505:. It has been shown that tetracyclines are not only active against broad spectrum of bacteria, but also against viruses, protozoa that lack mitochondria and some noninfectious conditions. The binding of tetracyclines to cellular dsRNA (double stranded RNA) may be an explanation for their wide range of effect. It can also be attributed to the nature of ribosomal protein synthesis pathways among bacteria. Incyclinide was announced to be ineffective for rosacea in September 2007. Several trials have examined modified and unmodified tetracyclines for the treatment of human cancers; of those, very promising results were achieved with CMT-3 for patients with
27:
731:
tetracycline platform towards derivatives with increased potency as well as efficacy against tetracycline-resistant bacteria, with improved pharmacokinetic and chemical properties. Shortly after the introduction of tetracycline therapy, the first tetracycline-resistant bacterial pathogen was identified. Since then, tetracycline-resistant bacterial pathogens have continued to be identified, limiting tetracycline's effectiveness in treatment of bacterial disease.
692:
semisynthetic tetracyclines had entered the market, and now most antibiotic discoveries are of novel active derivatives of older compounds. Other tetracyclines were identified later, either as naturally occurring molecules, e.g., tetracycline from S. aureofaciens, S. rimosus, and S. viridofaciens and dimethyl-chlortetracycline from S. aureofaciens, or as products of semisynthetic approaches, e.g., methacycline, doxycycline, and minocycline.
1663:
3548:
1667:
379:. It increases the risk of sunburn under exposure to light from the sun or other sources. This may be of particular importance for those intending to take on vacations long-term doxycycline as a malaria prophylaxis. They may cause stomach or bowel upsets, and, on rare occasions, allergic reactions. Very rarely, severe headache and vision problems may be signs of dangerous
671:(terramycin) was isolated in 1949 by Alexander Finlay from a soil sample collected on the grounds of a factory in Terre Haute, Indiana. It came from a similar soil bacterium named Streptomyces rimosus. From the beginning, terramycin was a molecule enveloped in controversy. It was the subject of the first mass-marketing campaign by a modern pharmaceutical company.
549:, a class of antibiotic destructase, modifies the tetracycline antibiotic at their oxidative soft spot leading to an inactivation of the tetracycline antibiotic. For example, the oxireductase makes a modification on the C11a site of oxytetracycline. Both Mgchelation and ribosome binding are required for the
518:
group and a C1-C3 diketo substructure. Removal of the dimethylamine group at C4 reduces antibacterial activity. Replacement of the carboxylamine group at C2 results in reduced antibacterial activity but it is possible to add substituents to the amide nitrogen to get more soluble analogs like the prodrug
452:
Tetracycline use should be avoided in pregnant or lactating women, and in children with developing teeth because they may result in permanent staining (dark yellow-gray teeth with a darker horizontal band that goes across the top and bottom rows of teeth), and possibly affect the growth of teeth and
140:
but is still considered as the parent compound for nomenclature purposes. Tetracyclines are among the cheapest classes of antibiotics available and have been used extensively in prophylaxis and in treatment of human and animal infections, as well as at subtherapeutic levels in animal feed as growth
734:
Glycylcyclines and fluorocyclines are new classes of antibiotics derived from tetracycline. These tetracycline analogues are specifically designed to overcome two common mechanisms of tetracycline resistance, namely resistance mediated by acquired efflux pumps and/or ribosomal protection. In 2005,
691:
itself as a synthetic product. In 1955, Conover discovered that hydrogenolysis of aureomycin gives a deschloro product that is just as active as the original product. This proved for the first time that chemically modified antibiotics could have biological activity. Within a few years, a number of
646:
The history of the tetracyclines involves the collective contributions of thousands of dedicated researchers, scientists, clinicians, and business executives. Tetracyclines were discovered in the 1940s, first reported in scientific literature in 1948, and exhibited activity against a wide range of
207:
can become resistant to tetracyclines, resulting in overgrowth of resistant organisms. The widespread use of tetracyclines is thought to have contributed to an increase in the number of tetracycline-resistant organisms, in turn rendering certain infections more resilient to treatment. Tetracycline
517:
Tetracyclines are composed of a rigid skeleton of 4 fused rings. The rings structure of tetracyclines is divided into an upper modifiable region and a lower non modifiable region. An active tetracycline requires a C10 phenol as well as a C11-C12 keto-enol substructure in conjugation with a 12a-OH
3061:
Solomkin J, Evans D, Slepavicius A, Lee P, Marsh A, Tsai L, et al. (March 2017). "Assessing the
Efficacy and Safety of Eravacycline vs Ertapenem in Complicated Intra-abdominal Infections in the Investigating Gram-Negative Infections Treated With Eravacycline (IGNITE 1) Trial: A Randomized
183:
Tetracyclines all have the same antibacterial spectrum, although there are differences in species' sensitivity to types of tetracyclines. Tetracyclines inhibit protein synthesis in both bacterial and human cells. Bacteria have a system that allows tetracyclines to be transported into the cell,
440:, a potentially fatal disease affecting proximal tubular function in the nephrons of the kidney. Prescriptions of these drugs should be discarded once expired because they can cause hepatotoxicity. It was once believed that tetracycline antibiotics impair the effectiveness of many types of
522:. The simplest tetracycline with measurable antibacterial activity is 6-deoxy-6-demethyltetracycline and its structure is often considered to be the minimum pharmacophore for the tetracycle class of antibiotics. C5-C9 can be modified to make derivatives with varying antibacterial activity.
730:
Tetracyclines were noted for their broad spectrum antibacterial activity and were commercialized with clinical success beginning in the late 1940s to the early 1950s. The second-generation semisynthetic analogs and more recent third-generation compounds show the continued evolution of the
751:
binds to the bacterial 30S ribosome, blocking the entry of transfer RNA. This ultimately prevents protein synthesis and thus inhibiting bacterial growth. However, the addition of an N,N,-dimethylglycylamido group at the 9 position of the minocycline molecule increases the affinity of
556:
In the most common mechanism of reaction, efflux, various resistance genes encode a membrane protein that actively pumps tetracycline out of the cell by exchanging a proton for a tetracycline cation complex. This exchange leads to a reduced cytoplasmic concentration of tetracycline.
444:. Recent research has shown no significant loss of effectiveness in oral contraceptives while using most tetracyclines. Despite these studies, many physicians still recommend the use of barrier contraception for people taking any tetracyclines to prevent unwanted pregnancy.
3406:
Zhu, Z., Zheng, T., Lee, C. G., Homer, R. J., & Elias, J. A. (2002). Tetracycline-controlled transcriptional regulation systems: advances and application in transgenic animal modeling. Seminars in Cell & Developmental
Biology, 13(2), 121β128.
399:
under 8 years of age. Some adults also experience teeth discoloration (mild grey hue) after use. They are, however, safe to use in the first 18 weeks of pregnancy. Some patients taking tetracyclines require medical supervision because they can cause
1023:. The mechanism of action for the antibacterial effect of tetracyclines relies on disrupting protein translation in bacteria, thereby damaging the ability of microbes to grow and repair; however protein translation is also disrupted in eukaryotic
457:, but the number of reports is too small to be sure if there actually is any risk. In tetracycline preparation, stability must be considered in order to avoid formation of toxic epi-anhydrotetracyclines.
743:, alterations to the molecule resulted in its expanded spectrum of activity and decreased susceptibility to the development of resistance when compared with other tetracycline antibiotics. Like
739:, the first member of a new subgroup of tetracyclines named glycylcyclines, was introduced to treat infections that are resistant to other antimicrobials. Although it is structurally related to
216:
of tetracyclines or for a protein that protects bacterial ribosomes from the action of tetracyclines. Furthermore, a limited number of bacteria acquire resistance to tetracyclines by mutations.
2059:
Ryan ME, Usman A, Ramamurthy NS, Golub LM, Greenwald RA (February 2001). "Excessive matrix metalloproteinase activity in diabetes: inhibition by tetracycline analogues with zinc reactivity".
453:
bones. Usage during the first 12 weeks of pregnancy does not appear to increase the risk of any major birth defects. There may be a small increased risk for minor birth defects such as an
57:
or produced semi-synthetically from those isolated compounds. Tetracycline molecules comprise a linear fused tetracyclic nucleus (rings designated A, B, C and D) to which a variety of
3580:
602:) be taken with a full glass of water, either two hours after eating or two hours before eating. This is partly because most tetracyclines bind with food and also easily with
2909:
3337:
1385:
Critically important antimicrobials for human medicine : ranking of antimicrobial agents for risk management of antimicrobial resistance due to non-human use
224:
Tetracyclines are generally used in the treatment of infections of the urinary tract, respiratory tract, and the intestines and are also used in the treatment of
3018:
Zhanel GG, Cheung D, Adam H, Zelenitsky S, Golden A, Schweizer F, et al. (April 2016). "Review of
Eravacycline, a Novel Fluorocycline Antibacterial Agent".
1702:
Deboyser D, Goethals F, Krack G, Roberfroid M (March 1989). "Investigation into the mechanism of tetracycline-induced steatosis: study in isolated hepatocytes".
675:
advertised the drug heavily in medical journals, eventually spending twice as much on marketing as it did to discover and develop terramycin. Still, it turned
3573:
1019:
biomedical research experiments involving bacteria as well in experiments in eukaryotic cells and organisms with inducible protein expression systems using
638:
can be taken with dairy products because it does not chelate calcium as readily, although dairy products do decrease absorption of minocycline slightly.
1078:
1020:
61:
are attached. Tetracyclines are named after their four ("tetra-") hydrocarbon rings ("-cycl-") derivation ("-ine"). They are defined as a subclass of
3566:
2164:"Tetracycline: Classification, Structure Activity Relationship and Mechanism of Action as a Theranostic Agent for Infectious Lesions-A Mini Review"
1772:
Ekwall B, Acosta D (1982). "In vitro comparative toxicity of selected drugs and chemicals in HeLa cells, Chang liver cells, and rat hepatocytes".
485:. This mechanism does not add to their antibiotic effects, but has led to extensive research on chemically modified tetracyclines or CMTs (like
432:. Antacids containing aluminium and calcium reduce the absorption of all tetracyclines, and dairy products reduce absorption greatly for all but
1842:
DrΓ©no B, Bettoli V, Ochsendorf F, Layton A, Mobacken H, Degreef H (2004). "European recommendations on the use of oral antibiotics for acne".
1508:
Taylor, MJ; Makunde, WH; McGarry, HF; Turner, JD; Mand, S; Hoerauf, A (June 2005). "Macrofilaricidal activity after doxycycline treatment of
3154:
1055:
in the USA. However, this is an invasive procedure for the animal and labour-intensive for the researcher. Therefore, other dyes such as
416:
Tetracyclines should be used with caution by those with liver impairment. Also, because the molecules are soluble in water it can worsen
195:. Tetracyclines remain the treatment of choice for some specific indications. Because not all of the tetracycline administered orally is
667:
was scouring the globe for new antibiotics. Soil samples were collected from jungles, deserts, mountaintops, and oceans. But ultimately
1688:
69:
of polycyclic naphthacene carboxamide. While all tetracyclines have a common structure, they differ from each other by the presence of
481:
complex. Some studies have shown that tetracyclines may bind to both 16S and 23S rRNAs. Tetracyclines also have been found to inhibit
3552:
768:
was the first tetracycline approved in over 20 years, other, newer versions of tetracyclines are currently in human clinical trials.
2120:
Richards C, Pantanowitz L, Dezube BJ (February 2011). "Antimicrobial and non-antimicrobial tetracyclines in human cancer trials".
19:
This article is about the group of antibiotics known as the tetracyclines. For the specific antibiotic called "tetracycline", see
3558:
1917:
1416:
Simonart T, Dramaix M, De
Maertelaer V (February 2008). "Efficacy of tetracyclines in the treatment of acne vulgaris: a review".
626:
and preparations containing iron should be avoided near the time of taking the drug. Partial exceptions to these rules occur for
2948:
1340:
Sloan B, Scheinfeld N (September 2008). "The use and safety of doxycycline hyclate and other second-generation tetracyclines".
718:
light β the deposits are fluorescent, just as are modern ones. Armelagos suggested that this was due to ingestion of the local
950:(formerly known as TP-434) received FDA approval on August 27, 2018, for treatment of complicated intra-abdominal infections.
4376:
2650:
1231:
1047:, a UV lamp can be used to check if it is in a tooth pulled from an animal. For example, it was used to check uptake of oral
655:, a 73-year-old emeritus professor of botany employed by American Cyanamid β Lederle Laboratories, under the leadership of
384:
380:
2730:
2332:"Tetracycline resistance determinants: mechanisms of action, regulation of expression, genetic mobility, and distribution"
714:
period (around AD 350) had deposits of tetracycline in their bones, detectable through analyses of cross-sections through
553:
of oxytetracycline and the modification attenuate the binding, leading to inactivation of the oxytetracycline antibiotic.
1633:
2848:
764:. This allows for an expanded spectrum of activity and decreased susceptibility to the development of resistance. While
647:
microorganisms. The first members of the tetracycline group to be described were chlortetracycline and oxytetracycline.
3341:
683:
group, led by
Francis A. Hochstein, in loose collaboration with and Robert Burns Woodward, determined the structure of
659:. Duggar derived the substance from a Missouri soil sample, golden-colored, fungus-like, soil-dwelling bacterium named
4420:
1392:
1268:
1167:"Tetracycline antibiotics: mode of action, applications, molecular biology, and epidemiology of bacterial resistance"
1083:
993:
780:
4393:
3290:"Microbiological Profile of Sarecycline, a Novel Targeted Spectrum Tetracycline for the Treatment of Acne Vulgaris"
3419:"Tetracyclines Disturb Mitochondrial Function across Eukaryotic Models: A Call for Caution in Biomedical Research"
3516:
152:) and are only effective against multiplying microorganisms. They are short-acting and passively diffuse through
1941:
1737:
Amacher DE, Martin BA (December 1997). "Tetracycline-induced steatosis in primary canine hepatocyte cultures".
184:
whereas human cells do not. Human cells therefore are spared the effects of tetracycline on protein synthesis.
560:
In ribosomal protection, a resistance gene encodes a protein that can have several effects, depending on what
2094:
1807:
Archer JS, Archer DF (June 2002). "Oral contraceptive efficacy and antibiotic interaction: a myth debunked".
574:
binding to the ribosome and distorting the structure to still allow t-RNA binding while tetracycline is bound
236:; however, their use for these indications is less popular than it once was due to widespread development of
395:
in the fetus as they develop in infancy. For this same reason, tetracyclines are contraindicated for use in
989:
429:
336:
963:(formerly known as WC 3035) received FDA approval on October 1, 2018, for treatment of moderate to severe
3593:
1382:
466:
4081:
3985:
3636:
2772:
968:
48:
compounds that have a common basic structure and are either isolated directly from several species of
4325:
660:
619:
482:
196:
3468:"Tetracycline antibiotics impair mitochondrial function and its experimental use confounds research"
1883:
531:
321:
209:
192:
3588:
4381:
1461:"Comparative susceptibility of anaerobic bacteria to minocycline, doxycycline, and tetracycline"
1247:
Blackwood RK, English AR (1970). "StructureβActivity
Relationships in the Tetracycline Series".
651:(Aureomycin) was first discovered as an ordinary item in 1945 and initially endorsed in 1948 by
240:
in the causative organisms. Tetracyclines are widely used in the treatment of moderately severe
3727:
1878:
441:
200:
113:
66:
2529:
DΓΆnhΓΆfer A, Franckenberg S, Wickles S, Berninghausen O, Beckmann R, Wilson DN (October 2012).
4425:
3385:
3363:
3241:
3219:
719:
656:
652:
539:
470:
301:
237:
213:
169:
161:
82:
2639:
367:, although drug-resistance is mounting and their effect on overall mortality is questioned.
4034:
2924:
2814:
2684:
2542:
2485:
392:
173:
104:
Tetracyclines were discovered in the 1940s and exhibited activity against a wide range of
8:
3663:
3417:
Moullan N, Mouchiroud L, Wang X, Ryu D, Williams EG, Mottis A, et al. (March 2015).
3107:"Functional, biophysical, and structural bases for antibacterial activity of tigecycline"
699:
550:
360:
225:
2928:
2818:
2688:
2546:
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from binding to the A site of the ribosome. They also bind to some extent the bacterial
3492:
3467:
3443:
3418:
3314:
3289:
3131:
3106:
3087:
3043:
2708:
2565:
2530:
2506:
2473:
2472:
Li W, Atkinson GC, Thakor NS, Allas U, Lu CC, Chan KY, et al. (12 February 2013).
2446:
2421:
2397:
2372:
2348:
2331:
2307:
2282:
2233:
2206:
1994:
1969:
1580:
1537:
1441:
1365:
1317:
1290:
564:
is transferred. Twelve classes of ribosomal protection genes/proteins have been found.
274:
264:). Anaerobic bacteria are not as susceptible to tetracyclines as are aerobic bacteria.
2614:
2589:
1924:
1892:
1611:
1525:
1485:
1460:
1260:
4305:
4301:
3870:
3497:
3448:
3319:
3263:
3201:
3180:"Pharmacokinetics and pharmacodynamics of the tetracyclines including glycylcyclines"
3136:
3079:
3035:
3000:
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2830:
2700:
2696:
2646:
2619:
2605:
2570:
2511:
2451:
2402:
2353:
2312:
2238:
2207:"Classification Framework and Chemical Biology of Tetracycline-Structure-Based Drugs"
2137:
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1999:
1896:
1851:
1824:
1789:
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1719:
1715:
1682:
1615:
1572:
1529:
1490:
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1429:
1398:
1388:
1357:
1322:
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1227:
1196:
1191:
1166:
812:
648:
425:
157:
133:
58:
3091:
3047:
2712:
2672:
2283:"The Tetracycline Destructases: A Novel Family of Tetracycline-Inactivating Enzymes"
2045:
1641:
1584:
1541:
1369:
634:, which may be taken with food (though not iron, antacids, or calcium supplements).
4353:
4297:
3925:
3487:
3479:
3438:
3430:
3309:
3301:
3191:
3126:
3118:
3071:
3027:
2990:
2932:
2890:
2822:
2692:
2609:
2601:
2560:
2550:
2501:
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2441:
2433:
2392:
2384:
2343:
2302:
2298:
2294:
2228:
2218:
2178:
2163:
2129:
2068:
2041:
1989:
1981:
1888:
1816:
1781:
1746:
1711:
1607:
1564:
1521:
1480:
1472:
1445:
1425:
1349:
1312:
1302:
1256:
1219:
1186:
1182:
1178:
900:
703:
478:
437:
3613:
3483:
2875:
2752:
2183:
1383:
WHO Advisory Group on
Integrated Surveillance of Antimicrobial Resistance (2017).
1111:
469:. They inhibit the initiation of translation in variety of ways by binding to the
4344:
4339:
4051:
3920:
3915:
3466:
Chatzispyrou IA, Held NM, Mouchiroud L, Auwerx J, Houtkooper RH (November 2015).
3434:
824:
684:
668:
591:
454:
284:
253:
153:
137:
86:
3609:
3605:
3601:
3597:
2826:
2388:
4387:
4204:
4134:
4119:
3880:
3765:
3753:
3631:
3075:
2908:
Bassett EJ, Keith MS, Armelagos GJ, Martin DL, Villanueva AR (September 1980).
2535:
Proceedings of the
National Academy of Sciences of the United States of America
2223:
2133:
1970:"rRNA Binding Sites and the Molecular Mechanism of Action of the Tetracyclines"
1923:. Organization of Teratology Information Specialists. July 2010. Archived from
1555:
Bhattacharya SK (February 2003). "An evaluation of current cholera treatment".
1048:
836:
595:
546:
506:
474:
417:
405:
289:
165:
145:
121:
105:
42:
3031:
2590:"Ribosomal protection proteins and their mechanism of tetracycline resistance"
1785:
4414:
4349:
4293:
4285:
4247:
4237:
4209:
4189:
4179:
4174:
4139:
4124:
4061:
4056:
3980:
3945:
3733:
3105:
Olson MW, Ruzin A, Feyfant E, Rush TS, O'Connell J, Bradford PA (June 2006).
2852:
2474:"Mechanism of tetracycline resistance by ribosomal protection protein Tet(O)"
2422:"Mosaic tetracycline resistance genes encoding ribosomal protection proteins"
2072:
1568:
1402:
1353:
1307:
1068:
964:
587:
388:
376:
241:
177:
149:
109:
98:
2936:
2555:
1869:
DeRossi SS, Hersh EV (October 2002). "Antibiotics and oral contraceptives".
1820:
1223:
1007:
Members of the tetracycline class of antibiotics are often used as research
473:, which is made up of 16S rRNA and 21 proteins. They inhibit the binding of
4333:
4329:
4257:
4194:
4164:
4129:
4099:
3935:
3910:
3895:
3885:
3875:
3849:
3790:
3738:
3685:
3658:
3648:
3501:
3452:
3323:
3205:
3140:
3083:
3039:
3004:
2834:
2802:
2704:
2623:
2574:
2515:
2455:
2406:
2316:
2242:
2141:
2080:
2003:
1900:
1855:
1828:
1750:
1619:
1576:
1533:
1437:
1361:
1326:
1284:
1282:
1280:
1200:
1073:
1024:
976:
939:
876:
863:
797:
761:
696:
688:
599:
348:
269:
249:
50:
31:
20:
2944:
2894:
2357:
1793:
1758:
1723:
1494:
1035:
in wildlife to check if wild animals are consuming a bait that contains a
722:(very much like the Egyptian beer), made from contaminated stored grains.
375:
Side-effects from tetracyclines are not common, but of particular note is
4319:
4265:
4242:
4169:
4154:
4149:
4066:
3953:
3930:
3905:
3900:
3890:
3865:
3709:
3680:
3305:
3196:
3179:
3122:
2437:
1985:
1056:
1040:
955:
924:
912:
888:
848:
765:
757:
753:
748:
744:
740:
736:
715:
635:
631:
627:
519:
486:
433:
421:
352:
340:
313:
309:
265:
261:
257:
229:
125:
117:
26:
3517:"A Review of Biomarkers Used For Wildlife Damage and Disease Management"
2910:"Tetracycline-labeled human bone from ancient Sudanese Nubia (A.D. 350)"
2528:
1942:"Mechanism of Action of Tetracyclines - Animations - PharmaXChange.info"
1277:
300:. Tetracyclines remain the treatment of choice for infections caused by
4315:
4275:
4270:
4219:
4199:
4184:
4159:
4114:
4109:
4043:
4014:
3994:
3814:
3809:
3800:
3795:
3780:
3775:
3723:
3675:
3589:
3155:"How Paratek hopes to succeed in antibiotics despite Tetraphase's fail"
2497:
1548:
1476:
344:
328:
317:
297:
65:, having an octahydrotetracene-2-carboxamide skeleton and are known as
62:
45:
4144:
4104:
4091:
4024:
4019:
4009:
4004:
3999:
3830:
3785:
3748:
3743:
3714:
3704:
3694:
1032:
607:
603:
590:, short-acting tetracyclines (plain tetracycline, chlortetracycline,
567:
Possible mechanisms of action of these protective proteins include:
545:
Inactivation is the rarest type of resistance, where NADPH-dependent
401:
233:
204:
90:
542:, ribosomal protection, reduced permeability and ribosome mutation.
4229:
3699:
3670:
2995:
2978:
1218:. International Union of Pure and Applied Chemistry (IUPAC). 2009.
1028:
623:
502:
498:
396:
356:
305:
188:
129:
78:
54:
711:
436:. The breakdown products of tetracyclines are toxic and can cause
4214:
1052:
1044:
1036:
1008:
615:
490:
364:
293:
279:
245:
94:
3465:
363:. They may have a role in reducing the duration and severity of
85:
do not change their broad antibacterial activity, but do affect
4311:
3547:
1701:
680:
676:
672:
664:
535:
332:
191:, although their usefulness has been reduced with the onset of
74:
70:
2588:
Connell SR, Tracz DM, Nierhaus KH, Taylor DE (December 2003).
1591:
420:(this is not true of the lipid-soluble agents doxycycline and
3524:
Proceedings of the 12th
Wildlife Damage Management Conference
707:
2531:"Structural basis for TetM-mediated tetracycline resistance"
2280:
2017:
Spreitzer H (July 2, 2007). "Neue
Wirkstoffe β Incyclinid".
1841:
1730:
1415:
296:
treatment and prophylaxis, as well as treating elephantitis
3338:"Antibiotic Firm Paratek Joins IPO Queue; Aiming for $ 92M"
3060:
2907:
1634:"Drugs and their categories in pregnancy and breastfeeding"
1387:(5th revision 2016 ed.). : World Health Organization.
611:
561:
494:
3017:
2587:
2281:
Forsberg KJ, Patel S, Wencewicz TA, Dantas G (July 2015).
1507:
756:
for the ribosomal target up to 5 times when compared with
3971:
3622:
3288:
Zhanel G, Critchley I, Lin LY, Alvandi N (January 2019).
3287:
2171:
Biomedical Journal of Scientific & Technical Research
2119:
1059:
that can be detected in hair and whiskers are preferred.
985:
679:, then a small company, into a pharmaceutical giant. The
3416:
2058:
1512:: a double-blind, randomised placebo-controlled trial".
663:. About the same time as Lederle discovered aureomycin,
586:
When ingested, it is usually recommended that the more
2419:
1695:
1031:
experimental results. It can be used as an artificial
3104:
2471:
2095:"CollaGenex says incyclinide ineffective for rosacea"
1765:
2420:
Warburton PJ, Amodeo N, Roberts AP (December 2016).
2032:
Viera MH, Perez OA, Berman B (2007). "Incyclinide".
687:, enabling Lloyd H. Conover to successfully produce
2883:
Journal of the American Society of Brewing Chemists
771:
577:
binding to the ribosome and dislodging tetracycline
571:
blocking tetracyclines from binding to the ribosome
2638:
1079:Tetracycline controlled transcriptional activation
1021:tetracycline-controlled transcriptional activation
512:
2636:
2257:"Tetracycline β Structure-activity relationships"
4412:
2805:(January 1950). "Terramycin, a new antibiotic".
2031:
1288:
1246:
132:. Tetracycline itself was discovered later than
2323:
2161:
1339:
618:, which reduces their ability to be completely
148:) rather than killers of the infectious agent (
34:with atoms and four rings numbered and labeled.
3508:
1809:Journal of the American Academy of Dermatology
1458:
988:approval on October 2, 2018, for treatment of
3574:
3177:
2972:
2970:
2968:
2113:
1736:
1177:(2): 232β60, second page, table of contents.
1164:
3459:
3410:
3281:
3098:
2731:"Tetracycline: History, Properties and Uses"
1868:
1862:
1835:
1806:
1800:
1771:
1554:
1106:
1104:
1102:
1100:
1098:
2800:
2377:Cold Spring Harbor Perspectives in Medicine
2162:Tariq S, Rizvi SF, Anwar U (25 July 2018).
1963:
1961:
1959:
1459:Chow AW, Patten V, Guze LB (January 1975).
1002:
4042:
3581:
3567:
2965:
2677:Annals of the New York Academy of Sciences
2670:
1171:Microbiology and Molecular Biology Reviews
525:
187:Tetracyclines retain an important role in
3514:
3491:
3442:
3313:
3195:
3184:The Journal of Antimicrobial Chemotherapy
3130:
2994:
2724:
2722:
2666:
2664:
2662:
2613:
2564:
2554:
2505:
2445:
2426:The Journal of Antimicrobial Chemotherapy
2413:
2396:
2373:"Tetracycline Antibiotics and Resistance"
2347:
2306:
2232:
2222:
2182:
2157:
2155:
2153:
2151:
2052:
2016:
1993:
1882:
1484:
1316:
1306:
1190:
1160:
1158:
1156:
1154:
1152:
1095:
180:components to leak from bacterial cells.
2641:Drug Interactions in Infectious Diseases
2522:
2370:
2364:
2274:
2200:
2198:
2196:
2194:
1967:
1956:
1289:Markley JL, Wencewicz TA (30 May 2018).
1216:IUPAC Compendium of Chemical Terminology
1150:
1148:
1146:
1144:
1142:
1140:
1138:
1136:
1134:
1132:
424:). They may increase muscle weakness in
156:in the bacterial membrane. They inhibit
25:
2976:
2581:
2329:
2249:
1912:
1910:
1409:
160:by binding reversibly to the bacterial
4413:
3011:
2873:
2766:
2764:
2762:
2728:
2719:
2659:
2148:
1687:: CS1 maint: archived copy as title (
984:(formerly known as PTK-0796) received
460:
3562:
3294:Antimicrobial Agents and Chemotherapy
3111:Antimicrobial Agents and Chemotherapy
2594:Antimicrobial Agents and Chemotherapy
2467:
2465:
2204:
2191:
1974:Antimicrobial Agents and Chemotherapy
1597:
1465:Antimicrobial Agents and Chemotherapy
1129:
228:, especially in patients allergic to
144:Tetracyclines are growth inhibitors (
3178:Agwuh KN, MacGowan A (August 2006).
3054:
2671:Nelson ML, Levy SB (December 2011).
1907:
1207:
447:
385:idiopathic intracranial hypertension
3270:. U.S. National Library of Medicine
2876:"Archaeology of ancient Egypt beer"
2759:
1704:Toxicology and Applied Pharmacology
1291:"Tetracycline-Inactivating Enzymes"
381:secondary intracranial hypertension
13:
2673:"The history of the tetracyclines"
2462:
2349:10.1111/j.1574-6976.1996.tb00251.x
1739:Fundamental and Applied Toxicology
1418:The British Journal of Dermatology
1240:
994:skin and skin structure infections
203:, the bacterial population of the
14:
4437:
3540:
3407:doi:10.1016/s1084-9521(02)00018-6
2637:Piscitelli SC, Rodvold K (2005).
1557:Expert Opinion on Pharmacotherapy
1165:Chopra I, Roberts M (June 2001).
1084:Animal Drug Availability Act 1996
581:
391:due to the likelihood of causing
16:Type of broad-spectrum antibiotic
3546:
2697:10.1111/j.1749-6632.2011.06354.x
2606:10.1128/AAC.47.12.3675-3681.2003
2019:Γsterreichische Apothekerzeitung
1598:Parsi VK (May 2001). "Cholera".
1430:10.1111/j.1365-2133.2007.08286.x
1249:Advances in Applied Microbiology
772:List of tetracycline antibiotics
3400:
3378:
3356:
3330:
3256:
3234:
3212:
3171:
3147:
2901:
2867:
2841:
2794:
2770:
2745:
2630:
2087:
2046:10.1358/dof.2007.032.03.1083308
2025:
2010:
1934:
1871:Dental Clinics of North America
1844:European Journal of Dermatology
1656:
1626:
1600:Primary Care Update for Ob/Gyns
1501:
513:Structure-activity relationship
370:
219:
208:resistance is often due to the
4082:transpeptidation/translocation
3242:"Drug Trial Snapshot: Seysara"
2979:"Tetracycline therapy: update"
2733:. Nottingham, UK: UKEssays.com
2299:10.1016/j.chembiol.2015.05.017
1452:
1376:
1333:
1183:10.1128/MMBR.65.2.232-260.2001
725:
538:inactivation of tetracycline,
1:
3484:10.1158/0008-5472.CAN-15-1626
3386:"Drug Trial Snapshot: Nuzyra"
3364:"Drug Trial Snapshot: Nuzyra"
3220:"Drug Trial Snapshot: Xerava"
2184:10.26717/BJSTR.2018.07.001475
1893:10.1016/S0011-8532(02)00017-4
1612:10.1016/S1068-607X(00)00086-X
1526:10.1016/S0140-6736(05)66591-9
1342:Expert Opinion on Drug Safety
1261:10.1016/S0065-2164(08)70405-2
1089:
622:by the body. Dairy products,
465:Tetracycline antibiotics are
212:of new genes, which code for
3435:10.1016/j.celrep.2015.02.034
2983:Clinical Infectious Diseases
2977:Roberts MC (February 2003).
2753:"The Pharmaceutical Century"
2729:Essays, UK (November 2013).
1918:"Tetracycline and Pregnancy"
1774:Drug and Chemical Toxicology
1716:10.1016/0041-008X(89)90252-4
1027:leading to effects that may
990:community-acquired pneumonia
467:protein synthesis inhibitors
430:systemic lupus erythematosus
337:Rocky Mountain spotted fever
7:
2827:10.1126/science.111.2874.85
2389:10.1101/cshperspect.a025387
2330:Roberts MC (October 1996).
2061:Current Medicinal Chemistry
2021:(in German) (14/2007): 655.
1968:Chukwudi CU (August 2016).
1062:
1039:or medication. Since it is
411:
282:) and is effective against
272:treatment for infection by
10:
4442:
3515:Fry TL, Dunbar MR (2007).
3076:10.1001/jamasurg.2016.4237
2371:Grossman TH (April 2016).
2224:10.3390/antibiotics1010001
2134:10.1016/j.phrs.2010.10.008
641:
288:, the infectious agent of
18:
4371:
4326:Quinupristin/dalfopristin
4284:
4256:
4228:
4090:
4079:
4033:
3979:
3970:
3944:
3858:
3843:
3823:
3762:
3645:
3630:
3621:
3594:inhibit protein synthesis
3032:10.1007/s40265-016-0545-8
2336:FEMS Microbiology Reviews
1786:10.3109/01480548209041054
1295:Frontiers in Microbiology
943:
852:
801:
661:Streptomyces aureofaciens
483:matrix metalloproteinases
359:). They are also used in
4421:Tetracycline antibiotics
3845:Tetracycline antibiotics
3553:Tetracycline antibiotics
2122:Pharmacological Research
2073:10.2174/0929867013373598
1569:10.1517/14656566.4.2.141
1354:10.1517/14740338.7.5.571
1308:10.3389/fmicb.2018.01058
1003:Use as research reagents
2937:10.1126/science.7001623
2556:10.1073/pnas.1208037109
2287:Chemistry & Biology
1821:10.1067/mjd.2002.120448
1224:10.1351/goldbook.T06287
1116:Encyclopedia Britannica
881:12 hours (intermediate)
841:12 hours (intermediate)
526:Mechanism of resistance
489:) for the treatment of
214:energy-dependent efflux
2849:"Lemelson-MIT Program"
1751:10.1006/faat.1997.2389
695:Research conducted by
442:hormonal contraception
345:spirochetal infections
292:. It is also used for
201:gastrointestinal tract
114:gram-negative bacteria
35:
2895:10.1094/ASBCJ-54-0003
2478:Nature Communications
2261:University of Bristol
2205:Fuoco D (June 2012).
871:(no longer marketed)
657:Yellapragada Subbarow
653:Benjamin Minge Duggar
501:and various types of
471:30S ribosomal subunit
193:antibiotic resistance
170:50S ribosomal subunit
162:30S ribosomal subunit
29:
4035:Peptidyl transferase
3555:at Wikimedia Commons
3306:10.1128/AAC.01297-18
3123:10.1128/AAC.01499-05
2773:"The teteracyclines"
1986:10.1128/AAC.00594-16
1644:on 14 September 2009
1510:Wuchereria bancrofti
967:. Sarecycline is a
706:showed that ancient
393:teeth discolouration
387:. Tetracyclines are
174:cytoplasmic membrane
30:Skeletal formula of
3664:Dihydrostreptomycin
2929:1980Sci...209.1532B
2819:1950Sci...111...85F
2689:2011NYASA1241...17N
2547:2012PNAS..10916900D
2490:2013NatCo...4.1477L
2101:. 26 September 2016
2034:Drugs of the Future
802:Naturally occurring
700:George J. Armelagos
551:biological activity
534:to tetracycline by
461:Mechanism of action
361:veterinary medicine
164:and preventing the
89:properties such as
4398:Never to phase III
3344:on 18 October 2017
3197:10.1093/jac/dkl224
2498:10.1038/ncomms2470
2438:10.1093/jac/dkw304
1477:10.1128/aac.7.1.46
275:Bacillus anthracis
268:is also used as a
172:and may alter the
36:
4408:
4407:
4367:
4366:
4363:
4362:
4075:
4074:
3966:
3965:
3962:
3961:
3871:Chlortetracycline
3839:
3838:
3551:Media related to
3429:(10): 1681β1691.
3062:Clinical Trial".
2874:Samuel D (1996).
2652:978-1-58829-455-5
2432:(12): 3333β3339.
1520:(9477): 2116β21.
1233:978-0-9678550-9-7
1214:"Tetracyclines".
1000:
999:
905:6β8 hours (short)
868:6β8 hours (short)
856:6β8 hours (short)
829:6β8 hours (short)
817:6β8 hours (short)
813:Chlortetracycline
805:6β8 hours (short)
649:Chlortetracycline
530:Cells can become
448:Contraindications
426:myasthenia gravis
158:protein synthesis
134:chlortetracycline
59:functional groups
4433:
4088:
4087:
4040:
4039:
3977:
3976:
3926:Rolitetracycline
3856:
3855:
3643:
3642:
3628:
3627:
3583:
3576:
3569:
3560:
3559:
3550:
3535:
3534:
3532:
3531:
3521:
3512:
3506:
3505:
3495:
3463:
3457:
3456:
3446:
3414:
3408:
3404:
3398:
3397:
3395:
3393:
3382:
3376:
3375:
3373:
3371:
3360:
3354:
3353:
3351:
3349:
3340:. Archived from
3334:
3328:
3327:
3317:
3285:
3279:
3278:
3276:
3275:
3260:
3254:
3253:
3251:
3249:
3238:
3232:
3231:
3229:
3227:
3216:
3210:
3209:
3199:
3175:
3169:
3168:
3166:
3165:
3151:
3145:
3144:
3134:
3102:
3096:
3095:
3058:
3052:
3051:
3015:
3009:
3008:
2998:
2974:
2963:
2962:
2960:
2959:
2953:
2947:. Archived from
2923:(4464): 1532β4.
2914:
2905:
2899:
2898:
2880:
2871:
2865:
2864:
2862:
2860:
2855:on 18 March 2003
2851:. Archived from
2845:
2839:
2838:
2798:
2792:
2791:
2789:
2787:
2777:
2768:
2757:
2756:
2749:
2743:
2742:
2740:
2738:
2726:
2717:
2716:
2668:
2657:
2656:
2645:. Humana Press.
2644:
2634:
2628:
2627:
2617:
2585:
2579:
2578:
2568:
2558:
2526:
2520:
2519:
2509:
2469:
2460:
2459:
2449:
2417:
2411:
2410:
2400:
2368:
2362:
2361:
2351:
2327:
2321:
2320:
2310:
2278:
2272:
2271:
2269:
2267:
2253:
2247:
2246:
2236:
2226:
2202:
2189:
2188:
2186:
2168:
2159:
2146:
2145:
2117:
2111:
2110:
2108:
2106:
2091:
2085:
2084:
2056:
2050:
2049:
2029:
2023:
2022:
2014:
2008:
2007:
1997:
1965:
1954:
1953:
1951:
1949:
1938:
1932:
1931:
1929:
1922:
1914:
1905:
1904:
1886:
1866:
1860:
1859:
1839:
1833:
1832:
1804:
1798:
1797:
1769:
1763:
1762:
1734:
1728:
1727:
1699:
1693:
1692:
1686:
1678:
1676:
1675:
1666:. Archived from
1660:
1654:
1653:
1651:
1649:
1640:. Archived from
1630:
1624:
1623:
1595:
1589:
1588:
1552:
1546:
1545:
1505:
1499:
1498:
1488:
1456:
1450:
1449:
1413:
1407:
1406:
1380:
1374:
1373:
1337:
1331:
1330:
1320:
1310:
1286:
1275:
1274:
1244:
1238:
1237:
1211:
1205:
1204:
1194:
1162:
1127:
1126:
1124:
1122:
1108:
981:16+ hours (long)
960:16+ hours (long)
947:16+ hours (long)
932:16+ hours (long)
917:16+ hours (long)
901:Rolitetracycline
893:16+ hours (long)
776:
775:
704:Emory University
702:and his team at
479:mRNA translation
438:Fanconi syndrome
383:, also known as
128:, and protozoan
4441:
4440:
4436:
4435:
4434:
4432:
4431:
4430:
4411:
4410:
4409:
4404:
4403:
4388:Clinical trials
4359:
4345:Streptogramin B
4340:Streptogramin A
4280:
4252:
4224:
4071:
4052:Chloramphenicol
4029:
3983:
3958:
3940:
3921:Penimepicycline
3916:Oxytetracycline
3847:
3835:
3819:
3758:
3634:
3632:Aminoglycosides
3617:
3587:
3543:
3538:
3529:
3527:
3519:
3513:
3509:
3472:Cancer Research
3464:
3460:
3415:
3411:
3405:
3401:
3391:
3389:
3384:
3383:
3379:
3369:
3367:
3362:
3361:
3357:
3347:
3345:
3336:
3335:
3331:
3286:
3282:
3273:
3271:
3262:
3261:
3257:
3247:
3245:
3240:
3239:
3235:
3225:
3223:
3218:
3217:
3213:
3176:
3172:
3163:
3161:
3159:Bizjournals.com
3153:
3152:
3148:
3103:
3099:
3059:
3055:
3016:
3012:
2975:
2966:
2957:
2955:
2951:
2912:
2906:
2902:
2878:
2872:
2868:
2858:
2856:
2847:
2846:
2842:
2799:
2795:
2785:
2783:
2775:
2769:
2760:
2751:
2750:
2746:
2736:
2734:
2727:
2720:
2669:
2660:
2653:
2635:
2631:
2600:(12): 3675β81.
2586:
2582:
2541:(42): 16900β5.
2527:
2523:
2470:
2463:
2418:
2414:
2369:
2365:
2328:
2324:
2279:
2275:
2265:
2263:
2255:
2254:
2250:
2203:
2192:
2166:
2160:
2149:
2118:
2114:
2104:
2102:
2093:
2092:
2088:
2057:
2053:
2030:
2026:
2015:
2011:
1966:
1957:
1947:
1945:
1940:
1939:
1935:
1927:
1920:
1916:
1915:
1908:
1884:10.1.1.620.9933
1867:
1863:
1840:
1836:
1805:
1801:
1770:
1766:
1735:
1731:
1700:
1696:
1680:
1679:
1673:
1671:
1664:"Archived copy"
1662:
1661:
1657:
1647:
1645:
1632:
1631:
1627:
1596:
1592:
1553:
1549:
1506:
1502:
1457:
1453:
1414:
1410:
1395:
1381:
1377:
1338:
1334:
1287:
1278:
1271:
1245:
1241:
1234:
1213:
1212:
1208:
1163:
1130:
1120:
1118:
1110:
1109:
1096:
1092:
1065:
1005:
969:narrow-spectrum
825:Oxytetracycline
774:
728:
685:oxytetracycline
669:oxytetracycline
644:
592:oxytetracycline
584:
528:
515:
463:
455:inguinal hernia
450:
428:and exacerbate
414:
373:
285:Yersinia pestis
254:oxytetracycline
222:
138:oxytetracycline
93:and binding to
87:pharmacological
41:are a group of
24:
17:
12:
11:
5:
4439:
4429:
4428:
4423:
4406:
4405:
4402:
4401:
4400:
4399:
4396:
4385:
4379:
4373:
4372:
4369:
4368:
4365:
4364:
4361:
4360:
4358:
4357:
4347:
4342:
4337:
4323:
4309:
4290:
4288:
4286:Streptogramins
4282:
4281:
4279:
4278:
4273:
4268:
4262:
4260:
4254:
4253:
4251:
4250:
4245:
4240:
4234:
4232:
4226:
4225:
4223:
4222:
4217:
4212:
4207:
4205:Troleandomycin
4202:
4197:
4192:
4187:
4182:
4177:
4172:
4167:
4162:
4157:
4152:
4147:
4142:
4137:
4135:Flurithromycin
4132:
4127:
4122:
4120:Clarithromycin
4117:
4112:
4107:
4102:
4096:
4094:
4085:
4077:
4076:
4073:
4072:
4070:
4069:
4064:
4059:
4054:
4048:
4046:
4037:
4031:
4030:
4028:
4027:
4022:
4017:
4012:
4007:
4002:
3997:
3991:
3989:
3974:
3968:
3967:
3964:
3963:
3960:
3959:
3957:
3956:
3950:
3948:
3946:Glycylcyclines
3942:
3941:
3939:
3938:
3933:
3928:
3923:
3918:
3913:
3908:
3903:
3898:
3893:
3888:
3883:
3881:Demeclocycline
3878:
3873:
3868:
3862:
3860:
3853:
3841:
3840:
3837:
3836:
3834:
3833:
3827:
3825:
3821:
3820:
3818:
3817:
3812:
3806:
3805:
3804:
3803:
3798:
3793:
3788:
3783:
3772:
3770:
3766:Micromonospora
3760:
3759:
3757:
3756:
3754:Nourseothricin
3751:
3746:
3741:
3736:
3731:
3720:
3719:
3718:
3717:
3712:
3707:
3702:
3691:
3690:
3689:
3688:
3683:
3678:
3667:
3666:
3661:
3655:
3653:
3640:
3625:
3619:
3618:
3590:Antibacterials
3586:
3585:
3578:
3571:
3563:
3557:
3556:
3542:
3541:External links
3539:
3537:
3536:
3507:
3478:(21): 4446β9.
3458:
3409:
3399:
3377:
3355:
3329:
3280:
3255:
3233:
3211:
3170:
3146:
3117:(6): 2156β66.
3097:
3070:(3): 224β232.
3053:
3010:
2996:10.1086/367622
2964:
2900:
2866:
2840:
2793:
2758:
2744:
2718:
2658:
2651:
2629:
2580:
2521:
2461:
2412:
2383:(4): a025387.
2363:
2322:
2273:
2248:
2190:
2147:
2112:
2086:
2051:
2040:(3): 209β214.
2024:
2009:
1980:(8): 4433β41.
1955:
1933:
1930:on 2011-08-27.
1906:
1861:
1834:
1799:
1764:
1729:
1694:
1655:
1625:
1606:(3): 106β109.
1590:
1547:
1500:
1451:
1408:
1393:
1375:
1332:
1276:
1269:
1239:
1232:
1206:
1128:
1112:"Tetracycline"
1093:
1091:
1088:
1087:
1086:
1081:
1076:
1071:
1064:
1061:
1049:rabies vaccine
1004:
1001:
998:
997:
982:
979:
973:
972:
961:
958:
952:
951:
948:
945:
942:
936:
935:
933:
930:
929:Glycylcyclines
927:
921:
920:
918:
915:
909:
908:
906:
903:
897:
896:
894:
891:
885:
884:
882:
879:
873:
872:
869:
866:
860:
859:
857:
854:
853:Semi-synthetic
851:
845:
844:
842:
839:
837:Demeclocycline
833:
832:
830:
827:
821:
820:
818:
815:
809:
808:
806:
803:
800:
794:
793:
790:
787:
784:
773:
770:
727:
724:
710:from the post-
697:anthropologist
643:
640:
596:demeclocycline
583:
582:Administration
580:
579:
578:
575:
572:
547:oxidoreductase
527:
524:
514:
511:
507:Kaposi Sarcoma
475:aminoacyl-tRNA
462:
459:
449:
446:
418:kidney failure
413:
410:
406:liver toxicity
372:
369:
290:bubonic plague
221:
218:
166:aminoacyl tRNA
154:porin channels
146:bacteriostatic
122:mycoplasmatota
106:microorganisms
81:groups. These
43:broad-spectrum
15:
9:
6:
4:
3:
2:
4438:
4427:
4424:
4422:
4419:
4418:
4416:
4397:
4395:
4392:
4391:
4389:
4386:
4383:
4380:
4378:
4375:
4374:
4370:
4355:
4351:
4350:Virginiamycin
4348:
4346:
4343:
4341:
4338:
4335:
4331:
4327:
4324:
4321:
4317:
4313:
4310:
4307:
4303:
4299:
4295:
4294:Pristinamycin
4292:
4291:
4289:
4287:
4283:
4277:
4274:
4272:
4269:
4267:
4264:
4263:
4261:
4259:
4255:
4249:
4248:Solithromycin
4246:
4244:
4241:
4239:
4238:Telithromycin
4236:
4235:
4233:
4231:
4227:
4221:
4218:
4216:
4213:
4211:
4210:Tulathromycin
4208:
4206:
4203:
4201:
4198:
4196:
4193:
4191:
4190:Telithromycin
4188:
4186:
4183:
4181:
4180:Solithromycin
4178:
4176:
4175:Roxithromycin
4173:
4171:
4168:
4166:
4163:
4161:
4158:
4156:
4153:
4151:
4148:
4146:
4143:
4141:
4140:Gamithromycin
4138:
4136:
4133:
4131:
4128:
4126:
4125:Dirithromycin
4123:
4121:
4118:
4116:
4113:
4111:
4108:
4106:
4103:
4101:
4098:
4097:
4095:
4093:
4089:
4086:
4083:
4078:
4068:
4065:
4063:
4062:Thiamphenicol
4060:
4058:
4057:Azidamfenicol
4055:
4053:
4050:
4049:
4047:
4045:
4041:
4038:
4036:
4032:
4026:
4023:
4021:
4018:
4016:
4013:
4011:
4008:
4006:
4003:
4001:
3998:
3996:
3993:
3992:
3990:
3987:
3982:
3981:Oxazolidinone
3978:
3975:
3973:
3969:
3955:
3952:
3951:
3949:
3947:
3943:
3937:
3934:
3932:
3929:
3927:
3924:
3922:
3919:
3917:
3914:
3912:
3909:
3907:
3904:
3902:
3899:
3897:
3894:
3892:
3889:
3887:
3884:
3882:
3879:
3877:
3874:
3872:
3869:
3867:
3864:
3863:
3861:
3859:Tetracyclines
3857:
3854:
3851:
3846:
3842:
3832:
3829:
3828:
3826:
3822:
3816:
3813:
3811:
3808:
3807:
3802:
3799:
3797:
3794:
3792:
3789:
3787:
3784:
3782:
3779:
3778:
3777:
3774:
3773:
3771:
3768:
3767:
3761:
3755:
3752:
3750:
3747:
3745:
3742:
3740:
3737:
3735:
3734:Spectinomycin
3732:
3729:
3725:
3722:
3721:
3716:
3713:
3711:
3708:
3706:
3703:
3701:
3698:
3697:
3696:
3693:
3692:
3687:
3684:
3682:
3679:
3677:
3674:
3673:
3672:
3669:
3668:
3665:
3662:
3660:
3657:
3656:
3654:
3651:
3650:
3644:
3641:
3638:
3633:
3629:
3626:
3624:
3620:
3615:
3611:
3607:
3603:
3599:
3595:
3591:
3584:
3579:
3577:
3572:
3570:
3565:
3564:
3561:
3554:
3549:
3545:
3544:
3525:
3518:
3511:
3503:
3499:
3494:
3489:
3485:
3481:
3477:
3473:
3469:
3462:
3454:
3450:
3445:
3440:
3436:
3432:
3428:
3424:
3420:
3413:
3403:
3387:
3381:
3365:
3359:
3343:
3339:
3333:
3325:
3321:
3316:
3311:
3307:
3303:
3299:
3295:
3291:
3284:
3269:
3265:
3264:"Sarecycline"
3259:
3243:
3237:
3221:
3215:
3207:
3203:
3198:
3193:
3190:(2): 256β65.
3189:
3185:
3181:
3174:
3160:
3156:
3150:
3142:
3138:
3133:
3128:
3124:
3120:
3116:
3112:
3108:
3101:
3093:
3089:
3085:
3081:
3077:
3073:
3069:
3065:
3057:
3049:
3045:
3041:
3037:
3033:
3029:
3026:(5): 567β88.
3025:
3021:
3014:
3006:
3002:
2997:
2992:
2988:
2984:
2980:
2973:
2971:
2969:
2954:on 2016-03-04
2950:
2946:
2942:
2938:
2934:
2930:
2926:
2922:
2918:
2911:
2904:
2896:
2892:
2888:
2884:
2877:
2870:
2854:
2850:
2844:
2836:
2832:
2828:
2824:
2820:
2816:
2812:
2808:
2804:
2797:
2781:
2774:
2767:
2765:
2763:
2754:
2748:
2732:
2725:
2723:
2714:
2710:
2706:
2702:
2698:
2694:
2690:
2686:
2682:
2678:
2674:
2667:
2665:
2663:
2654:
2648:
2643:
2642:
2633:
2625:
2621:
2616:
2611:
2607:
2603:
2599:
2595:
2591:
2584:
2576:
2572:
2567:
2562:
2557:
2552:
2548:
2544:
2540:
2536:
2532:
2525:
2517:
2513:
2508:
2503:
2499:
2495:
2491:
2487:
2483:
2479:
2475:
2468:
2466:
2457:
2453:
2448:
2443:
2439:
2435:
2431:
2427:
2423:
2416:
2408:
2404:
2399:
2394:
2390:
2386:
2382:
2378:
2374:
2367:
2359:
2355:
2350:
2345:
2341:
2337:
2333:
2326:
2318:
2314:
2309:
2304:
2300:
2296:
2293:(7): 888β97.
2292:
2288:
2284:
2277:
2262:
2258:
2252:
2244:
2240:
2235:
2230:
2225:
2220:
2216:
2212:
2208:
2201:
2199:
2197:
2195:
2185:
2180:
2176:
2172:
2165:
2158:
2156:
2154:
2152:
2143:
2139:
2135:
2131:
2127:
2123:
2116:
2100:
2096:
2090:
2082:
2078:
2074:
2070:
2067:(3): 305β16.
2066:
2062:
2055:
2047:
2043:
2039:
2035:
2028:
2020:
2013:
2005:
2001:
1996:
1991:
1987:
1983:
1979:
1975:
1971:
1964:
1962:
1960:
1944:. 27 May 2011
1943:
1937:
1926:
1919:
1913:
1911:
1902:
1898:
1894:
1890:
1885:
1880:
1877:(4): 653β64.
1876:
1872:
1865:
1857:
1853:
1849:
1845:
1838:
1830:
1826:
1822:
1818:
1815:(6): 917β23.
1814:
1810:
1803:
1795:
1791:
1787:
1783:
1780:(3): 219β31.
1779:
1775:
1768:
1760:
1756:
1752:
1748:
1745:(2): 256β63.
1744:
1740:
1733:
1725:
1721:
1717:
1713:
1709:
1705:
1698:
1690:
1684:
1670:on 2016-04-09
1669:
1665:
1659:
1643:
1639:
1638:www.tg.org.au
1635:
1629:
1621:
1617:
1613:
1609:
1605:
1601:
1594:
1586:
1582:
1578:
1574:
1570:
1566:
1562:
1558:
1551:
1543:
1539:
1535:
1531:
1527:
1523:
1519:
1515:
1511:
1504:
1496:
1492:
1487:
1482:
1478:
1474:
1470:
1466:
1462:
1455:
1447:
1443:
1439:
1435:
1431:
1427:
1424:(2): 208β16.
1423:
1419:
1412:
1404:
1400:
1396:
1394:9789241512220
1390:
1386:
1379:
1371:
1367:
1363:
1359:
1355:
1351:
1347:
1343:
1336:
1328:
1324:
1319:
1314:
1309:
1304:
1300:
1296:
1292:
1285:
1283:
1281:
1272:
1270:9780120026135
1266:
1262:
1258:
1254:
1250:
1243:
1235:
1229:
1225:
1221:
1217:
1210:
1202:
1198:
1193:
1188:
1184:
1180:
1176:
1172:
1168:
1161:
1159:
1157:
1155:
1153:
1151:
1149:
1147:
1145:
1143:
1141:
1139:
1137:
1135:
1133:
1117:
1113:
1107:
1105:
1103:
1101:
1099:
1094:
1085:
1082:
1080:
1077:
1075:
1072:
1070:
1069:Glycylcycline
1067:
1066:
1060:
1058:
1054:
1050:
1046:
1043:and binds to
1042:
1038:
1034:
1030:
1026:
1022:
1018:
1014:
1010:
995:
991:
987:
983:
980:
978:
975:
974:
970:
966:
965:acne vulgaris
962:
959:
957:
954:
953:
949:
946:
941:
938:
937:
934:
931:
928:
926:
923:
922:
919:
916:
914:
911:
910:
907:
904:
902:
899:
898:
895:
892:
890:
887:
886:
883:
880:
878:
875:
874:
870:
867:
865:
862:
861:
858:
855:
850:
847:
846:
843:
840:
838:
835:
834:
831:
828:
826:
823:
822:
819:
816:
814:
811:
810:
807:
804:
799:
796:
795:
791:
788:
785:
782:
778:
777:
769:
767:
763:
759:
755:
750:
746:
742:
738:
732:
723:
721:
717:
713:
709:
705:
701:
698:
693:
690:
686:
682:
678:
674:
670:
666:
662:
658:
654:
650:
639:
637:
633:
629:
625:
621:
617:
613:
609:
605:
601:
597:
593:
589:
588:water-soluble
576:
573:
570:
569:
568:
565:
563:
558:
554:
552:
548:
543:
541:
537:
533:
523:
521:
510:
508:
504:
500:
496:
492:
488:
484:
480:
476:
472:
468:
458:
456:
445:
443:
439:
435:
431:
427:
423:
419:
409:
407:
403:
398:
394:
390:
386:
382:
378:
377:phototoxicity
368:
366:
362:
358:
354:
350:
346:
342:
338:
334:
330:
326:
324:
319:
315:
311:
307:
303:
299:
295:
291:
287:
286:
281:
277:
276:
271:
267:
263:
259:
255:
251:
247:
243:
239:
235:
231:
227:
217:
215:
211:
206:
202:
198:
194:
190:
185:
181:
179:
178:intracellular
175:
171:
167:
163:
159:
155:
151:
150:bacteriocidal
147:
142:
139:
135:
131:
127:
123:
119:
115:
111:
110:gram-positive
107:
102:
100:
96:
92:
88:
84:
83:modifications
80:
76:
72:
68:
64:
60:
56:
53:
52:
47:
44:
40:
39:Tetracyclines
33:
28:
22:
4426:Hepatotoxins
4334:Quinupristin
4330:Dalfopristin
4258:Lincosamides
4195:Tildipirosin
4165:Oleandomycin
4130:Erythromycin
4100:Azithromycin
3936:Tetracycline
3911:Omadacycline
3896:Meclocycline
3886:Eravacycline
3876:Clomocycline
3844:
3791:Micronomicin
3764:
3739:Hygromycin B
3728:+loteprednol
3686:Ribostamycin
3659:Streptomycin
3649:Streptomyces
3647:
3528:. Retrieved
3523:
3510:
3475:
3471:
3461:
3426:
3423:Cell Reports
3422:
3412:
3402:
3390:. Retrieved
3380:
3368:. Retrieved
3358:
3346:. Retrieved
3342:the original
3332:
3297:
3293:
3283:
3272:. Retrieved
3267:
3258:
3246:. Retrieved
3236:
3224:. Retrieved
3214:
3187:
3183:
3173:
3162:. Retrieved
3158:
3149:
3114:
3110:
3100:
3067:
3064:JAMA Surgery
3063:
3056:
3023:
3019:
3013:
2989:(4): 462β7.
2986:
2982:
2956:. Retrieved
2949:the original
2920:
2916:
2903:
2886:
2882:
2869:
2857:. Retrieved
2853:the original
2843:
2813:(2874): 85.
2810:
2806:
2796:
2784:. Retrieved
2782:. Baran labs
2779:
2747:
2735:. Retrieved
2683:(1): 17β32.
2680:
2676:
2640:
2632:
2597:
2593:
2583:
2538:
2534:
2524:
2481:
2477:
2429:
2425:
2415:
2380:
2376:
2366:
2339:
2335:
2325:
2290:
2286:
2276:
2264:. Retrieved
2260:
2251:
2214:
2210:
2174:
2170:
2128:(2): 151β6.
2125:
2121:
2115:
2103:. Retrieved
2098:
2089:
2064:
2060:
2054:
2037:
2033:
2027:
2018:
2012:
1977:
1973:
1946:. Retrieved
1936:
1925:the original
1874:
1870:
1864:
1850:(6): 391β9.
1847:
1843:
1837:
1812:
1808:
1802:
1777:
1773:
1767:
1742:
1738:
1732:
1710:(3): 473β9.
1707:
1703:
1697:
1672:. Retrieved
1668:the original
1658:
1646:. Retrieved
1642:the original
1637:
1628:
1603:
1599:
1593:
1563:(2): 141β6.
1560:
1556:
1550:
1517:
1513:
1509:
1503:
1468:
1464:
1454:
1421:
1417:
1411:
1384:
1378:
1348:(5): 571β7.
1345:
1341:
1335:
1298:
1294:
1252:
1248:
1242:
1215:
1209:
1174:
1170:
1119:. Retrieved
1115:
1074:Eravacycline
1025:mitochondria
1016:
1012:
1006:
977:Omadacycline
971:antibiotic.
940:Eravacycline
877:Methacycline
864:Meclocycline
798:Tetracycline
779:Antibiotic (
762:tetracycline
733:
729:
720:ancient beer
694:
689:tetracycline
645:
600:methacycline
585:
566:
559:
555:
544:
529:
516:
464:
451:
415:
374:
371:Side effects
349:Lyme disease
322:
283:
273:
270:prophylactic
250:tetracycline
223:
220:Medical uses
186:
182:
143:
103:
51:Streptomyces
49:
38:
37:
32:tetracycline
21:tetracycline
4384:from market
4320:Linopristin
4266:Clindamycin
4243:Cethromycin
4170:Rokitamycin
4155:Midecamycin
4150:Kitasamycin
4067:Florfenicol
4044:Amphenicols
3988:inhibitors)
3954:Tigecycline
3931:Sarecycline
3906:Minocycline
3901:Metacycline
3891:Lymecycline
3866:Doxycycline
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3681:Paromomycin
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2889:(1): 3β12.
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2217:(1): 1β13.
2211:Antibiotics
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1057:rhodamine B
1041:fluorescent
956:Sarecycline
925:Tigecycline
913:Doxycycline
889:Minocycline
849:Lymecycline
766:tigecycline
758:minocycline
754:tigecycline
749:tigecycline
745:minocycline
741:minocycline
737:tigecycline
726:Development
716:ultraviolet
636:Minocycline
632:minocycline
628:doxycycline
520:lymecycline
487:incyclinide
434:minocycline
422:minocycline
353:borreliosis
341:brucellosis
323:L. venereum
314:salpingitis
310:psittacosis
266:Doxycycline
262:minocycline
258:doxycycline
210:acquisition
141:promoters.
126:rickettsiae
118:chlamydiota
67:derivatives
63:polyketides
4415:Categories
4316:Flopristin
4276:Pirlimycin
4271:Lincomycin
4220:Tylvalosin
4200:Tilmicosin
4185:Spiramycin
4160:Miocamycin
4115:Carrimycin
4110:Carbomycin
4092:Macrolides
4015:Ranbezolid
3995:Eperezolid
3986:initiation
3815:Astromicin
3810:Verdamicin
3801:Isepamicin
3796:Plazomicin
3781:Netilmicin
3776:Gentamicin
3724:Tobramycin
3676:Framycetin
3637:initiation
3530:2017-05-03
3392:8 February
3370:8 February
3274:2020-06-07
3248:8 February
3164:2017-03-13
2958:2014-06-19
1674:2019-04-16
1648:3 February
1090:References
992:and acute
389:teratogens
329:Rickettsia
318:urethritis
298:filariasis
238:resistance
234:macrolides
108:including
46:antibiotic
4394:Phase III
4382:Withdrawn
4230:Ketolides
4145:Josamycin
4105:Boromycin
4025:Tedizolid
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4010:Radezolid
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4000:Linezolid
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3715:Dibekacin
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3695:Kanamycin
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536:enzymatic
532:resistant
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499:diabetes
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