40:
630:
607:
1873:
31:
1916:
6460:
1743:
Colchicine has one stereocenter located at carbon 7. The natural configuration of this stereocenter is S. The molecule also contains one chiral axis - the single bond between rings A and C. The natural configuration of this axis is aS. Although colchicine has four stereoisomers, the only one found in
1714:
Before the
Colcrys approval, unapproved colchicine products were being illegally sold in the United States for under 10 cents a pill. These products were also labeled in an unsafe manner and not manufactured under FDA inspection. URL conducted one Phase 3 clinical trial and at least 12 other trials
913:
Colchicine is an alternative for those unable to tolerate NSAIDs when treating gout. Low doses (1.2 mg in one hour, followed by 0.6 mg an hour later) appear to be well tolerated and may reduce gout symptoms and pain, perhaps as effectively as NSAIDs. At higher doses, side effects (primarily
1683:
attacks. The only placebo control trial conducted using colchicine for acute gout attacks instructed physicians to give colchicine until pain relief or toxicity. All patients on the colchicine arm had adverse events. Despite its toxicity, unapproved oral colchicine was still prescribed using this
1269:
In the United States, several hundred cases of colchicine toxicity are reported annually, about 10% of which end with serious morbidity or mortality. Many of these cases are intentional overdoses, but others were accidental; for example, if the drug were not dosed appropriately for kidney function.
1232:
Because colchicine is so toxic, chemists are continuing to try to synthesize derivatives of the molecule that decrease the toxicity. The most important aspect of these derivatives is that they keep the tropolone ring (the ring with the methoxy group and the carbonyl) intact to retain the mechanistic
4565:
Terkeltaub RA, Furst DE, Bennett K, Kook KA, Crockett RS, Davis MW (April 2010). "High versus low dosing of oral colchicine for early acute gout flare: Twenty-four-hour outcome of the first multicenter, randomized, double-blind, placebo-controlled, parallel-group, dose-comparison colchicine study".
1976:
in plant cells to produce new or improved varieties, strains, and cultivars. When used to induce polyploidy in plants, colchicine cream is usually applied to a growth point of the plant, such as an apical tip, shoot, or sucker. Seeds can be presoaked in a colchicine solution before planting. Since
1752:
Colchicine is a light-sensitive compound, so needs to be stored in a dark bottle. Upon exposure to light, colchicine undergoes photoisomerization and transforms into structural isomers, called lumicolchicine. After this transformation, colchicine is no longer effective in its mechanistic binding to
1220:
No specific antidote for colchicine is known, but supportive care is used in cases of overdose. In the immediate period after an overdose, monitoring for gastrointestinal symptoms, cardiac dysrhythmias, and respiratory depression is appropriate, and may require gastrointestinal decontamination with
1075:
According to one review, colchicine poisoning by overdose (range of acute doses of 7 to 26 mg) begins with a gastrointestinal phase occurring 10–24 hours after ingestion, followed by multiple organ dysfunction occurring 24 hours to 7 days after ingestion, after which the affected person either
1799:
of 0.6 to 1.2 mg per day, or a high-dose amount of up to 4.8 mg in the first 6 hours of a gout episode. With an oral dose of 0.6 mg, peak blood levels occur within one to two hours. For treating gout, the initial effects of colchicine occur in a window of 12 to 24 hours, with a peak
2001:
instead of diploid). While this would be fatal in most higher animal cells, in plant cells, it is not only usually well-tolerated, but also frequently results in larger, hardier, faster-growing, and in general more desirable plants than the normally diploid parents. For this reason, this type of
1315:, or those who have liver or kidney disease, should not take colchicine, as these drugs and conditions may interfere with colchicine metabolism and raise its blood levels, potentially increasing its toxicity abruptly. Symptoms of toxicity include gastrointestinal upset, fever,
1695:, acute gout flares, and for the prophylaxis of gout flares). This resulted in a 3-year regulatory market exclusivity in the acute and chronic gout indications and a 7-year exclusity on the FMF indication. In addition, there are 17 patents on colchicine, listed in the FDA
1867:-formyldemecolcine hydrolyzes then to generate the molecule demecolcine, which also goes through an oxidative demethylation that generates deacetylcolchicine. The molecule of colchicine appears finally after addition of acetyl-coenzyme A to deacetylcolchicine.
1667:
to the FD&C Act gave the FDA the authority to also require efficacy as a condition for drug approval. Drugs approved after June 24, 1938, but before 1962 had a limited time to be reviewed for efficacy in order to remain on the market. This was known as the
2029:
triploid plants not readily propagated vegetatively cannot produce a second-generation crop from the seeds (if any) of the triploid crop and need to buy triploid seed from a supplier each year. Many sterile triploid plants, including some trees and
4299:
976:, as it may only be useful for the treatment of chondritis and mild skin symptoms. It is a component of therapy for several other conditions, including pericarditis, pulmonary fibrosis, biliary cirrhosis, various vasculitides, pseudogout,
1702:
At the time of approval, there were no FDA approved single agent colchicine products (brand or generic) in the United States. The unapproved, illegally marketed colchicine products were forcibly removed by the FDA in
October 2010.
5901:
4075:"Examen chimique des plusieurs végétaux de la famille des colchicées, et du principe actif qu'ils renferment. [Cévadille (veratrum sabadilla); hellébore blanc (veratrum album); colchique commun (colchicum autumnale)]"
1626:
made an important contribution when he suggested that, among the molecule's three rings, two were seven-member rings. Its pain-relieving and anti-inflammatory effects for gout were linked to its ability to bind with tubulin.
5889:
1800:
within 48 to 72 hours. It has a narrow therapeutic window, requiring monitoring of the subject for potential toxicity. Colchicine is not a general pain-relief drug, and is not used to treat pain in other disorders.
1655:—through which the FDA sought more rigorous testing of efficacy and safety of colchicine and other unapproved drugs. This program was in response to multiple deaths caused by "unapproved products.". After the
4097:
1622:. In 1833, P. L. Geiger purified an active ingredient, which he named colchicine. It quickly became a popular remedy for gout. The determination of colchicine's structure required decades, although in 1945,
5748:
1478:
mediators. Apart from inhibiting mitosis, colchicine inhibits neutrophil motility and activity, leading to a net anti-inflammatory effect, which has efficacy for inhibiting or preventing gout inflammation.
6141:
3752:
Schwier NC, Cornelio CK, Boylan PM (April 2022). "A systematic review of the drug-drug interaction between statins and colchicine: Patient characteristics, etiologies, and clinical management strategies".
1711:
The events that lead to the approval of
Colcrys, the clearance of the illegally sold non-FDA approved colchicine products, Colcrys pricing and the sale of URL Pharma still are controversial today.
1083:
and be absorbed into the body, causing systemic toxicity. Symptoms of colchicine overdose start 2 to 24 hours after the toxic dose has been ingested, and include burning in the mouth and throat,
5897:
5885:
5743:
999:. In people with recent myocardial infarction (recent heart attack), it has been found to reduce risk of future cardiovascular events. Its clinical use may grow to include this indication.
696:
2787:
1047:
Deaths – both accidental and intentional – have resulted from overdose of colchicine. Typical side effects of moderate doses may include gastrointestinal upset, diarrhea, and
4253:
3874:
Cisternino S, Rousselle C, Debray M, Scherrmann JM (October 2003). "In vivo saturation of the transport of vinblastine and colchicine by P-glycoprotein at the rat blood-brain barrier".
4166:
Dewar did not prove the structure of colchicine; he merely suggested that it contained two seven-membered rings. Colchicine's structure was determined by X-ray crystallography in 1952
262:
3047:"Safety of colchicine and NSAID prophylaxis when initiating urate-lowering therapy for gout: propensity score-matched cohort studies in the UK Clinical Practice Research Datalink"
2470:
1106:
If the affected persons survive the gastrointestinal phase of toxicity, they may experience multiple organ failure and critical illness. This includes kidney damage, which causes
1679:
drug that was implicated in numerous death leading to the FDA forcefully removing injectable colchicine from the US Market. At this time oral colchicine was being used to treat
1659:
was signed into law in June 24, 1938, the FDA had the regulatory authority to mandate drugs be reviewed for safety prior to approval. Drugs approved prior to June 24, 1938 were
980:, calcinosis, scleroderma, and amyloidosis. Research regarding the efficacy of colchicine in many of these diseases has not been performed. It is also used in the treatment of
5893:
6063:
5341:
2291:"2012 American College of Rheumatology guidelines for management of gout. Part 1: systematic nonpharmacologic and pharmacologic therapeutic approaches to hyperuricemia"
1292:
involved in drug and toxin metabolism. Fatal drug interactions have occurred when colchicine was taken with other drugs that inhibit P-glycoprotein and CYP3A4, such as
6525:
2106:
1392:
of joints. These crystal deposits cause inflammatory arthritis, which is initiated and sustained by mechanisms involving various proinflammatory mediators, such as
2046:
and do not drop undesirable fruit and seed litter. In certain species, colchicine-induced triploidy has been used to create "seedless" fruit, such as seedless
1696:
5973:
5857:
5783:
3094:
4547:
5847:
5278:
217:
917:
For treating gout symptoms, colchicine is taken orally, with or without food, as symptoms first appear. Subsequent doses may be needed if symptoms worsen.
6277:
5881:
5852:
4472:
Ahern MJ, Reid C, Gordon TP, McCredie M, Brooks PM, Jones M (June 1987). "Does colchicine work? The results of the first controlled study in acute gout".
3631:
Finkelstein Y, Aks SE, Hutson JR, Juurlink DN, Nguyen P, Dubnov-Raz G, et al. (June 2010). "Colchicine poisoning: the dark side of an ancient drug".
5738:
5733:
3831:
Drion N, Lemaire M, Lefauconnier JM, Scherrmann JM (October 1996). "Role of P-glycoprotein in the blood-brain transport of colchicine and vinblastine".
1241:
With overdoses, colchicine becomes toxic as an extension of its cellular mechanism of action via binding to tubulin. Cells so affected undergo impaired
5872:
3183:
Nelson K, Fuster V, Ridker PM (August 2023). "Low-Dose
Colchicine for Secondary Prevention of Coronary Artery Disease: JACC Review Topic of the Week".
2085:. Wheat is typically tetraploid and rye diploid, with their triploid hybrid infertile; treatment of triploid triticale with colchicine gives fertile
1766:
738:
InChI=1S/C22H25NO6/c1-12(24)23-16-8-6-13-10-19(27-3)21(28-4)22(29-5)20(13)14-7-9-18(26-2)17(25)11-15(14)16/h7,9-11,16H,6,8H2,1-5H3,(H,23,24)/t16-/m0/s1
1672:(DESI). As of today there are only a handful of drugs still on the DESI list and in 2006, the FDA stated it was not aware of any grandfathered drugs.
6436:
6202:
2340:"2012 American College of Rheumatology guidelines for management of gout. Part 2: therapy and antiinflammatory prophylaxis of acute gouty arthritis"
5553:
4645:
4521:
1989:; half the resulting daughter cells, therefore, contain no chromosomes, while the other half contain double the usual number of chromosomes (i.e.,
1855:-methylation directed by S-adenosylmethionine. Two oxidation steps followed by the cleavage of the cyclopropane ring lead to the formation of the
5837:
4968:
4743:
Sagorin C, Ertel NH, Wallace SL (March 1972). "Photoisomerization of colchicine. Loss of significant antimitotic activity in human lymphocytes".
6039:
6035:
6031:
6023:
3410:
Portincasa P (2016). "Colchicine, Biologic Agents and More for the
Treatment of Familial Mediterranean Fever. The Old, the New, and the Rare".
948:. As an anti-inflammatory drug, Lodoco in a dose of 0.5 mg per day reduced the rate of cardiovascular events by 31% in people with established
896:
in plant cells are doubled. This frequently results in larger, hardier, faster-growing, and in general more desirable plants than the normally
6332:
6327:
6317:
115:
4828:
Leete E (1963). "The biosynthesis of the alkaloids of
Colchicum: The incorporation of phenylalaline-2-C14 into colchicine and demecolcine".
1675:
By 2006, URL Pharma decided to research colchicine to see if this unapproved product could gain legal FDA approval. Colchicine was a narrow
873:), was used as early as 1500 BC to treat joint swelling. It was approved for medical use in the United States in 1961. It is available as a
6282:
710:
1769:(42 U.S.C. 11002) and is subject to strict reporting requirements by facilities that produce, store, or use it in significant quantities.
6425:
6385:
6267:
6159:
5793:
5646:
5463:
5419:
2474:
6252:
6151:
5822:
5630:
6390:
5907:
5525:
5271:
2264:
2212:
2187:
2162:
3446:
1396:. Colchicine accumulates in white blood cells and affects them in a variety of ways - decreasing motility, mobilization (especially
1795:
Colchicine is typically prescribed to mitigate or prevent the onset of gout, or its continuing symptoms and pain, using a low-dose
2061:
The ability of colchicine to induce polyploidy can be also exploited to render infertile hybrids fertile, for example in breeding
6247:
1270:
Most cases of colchicine toxicity occur in adults. Many of these adverse events resulted from the use of intravenous colchicine.
2137:
4359:
4077:[Chemical examination of several plants of the meadow saffron family, and of the active principle that they contain.].
1762:
6515:
6495:
5222:
4057:
3386:
2640:
2616:
2507:
2398:
2248:
2445:
5264:
3266:
Puéchal X, Terrier B, Mouthon L, Costedoat-Chalumeau N, Guillevin L, Le Jeunne C (March 2014). "Relapsing polychondritis".
1656:
5182:
4961:
793:
4906:
3447:"Colchicine for primary prevention of atrial fibrillation after open-heart surgery: Systematic review and meta-analysis"
1669:
1612:
755:
166:
6418:
2965:"Management of Gout: A Systematic Review in Support of an American College of Physicians Clinical Practice Guideline"
2791:
1955:
730:
92:
5239:
4779:"40 CFR Appendix A to Part 355, The List of Extremely Hazardous Substances and Their Threshold Planning Quantities"
789:
1079:
Colchicine can be toxic when ingested, inhaled, or absorbed in the eyes. It can cause a temporary clouding of the
6505:
6500:
2765:
1474:
Generally, colchicine appears to inhibit multiple proinflammatory mechanisms, while enabling increased levels of
381:
247:
147:
4419:"Deaths from Intravenous Colchicine Resulting from a Compounding Pharmacy Error --- Oregon and Washington, 2007"
4954:
3006:"Management of Acute and Recurrent Gout: A Clinical Practice Guideline From the American College of Physicians"
1937:
3969:
1715:
to gain the approval of
Colcrys. URL Pharma priced Colcrys at $ 4.85 a pill drawing the ire of many groups.
920:
There is preliminary evidence that daily colchicine (0.6 mg twice daily) may be effective as a long-term
455:
6188:
1691:
In July 2009, the FDA approved colchicine as a monotherapy for the treatment of three different indications (
1403:
Under preliminary research are various mechanisms by which colchicine may interfere with gout inflammation:
6411:
6217:
4258:
1692:
1685:
1684:
dosing regimen. In addition, at this time, oral colchicine was also used to treat the often fatal disease
1648:
981:
824:
777:
625:
506:
4609:
Kesselheim AS, Solomon DH (June 2010). "Incentives for drug development--the curious case of colchicine".
4332:
3678:
1591:
use waned over time, likely due to the severe gastrointestinal side effects preparations caused. In 1763,
4855:
Herbert RB (February 2001). "The biosynthesis of plant alkaloids and nitrogenous microbial metabolites".
1933:
1652:
1488:
586:
3996:"History of the use of colchicum and related medicaments in gout; with suggestions for further research"
3231:
Cocco G, Chu DC, Pandolfi S (December 2010). "Colchicine in clinical medicine. A guide for internists".
1831:, another plant of the family Colchicaceae, resulted in its incorporation into colchicine. However, the
6520:
6450:
5076:
4935:
3594:
2788:"Information for Healthcare Professionals: New Safety Information for Colchicine (marketed as Colcrys)"
1282:
6059:
1735:
Colchicine has a melting point of 142-150 °C. It has a molecular weight of 399.4 grams per mole.
877:. In 2021, it was the 184th most commonly prescribed medication in the United States, with more than 2
575:
2963:
Shekelle PG, Newberry SJ, FitzGerald JD, Motala A, O'Hanlon CE, Tariq A, et al. (January 2017).
1719:
1664:
6490:
4443:
3045:
Roddy E, Bajpai R, Forrester H, Partington RJ, Mallen CD, Clarson LE, et al. (December 2023).
973:
602:
5367:
5298:
5227:
4778:
2022:
1926:
1131:
816:
203:
105:
3536:
Nidorf SM, Fiolet AT, Mosterd A, Eikelboom JW, Schut A, Opstal TS, et al. (November 2020).
1019:). About 10–20% of a colchicine dose is excreted unchanged by the kidneys; it is not removed by
6067:
5660:
5496:
5336:
1978:
1780:
for colchicine are
Colcrys or Mitigare, which are manufactured as a dark– and light-blue
945:
835:
327:
4698:
4047:
2238:
969:
781:
555:
6535:
6510:
6347:
6234:
5802:
5708:
5304:
4074:
2606:
2388:
1824:
1663:, as long as their manufacturing, ingredients and labeling remained unchanged. In 1962, the
953:
785:
446:
3095:"How common are side-effects of treatment to prevent gout flares when starting allopurinol?"
6375:
6075:
5620:
5586:
4211:
4181:
4141:
3004:
Qaseem A, Harris RP, Forciea MA, Denberg TD, Barry MJ, Boyd C, et al. (January 2017).
1583:
1562:
1538:
1304:
1202:
850:), and the medication can be deadly in overdose. Whether colchicine is safe for use during
812:
515:
350:
2338:
Khanna D, Khanna PP, Fitzgerald JD, Singh MK, Bae S, Neogi T, et al. (October 2012).
2289:
Khanna D, Fitzgerald JD, Khanna PP, Bae S, Singh MK, Neogi T, et al. (October 2012).
1242:
495:
8:
6480:
6055:
5574:
5459:
4418:
3705:"Quantum-chemical, NMR, FT IR, and ESI MS studies of complexes of colchicine with Zn(II)"
1888:
1623:
1509:
1210:
1143:
1139:
1027:
may result. The presentation includes a progressive onset of proximal weakness, elevated
992:
977:
866:
401:
210:
4697:
Sapra S, Bhalla Y, Sharma S, Singh G, Nepali K, Budhiraja A, et al. (13 May 2012).
4215:
4185:
4145:
3975:. Center for Drug Evaluation and Research, US Food and Drug Administration. 30 July 2009
3844:
3597:. Centers for Disease Control and Prevention, US Department of Health and Human Services
3335:
3310:
3071:
3046:
1784:
having a dose of 0.6 mg. Colchicine is also prepared as a white, yellow, or purple
1254:
629:
606:
410:
39:
6485:
6223:
5475:
5290:
4718:
4591:
4485:
4157:
4020:
3995:
3943:
3918:
3899:
3856:
3778:
3729:
3704:
3656:
3518:
3291:
3208:
3110:
2875:
2850:
2823:
2806:
2738:
2364:
2339:
2315:
2290:
2054:). Since most triploids do not produce pollen themselves, such plants usually require
1781:
1660:
1631:
1222:
874:
177:
3423:
6530:
5832:
5712:
5514:
5153:
4872:
4760:
4626:
4595:
4583:
4489:
4400:
4307:
4236:
4053:
4025:
3948:
3891:
3848:
3813:
3782:
3770:
3734:
3648:
3569:
3522:
3510:
3469:
3427:
3392:
3382:
3377:
Hoffman RS, Nelson LS, Goldfrank LR, Howland MA, Lewin NA, Smith SW (11 April 2019).
3340:
3295:
3283:
3248:
3212:
3200:
3114:
3076:
3027:
2986:
2880:
2828:
2730:
2612:
2587:
2503:
2394:
2369:
2320:
2244:
1982:
1902:
peak in the summer, and range from 0.1% in the flower to 0.8% in the bulb and seeds.
1848:
1796:
1789:
1676:
1604:
1475:
1467:
1147:
1096:
1011:) regimens of oral colchicine are absolutely contraindicated in people with advanced
957:
831:
299:
286:
274:
139:
4722:
3903:
3860:
3660:
2849:
McKenzie BJ, Wechalekar MD, Johnston RV, Schlesinger N, Buchbinder R (August 2021).
2582:
2565:
1440:
6093:
5922:
5490:
5486:
5315:
5287:
4864:
4837:
4752:
4710:
4618:
4575:
4481:
4390:
4219:
4189:
4161:
4149:
4113:
4015:
4007:
3938:
3930:
3883:
3840:
3805:
3762:
3724:
3716:
3640:
3559:
3549:
3500:
3461:
3419:
3330:
3326:
3322:
3275:
3240:
3192:
3102:
3066:
3058:
3017:
2976:
2870:
2866:
2862:
2818:
2742:
2722:
2577:
2471:"Colchicine for acute gout: updated information about dosing and drug interactions"
2359:
2351:
2310:
2302:
2043:
1894:
1618:
Colchicine was first isolated in 1820 by French chemists P. S. Pelletier and J. B.
1561:
to treat gout probably dates to around 550 AD, as the "hermodactyl" recommended by
1447:
1135:
1023:. Cumulative toxicity is a high probability in this clinical setting, and a severe
642:
309:
230:
57:
4273:
2662:
2632:
2419:
1578:
125:
6464:
5983:
5827:
5798:
5668:
5530:
5520:
5482:
5085:
4671:
3809:
3644:
3505:
3488:
3465:
3279:
2726:
1785:
1190:
1186:
1028:
1016:
996:
968:
Colchicine is also used as an anti-inflammatory agent for long-term treatment of
949:
847:
834:, so overdosing is a significant risk. Common side effects of colchicine include
797:
435:
337:
317:
940:
In June 2023, the U.S. FDA approved a low-dose regimen of colchicine (tradename
6370:
6272:
5942:
5862:
5696:
5471:
5429:
5233:
5021:
5011:
4806:
3244:
3196:
3106:
2695:
2561:
1969:
1496:
1385:
1297:
1279:
1226:
1092:
1064:
1059:, and cause hair loss. All of these side effects can result from inhibition of
1032:
1012:
956:. Colchicine was most effective in combination therapy with lipid-lowering and
929:
885:
843:
5256:
4714:
4522:"Orange Book: Approved Drug Products with Therapeutic Equivalence Evaluations"
4395:
4378:
4194:
4169:
3887:
3720:
3595:"CDC - The Emergency Response Safety and Health Database: Biotoxin: Cochicine"
3396:
1997:), and lead to cell nuclei with double the usual number of chromosomes (i.e.,
800:
in the treatment of gout. Other uses for colchicine include the management of
6474:
6101:
6011:
5958:
5927:
5680:
5600:
5559:
5510:
5467:
5439:
5198:
5016:
4507:
4311:
4223:
4117:
2111:
1851:
involving the intermediate isoandrocymbine. The resulting molecule undergoes
1816:
1522:
1461:
1332:
1159:
1123:
1024:
855:
618:
4946:
4379:"Unapproved drugs in the United States and the Food and Drug Administration"
4170:"An x-ray diffraction determination of the chemical structure of colchicine"
3309:
Alabed S, Cabello JB, Irving GJ, Qintar M, Burls A, Nelson L (August 2014).
3156:
3062:
2941:
2515:
1847:-autumnaline. That biosynthetic pathway occurs primarily through a phenolic
1642:
6135:
6079:
6071:
6027:
5995:
5605:
5582:
5139:
5042:
4982:
4876:
4756:
4630:
4587:
4404:
4029:
3952:
3895:
3817:
3774:
3738:
3652:
3573:
3514:
3473:
3431:
3344:
3287:
3252:
3204:
3080:
3031:
2990:
2884:
2832:
2734:
2591:
2373:
2324:
2035:
2026:
1809:
1630:
The full synthesis of colchicine was achieved by the Swiss organic chemist
1518:
1432:
1312:
1308:
1293:
1173:
Long-term exposure to colchicine can lead to toxicity, particularly of the
1163:
1127:
1020:
1008:
859:
839:
801:
225:
22:
5331:
4764:
4493:
4132:
Dewar MJ (3 February 1945). "Structure of colchicine". Letters to Editor.
3852:
3554:
3537:
1381:
6380:
6297:
6163:
6105:
6097:
5987:
5842:
5763:
5753:
5700:
5650:
5549:
5534:
5506:
5377:
5207:
5202:
5128:
5093:
5052:
5047:
4622:
4011:
2713:
Chen LX, Schumacher HR (October 2008). "Gout: an evidence-based review".
2055:
2039:
2002:
genetic manipulation is frequently used in breeding plants commercially.
1836:
1722:, acquired URL Pharma for $ 800 million including the rights to Colcrys.
1550:
1408:
1389:
1246:
1174:
1052:
1048:
1036:
985:
925:
921:
133:
4841:
3934:
3265:
928:
to reduce the risk of increased uric acid levels and acute gout flares;
475:
6337:
6312:
6292:
6287:
6262:
6167:
6155:
6127:
6045:
6019:
6015:
6001:
5991:
5962:
5950:
5946:
5917:
5912:
5867:
5806:
5788:
5692:
5676:
5672:
5654:
5638:
5590:
5578:
5564:
5501:
5424:
5382:
5177:
5119:
5103:
5098:
5037:
5006:
4991:
4545:
4357:
3564:
3487:
Imazio M, Andreis A, Brucato A, Adler Y, De
Ferrari GM (October 2020).
3445:
Lennerz C, Barman M, Tantawy M, Sopher M, Whittaker P (December 2017).
2047:
1998:
1990:
1973:
1940: in this section. Unsourced material may be challenged and removed.
1872:
1813:
1777:
1514:
1425:
1397:
1352:
1344:
1324:
1250:
1115:
893:
889:
769:
672:
486:
4579:
3766:
2473:. National Prescribing Service, Australia. 14 May 2010. Archived from
2355:
2306:
2107:"Health product highlights 2021: Annexes of products approved in 2021"
1162:. Recovery may begin within six to eight days and begins with rebound
6365:
6322:
6307:
6302:
6173:
6117:
6113:
6006:
5937:
5877:
5817:
5812:
5778:
5688:
5684:
5625:
5615:
5594:
5540:
5444:
5411:
5193:
5057:
4868:
4153:
3022:
3005:
2981:
2964:
2848:
2086:
2062:
2014:
2010:
1856:
1835:
ring of colchicine resulted from the expansion of the tyrosine ring.
1832:
1454:
1377:
1348:
1340:
1336:
1328:
1167:
1151:
1111:
1076:
declines into multiple organ failure or recovers over several weeks.
960:
medications. The mechanism for this effect of colchicine is unknown.
851:
820:
421:
363:
119:
1915:
6360:
6146:
6131:
6121:
6109:
5978:
5968:
5954:
5768:
5634:
5610:
5569:
5434:
5133:
5124:
5062:
4699:"Colchicine and its various physicochemical and biological aspects"
4274:"FDA Moves In On Unapproved Cough Suppressant Hydrocodone Products"
3873:
2006:
1820:
1619:
1608:
1574:
1534:
1458:
1436:
1393:
1320:
1214:
1155:
1107:
1100:
1088:
1035:. Colchicine toxicity can be potentiated by the concomitant use of
932:
may occur, though overall the risk of serious side effects is low.
838:
upset, particularly at high doses. Severe side effects may include
808:
535:
466:
161:
3830:
2005:
When such a tetraploid plant is crossed with a diploid plant, the
1843:
revealed that colchicine can be synthesized biosynthetically from
944:) to reduce the risk of further disorders in adults with existing
695:
6257:
6089:
5758:
5704:
5642:
5545:
5449:
5395:
5387:
5372:
5351:
5346:
5188:
4508:"FDA Approves Colchicine With Drug Interaction and Dose Warnings"
2766:"Colcrys (colchicine, USP) tablets 0.6 mg. Drug Approval Package"
1994:
1986:
1418:
1412:
1316:
1258:
1198:
1060:
897:
4646:"2,000% Drug Price Surge Is a Side Effect of FDA Safety Program"
3702:
3684:. Christchurch and Canterbury District Health Board, New Zealand
2962:
2390:
Pericardial
Diseases: Clinical Diagnostic Imaging Atlas with DVD
6085:
5403:
5359:
2502:(76 ed.). Pharmaceutical Press. 2018. pp. 1085–1086.
1466:
Inhibits release of glycoproteins that promote chemotaxis from
1356:
1289:
1286:
1206:
1178:
1119:
1080:
1056:
566:
343:
3044:
81:
5718:
3919:"Intravenous colchicine in the management of gouty arthritis"
3703:
Jankowski W, Kurek J, Barczyński P, Hoffmann M (April 2017).
3376:
2070:
2031:
2018:
1596:
1530:
1492:
1373:
1182:
1084:
686:
546:
72:
3970:"Colcrys (colchicine). Summary review for regulatory action"
3630:
3535:
2566:"Mechanism of action of colchicine in the treatment of gout"
591:
30:
6178:
6050:
5723:
4978:
3796:
Niel E, Scherrmann JM (December 2006). "Colchicine today".
2805:
Laubscher T, Dumont Z, Regier L, Jensen B (December 2009).
2804:
2337:
2058:
with a diploid parent to induce seedless fruit production.
1765:
in the United States as defined in Section 302 of the U.S.
1680:
1570:
1554:
1194:
773:
526:
4564:
3444:
3003:
2522:. National Institute for Health and Care Excellence (NICE)
1099:
due to extreme vascular damage and fluid loss through the
66:
5664:
3486:
3308:
2288:
2078:
1643:
Colcrys, the Unapproved Drugs Initiative, and controversy
1355:
may experience colchicine toxicity. Grapefruit juice and
75:
2608:
The Search for Human Chromosomes: A History of Discovery
1319:, low blood cell counts, and organ failure. People with
984:, in which it reduces attacks and the long-term risk of
4471:
4358:
Center for Drug Evaluation and Research (16 May 2024).
4333:"AP: Millions Spent On Unapproved Medicines - CBS News"
2696:"Modern Genetic Analysis: Changes in Chromosome Number"
1545:
extract was first described as a treatment for gout in
1411:
polymerization by binding to its constitutive protein,
4696:
3538:"Colchicine in Patients with Chronic Coronary Disease"
3128:
2693:
827:
removed all injectable colchicine from the US market.
718:
CC(=O)N1CCC2=CC(=C(C(=C2C3=CC=C(C(=O)C=C13)OC)OC)OC)OC
6448:
6189:
4637:
3751:
3489:"Colchicine for acute and chronic coronary syndromes"
93:
84:
78:
63:
4246:
4167:
2560:
69:
4892:
Medicinal natural products: A biosynthetic approach
4742:
4200:Its total synthesis was first accomplished in 1959
2768:. US Food and Drug Administration. 17 February 2010
1905:
1507:
The plant source of colchicine, the autumn crocus (
1185:. Effects of long-term colchicine toxicity include
935:
858:appears to be safe. Colchicine works by decreasing
454:
60:
4771:
3182:
1767:Emergency Planning and Community Right-to-Know Act
1146:. Neurologic symptoms are also evident, including
4608:
4376:
4202:Eschenmoser A (1959). "Synthese des Colchicins".
4072:
1189:, thrombocytopenia, low white blood cell counts,
6526:Drugs developed by Takeda Pharmaceutical Company
6472:
4546:Center for Drug Evaluation and Research (2009).
4444:"Federal Register / Vol. 73, No. 27 / Page 7565"
4100:[On some new poisonous organic alkalis]
3230:
2844:
2842:
1607:, who had gout himself and had written humorous
1595:was recorded as a remedy for dropsy (now called
1553:, in the first century AD. Use of the bulb-like
434:
5286:
4904:
4801:
4799:
4678:. National Center for Biotechnology Information
4558:
4098:"Ueber einige neue giftige organische Alkalien"
3372:
3370:
3368:
3366:
3364:
3362:
3360:
3358:
3356:
3354:
2446:"FDA Enforcement Against Injectable Colchicine"
2426:. American Society of Health-System Pharmacists
2236:
1063:, which may include neuromuscular toxicity and
409:
4548:"Colchicine (marketed as Colcrys) Information"
4474:Australian and New Zealand Journal of Medicine
4377:Nasr A, Lauterio TJ, Davis MW (October 2011).
4168:King MV, de Vries JL, Pepinsky R (July 1952).
3795:
2712:
1898:(glory lily). Concentrations of colchicine in
914:diarrhea, nausea, or vomiting) limit its use.
6348:
6235:
5272:
4976:
4962:
4940:Emergency Response Safety and Health Database
4643:
3916:
3185:Journal of the American College of Cardiology
2839:
1981:is driven by microtubules, colchicine alters
1359:can also increase colchicine concentrations.
4796:
3867:
3789:
3438:
3381:(Eleventh ed.). New York: McGraw-Hill.
3351:
3151:
3149:
2694:Griffiths AJ, Gelbart WM, Miller JH (1999).
2689:
2687:
2685:
2683:
1985:by inhibiting chromosome segregation during
165:
4360:"Drug Efficacy Study Implementation (DESI)"
4201:
4122:; colchicine is discussed on pages 274-276
3824:
3529:
3480:
3315:The Cochrane Database of Systematic Reviews
2855:The Cochrane Database of Systematic Reviews
2780:
2414:
2412:
2410:
2132:
2130:
1699:which may confer additional exclusivity.
1417:As availability of tubulin is essential to
5279:
5265:
4969:
4955:
4602:
4500:
3679:"Colchicine – extremely toxic in overdose"
3409:
2760:
2758:
2756:
2754:
2752:
2556:
2554:
2552:
2550:
2548:
2546:
2544:
2542:
2540:
2538:
2465:
2463:
1827:. Giving radioactive phenylalanine-2-C to
1772:
991:Colchicine is effective for prevention of
628:
605:
494:
4907:"The use of colchicine in plant breeding"
4394:
4193:
4019:
3942:
3728:
3672:
3670:
3563:
3553:
3504:
3334:
3178:
3176:
3174:
3146:
3070:
3021:
2980:
2936:
2934:
2932:
2930:
2928:
2926:
2924:
2922:
2920:
2918:
2916:
2914:
2874:
2822:
2680:
2581:
2386:
2363:
2314:
2243:. Elsevier Health Sciences. p. 177.
1956:Learn how and when to remove this message
1581:in the 16th century, and appeared in the
1261:, culminating in multiple organ failure.
514:
6437:Ionotropic glutamate receptor modulators
5316:
4049:Pharmacodynamic basis of herbal medicine
3226:
3224:
3222:
2956:
2912:
2910:
2908:
2906:
2904:
2902:
2900:
2898:
2896:
2894:
2807:"Taking the stress out of managing gout"
2706:
2564:, Lauterio TJ, Wolfe HR (October 2014).
2494:
2492:
2420:"Colchicine Monograph for Professionals"
2407:
2393:. Elsevier Health Sciences. p. 58.
2127:
1753:tubulin, so is not effective as a drug.
1603:plants were brought to North America by
1450:production in response to urate crystals
1236:
4854:
3993:
3964:
3962:
3745:
2749:
2535:
2460:
1443:activation, a component of inflammation
972:. It appears to have limited effect in
601:
474:
138:
6473:
4889:
4644:Langreth R, Koons C (6 October 2015).
4095:
3676:
3667:
3589:
3587:
3585:
3583:
3171:
2997:
2034:, are becoming increasingly valued in
1808:According to laboratory research, the
1730:
1611:about the disease during his stint as
1367:
619:
280:
6194:Tooltip N-Methyl-D-aspartate receptor
5260:
4950:
4827:
4131:
4045:
3626:
3624:
3622:
3620:
3618:
3616:
3614:
3612:
3233:European Journal of Internal Medicine
3219:
2891:
2798:
2489:
1424:Inhibits activation and migration of
1170:as organ functions return to normal.
574:
554:
293:
156:
124:
5886:4-hydroxyquinoline-3-carboxylic acid
5744:4-Phenyl-4-formyl-N-methylpiperidine
3959:
2663:"Colchicine - Drug Usage Statistics"
2643:from the original on 15 January 2024
2604:
1938:adding citations to reliable sources
1909:
1747:
1657:Federal Food, Drug, and Cosmetic Act
1273:
1002:
794:nonsteroidal anti-inflammatory drugs
229:
16:Medication mainly used to treat gout
5709:trichloroethane (methyl chloroform)
4611:The New England Journal of Medicine
3917:Graham W, Roberts JB (March 1953).
3845:10.1046/j.1471-4159.1996.67041688.x
3580:
3542:The New England Journal of Medicine
3454:International Journal of Cardiology
3379:Goldfrank's toxicologic emergencies
1744:nature is the aS,7s configuration.
1725:
1718:In 2012, Asia's biggest drugmaker,
1482:
963:
534:
425:
13:
6313:Pesampator (BIIB-104, PF-04958242)
4486:10.1111/j.1445-5994.1987.tb01232.x
4300:"Unapproved Drugs Called 'Threat'"
4073:Pelletier PS, Caventou JB (1820).
3609:
2500:British national formulary: BNF 76
2021:), although many triploids can be
1871:
1670:Drug Efficacy Study Implementation
1613:United States Ambassador to France
1513:), was described for treatment of
1376:results from the precipitation of
1042:
14:
6547:
4928:
4783:LII / Legal Information Institute
4254:"FDA Unapproved Drugs Initiative"
3424:10.2174/0929867323666151117121706
2792:U.S. Food and Drug Administration
1435:complex found in neutrophils and
952:and by 23% in people with recent
256:
188:
6458:
4079:Annales de Chimie et de Physique
4035:(free BMJ registration required)
4000:Annals of the Rheumatic Diseases
3923:Annals of the Rheumatic Diseases
3051:Annals of the Rheumatic Diseases
2715:Journal of Clinical Rheumatology
2237:Schachner LA, Hansen RC (2011).
1914:
1906:Botanical use and seedless fruit
1886:Colchicine may be purified from
1792:) having a dose of 0.6 mg.
1651:(FDA) safety program called the
1637:
1421:, colchicine may inhibit mitosis
1118:that can last for several days;
936:Risk of cardiovascular disorders
930:adverse gastrointestinal effects
790:American College of Rheumatology
659:
653:
56:
38:
29:
4905:Dermen H, Emsweller SL (1961).
4898:
4883:
4848:
4821:
4736:
4690:
4664:
4539:
4514:
4465:
4436:
4411:
4370:
4351:
4325:
4292:
4266:
4230:
4125:
4089:
4066:
4039:
3987:
3910:
3696:
3403:
3302:
3259:
3121:
3087:
3038:
2655:
2625:
2598:
2583:10.1016/j.clinthera.2014.07.017
2438:
2380:
2265:"Drugs@FDA: FDA-Approved Drugs"
2213:"Drugs@FDA: FDA-Approved Drugs"
2188:"Drugs@FDA: FDA-Approved Drugs"
2163:"Drugs@FDA: FDA-Approved Drugs"
1925:needs additional citations for
1881:
1803:
1362:
1264:
903:
865:Colchicine, in the form of the
854:is unclear, but its use during
743:Key:IAKHMKGGTNLKSZ-INIZCTEOSA-N
3327:10.1002/14651858.CD010652.pub2
2867:10.1002/14651858.CD006190.pub3
2448:. The Rheumatologist. May 2008
2331:
2282:
2257:
2230:
2205:
2180:
2155:
2099:
1706:
1278:Colchicine interacts with the
1257:, and interrupted function of
662:
647:
269:
1:
6412:Receptor/signaling modulators
6353:Tooltip Glycine transporter 2
6263:Bitopertin (RG1678/RO4917838)
6240:Tooltip Glycine transporter 1
4243:. Accessed 24 September 2023.
3994:Hartung EF (September 1954).
3709:Journal of Molecular Modeling
3311:"Colchicine for pericarditis"
2344:Arthritis Care & Research
2295:Arthritis Care & Research
2092:
1968:Colchicine is widely used in
1763:extremely hazardous substance
1756:
1142:leading to potentially fatal
1051:. High doses can also damage
884:Colchicine is widely used in
6516:Peripherally selective drugs
6496:Glycine receptor antagonists
6430:receptor positive modulators
4936:"Colchicine : Biotoxin"
4259:Food and Drug Administration
3810:10.1016/j.jbspin.2006.03.006
3645:10.3109/15563650.2010.495348
3506:10.1136/heartjnl-2020-317108
3466:10.1016/j.ijcard.2017.08.039
3280:10.1016/j.jbspin.2014.01.001
2727:10.1097/RHU.0b013e3181896921
2240:Pediatric Dermatology E-Book
1738:
1693:familial Mediterranean fever
1686:Familial Mediterranean fever
1649:Food and Drug Administration
1533:medical text. It is a toxic
1382:crystals of monosodium urate
1233:properties of the molecule.
982:familial Mediterranean fever
842:(low blood cell counts) and
784:, and to reduce the risk of
778:familial Mediterranean fever
7:
5077:Xanthine oxidase inhibitors
4703:Medicinal Chemical Research
3412:Current Medicinal Chemistry
3010:Annals of Internal Medicine
2969:Annals of Internal Medicine
2944:. Drugs.com. 1 January 2017
2851:"Colchicine for acute gout"
2532:Available online in UK only
2042:because they do not become
1812:of colchicine involves the
1653:Unapproved Drugs Initiative
1489:peripherally selective drug
1487:Colchicine appears to be a
1116:low white blood cell counts
1070:
10:
6552:
5468:chlorobutanol (chloretone)
4894:. Wiley. pp. 360–362.
4809:. Drugs.com. 6 August 2018
3245:10.1016/j.ejim.2010.09.010
3197:10.1016/j.jacc.2023.05.055
3107:10.3310/nihrevidence_62005
2702:. W. H. Freeman, New York.
2520:British national formulary
1577:, and were recommended by
1502:
1158:; children may experience
772:used to prevent and treat
637:Chemical and physical data
6403:
6346:
6233:
6216:
6187:
5583:pregnenolone (eltanolone)
5560:Glutamic acid (glutamate)
5314:
5297:
5217:
5170:
5152:
5112:
5084:
5075:
5030:
4999:
4990:
4715:10.1007/s00044-012-0077-z
4396:10.1007/s12325-011-0059-4
4195:10.1107/S0365110X52001313
3721:10.1007/s00894-017-3306-z
3159:. Drugs.com. 23 June 2023
2811:Canadian Family Physician
1720:Takeda Pharmaceutical Co.
1665:Kefauver-Harris Amendment
1599:) among other illnesses.
1495:uptake due to binding to
1372:In gout, inflammation in
892:, in which the number of
862:via multiple mechanisms.
751:
726:
706:
684:
671:
641:
636:
617:
585:
565:
545:
525:
505:
485:
465:
445:
420:
400:
377:
372:
362:
349:
336:
326:
316:
308:
246:
241:
216:
202:
176:
146:
132:
114:
110:Colcrys, Mitigare, others
104:
51:
46:
37:
28:
6419:GABA receptor modulators
5321:Tooltip Glycine receptor
4745:Arthritis and Rheumatism
4568:Arthritis and Rheumatism
4278:www.medicalnewstoday.com
4239:The Franklin Institute.
4224:10.1002/ange.19590712002
4118:10.1002/jlac.18330070312
2611:. Springer. p. 88.
1428:to sites of inflammation
974:relapsing polychondritis
830:Colchicine has a narrow
392:-heptalen-7-yl]acetamide
6064:3β-androsterone sulfate
6060:3α-androsterone sulfate
4857:Natural Product Reports
3888:10.1023/a:1026187301648
3063:10.1136/ard-2023-224154
2700:Modern Genetic Analysis
2023:propagated vegetatively
1839:feeding experiments of
1773:Formulations and dosing
1761:It is classified as an
1569:corms were used by the
1132:bone marrow suppression
946:cardiovascular diseases
908:
881:million prescriptions.
817:route of administration
792:recommends colchicine,
6506:Microtubule inhibitors
6501:Benzodihydroheptalenes
6308:ORG-25935 (SCH-900435)
5497:Alkylbenzene sulfonate
4757:10.1002/art.1780150213
4526:www.accessdata.fda.gov
4174:Acta Crystallographica
2269:www.accessdata.fda.gov
2217:www.accessdata.fda.gov
2192:www.accessdata.fda.gov
2167:www.accessdata.fda.gov
2009:offspring are usually
1979:chromosome segregation
1876:
1103:, which can be fatal.
1101:gastrointestinal tract
819:for colchicine can be
342:Metabolism, partly by
6381:Opiranserin (VVZ-149)
5681:diethyl ether (ether)
4106:Annalen der Pharmacie
3555:10.1056/NEJMoa2021372
2633:"The Top 300 of 2021"
2570:Clinical Therapeutics
2387:Hutchison SJ (2009).
1875:
1305:macrolide antibiotics
1237:Mechanism of toxicity
1211:peripheral neuropathy
1122:; muscular weakness;
954:myocardial infarction
786:myocardial infarction
6076:pregnenolone sulfate
6056:Neuroactive steroids
6014:constituents (e.g.,
5974:Cyanotriphenylborate
5935:Negative modulators:
5858:N,N-Dimethylmuscimol
5784:Cyanotriphenylborate
5621:Tetrahydrocannabinol
5587:pregnenolone acetate
5575:Neuroactive steroids
5548:constituents (e.g.,
5457:Positive modulators:
4623:10.1056/NEJMp1003126
4012:10.1136/ard.13.3.190
2721:(5 Suppl): S55–S62.
2138:"Colchicine capsule"
1934:improve this article
1863:-formyldemecolcine.
1584:London Pharmacopoeia
1563:Alexander of Tralles
1551:Pedanius Dioscorides
1539:secondary metabolite
1431:Interferes with the
1203:vesicular dermatitis
1015:(including those on
807:Colchicine is taken
6068:deoxycorticosterone
5848:N-Methylbicuculline
4842:10.1021/ja00905a030
4807:"Colchicine images"
4383:Advances in Therapy
4306:. 31 January 2024.
4280:. 29 September 2007
4216:1959AngCh..71..637S
4186:1952AcCry...5..437K
4146:1945Natur.155..141D
3935:10.1136/ard.12.1.16
3633:Clinical Toxicology
3101:. 6 February 2024.
2013:(unable to produce
1892:(autumn crocus) or
1889:Colchicum autumnale
1731:Physical properties
1510:Colchicum autumnale
1368:Mechanism of action
1144:respiratory failure
1140:ascending paralysis
1031:, and sensorimotor
993:atrial fibrillation
978:spondyloarthropathy
871:Colchicum autumnale
823:, and in 2008, the
289:(Prescription only)
265:(Prescription only)
25:
6278:Glycyldodecylamide
5882:4-hydroxyquinoline
5853:N-Methylstrychnine
5244:Never to phase III
5154:Mitotic inhibitors
4942:. 8 November 2017.
4890:Dewick PM (2009).
4339:. 24 November 2008
4237:Albert Eschenmoser
4096:Geiger PL (1833).
1877:
1859:ring contained by
1632:Albert Eschenmoser
1223:activated charcoal
875:generic medication
811:. The parenteral (
21:
6521:Pyrogallol ethers
6446:
6445:
6399:
6398:
6371:Ethanol (alcohol)
6273:Ethanol (alcohol)
6227:
6212:
6211:
5833:Isonipecotic acid
5739:2-Nitrostrychnine
5734:2-Aminostrychnine
5713:trichloroethylene
5515:sodium thiopental
5472:ethanol (alcohol)
5414:
5406:
5398:
5390:
5362:
5354:
5308:
5254:
5253:
5148:
5147:
5071:
5070:
4836:(22): 3666–3669.
4617:(22): 2045–2047.
4580:10.1002/art.27327
4453:. 8 February 2008
4204:Angewandte Chemie
4140:(3927): 141–142.
4059:978-0-8493-7050-2
4046:Ebadi MS (2007).
3767:10.1002/phar.2674
3677:Doogue M (2014).
3548:(19): 1838–1847.
3499:(20): 1555–1560.
3388:978-1-259-85961-8
3057:(12): 1618–1625.
2817:(12): 1209–1212.
2618:978-3-319-26336-6
2576:(10): 1465–1479.
2509:978-0-85711-338-2
2400:978-1-4160-5274-6
2356:10.1002/acr.21773
2350:(10): 1447–1461.
2307:10.1002/acr.21772
2301:(10): 1431–1446.
2250:978-0-7234-3665-2
2056:cross-pollination
2052:Citrullus lanatus
1983:cellular division
1966:
1965:
1958:
1849:coupling reaction
1748:Light sensitivity
1677:therapeutic index
1605:Benjamin Franklin
1547:De Materia Medica
1476:anti-inflammatory
1400:), and adhesion.
1274:Drug interactions
1255:cellular motility
1205:, kidney damage,
1097:hypovolemic shock
1095:. This can cause
1039:-lowering drugs.
1003:Contraindications
958:anti-inflammatory
832:therapeutic index
763:
762:
697:Interactive image
587:CompTox Dashboard
297:
284:
272:
260:
192:
159:
6543:
6463:
6462:
6461:
6454:
6354:
6350:
6241:
6237:
6231:
6230:
6221:
6195:
6191:
6094:dextromethorphan
5984:Dihydropyridines
5923:Thiocolchicoside
5873:Pseudostrychnine
5813:Gaboxadol (THIP)
5807:anandamide (AEA)
5799:Endocannabinoids
5531:Dihydropyridines
5491:trifluoroethanol
5487:trichloroethanol
5412:
5404:
5396:
5388:
5360:
5352:
5322:
5318:
5312:
5311:
5302:
5288:Glycine receptor
5281:
5274:
5267:
5258:
5257:
5086:purine analogues
5082:
5081:
4997:
4996:
4971:
4964:
4957:
4948:
4947:
4943:
4922:
4921:
4919:
4917:
4902:
4896:
4895:
4887:
4881:
4880:
4869:10.1039/A809393H
4852:
4846:
4845:
4830:J. Am. Chem. Soc
4825:
4819:
4818:
4816:
4814:
4803:
4794:
4793:
4791:
4789:
4775:
4769:
4768:
4740:
4734:
4733:
4731:
4729:
4694:
4688:
4687:
4685:
4683:
4668:
4662:
4661:
4659:
4657:
4641:
4635:
4634:
4606:
4600:
4599:
4574:(4): 1060–1068.
4562:
4556:
4555:
4543:
4537:
4536:
4534:
4532:
4518:
4512:
4511:
4504:
4498:
4497:
4469:
4463:
4462:
4460:
4458:
4448:
4440:
4434:
4433:
4431:
4429:
4415:
4409:
4408:
4398:
4374:
4368:
4367:
4355:
4349:
4348:
4346:
4344:
4329:
4323:
4322:
4320:
4318:
4296:
4290:
4289:
4287:
4285:
4270:
4264:
4263:
4250:
4244:
4234:
4228:
4227:
4199:
4197:
4165:
4154:10.1038/155141d0
4129:
4123:
4121:
4103:
4093:
4087:
4086:
4070:
4064:
4063:
4043:
4037:
4033:
4023:
3991:
3985:
3984:
3982:
3980:
3974:
3966:
3957:
3956:
3946:
3914:
3908:
3907:
3871:
3865:
3864:
3828:
3822:
3821:
3798:Joint Bone Spine
3793:
3787:
3786:
3749:
3743:
3742:
3732:
3700:
3694:
3693:
3691:
3689:
3683:
3674:
3665:
3664:
3628:
3607:
3606:
3604:
3602:
3591:
3578:
3577:
3567:
3557:
3533:
3527:
3526:
3508:
3484:
3478:
3477:
3451:
3442:
3436:
3435:
3407:
3401:
3400:
3374:
3349:
3348:
3338:
3306:
3300:
3299:
3268:Joint Bone Spine
3263:
3257:
3256:
3228:
3217:
3216:
3180:
3169:
3168:
3166:
3164:
3153:
3144:
3143:
3141:
3139:
3125:
3119:
3118:
3091:
3085:
3084:
3074:
3042:
3036:
3035:
3025:
3023:10.7326/M16-0570
3001:
2995:
2994:
2984:
2982:10.7326/M16-0461
2960:
2954:
2953:
2951:
2949:
2938:
2889:
2888:
2878:
2846:
2837:
2836:
2826:
2802:
2796:
2795:
2784:
2778:
2777:
2775:
2773:
2762:
2747:
2746:
2710:
2704:
2703:
2691:
2678:
2677:
2675:
2673:
2659:
2653:
2652:
2650:
2648:
2629:
2623:
2622:
2605:Wall WJ (2015).
2602:
2596:
2595:
2585:
2558:
2533:
2531:
2529:
2527:
2513:
2496:
2487:
2486:
2484:
2482:
2467:
2458:
2457:
2455:
2453:
2442:
2436:
2435:
2433:
2431:
2416:
2405:
2404:
2384:
2378:
2377:
2367:
2335:
2329:
2328:
2318:
2286:
2280:
2279:
2277:
2275:
2261:
2255:
2254:
2234:
2228:
2227:
2225:
2223:
2209:
2203:
2202:
2200:
2198:
2184:
2178:
2177:
2175:
2173:
2159:
2153:
2152:
2150:
2148:
2134:
2125:
2124:
2122:
2120:
2103:
2044:invasive species
1961:
1954:
1950:
1947:
1941:
1918:
1910:
1895:Gloriosa superba
1726:Sources and uses
1483:Pharmacokinetics
1448:superoxide anion
1243:protein assembly
1136:thrombocytopenia
1108:low urine output
1091:, diarrhea, and
970:Behçet's disease
964:Other conditions
880:
836:gastrointestinal
782:Behçet's disease
759:
758:
699:
679:
664:
661:
655:
649:
632:
621:
610:
609:
595:
593:
578:
558:
538:
518:
498:
478:
458:
438:
428:
427:
413:
354:
295:
292:
282:
279:
271:
268:
258:
255:
233:
190:
187:
169:
158:
155:
142:
128:
96:
91:
90:
87:
86:
83:
80:
77:
74:
71:
68:
65:
62:
42:
33:
26:
24:
20:
6551:
6550:
6546:
6545:
6544:
6542:
6541:
6540:
6491:Antigout agents
6471:
6470:
6469:
6459:
6457:
6449:
6447:
6442:
6429:
6395:
6352:
6342:
6253:ALX-5407 (NFPS)
6239:
6220:
6208:
6193:
6183:
5943:Benzodiazepines
5828:Isobutyric acid
5669:chloral hydrate
5521:Chlormethiazole
5483:tribromoethanol
5479:-butanol (2M2P)
5320:
5301:
5293:
5285:
5255:
5250:
5249:
5234:Clinical trials
5213:
5166:
5144:
5108:
5067:
5026:
4986:
4977:Drugs used for
4975:
4934:
4931:
4926:
4925:
4915:
4913:
4903:
4899:
4888:
4884:
4853:
4849:
4826:
4822:
4812:
4810:
4805:
4804:
4797:
4787:
4785:
4777:
4776:
4772:
4741:
4737:
4727:
4725:
4695:
4691:
4681:
4679:
4670:
4669:
4665:
4655:
4653:
4642:
4638:
4607:
4603:
4563:
4559:
4544:
4540:
4530:
4528:
4520:
4519:
4515:
4506:
4505:
4501:
4470:
4466:
4456:
4454:
4446:
4442:
4441:
4437:
4427:
4425:
4417:
4416:
4412:
4389:(10): 842–856.
4375:
4371:
4356:
4352:
4342:
4340:
4337:www.cbsnews.com
4331:
4330:
4326:
4316:
4314:
4304:Washington Post
4298:
4297:
4293:
4283:
4281:
4272:
4271:
4267:
4252:
4251:
4247:
4235:
4231:
4210:(20): 637–640.
4130:
4126:
4101:
4094:
4090:
4071:
4067:
4060:
4044:
4040:
3992:
3988:
3978:
3976:
3972:
3968:
3967:
3960:
3915:
3911:
3882:(10): 1607–11.
3872:
3868:
3829:
3825:
3794:
3790:
3755:Pharmacotherapy
3750:
3746:
3701:
3697:
3687:
3685:
3681:
3675:
3668:
3629:
3610:
3600:
3598:
3593:
3592:
3581:
3534:
3530:
3485:
3481:
3449:
3443:
3439:
3408:
3404:
3389:
3375:
3352:
3321:(8): CD010652.
3307:
3303:
3264:
3260:
3229:
3220:
3181:
3172:
3162:
3160:
3155:
3154:
3147:
3137:
3135:
3127:
3126:
3122:
3093:
3092:
3088:
3043:
3039:
3002:
2998:
2961:
2957:
2947:
2945:
2940:
2939:
2892:
2861:(8): CD006190.
2847:
2840:
2803:
2799:
2786:
2785:
2781:
2771:
2769:
2764:
2763:
2750:
2711:
2707:
2692:
2681:
2671:
2669:
2661:
2660:
2656:
2646:
2644:
2631:
2630:
2626:
2619:
2603:
2599:
2559:
2536:
2525:
2523:
2514:
2510:
2498:
2497:
2490:
2480:
2478:
2477:on 30 June 2012
2469:
2468:
2461:
2451:
2449:
2444:
2443:
2439:
2429:
2427:
2418:
2417:
2408:
2401:
2385:
2381:
2336:
2332:
2287:
2283:
2273:
2271:
2263:
2262:
2258:
2251:
2235:
2231:
2221:
2219:
2211:
2210:
2206:
2196:
2194:
2186:
2185:
2181:
2171:
2169:
2161:
2160:
2156:
2146:
2144:
2136:
2135:
2128:
2118:
2116:
2115:. 3 August 2022
2105:
2104:
2100:
2095:
1962:
1951:
1945:
1942:
1931:
1919:
1908:
1884:
1806:
1775:
1759:
1750:
1741:
1733:
1728:
1709:
1645:
1640:
1505:
1485:
1470:and neutrophils
1380:as needle-like
1370:
1365:
1276:
1267:
1239:
1191:aplastic anemia
1187:agranulocytosis
1073:
1045:
1043:Adverse effects
1029:creatine kinase
1005:
997:cardiac surgery
966:
950:atherosclerosis
938:
924:when used with
911:
906:
878:
848:skeletal muscle
754:
752:
747:
744:
739:
734:
733:
722:
719:
714:
713:
702:
677:
667:
658:
652:
613:
589:
581:
561:
541:
521:
501:
481:
461:
441:
424:
416:
396:
393:
385:
384:
358:26.6-31.2 hours
352:
328:Protein binding
318:Bioavailability
310:Pharmacokinetic
304:
237:
205:
198:
179:
172:
94:
59:
55:
17:
12:
11:
5:
6549:
6539:
6538:
6533:
6528:
6523:
6518:
6513:
6508:
6503:
6498:
6493:
6488:
6483:
6468:
6467:
6444:
6443:
6441:
6440:
6433:
6427:
6422:
6415:
6408:
6404:
6401:
6400:
6397:
6396:
6394:
6393:
6388:
6383:
6378:
6373:
6368:
6363:
6357:
6355:
6344:
6343:
6341:
6340:
6335:
6330:
6325:
6320:
6315:
6310:
6305:
6300:
6295:
6290:
6285:
6280:
6275:
6270:
6265:
6260:
6255:
6250:
6244:
6242:
6228:
6214:
6213:
6210:
6209:
6207:
6206:
6198:
6196:
6185:
6184:
6182:
6181:
6176:
6171:
6149:
6144:
6139:
6125:
6083:
6053:
6048:
6043:
6009:
6004:
5999:
5981:
5976:
5971:
5966:
5940:
5931:
5930:
5925:
5920:
5915:
5910:
5905:
5875:
5870:
5865:
5863:Nipecotic acid
5860:
5855:
5850:
5845:
5840:
5835:
5830:
5825:
5820:
5815:
5810:
5796:
5791:
5786:
5781:
5776:
5771:
5766:
5761:
5756:
5751:
5746:
5741:
5736:
5727:
5726:
5721:
5716:
5697:methoxyflurane
5658:
5628:
5623:
5618:
5613:
5608:
5603:
5598:
5572:
5567:
5562:
5557:
5554:ginsenoside-Rf
5543:
5538:
5528:
5523:
5518:
5504:
5499:
5494:
5453:
5452:
5447:
5442:
5437:
5432:
5430:Picolinic acid
5427:
5422:
5417:
5409:
5401:
5393:
5385:
5380:
5375:
5370:
5365:
5357:
5349:
5344:
5339:
5334:
5325:
5323:
5309:
5295:
5294:
5284:
5283:
5276:
5269:
5261:
5252:
5251:
5248:
5247:
5246:
5245:
5242:
5231:
5225:
5219:
5218:
5215:
5214:
5212:
5211:
5205:
5196:
5191:
5180:
5174:
5172:
5168:
5167:
5165:
5164:
5158:
5156:
5150:
5149:
5146:
5145:
5143:
5142:
5137:
5131:
5122:
5116:
5114:
5110:
5109:
5107:
5106:
5101:
5096:
5090:
5088:
5079:
5073:
5072:
5069:
5068:
5066:
5065:
5060:
5055:
5050:
5045:
5040:
5034:
5032:
5028:
5027:
5025:
5024:
5022:Isobromindione
5019:
5014:
5012:Sulfinpyrazone
5009:
5003:
5001:
4994:
4988:
4987:
4974:
4973:
4966:
4959:
4951:
4945:
4944:
4930:
4929:External links
4927:
4924:
4923:
4897:
4882:
4847:
4820:
4795:
4770:
4751:(2): 213–217.
4735:
4689:
4663:
4636:
4601:
4557:
4538:
4513:
4499:
4480:(3): 301–304.
4464:
4435:
4410:
4369:
4350:
4324:
4291:
4265:
4245:
4229:
4180:(4): 437–440.
4124:
4112:(3): 269–280.
4088:
4065:
4058:
4038:
4006:(3): 190–200.
3986:
3958:
3909:
3866:
3839:(4): 1688–93.
3823:
3788:
3761:(4): 320–333.
3744:
3695:
3666:
3639:(5): 407–414.
3608:
3579:
3528:
3479:
3437:
3402:
3387:
3350:
3301:
3274:(2): 118–124.
3258:
3239:(6): 503–508.
3218:
3191:(7): 648–660.
3170:
3145:
3120:
3086:
3037:
2996:
2955:
2890:
2838:
2797:
2779:
2748:
2705:
2679:
2654:
2624:
2617:
2597:
2534:
2508:
2488:
2459:
2437:
2406:
2399:
2379:
2330:
2281:
2256:
2249:
2229:
2204:
2179:
2154:
2126:
2097:
2096:
2094:
2091:
2081:Secale cereale
2025:. Growers of
1970:plant breeding
1964:
1963:
1922:
1920:
1913:
1907:
1904:
1883:
1880:
1879:
1878:
1805:
1802:
1774:
1771:
1758:
1755:
1749:
1746:
1740:
1737:
1732:
1729:
1727:
1724:
1708:
1705:
1644:
1641:
1639:
1636:
1504:
1501:
1497:P-glycoprotein
1484:
1481:
1472:
1471:
1468:synovial cells
1464:
1451:
1444:
1441:interleukin-1β
1429:
1422:
1415:
1386:synovial fluid
1384:in and around
1369:
1366:
1364:
1361:
1303:People taking
1298:clarithromycin
1280:P-glycoprotein
1275:
1272:
1266:
1263:
1238:
1235:
1227:gastric lavage
1160:hallucinations
1093:abdominal pain
1072:
1069:
1065:rhabdomyolysis
1044:
1041:
1033:polyneuropathy
1013:kidney failure
1004:
1001:
965:
962:
937:
934:
910:
907:
905:
902:
886:plant breeding
844:rhabdomyolysis
761:
760:
749:
748:
746:
745:
742:
740:
737:
729:
728:
727:
724:
723:
721:
720:
717:
709:
708:
707:
704:
703:
701:
700:
692:
690:
682:
681:
675:
669:
668:
665:
656:
650:
645:
639:
638:
634:
633:
623:
615:
614:
612:
611:
598:
596:
583:
582:
580:
579:
571:
569:
563:
562:
560:
559:
551:
549:
543:
542:
540:
539:
531:
529:
523:
522:
520:
519:
511:
509:
503:
502:
500:
499:
491:
489:
483:
482:
480:
479:
471:
469:
463:
462:
460:
459:
451:
449:
443:
442:
440:
439:
431:
429:
418:
417:
415:
414:
406:
404:
398:
397:
395:
394:
388:
380:
379:
378:
375:
374:
370:
369:
366:
360:
359:
356:
347:
346:
340:
334:
333:
330:
324:
323:
320:
314:
313:
306:
305:
303:
302:
290:
277:
266:
252:
250:
244:
243:
239:
238:
236:
235:
222:
220:
214:
213:
208:
206:administration
200:
199:
197:
196:
194:
184:
182:
174:
173:
171:
170:
152:
150:
144:
143:
136:
130:
129:
122:
112:
111:
108:
102:
101:
53:
49:
48:
44:
43:
35:
34:
15:
9:
6:
4:
3:
2:
6548:
6537:
6534:
6532:
6529:
6527:
6524:
6522:
6519:
6517:
6514:
6512:
6509:
6507:
6504:
6502:
6499:
6497:
6494:
6492:
6489:
6487:
6484:
6482:
6479:
6478:
6476:
6466:
6456:
6455:
6452:
6439:
6438:
6434:
6432:
6431:
6423:
6421:
6420:
6416:
6414:
6413:
6409:
6406:
6405:
6402:
6392:
6389:
6387:
6384:
6382:
6379:
6377:
6374:
6372:
6369:
6367:
6364:
6362:
6359:
6358:
6356:
6351:
6345:
6339:
6336:
6334:
6331:
6329:
6326:
6324:
6321:
6319:
6316:
6314:
6311:
6309:
6306:
6304:
6301:
6299:
6296:
6294:
6291:
6289:
6286:
6284:
6281:
6279:
6276:
6274:
6271:
6269:
6266:
6264:
6261:
6259:
6256:
6254:
6251:
6249:
6246:
6245:
6243:
6238:
6232:
6229:
6225:
6219:
6215:
6204:
6200:
6199:
6197:
6192:
6186:
6180:
6177:
6175:
6172:
6169:
6165:
6161:
6157:
6153:
6150:
6148:
6145:
6143:
6140:
6137:
6133:
6129:
6126:
6123:
6119:
6115:
6111:
6107:
6103:
6102:levomethadone
6099:
6095:
6091:
6087:
6084:
6081:
6077:
6073:
6069:
6065:
6061:
6057:
6054:
6052:
6049:
6047:
6044:
6041:
6037:
6033:
6029:
6025:
6021:
6017:
6013:
6010:
6008:
6005:
6003:
6000:
5997:
5993:
5989:
5985:
5982:
5980:
5977:
5975:
5972:
5970:
5967:
5964:
5960:
5959:flunitrazepam
5956:
5952:
5948:
5944:
5941:
5939:
5936:
5933:
5932:
5929:
5926:
5924:
5921:
5919:
5916:
5914:
5911:
5909:
5906:
5903:
5899:
5895:
5891:
5887:
5883:
5879:
5876:
5874:
5871:
5869:
5866:
5864:
5861:
5859:
5856:
5854:
5851:
5849:
5846:
5844:
5841:
5839:
5838:Isostrychnine
5836:
5834:
5831:
5829:
5826:
5824:
5821:
5819:
5816:
5814:
5811:
5808:
5804:
5800:
5797:
5795:
5792:
5790:
5787:
5785:
5782:
5780:
5777:
5775:
5772:
5770:
5767:
5765:
5762:
5760:
5757:
5755:
5752:
5750:
5747:
5745:
5742:
5740:
5737:
5735:
5732:
5729:
5728:
5725:
5722:
5720:
5717:
5714:
5710:
5706:
5702:
5698:
5694:
5690:
5686:
5682:
5678:
5674:
5670:
5666:
5662:
5659:
5656:
5652:
5648:
5644:
5640:
5636:
5632:
5629:
5627:
5624:
5622:
5619:
5617:
5614:
5612:
5609:
5607:
5604:
5602:
5601:Nitrous oxide
5599:
5596:
5592:
5588:
5584:
5580:
5576:
5573:
5571:
5568:
5566:
5563:
5561:
5558:
5555:
5551:
5547:
5544:
5542:
5539:
5536:
5532:
5529:
5527:
5524:
5522:
5519:
5516:
5512:
5511:pentobarbital
5508:
5505:
5503:
5500:
5498:
5495:
5492:
5488:
5484:
5480:
5478:
5473:
5469:
5465:
5461:
5458:
5455:
5454:
5451:
5448:
5446:
5443:
5441:
5440:Quisqualamine
5438:
5436:
5433:
5431:
5428:
5426:
5423:
5421:
5418:
5416:
5410:
5408:
5402:
5400:
5394:
5392:
5386:
5384:
5381:
5379:
5376:
5374:
5371:
5369:
5366:
5364:
5358:
5356:
5350:
5348:
5345:
5343:
5340:
5338:
5335:
5333:
5330:
5327:
5326:
5324:
5319:
5313:
5310:
5306:
5300:
5296:
5292:
5289:
5282:
5277:
5275:
5270:
5268:
5263:
5262:
5259:
5243:
5241:
5238:
5237:
5235:
5232:
5229:
5226:
5224:
5221:
5220:
5216:
5209:
5206:
5204:
5200:
5199:Urate oxidase
5197:
5195:
5192:
5190:
5187:
5184:
5181:
5179:
5176:
5175:
5173:
5169:
5163:
5160:
5159:
5157:
5155:
5151:
5141:
5138:
5135:
5132:
5130:
5126:
5123:
5121:
5118:
5117:
5115:
5111:
5105:
5102:
5100:
5097:
5095:
5092:
5091:
5089:
5087:
5083:
5080:
5078:
5074:
5064:
5061:
5059:
5056:
5054:
5051:
5049:
5046:
5044:
5041:
5039:
5036:
5035:
5033:
5029:
5023:
5020:
5018:
5017:Benzbromarone
5015:
5013:
5010:
5008:
5005:
5004:
5002:
4998:
4995:
4993:
4989:
4984:
4980:
4972:
4967:
4965:
4960:
4958:
4953:
4952:
4949:
4941:
4937:
4933:
4932:
4912:
4908:
4901:
4893:
4886:
4878:
4874:
4870:
4866:
4862:
4858:
4851:
4843:
4839:
4835:
4831:
4824:
4808:
4802:
4800:
4784:
4780:
4774:
4766:
4762:
4758:
4754:
4750:
4746:
4739:
4724:
4720:
4716:
4712:
4708:
4704:
4700:
4693:
4677:
4673:
4667:
4651:
4650:Bloomberg.com
4647:
4640:
4632:
4628:
4624:
4620:
4616:
4612:
4605:
4597:
4593:
4589:
4585:
4581:
4577:
4573:
4569:
4561:
4553:
4549:
4542:
4527:
4523:
4517:
4509:
4503:
4495:
4491:
4487:
4483:
4479:
4475:
4468:
4452:
4445:
4439:
4424:
4420:
4414:
4406:
4402:
4397:
4392:
4388:
4384:
4380:
4373:
4365:
4361:
4354:
4338:
4334:
4328:
4313:
4309:
4305:
4301:
4295:
4279:
4275:
4269:
4261:
4260:
4255:
4249:
4242:
4238:
4233:
4225:
4221:
4217:
4213:
4209:
4205:
4196:
4191:
4187:
4183:
4179:
4175:
4171:
4163:
4159:
4155:
4151:
4147:
4143:
4139:
4135:
4128:
4119:
4115:
4111:
4108:(in German).
4107:
4099:
4092:
4084:
4080:
4076:
4069:
4061:
4055:
4052:. CRC Press.
4051:
4050:
4042:
4036:
4031:
4027:
4022:
4017:
4013:
4009:
4005:
4001:
3997:
3990:
3971:
3965:
3963:
3954:
3950:
3945:
3940:
3936:
3932:
3928:
3924:
3920:
3913:
3905:
3901:
3897:
3893:
3889:
3885:
3881:
3877:
3870:
3862:
3858:
3854:
3850:
3846:
3842:
3838:
3834:
3827:
3819:
3815:
3811:
3807:
3803:
3799:
3792:
3784:
3780:
3776:
3772:
3768:
3764:
3760:
3756:
3748:
3740:
3736:
3731:
3726:
3722:
3718:
3714:
3710:
3706:
3699:
3680:
3673:
3671:
3662:
3658:
3654:
3650:
3646:
3642:
3638:
3634:
3627:
3625:
3623:
3621:
3619:
3617:
3615:
3613:
3596:
3590:
3588:
3586:
3584:
3575:
3571:
3566:
3561:
3556:
3551:
3547:
3543:
3539:
3532:
3524:
3520:
3516:
3512:
3507:
3502:
3498:
3494:
3490:
3483:
3475:
3471:
3467:
3463:
3459:
3455:
3448:
3441:
3433:
3429:
3425:
3421:
3417:
3413:
3406:
3398:
3394:
3390:
3384:
3380:
3373:
3371:
3369:
3367:
3365:
3363:
3361:
3359:
3357:
3355:
3346:
3342:
3337:
3332:
3328:
3324:
3320:
3316:
3312:
3305:
3297:
3293:
3289:
3285:
3281:
3277:
3273:
3269:
3262:
3254:
3250:
3246:
3242:
3238:
3234:
3227:
3225:
3223:
3214:
3210:
3206:
3202:
3198:
3194:
3190:
3186:
3179:
3177:
3175:
3158:
3152:
3150:
3134:
3130:
3124:
3116:
3112:
3108:
3104:
3100:
3099:NIHR Evidence
3096:
3090:
3082:
3078:
3073:
3068:
3064:
3060:
3056:
3052:
3048:
3041:
3033:
3029:
3024:
3019:
3015:
3011:
3007:
3000:
2992:
2988:
2983:
2978:
2974:
2970:
2966:
2959:
2943:
2937:
2935:
2933:
2931:
2929:
2927:
2925:
2923:
2921:
2919:
2917:
2915:
2913:
2911:
2909:
2907:
2905:
2903:
2901:
2899:
2897:
2895:
2886:
2882:
2877:
2872:
2868:
2864:
2860:
2856:
2852:
2845:
2843:
2834:
2830:
2825:
2820:
2816:
2812:
2808:
2801:
2793:
2789:
2783:
2767:
2761:
2759:
2757:
2755:
2753:
2744:
2740:
2736:
2732:
2728:
2724:
2720:
2716:
2709:
2701:
2697:
2690:
2688:
2686:
2684:
2668:
2664:
2658:
2642:
2638:
2634:
2628:
2620:
2614:
2610:
2609:
2601:
2593:
2589:
2584:
2579:
2575:
2571:
2567:
2563:
2557:
2555:
2553:
2551:
2549:
2547:
2545:
2543:
2541:
2539:
2521:
2517:
2511:
2505:
2501:
2495:
2493:
2476:
2472:
2466:
2464:
2447:
2441:
2425:
2421:
2415:
2413:
2411:
2402:
2396:
2392:
2391:
2383:
2375:
2371:
2366:
2361:
2357:
2353:
2349:
2345:
2341:
2334:
2326:
2322:
2317:
2312:
2308:
2304:
2300:
2296:
2292:
2285:
2270:
2266:
2260:
2252:
2246:
2242:
2241:
2233:
2218:
2214:
2208:
2193:
2189:
2183:
2168:
2164:
2158:
2143:
2139:
2133:
2131:
2114:
2113:
2112:Health Canada
2108:
2102:
2098:
2090:
2088:
2084:
2082:
2076:
2074:
2068:
2066:
2065:Triticosecale
2063:triticale (×
2059:
2057:
2053:
2049:
2045:
2041:
2037:
2033:
2028:
2024:
2020:
2016:
2012:
2008:
2003:
2000:
1996:
1992:
1988:
1984:
1980:
1975:
1971:
1960:
1957:
1949:
1946:February 2016
1939:
1935:
1929:
1928:
1923:This section
1921:
1917:
1912:
1911:
1903:
1901:
1897:
1896:
1891:
1890:
1874:
1870:
1869:
1868:
1866:
1862:
1858:
1854:
1850:
1846:
1842:
1838:
1834:
1830:
1829:C. byzantinum
1826:
1822:
1818:
1817:phenylalanine
1815:
1811:
1801:
1798:
1793:
1791:
1787:
1783:
1779:
1770:
1768:
1764:
1754:
1745:
1736:
1723:
1721:
1716:
1712:
1704:
1700:
1698:
1694:
1689:
1687:
1682:
1678:
1673:
1671:
1666:
1662:
1661:grandfathered
1658:
1654:
1650:
1647:In 2006 U.S.
1638:United States
1635:
1633:
1628:
1625:
1624:Michael Dewar
1621:
1616:
1614:
1610:
1606:
1602:
1598:
1594:
1590:
1586:
1585:
1580:
1579:Ambroise Paré
1576:
1572:
1568:
1564:
1560:
1556:
1552:
1548:
1544:
1540:
1536:
1532:
1529:1500 BC), an
1528:
1524:
1523:Ebers Papyrus
1520:
1516:
1512:
1511:
1500:
1498:
1494:
1491:with limited
1490:
1480:
1477:
1469:
1465:
1463:
1462:degranulation
1460:
1456:
1452:
1449:
1445:
1442:
1439:that mediate
1438:
1434:
1430:
1427:
1423:
1420:
1416:
1414:
1410:
1406:
1405:
1404:
1401:
1399:
1395:
1391:
1387:
1383:
1379:
1375:
1360:
1358:
1354:
1350:
1346:
1342:
1338:
1334:
1333:fosamprenavir
1330:
1326:
1322:
1318:
1314:
1310:
1306:
1301:
1299:
1295:
1291:
1288:
1284:
1281:
1271:
1262:
1260:
1256:
1252:
1248:
1245:with reduced
1244:
1234:
1230:
1228:
1224:
1218:
1216:
1212:
1208:
1204:
1200:
1196:
1192:
1188:
1184:
1180:
1176:
1171:
1169:
1165:
1161:
1157:
1153:
1149:
1145:
1141:
1137:
1133:
1129:
1125:
1124:liver failure
1121:
1117:
1113:
1109:
1104:
1102:
1098:
1094:
1090:
1086:
1082:
1077:
1068:
1066:
1062:
1058:
1054:
1050:
1040:
1038:
1034:
1030:
1026:
1025:neuromyopathy
1022:
1018:
1014:
1010:
1000:
998:
994:
989:
987:
983:
979:
975:
971:
961:
959:
955:
951:
947:
943:
933:
931:
927:
923:
918:
915:
901:
899:
895:
891:
887:
882:
876:
872:
868:
867:autumn crocus
863:
861:
857:
856:breastfeeding
853:
849:
845:
841:
837:
833:
828:
826:
822:
818:
814:
810:
805:
803:
799:
795:
791:
787:
783:
779:
775:
771:
767:
757:
750:
741:
736:
735:
732:
725:
716:
715:
712:
705:
698:
694:
693:
691:
688:
683:
676:
674:
670:
646:
644:
640:
635:
631:
627:
624:
622:
620:ECHA InfoCard
616:
608:
604:
603:DTXSID5024845
600:
599:
597:
588:
584:
577:
573:
572:
570:
568:
564:
557:
553:
552:
550:
548:
544:
537:
533:
532:
530:
528:
524:
517:
513:
512:
510:
508:
504:
497:
493:
492:
490:
488:
484:
477:
473:
472:
470:
468:
464:
457:
453:
452:
450:
448:
444:
437:
433:
432:
430:
423:
419:
412:
408:
407:
405:
403:
399:
391:
387:
386:
383:
376:
371:
367:
365:
361:
357:
355:
348:
345:
341:
339:
335:
331:
329:
325:
321:
319:
315:
311:
307:
301:
291:
288:
278:
276:
267:
264:
254:
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232:
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215:
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201:
195:
186:
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153:
151:
149:
145:
141:
137:
135:
131:
127:
123:
121:
117:
113:
109:
107:
103:
99:
98:
89:
54:
52:Pronunciation
50:
47:Clinical data
45:
41:
36:
32:
27:
19:
6536:Plant toxins
6511:Orphan drugs
6435:
6424:
6417:
6410:
6136:picrotoxinin
6080:progesterone
6072:DHEA sulfate
6040:ginkgolide M
6036:ginkgolide J
6032:ginkgolide C
6028:ginkgolide B
6024:ginkgolide A
5996:nitrendipine
5934:
5773:
5731:Antagonists:
5730:
5606:Penicillin G
5550:ginsenosides
5507:Barbiturates
5476:
5456:
5337:β-ABA (BABA)
5328:
5185:
5161:
5140:Topiroxostat
5134:Myo-inositol
5043:Atorvastatin
4939:
4914:. Retrieved
4910:
4900:
4891:
4885:
4863:(1): 50–65.
4860:
4856:
4850:
4833:
4829:
4823:
4811:. Retrieved
4786:. Retrieved
4782:
4773:
4748:
4744:
4738:
4726:. Retrieved
4706:
4702:
4692:
4680:. Retrieved
4675:
4672:"Colchicine"
4666:
4654:. Retrieved
4649:
4639:
4614:
4610:
4604:
4571:
4567:
4560:
4551:
4541:
4529:. Retrieved
4525:
4516:
4510:. July 2009.
4502:
4477:
4473:
4467:
4455:. Retrieved
4450:
4438:
4426:. Retrieved
4422:
4413:
4386:
4382:
4372:
4363:
4353:
4341:. Retrieved
4336:
4327:
4315:. Retrieved
4303:
4294:
4282:. Retrieved
4277:
4268:
4257:
4248:
4240:
4232:
4207:
4203:
4177:
4173:
4137:
4133:
4127:
4109:
4105:
4091:
4082:
4078:
4068:
4048:
4041:
4034:
4003:
3999:
3989:
3977:. Retrieved
3929:(1): 16–19.
3926:
3922:
3912:
3879:
3875:
3869:
3836:
3832:
3826:
3804:(6): 672–8.
3801:
3797:
3791:
3758:
3754:
3747:
3712:
3708:
3698:
3686:. Retrieved
3636:
3632:
3599:. Retrieved
3545:
3541:
3531:
3496:
3492:
3482:
3457:
3453:
3440:
3418:(1): 60–86.
3415:
3411:
3405:
3378:
3318:
3314:
3304:
3271:
3267:
3261:
3236:
3232:
3188:
3184:
3161:. Retrieved
3136:. Retrieved
3132:
3123:
3098:
3089:
3054:
3050:
3040:
3016:(1): 58–68.
3013:
3009:
2999:
2975:(1): 37–51.
2972:
2968:
2958:
2946:. Retrieved
2942:"Colchicine"
2858:
2854:
2814:
2810:
2800:
2782:
2770:. Retrieved
2718:
2714:
2708:
2699:
2670:. Retrieved
2666:
2657:
2645:. Retrieved
2636:
2627:
2607:
2600:
2573:
2569:
2524:. Retrieved
2519:
2516:"Colchicine"
2499:
2479:. Retrieved
2475:the original
2450:. Retrieved
2440:
2428:. Retrieved
2423:
2389:
2382:
2347:
2343:
2333:
2298:
2294:
2284:
2272:. Retrieved
2268:
2259:
2239:
2232:
2220:. Retrieved
2216:
2207:
2195:. Retrieved
2191:
2182:
2170:. Retrieved
2166:
2157:
2145:. Retrieved
2141:
2117:. Retrieved
2110:
2101:
2080:
2072:
2064:
2060:
2051:
2036:horticulture
2004:
1972:by inducing
1967:
1952:
1943:
1932:Please help
1927:verification
1924:
1900:C. autumnale
1899:
1893:
1887:
1885:
1882:Purification
1864:
1860:
1852:
1844:
1841:C. autumnale
1840:
1828:
1810:biosynthesis
1807:
1804:Biosynthesis
1797:prescription
1794:
1776:
1760:
1751:
1742:
1734:
1717:
1713:
1710:
1701:
1690:
1674:
1646:
1629:
1617:
1600:
1592:
1588:
1582:
1566:
1558:
1546:
1542:
1526:
1508:
1506:
1486:
1473:
1433:inflammasome
1402:
1390:soft tissues
1371:
1363:Pharmacology
1313:cyclosporine
1309:ketoconazole
1302:
1294:erythromycin
1277:
1268:
1265:Epidemiology
1240:
1231:
1219:
1193:, alopecia,
1172:
1164:leukocytosis
1128:hepatomegaly
1112:bloody urine
1105:
1078:
1074:
1046:
1021:hemodialysis
1009:prophylactic
1006:
990:
967:
941:
939:
919:
916:
912:
904:Medical uses
883:
870:
864:
860:inflammation
840:pancytopenia
829:
806:
802:pericarditis
796:(NSAIDs) or
765:
764:
753:
389:
351:Elimination
248:Legal status
242:Legal status
148:License data
18:
6333:SSR-504,734
6328:SSR-103,800
6318:PF-03463275
6298:Mardepodect
6218:Transporter
6164:tropisetron
6106:levorphanol
6098:dextrorphan
6020:ginkgolides
5988:nicardipine
5843:Laudanosine
5764:Cacotheline
5754:Bicuculline
5701:sevoflurane
5651:tropisetron
5535:nicardipine
5378:Hypotaurine
5230:from market
5208:Pegloticase
5203:Rasburicase
5129:Phytic acid
5094:Allopurinol
5053:Guaifenesin
5048:Fenofibrate
4992:Uricosurics
4911:archive.org
4652:. Bloomberg
4451:govinfo.gov
4423:www.cdc.gov
3833:J Neurochem
3601:31 December
3565:2066/229130
3460:: 127–137.
3163:19 February
2089:triticale.
2048:watermelons
2040:landscaping
1993:instead of
1837:Radioactive
1814:amino acids
1778:Trade names
1707:Controversy
1697:Orange Book
1453:Interrupts
1426:neutrophils
1409:microtubule
1317:muscle pain
1283:transporter
1259:heart cells
1247:endocytosis
1175:bone marrow
1053:bone marrow
1049:neutropenia
1037:cholesterol
1007:Long-term (
986:amyloidosis
926:allopurinol
922:prophylaxis
894:chromosomes
846:(damage to
776:, to treat
680: g·mol
626:100.000.544
556:CHEBI:27882
373:Identifiers
368:Feces (65%)
134:MedlinePlus
106:Trade names
6481:Acetamides
6475:Categories
6338:Tilapertin
6293:LY-2365109
6288:Iclepertin
6283:GSK1018921
6168:zatosetron
6156:bemesetron
6128:Picrotoxin
6046:Imipramine
6016:bilobalide
6002:Furosemide
5992:nifedipine
5963:flurazepam
5951:clonazepam
5947:bromazepam
5918:Strychnine
5913:Sinomenine
5878:Quinolines
5868:Pitrazepin
5789:Dendrobine
5774:Colchicine
5693:isoflurane
5677:desflurane
5673:chloroform
5655:zatosetron
5639:bemesetron
5591:minaxolone
5579:alfaxolone
5565:Ivermectin
5502:Anandamide
5425:Milacemide
5415:-Threonine
5383:Ivermectin
5291:modulators
5178:Cinchophen
5162:Colchicine
5120:Febuxostat
5104:Tisopurine
5099:Oxypurinol
5038:Amlodipine
5007:Probenecid
4728:7 November
4709:(2): 531.
4682:7 November
4656:27 October
3715:(4): 127.
3397:1020416505
2672:14 January
2647:14 January
2526:26 January
2093:References
1999:tetraploid
1991:tetraploid
1974:polyploidy
1825:precursors
1757:Regulation
1634:in 1959.
1573:physician
1515:rheumatism
1398:chemotaxis
1353:saquinavir
1345:nelfinavir
1325:atazanavir
1285:, and the
1251:exocytosis
1055:, lead to
890:polyploidy
888:to induce
813:injectable
770:medication
766:Colchicine
685:3D model (
673:Molar mass
516:SML2Y3J35T
487:ChemSpider
447:IUPHAR/BPS
402:CAS Number
382:IUPAC name
338:Metabolism
167:Colchicine
97:-chiss-een
23:Colchicine
6486:Alkaloids
6386:ORG-25543
6366:Amoxapine
6323:Sarcosine
6303:ORG-24598
6268:CP-802079
6174:Verapamil
6160:LY-278584
6152:Tropeines
6118:pethidine
6114:oripavine
6007:Genistein
5938:Amiloride
5818:Gelsemine
5794:Diaboline
5779:Colubrine
5689:halothane
5685:enflurane
5661:Volatiles
5647:LY-278584
5631:Tropeines
5626:Triclofos
5616:Tamoxifen
5595:ORG-20599
5541:Etomidate
5464:brometone
5445:Sarcosine
5420:MDL-27531
5332:β-Alanine
5329:Agonists:
5240:Phase III
5228:Withdrawn
5194:Sevelamer
5125:Inositols
5058:Lesinurad
5031:secondary
4813:21 August
4596:205424044
4312:0190-8286
3979:19 August
3876:Pharm Res
3783:246903117
3688:23 August
3523:220305546
3296:205754989
3213:260715494
3115:267539627
2948:19 August
2772:19 August
2562:Dalbeth N
2424:Drugs.com
2087:hexaploid
2017:seeds or
1857:tropolone
1833:tropolone
1739:Structure
1601:Colchicum
1593:Colchicum
1589:Colchicum
1587:of 1618.
1567:Colchicum
1559:Colchicum
1543:Colchicum
1455:mast cell
1446:Inhibits
1437:monocytes
1407:Inhibits
1394:cytokines
1378:uric acid
1349:ritonavir
1341:lopinavir
1337:indinavir
1329:darunavir
1152:confusion
900:parents.
852:pregnancy
576:ChEMBL107
364:Excretion
353:half-life
204:Routes of
178:Pregnancy
126:Monograph
120:Drugs.com
6531:Tropones
6465:Medicine
6407:See also
6361:ALX-1393
6224:blockers
6205:instead.
6147:Riluzole
6132:picrotin
6122:thebaine
6110:morphine
5979:Daidzein
5969:Corymine
5955:diazepam
5890:5,7-CIQA
5823:iso-THAZ
5769:Caffeine
5635:atropine
5611:Propofol
5570:Ketamine
5460:Alcohols
5435:Propofol
5399:-Proline
5391:-Alanine
5355:-Alanine
5299:Receptor
5063:Losartan
4916:26 April
4877:11245400
4788:11 March
4723:13211030
4631:20393164
4588:20131255
4405:21894470
4085:: 69–81.
4030:13198053
3953:13031443
3904:10193442
3896:14620515
3861:38446612
3818:17067838
3775:35175631
3739:28321655
3661:33905426
3653:20586571
3574:32865380
3515:32611559
3474:28918897
3432:26572612
3345:25164988
3336:10645160
3288:24556284
3253:21111934
3205:37558377
3157:"Lodoco"
3081:37788904
3072:10646835
3032:27802508
2991:27802478
2885:34438469
2833:20008601
2735:18830092
2667:ClinCalc
2641:Archived
2637:ClinCalc
2592:25151572
2430:27 March
2374:23024029
2325:23024028
2147:27 March
2142:DailyMed
2119:25 March
2073:Triticum
2007:triploid
1821:tyrosine
1620:Caventou
1609:doggerel
1575:Avicenna
1535:alkaloid
1531:Egyptian
1519:swelling
1459:lysosome
1321:HIV/AIDS
1215:myopathy
1168:alopecia
1156:delirium
1148:seizures
1089:vomiting
1071:Toxicity
1017:dialysis
809:by mouth
798:steroids
756:(verify)
467:DrugBank
218:ATC code
211:By mouth
180:category
162:DailyMed
6391:VVZ-368
6258:ASP2535
6154:(e.g.,
6130:(i.e.,
6090:codeine
6088:(e.g.,
6086:Opioids
6058:(e.g.,
6022:(e.g.,
5986:(e.g.,
5945:(e.g.,
5908:RU-5135
5880:(e.g.,
5801:(e.g.,
5759:Brucine
5705:toluene
5667:(e.g.,
5643:cocaine
5633:(e.g.,
5577:(e.g.,
5552:(e.g.,
5546:Ginseng
5533:(e.g.,
5526:D12-116
5509:(e.g.,
5462:(e.g.,
5450:Taurine
5407:-Serine
5373:Glycine
5363:-Serine
5347:Caesium
5305:ligands
5189:aspirin
5000:primary
4765:5027606
4676:PubChem
4494:3314832
4212:Bibcode
4182:Bibcode
4162:4074312
4142:Bibcode
4021:1006735
3944:1030428
3853:8858954
3730:5393104
2876:8407279
2824:2793228
2743:6644013
2365:3662546
2316:3683400
2071:wheat (
2015:fertile
2011:sterile
1995:diploid
1987:mitosis
1782:capsule
1688:(FMF).
1571:Persian
1521:in the
1503:History
1419:mitosis
1413:tubulin
1357:statins
1323:taking
1199:purpura
1061:mitosis
898:diploid
678:399.443
643:Formula
476:DB01394
422:PubChem
411:64-86-8
273::
234:)
228: (
226:M04AC01
193: D
164::
140:a682711
6451:Portal
6012:Ginkgo
5902:7-TFQA
5749:αEMBTL
5342:β-AIBA
5223:WHO-EM
5186:except
5183:NSAIDs
4875:
4763:
4721:
4629:
4594:
4586:
4531:30 May
4492:
4457:29 May
4428:29 May
4403:
4343:29 May
4317:29 May
4310:
4284:29 May
4241:fi.edu
4160:
4134:Nature
4056:
4028:
4018:
3951:
3941:
3902:
3894:
3859:
3851:
3816:
3781:
3773:
3737:
3727:
3659:
3651:
3572:
3521:
3513:
3472:
3430:
3395:
3385:
3343:
3333:
3294:
3286:
3251:
3211:
3203:
3138:29 May
3133:LODOCO
3129:"Home"
3113:
3079:
3069:
3030:
2989:
2883:
2873:
2831:
2821:
2741:
2733:
2615:
2590:
2506:
2481:14 May
2452:29 May
2397:
2372:
2362:
2323:
2313:
2274:29 May
2247:
2222:29 May
2197:29 May
2172:29 May
2032:shrubs
2027:annual
2019:spores
1790:tablet
1374:joints
1290:enzyme
1287:CYP3A4
1213:, and
1207:anuria
1183:nerves
1181:, and
1179:kidney
1154:, and
1138:; and
1120:anemia
1081:cornea
1057:anemia
995:after
942:LODOCO
879:
821:lethal
788:. The
711:SMILES
567:ChEMBL
536:D00570
344:CYP3A4
332:35-44%
300:℞-only
298:
285:
275:℞-only
261:
160:
100:
6376:NAGly
6349:GlyT2
6248:ACPPB
6236:GlyT1
6190:NMDAR
5928:Tutin
5898:7-TFQ
5894:7-CIQ
5719:Xenon
5665:gases
5171:Other
5113:other
4719:S2CID
4592:S2CID
4447:(PDF)
4158:S2CID
4102:(PDF)
3973:(PDF)
3900:S2CID
3857:S2CID
3779:S2CID
3682:(PDF)
3657:S2CID
3519:S2CID
3493:Heart
3450:(PDF)
3292:S2CID
3209:S2CID
3111:S2CID
2739:S2CID
2079:rye (
2075:spp.)
2069:from
1597:edema
1555:corms
1527:circa
1493:brain
1351:, or
1311:, or
1085:fever
768:is a
731:InChI
687:JSmol
547:ChEBI
6426:GABA
6203:here
6201:See
6179:Zinc
6142:PMBA
6134:and
6051:NBQX
5803:2-AG
5724:Zinc
5477:tert
5368:GABA
5317:GlyR
4979:gout
4918:2016
4873:PMID
4815:2018
4790:2018
4761:PMID
4730:2021
4684:2021
4658:2015
4627:PMID
4584:PMID
4533:2024
4490:PMID
4459:2024
4430:2024
4401:PMID
4345:2024
4319:2024
4308:ISSN
4286:2024
4054:ISBN
4026:PMID
3981:2018
3949:PMID
3892:PMID
3849:PMID
3814:PMID
3771:PMID
3735:PMID
3690:2018
3649:PMID
3603:2015
3570:PMID
3511:PMID
3470:PMID
3428:PMID
3393:OCLC
3383:ISBN
3341:PMID
3319:2014
3284:PMID
3249:PMID
3201:PMID
3165:2024
3140:2024
3077:PMID
3028:PMID
2987:PMID
2950:2018
2881:PMID
2859:2021
2829:PMID
2774:2018
2731:PMID
2674:2024
2649:2024
2613:ISBN
2588:PMID
2528:2024
2504:ISBN
2483:2010
2454:2024
2432:2019
2395:ISBN
2370:PMID
2321:PMID
2276:2024
2245:ISBN
2224:2024
2199:2024
2174:2024
2149:2019
2121:2024
2077:and
2038:and
1819:and
1786:pill
1681:gout
1557:of
1537:and
1517:and
1457:and
1388:and
1195:rash
1166:and
1110:and
909:Gout
780:and
774:gout
527:KEGG
507:UNII
496:5933
456:2367
436:6167
312:data
116:AHFS
4983:M04
4865:doi
4838:doi
4753:doi
4711:doi
4619:doi
4615:362
4576:doi
4552:FDA
4482:doi
4391:doi
4364:FDA
4220:doi
4190:doi
4150:doi
4138:155
4114:doi
4016:PMC
4008:doi
3939:PMC
3931:doi
3884:doi
3841:doi
3806:doi
3763:doi
3725:PMC
3717:doi
3641:doi
3560:hdl
3550:doi
3546:383
3501:doi
3497:106
3462:doi
3458:249
3420:doi
3331:PMC
3323:doi
3276:doi
3241:doi
3193:doi
3103:doi
3067:PMC
3059:doi
3018:doi
3014:166
2977:doi
2973:166
2871:PMC
2863:doi
2819:PMC
2723:doi
2578:doi
2360:PMC
2352:doi
2311:PMC
2303:doi
1936:by
1845:(S)
1823:as
1549:by
1296:or
1225:or
825:FDA
804:.
592:EPA
426:CID
322:45%
287:POM
231:WHO
95:KOL
6477::
6166:,
6162:,
6158:,
6120:,
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6112:,
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4938:.
4909:.
4871:.
4861:18
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