594:
571:
970:. For example, in a phase II study involving men with advanced prostate cancer, high-dose itraconazole (600 mg/day) was associated with significant PSA responses and a delay in tumor progression. Itraconazole also showed activity in a phase II trial in men with non-small cell lung cancer when it was combined with the chemotherapy agent, pemetrexed. A recent review also highlights its use topically and orally in conjunction with other chemotherapeutic agents for advanced and metastatic basal cell carcinomas that cannot be treated surgically.
1002:, and if this is a problem, then half the dose can be given as oral solution and half as capsule to reduce the amount of cyclodextrin given. "Sporanox" itraconazole capsules should always be taken with food, as this improves absorption, however the manufacturers of "Lozanoc" assert that it may be taken "without regard to meals". Itraconazole oral solution should be taken an hour before food, or two hours after food (and likewise if a combination of capsules and oral solution are used). Itraconazole may be taken with orange juice or
1313:
987:. The three-layer structure of these blue capsules is complex because itraconazole is insoluble and is sensitive to pH. The complicated procedure not only requires a specialized machine to create it, but also the method used has manufacturing problems. Also, the pill is quite large, making it difficult for many patients to swallow. Parts of the processes of creating Sporanox were discovered by the Korean Patent Laid-open No. 10-2001-2590. The tiny blue pellets contained in the capsule are manufactured in
1334:
31:
2881:
4843:
1994:
1296:
by reducing elimination and increasing absorption of organic cation drugs. With conventional itraconazole preparations serum levels can vary greatly between patients, often resulting in serum concentrations lower than the therapeutic index. It has therefore been conventionally advised that patients
978:
Itraconazole is produced as blue 22 mm (0.87 in) capsules with tiny 1.5 mm (0.059 in) blue pellets inside. Each capsule contains 100 mg and is usually taken twice a day at twelve-hour intervals. The
Sporanox brand of itraconazole has been developed and marketed by
1267:
2 phosphorylation, trafficking, and cholesterol biosynthesis pathways. Evidence suggests the structural determinants for inhibition of hedgehog signaling by itraconazole are recognizably different from those associated with antiangiogenic activity.
743:
InChI=1S/C35H38Cl2N8O4/c1-3-25(2)45-34(46)44(24-40-45)29-7-5-27(6-8-29)41-14-16-42(17-15-41)28-9-11-30(12-10-28)47-19-31-20-48-35(49-31,21-43-23-38-22-39-43)32-13-4-26(36)18-33(32)37/h4-13,18,22-25,31H,3,14-17,19-21H2,1-2H3/t25?,31-,35-/m0/s1
669:
2438:"Itraconazole Side Chain Analogues: Structure–Activity Relationship Studies for Inhibition of Endothelial Cell Proliferation, Vascular Endothelial Growth Factor Receptor 2 (VEGFR2) Glycosylation, and Hedgehog Signaling"
1263:
and the exact molecular targets responsible remain unidentified. Functionally, the antiangiogenic activity of itraconazole has been shown to be linked to inhibition of glycosylation,
223:
1540:
Vasilev NA, Surov AO, Voronin AP, Drozd KV, Perlovich GL (April 2021). "Novel cocrystals of itraconazole: Insights from phase diagrams, formation thermodynamics and solubility".
1505:
936:
infections. According to the Johns
Hopkins Abx Guide, it has "negligible CSF penetration, however treatment has been successful for cryptococcal and coccidioidal meningitis".
1847:"Repurposing itraconazole as a treatment for advanced prostate cancer: a noncomparative randomized phase II trial in men with metastatic castration-resistant prostate cancer"
1324:. The two chiral centers in the dioxolane ring are fixed in relation to one another, and the triazolomethylene and aryloxymethylene dioxolane-ring substituents are always
1845:
Antonarakis ES, Heath EI, Smith DC, Rathkopf D, Blackford AL, Danila DC, King S, Frost A, Ajiboye AS, Zhao M, Mendonca J, Kachhap SK, Rudek MA, Carducci MA (2013).
4918:
2008:
178:
1756:
1992:, Lee KH, Park ES, Chi SC, "Composition comprising Itraconazole for oral administration", published 13 October 2005, assigned to FDL Inc.
2189:
Kim J, Tang JY, Gong R, Kim J, Lee JJ, Clemons KV, Chong CR, Chang KS, Fereshteh M, Gardner D, Reya T, Liu JO, Epstein EH, Stevens DA, Beachy PA (2010).
2240:"Itraconazole and arsenic trioxide inhibit hedgehog pathway activation and tumor growth associated with acquired resistance to smoothened antagonists"
4604:
4898:
2631:
Kunze KL, Nelson WL, Kharasch ED, Thummel KE, Isoherranen N (April 2006). "Stereochemical aspects of itraconazole metabolism in vitro and in vivo".
4888:
4584:
2053:
4629:
4594:
4569:
2079:
4674:
4619:
4564:
4559:
2238:
Kim J, Aftab BT, Tang JY, Kim D, Lee AH, Rezaee M, Kim J, Chen B, King EM, Borodovsky A, Riggins GJ, Epstein EH, Beachy PA, Rudin CM (2013).
61:
4305:
4300:
4295:
4285:
715:
2036:
1512:
4153:
2699:
4068:
1462:
Isoherranen N, Kunze KL, Allen KE, Nelson WL, Thummel KE (October 2004). "Role of itraconazole metabolites in CYP3A4 inhibition".
4123:
3685:
3629:
2913:
2173:
1739:
868:
2788:
2758:
2728:
2290:
Chong CR, Xu J, Lu J, Bhat S, Sullivan DJ, Liu JO (2007). "Inhibition of
Angiogenesis by the Antifungal Drug Itraconazole".
4010:
1896:"Phase 2 study of pemetrexed and itraconazole as second-line therapy for metastatic nonsquamous non-small-cell lung cancer"
1943:
Ip KH, McKerrow K (2021). "Itraconazole in the treatment of basal cell carcinoma: A case-based review of the literature".
760:
112:
4923:
1782:
2561:
Barone JA, Koh JG, Bierman RH, Colaizzi JL, Swanson KA, Gaffar MC, Moskovitz BL, Mechlinski W, Van de Velde V (1993).
1631:
735:
2106:
3646:
2019:
2610:
1894:
Rudin CM, Brahmer JR, Juergens RA, Hann CL, Ettinger DS, Sebree R, Smith R, Aftab BT, Huang P, Liu JO (May 2013).
1260:
1234:
1059:
used to make the syrup preparation can cause diarrhea. Side effects that may indicate a greater problem include:
874:
Recent research works suggest itraconazole (ITZ) could also be used in the treatment of cancer by inhibiting the
368:
208:
93:
1760:
4893:
3396:
4913:
4863:
2885:
2847:
2818:
1330:
to each other. The clinical formulation is a 1:1:1:1 mixture of four stereoisomers (two enantiomeric pairs).
1006:, as absorption is also improved by acid. Absorption of itraconazole is impaired when taken with an antacid,
2963:
4928:
3910:
2794:
2764:
2734:
2705:
2485:
Patterson TF, Peters J, Levine SM, Anzueto A, Bryan CL, Sako EY, Miller OL, Calhoon JH, Rinaldi MG (1996).
2087:
1354:
829:
589:
470:
867:
Itraconazole was patented in 1978 and approved for medical use in the United States in 1992. It is on the
4868:
4118:
3960:
3955:
3900:
1408:"FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)"
1248:
antifungal agents in that it is the only inhibitor in this class that has been shown to inhibit both the
550:
2563:"Food interaction and steady-state pharmacokinetics of itraconazole capsules in healthy male volunteers"
539:
4878:
4833:
3815:
2057:
1249:
963:
2091:
3678:
3464:
3434:
2906:
2852:
2823:
1647:
1407:
1358:
2191:"Itraconazole, a Commonly Used Antifungal that Inhibits Hedgehog Pathway Activity and Cancer Growth"
4260:
4178:
4073:
3810:
3329:
1304:, decreased sensitivity to co ingestion of food, and hence decreased variability of serum levels.
1046:
1039:
566:
3634:
3564:
1325:
149:
43:
4735:
3601:
3248:
933:
802:
291:
164:
1621:
1300:
A product (Lozanoc) licensed through the
European union decentralised procedure has increased
820:
include nausea, diarrhea, abdominal pain, rash, and headache. Severe side effects may include
4903:
4873:
4403:
4360:
1015:
980:
952:
778:
680:
519:
4908:
3712:
3671:
2899:
2390:
1774:
984:
959:
479:
459:
394:
334:
160:
1034:) and the range of adverse effects it produces is similar to the other azole antifungals:
8:
4883:
4476:
4443:
3391:
3207:
1147:
925:
810:
806:
385:
171:
156:
2394:
2054:"The Safety of Sporanox Capsules and Lamisil Tablets for the Treatment of Onychomycosis"
593:
570:
4103:
3930:
3820:
3717:
3554:
3524:
3519:
2656:
2462:
2437:
2413:
2378:
2354:
2329:
2264:
2239:
2215:
2190:
2141:
2114:
1968:
1920:
1895:
1871:
1846:
1822:
1797:
1703:
1676:
1565:
1487:
1077:
833:
794:
123:
2587:
2562:
2533:
2511:
2486:
4133:
3415:
2648:
2592:
2543:
2516:
2467:
2418:
2359:
2307:
2269:
2220:
2169:
2146:
1972:
1960:
1925:
1876:
1827:
1735:
1728:
1708:
1627:
1569:
1557:
1479:
1436:
1321:
1191:
782:
247:
235:
85:
1598:
1381:
1026:
Itraconazole is a relatively well-tolerated drug (although not as well tolerated as
71:
4695:
4659:
4654:
4225:
4098:
4093:
4060:
3890:
3747:
3722:
3559:
3509:
2640:
2582:
2574:
2534:
Fraga
Fuentes MD, GarcĂa DĂaz B, de Juana Velasco P, Bermejo Vicedo MT (1997). "".
2506:
2498:
2457:
2449:
2408:
2398:
2349:
2341:
2330:"Itraconazole Inhibits Angiogenesis and Tumor Growth in Non-Small Cell Lung Cancer"
2299:
2259:
2251:
2210:
2202:
2136:
2126:
2115:"Cardiac arrest provoked by itraconazole and amiodarone interaction: a case report"
1952:
1915:
1907:
1866:
1862:
1858:
1817:
1809:
1798:"Itraconazole inhibits angiogenesis and tumor growth in non-small cell lung cancer"
1698:
1688:
1677:"Inhibition of the hedgehog pathway for the treatment of cancer using Itraconazole"
1655:
1549:
1491:
1471:
1293:
1241:
CC-3, caution should be used when considering interactions with other medications.
1206:
1082:
875:
723:
O=C1N(/N=C\N1c2ccc(cc2)N7CCN(c6ccc(OC3O(OC3)(c4ccc(Cl)cc4Cl)Cn5ncnc5)cc6)CC7)C(C)CC
702:
606:
273:
191:
2660:
2345:
1989:
1813:
1553:
419:
4847:
4669:
3141:
3131:
1911:
1301:
1257:
988:
967:
685:
301:
281:
2029:
4720:
4679:
4230:
3640:
3571:
3514:
3484:
3469:
3237:
3126:
2084:
Safety
Labeling Changes Approved By FDA Center for Drug Evaluation and Research
1289:
1285:
948:
924:. Itraconazole is over 99% protein-bound and has virtually no penetration into
917:
913:
821:
798:
2674:
2379:"Cholesterol trafficking is required for mTOR activation in endothelial cells"
2255:
2206:
1312:
4857:
4486:
4255:
4163:
4005:
3795:
3474:
3370:
3344:
3151:
3103:
3069:
3024:
2994:
1437:"Sporanox 10 mg/mL Oral Solution - Summary of Product Characteristics (SmPC)"
1007:
940:
921:
909:
857:
845:
825:
790:
786:
692:
582:
260:
22:
2891:
2403:
2131:
4644:
4624:
4579:
4544:
4413:
4040:
4015:
3965:
3905:
3895:
3885:
3835:
3825:
3775:
3596:
3581:
3494:
3424:
3340:
3174:
3169:
3161:
3156:
3136:
3054:
3044:
3039:
3029:
3014:
3004:
2989:
2930:
2926:
2652:
2644:
2471:
2422:
2363:
2311:
2273:
2224:
2150:
1964:
1929:
1880:
1831:
1712:
1652:
World Health
Organization model list of essential medicines: 21st list 2019
1561:
1483:
1475:
1333:
1277:
1253:
1056:
1031:
999:
995:
899:
895:
186:
2596:
2547:
2520:
2502:
4770:
4755:
4745:
4710:
4664:
4649:
4634:
4574:
4549:
4517:
4507:
4502:
4466:
4461:
4433:
4408:
4320:
4310:
4240:
4235:
4168:
4050:
4045:
4030:
3950:
3915:
3870:
3855:
3845:
3840:
3830:
3805:
3780:
3770:
3615:
3576:
3534:
3504:
3405:
3349:
3285:
3273:
3121:
3113:
3108:
3079:
3074:
3064:
3059:
3034:
3009:
2578:
1350:
1196:
1171:
1142:
1027:
944:
904:
891:
853:
837:
817:
167:
79:
1693:
1660:
1346:
Itraconazole was approved for medical use in the United States in 1992.
958:
Itraconazole has been explored as an anticancer agent for patients with
439:
4805:
4795:
4785:
4725:
4609:
4599:
4512:
4497:
4489:
4451:
4428:
4423:
4388:
4378:
4350:
4325:
4290:
4265:
4220:
4205:
4200:
4143:
4083:
4078:
4035:
4000:
3995:
3990:
3985:
3945:
3940:
3935:
3920:
3875:
3865:
3860:
3790:
3785:
3765:
3732:
3694:
3605:
3586:
3549:
3544:
3529:
3499:
3479:
3444:
3364:
3359:
3354:
3315:
3294:
3259:
3212:
3049:
2999:
2984:
2948:
2922:
2112:
1230:
1201:
1167:
1162:
1137:
1126:
929:
861:
645:
450:
319:
2453:
2303:
1956:
376:(±)-1--4-methoxy]phenyl]-1-piperazinyl]phenyl]-Δ-1,2,4-triazolin-5-one
4800:
4780:
4760:
4750:
4740:
4715:
4705:
4614:
4554:
4539:
4527:
4471:
4456:
4418:
4398:
4393:
4373:
4368:
4340:
4330:
4245:
4210:
4195:
4158:
4148:
4128:
4088:
4020:
3925:
3850:
3727:
3591:
3539:
3268:
3227:
3193:
3019:
2975:
1281:
1180:
1176:
1157:
1132:
879:
841:
405:
347:
65:
2113:
Tsimogianni AM, Andrianakis I, Betrosian A, Douzinas E (July 2011).
4820:
4815:
4810:
4639:
4589:
4383:
4315:
4280:
4215:
4113:
4108:
4025:
3980:
3975:
3970:
3800:
3489:
3232:
3184:
3094:
2166:
2072:
1152:
1088:
1069:
849:
499:
430:
107:
1297:
take itraconazole after a fatty meal rather than prior to eating.
668:
4790:
4275:
4270:
4250:
4190:
4138:
3760:
3755:
3610:
3222:
2168:(Eleventh ed.). New York: McGraw Hill Medical. p. 397.
1225:
The mechanism of action of itraconazole is the same as the other
1097:
1506:"Sporanox (itraconazole) Capsules. Full Prescribing Information"
4765:
4700:
4345:
2880:
2487:"Systemic availability of itraconazole in lung transplantation"
1256:. These distinct activities are unrelated to inhibition of the
1238:
1064:
530:
352:
311:
30:
3663:
4775:
4730:
4335:
3737:
2959:
1844:
1725:
1264:
1245:
1226:
1185:
1103:
659:
510:
307:
2484:
2436:
Shi W, Nacev BA, Aftab BT, Head S, Rudin CM, Liu JO (2011).
2163:
1726:
Gilbert DN, Moellering, RC, Eliopoulos GM, Sande MA (2006).
555:
1461:
1121:
The following drugs should not be taken with itraconazole:
1003:
908:, which fluconazole is not. It is also licensed for use in
490:
2630:
2620:. UK Medicines and Health Care Products Regulatory Agency.
2327:
1795:
1229:
antifungals: it inhibits the fungal-mediated synthesis of
1646:
1415:
2560:
2056:. FDA Public Health Advisory. 9 May 2001. Archived from
1893:
1664:. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
1539:
1988:
939:
It is also prescribed for systemic infections, such as
869:
1244:
Itraconazole is pharmacologically distinct from other
4831:
1376:
1374:
890:
Itraconazole has a broader spectrum of activity than
707:
7.8 ± 0.4 × 10 mol/L (pH 1.6) mg/mL (20 °C)
2328:
Aftab BT, Dobromilskaya I, Liu JO, Rudin CM (2011).
1796:
Aftab BT, Dobromilskaya I, Liu JO, Rudin CM (2011).
1042:
levels are found in 4% of people taking itraconazole
1601:. The American Society of Health-System Pharmacists
1400:
2603:
1727:
1371:
2435:
2164:Trevor AJ, Katzung BG, Kruidering-Hall M (2015).
4855:
2618:Public Assessment Report Decentralised Procedure
418:
2383:Proceedings of the National Academy of Sciences
2237:
1619:
393:
2188:
2001:
1674:
1511:. Janssen Pharmaceuticals, Inc. Archived from
4919:World Health Organization essential medicines
3679:
2921:
2907:
2289:
2611:"Lozanoc 50 Mg Hard Capsules (Itraconazole)"
2376:
1754:
998:contained in the oral solution can cause an
928:. Therefore, it should not be used to treat
111:
2554:
2527:
2478:
1535:
1533:
3686:
3672:
2914:
2900:
2231:
1942:
1730:The Sanford Guide to antimicrobial therapy
1668:
1593:
1591:
1589:
1587:
1585:
1583:
1581:
1579:
1498:
994:The oral solution is better absorbed. The
592:
569:
458:
29:
16:Medication used to treat fungal infections
2586:
2510:
2461:
2412:
2402:
2353:
2263:
2214:
2140:
2130:
1984:
1982:
1919:
1870:
1821:
1702:
1692:
1659:
478:
4889:Drugs developed by Johnson & Johnson
2323:
2321:
2285:
2283:
1530:
1332:
1311:
955:drugs are inappropriate or ineffective.
324:Hydroxy-itraconazole, keto-itraconazole,
1734:. Antimicrobial Therapy, Incorporated.
1719:
1576:
902:). In particular, it is active against
565:
438:
84:
4856:
2789:"Itraconazole Orphan Drug Designation"
2759:"Itraconazole Orphan Drug Designation"
2729:"Itraconazole Orphan Drug Designation"
2048:
2046:
1979:
1640:
1626:. John Wiley & Sons. p. 503.
1613:
1542:International Journal of Pharmaceutics
1316:Chiral centers are marked by asterisks
583:
241:
4899:Lanosterol 14α-demethylase inhibitors
3667:
2895:
2377:Xu J, Dang Y, Ren YR, Liu JO (2010).
2318:
2280:
1675:Li K, Fang D, Xiong Z, Luo R (2019).
1654:. Geneva: World Health Organization.
538:
518:
286:~55%, maximal if taken with full meal
254:
102:
70:
4532:(piperazine attached via side chain)
1755:Pham P, Bartlett JG (24 July 2007).
1320:The itraconazole molecule has three
1237:. Because of its ability to inhibit
1045:"small but real risk" of developing
190:
2043:
1945:Australasian Journal of Dermatology
1382:"Itraconazole Use During Pregnancy"
1271:
1220:
498:
409:
13:
2700:"Itraconazole: FDA-Approved Drugs"
2080:"Sporanox (Itraconazole) Capsules"
2009:"Sporanox (Itraconazole Capsules)"
1783:U.S. National Institutes of Health
1337:Four diastereomers of itraconazole
973:
14:
4940:
2873:
2037:"SUBA Bioavailability Technology"
1775:"Search results for Itraconazole"
217:
134:
48:Sporanox, Sporaz, Orungal, others
4841:
2879:
629:
623:
617:
3693:
3397:thymidylate synthase inhibitors
2840:
2811:
2781:
2751:
2721:
2692:
2667:
2633:Drug Metabolism and Disposition
2624:
2429:
2370:
2182:
2157:
2119:Journal of Medical Case Reports
1936:
1887:
1838:
1789:
1767:
1759:. Johns Hopkins. Archived from
1748:
1620:Fischer J, Ganellin CR (2006).
1464:Drug Metabolism and Disposition
1261:lanosterol 14 alpha-demethylase
1215:
1116:
1021:
885:
748:Key:VHVPQPYKVGDNFY-ZPGVKDDISA-N
2442:Journal of Medicinal Chemistry
1863:10.1634/theoncologist.2012-314
1455:
1429:
1051:liver failure, sometimes fatal
840:. It is unclear if use during
635:
611:
230:
1:
2346:10.1158/0008-5472.CAN-11-0691
1814:10.1158/0008-5472.CAN-11-0691
1623:Analogue-based Drug Discovery
1554:10.1016/j.ijpharm.2021.120441
1364:
4183:(benzhydrylalkylpiperazines)
2795:Food and Drug Administration
2765:Food and Drug Administration
2735:Food and Drug Administration
2706:Food and Drug Administration
2567:Antimicrob. Agents Chemother
2491:Antimicrob. Agents Chemother
2088:Food and Drug Administration
1912:10.1097/JTO.0b013e31828c3950
1900:Journal of Thoracic Oncology
1355:Food and Drug Administration
1307:
7:
2675:"Itraconazole on Drugs.com"
2018:. June 2006. Archived from
10:
4945:
1341:
1250:hedgehog signaling pathway
1235:lanosterol 14α-demethylase
964:non-small cell lung cancer
852:family of medications. It
781:used to treat a number of
601:Chemical and physical data
4924:Phenylethanolamine ethers
4688:
4526:
4485:
4442:
4359:
4177:
4059:
3746:
3701:
3624:
3465:bromochlorosalicylanilide
3457:
3435:Aminoacyl tRNA synthetase
3433:
3414:
3390:
3383:
3328:
3307:
3284:
3258:
3247:
3206:
3183:
3093:
2974:
2958:
2947:
2938:
2853:European Medicines Agency
2824:European Medicines Agency
2256:10.1016/j.ccr.2012.11.017
2207:10.1016/j.ccr.2010.02.027
1648:World Health Organization
1359:European Medicines Agency
756:
731:
711:
701:
697:165 °C (329 °F)
691:
679:
657:
644:
605:
600:
581:
549:
529:
509:
489:
469:
449:
429:
404:
384:
364:
359:
346:
333:
318:
300:
290:
280:
272:
207:
202:
177:
148:
122:
92:
78:
60:
52:
42:
37:
28:
4261:Diphenylmethylpiperazine
4179:Diphenylalkylpiperazines
4074:3-Methylbenzylpiperazine
1047:congestive heart failure
1040:alanine aminotransferase
830:Stevens–Johnson syndrome
773:, sometimes abbreviated
2404:10.1073/pnas.0910872107
2132:10.1186/1752-1947-5-333
1681:OncoTargets and Therapy
4361:Pyrimidinylpiperazines
3249:Squalene monooxygenase
3086:Systemic: ketoconazole
2645:10.1124/dmd.105.008508
1476:10.1124/dmd.104.000315
1338:
1317:
934:central nervous system
848:is safe. It is in the
803:paracoccidioidomycosis
329:-desalkyl-itraconazole
4894:Janssen Pharmaceutica
4404:Pyrimidinylpiperazine
3705:(no additional rings)
3277:Systemic: terbinafine
2503:10.1128/AAC.40.9.2217
2090:(FDA). Archived from
2039:. Mayne Pharma Group.
1349:It was designated an
1336:
1315:
1016:proton pump inhibitor
985:Johnson & Johnson
981:Janssen Pharmaceutica
894:(but not as broad as
779:antifungal medication
4914:Triazole antifungals
4864:1,2,4-Triazol-3-ones
4736:Cyclohexylpiperazine
4689:Others/Uncategorized
4444:Pyridinylpiperazines
3713:Aminoethylpiperazine
3565:Whitfield's ointment
3392:Pyrimidine analogues
3208:Polyene antimycotics
2888:at Wikimedia Commons
2579:10.1128/aac.37.4.778
2292:ACS Chemical Biology
1763:on 28 November 2007.
1233:, via inhibition of
960:basal cell carcinoma
878:in a similar way to
4929:Sec-Butyl compounds
4487:Benzo(iso)thiazolyl
4477:Pyridinylpiperazine
2395:2010PNAS..107.4764X
1694:10.2147/OTT.S223119
1276:Itraconazole, like
1239:cytochrome P450 3A4
926:cerebrospinal fluid
860:or affecting their
854:stops fungal growth
703:Solubility in water
355:(35%), faeces (54%)
250:(Prescription only)
226:(Prescription only)
25:
4869:Belgian inventions
3931:Naphthylpiperazine
3821:Diphenylpiperazine
3718:Diethylcarbamazine
3702:Simple piperazines
3651:Never to phase III
3555:tribromometacresol
3525:sodium thiosulfate
3520:selenium disulfide
3416:Mitotic inhibitors
2094:on 26 October 2016
1779:ClinicalTrials.gov
1339:
1318:
1188:medicines such as
983:, a subsidiary of
834:allergic reactions
805:. It may be given
795:coccidioidomycosis
21:
4879:CYP3A4 inhibitors
4829:
4828:
4533:
4184:
4134:Methoxypiperamide
4061:Benzylpiperazines
3748:Phenylpiperazines
3706:
3661:
3660:
3453:
3452:
3379:
3378:
3330:β-glucan synthase
3324:
3323:
3303:
3302:
3202:
3201:
2884:Media related to
2799:. 30 October 2008
2454:10.1021/jm200944b
2304:10.1021/cb600362d
2175:978-0-07-182635-8
1957:10.1111/ajd.13655
1808:(21): 6764–6772.
1741:978-1-930808-30-0
1470:(10): 1121–1131.
1443:. 1 February 2018
1294:drug interactions
1192:dihydroergotamine
856:by affecting the
783:fungal infections
768:
767:
670:Interactive image
551:CompTox Dashboard
258:
245:
233:
221:
138:
105:
4936:
4846:
4845:
4844:
4837:
4696:6-Nitroquipazine
4660:Thiethylperazine
4655:Prochlorperazine
4531:
4226:Chlorbenzoxamine
4182:
4099:Chlorbenzoxamine
3891:Levodropropizine
3704:
3688:
3681:
3674:
3665:
3664:
3560:undecylenic acid
3510:potassium iodide
3388:
3387:
3256:
3255:
2972:
2971:
2956:
2955:
2945:
2944:
2916:
2909:
2902:
2893:
2892:
2883:
2867:
2866:
2864:
2862:
2844:
2838:
2837:
2835:
2833:
2828:. 23 August 2017
2815:
2809:
2808:
2806:
2804:
2785:
2779:
2778:
2776:
2774:
2769:. 16 August 2016
2755:
2749:
2748:
2746:
2744:
2725:
2719:
2718:
2716:
2714:
2696:
2690:
2689:
2687:
2685:
2671:
2665:
2664:
2628:
2622:
2621:
2615:
2607:
2601:
2600:
2590:
2558:
2552:
2551:
2531:
2525:
2524:
2514:
2482:
2476:
2475:
2465:
2433:
2427:
2426:
2416:
2406:
2374:
2368:
2367:
2357:
2325:
2316:
2315:
2287:
2278:
2277:
2267:
2235:
2229:
2228:
2218:
2186:
2180:
2179:
2161:
2155:
2154:
2144:
2134:
2110:
2104:
2103:
2101:
2099:
2076:
2070:
2069:
2067:
2065:
2050:
2041:
2040:
2033:
2027:
2026:
2024:
2013:
2005:
1999:
1998:
1997:
1993:
1986:
1977:
1976:
1940:
1934:
1933:
1923:
1891:
1885:
1884:
1874:
1842:
1836:
1835:
1825:
1793:
1787:
1786:
1771:
1765:
1764:
1752:
1746:
1745:
1733:
1723:
1717:
1716:
1706:
1696:
1672:
1666:
1665:
1663:
1644:
1638:
1637:
1617:
1611:
1610:
1608:
1606:
1595:
1574:
1573:
1537:
1528:
1527:
1525:
1523:
1517:
1510:
1502:
1496:
1495:
1459:
1453:
1452:
1450:
1448:
1433:
1427:
1426:
1424:
1422:
1412:nctr-crs.fda.gov
1404:
1398:
1397:
1395:
1393:
1378:
1272:Pharmacokinetics
1221:Pharmacodynamics
1207:methylergonovine
1083:loss of appetite
1000:osmotic diarrhea
876:hedgehog pathway
785:. This includes
764:
763:
672:
652:
637:
631:
625:
619:
613:
596:
585:
574:
573:
559:
557:
542:
522:
502:
482:
462:
442:
422:
412:
411:
397:
338:
263:
256:
253:
243:
240:
232:
229:
219:
216:
194:
136:
133:
115:
104:
101:
88:
74:
33:
26:
24:
20:
4944:
4943:
4939:
4938:
4937:
4935:
4934:
4933:
4854:
4853:
4852:
4842:
4840:
4832:
4830:
4825:
4684:
4670:Trifluoperazine
4605:Octomethothepin
4530:
4522:
4481:
4438:
4355:
4181:
4173:
4055:
3742:
3703:
3697:
3692:
3662:
3657:
3656:
3641:Clinical trials
3620:
3449:
3429:
3410:
3395:
3375:
3332:
3320:
3299:
3280:
3276:
3251:
3243:
3235:
3210:
3198:
3179:
3132:fosravuconazole
3089:
2965:
2964:lanosterol 14α-
2951:
2940:
2934:
2920:
2876:
2871:
2870:
2860:
2858:
2846:
2845:
2841:
2831:
2829:
2817:
2816:
2812:
2802:
2800:
2787:
2786:
2782:
2772:
2770:
2757:
2756:
2752:
2742:
2740:
2727:
2726:
2722:
2712:
2710:
2698:
2697:
2693:
2683:
2681:
2673:
2672:
2668:
2629:
2625:
2613:
2609:
2608:
2604:
2559:
2555:
2532:
2528:
2483:
2479:
2448:(20): 7363–74.
2434:
2430:
2375:
2371:
2340:(21): 6764–72.
2334:Cancer Research
2326:
2319:
2288:
2281:
2236:
2232:
2187:
2183:
2176:
2162:
2158:
2111:
2107:
2097:
2095:
2078:
2077:
2073:
2063:
2061:
2052:
2051:
2044:
2035:
2034:
2030:
2025:on 5 July 2008.
2022:
2011:
2007:
2006:
2002:
1995:
1987:
1980:
1941:
1937:
1892:
1888:
1843:
1839:
1802:Cancer Research
1794:
1790:
1773:
1772:
1768:
1753:
1749:
1742:
1724:
1720:
1673:
1669:
1645:
1641:
1634:
1618:
1614:
1604:
1602:
1597:
1596:
1577:
1538:
1531:
1521:
1519:
1515:
1508:
1504:
1503:
1499:
1460:
1456:
1446:
1444:
1435:
1434:
1430:
1420:
1418:
1406:
1405:
1401:
1391:
1389:
1388:. 20 March 2019
1380:
1379:
1372:
1367:
1353:by both the US
1344:
1310:
1302:bioavailability
1274:
1258:cytochrome P450
1223:
1218:
1213:
1119:
1114:
1024:
1011:
989:Beerse, Belgium
976:
974:Available forms
968:prostate cancer
888:
759:
757:
752:
749:
744:
739:
738:
727:
724:
719:
718:
686:Racemic mixture
675:
650:
640:
634:
628:
622:
616:
577:
553:
545:
525:
505:
485:
465:
445:
425:
408:
400:
380:
377:
372:
371:
336:
325:
292:Protein binding
282:Bioavailability
274:Pharmacokinetic
268:
261:
198:
151:
144:
125:
118:
17:
12:
11:
5:
4942:
4932:
4931:
4926:
4921:
4916:
4911:
4906:
4901:
4896:
4891:
4886:
4881:
4876:
4871:
4866:
4851:
4850:
4827:
4826:
4824:
4823:
4818:
4813:
4808:
4803:
4798:
4793:
4788:
4783:
4778:
4773:
4768:
4763:
4758:
4753:
4748:
4743:
4738:
4733:
4728:
4723:
4721:Cinepazic acid
4718:
4713:
4708:
4703:
4698:
4692:
4690:
4686:
4685:
4683:
4682:
4680:Zuclopenthixol
4677:
4672:
4667:
4662:
4657:
4652:
4647:
4642:
4637:
4632:
4627:
4622:
4617:
4612:
4607:
4602:
4597:
4592:
4587:
4585:Isofloxythepin
4582:
4577:
4572:
4567:
4562:
4557:
4552:
4547:
4542:
4536:
4534:
4524:
4523:
4521:
4520:
4515:
4510:
4505:
4500:
4494:
4492:
4483:
4482:
4480:
4479:
4474:
4469:
4464:
4459:
4454:
4448:
4446:
4440:
4439:
4437:
4436:
4431:
4426:
4421:
4416:
4411:
4406:
4401:
4396:
4391:
4386:
4381:
4376:
4371:
4365:
4363:
4357:
4356:
4354:
4353:
4348:
4343:
4338:
4333:
4328:
4323:
4318:
4313:
4308:
4303:
4298:
4293:
4288:
4283:
4278:
4273:
4268:
4263:
4258:
4253:
4248:
4243:
4238:
4233:
4231:Chlorcyclizine
4228:
4223:
4218:
4213:
4208:
4203:
4198:
4193:
4187:
4185:
4175:
4174:
4172:
4171:
4166:
4161:
4156:
4151:
4146:
4141:
4136:
4131:
4126:
4121:
4116:
4111:
4106:
4101:
4096:
4091:
4086:
4081:
4076:
4071:
4065:
4063:
4057:
4056:
4054:
4053:
4048:
4043:
4038:
4033:
4028:
4023:
4018:
4013:
4008:
4003:
3998:
3993:
3988:
3983:
3978:
3973:
3968:
3963:
3958:
3953:
3948:
3943:
3938:
3933:
3928:
3923:
3918:
3913:
3908:
3903:
3898:
3893:
3888:
3883:
3878:
3873:
3868:
3863:
3858:
3853:
3848:
3843:
3838:
3833:
3828:
3823:
3818:
3813:
3808:
3803:
3798:
3793:
3788:
3783:
3778:
3773:
3768:
3763:
3758:
3752:
3750:
3744:
3743:
3741:
3740:
3735:
3730:
3725:
3720:
3715:
3709:
3707:
3699:
3698:
3691:
3690:
3683:
3676:
3668:
3659:
3658:
3655:
3654:
3653:
3652:
3649:
3638:
3632:
3626:
3625:
3622:
3621:
3619:
3618:
3613:
3608:
3599:
3594:
3589:
3584:
3579:
3574:
3572:citronella oil
3568:
3567:
3562:
3557:
3552:
3547:
3542:
3537:
3532:
3527:
3522:
3517:
3515:salicylic acid
3512:
3507:
3502:
3497:
3492:
3487:
3485:crystal violet
3482:
3477:
3472:
3470:chlorophetanol
3467:
3461:
3459:
3455:
3454:
3451:
3450:
3448:
3447:
3440:
3438:
3431:
3430:
3428:
3427:
3420:
3418:
3412:
3411:
3409:
3408:
3401:
3399:
3385:
3381:
3380:
3377:
3376:
3374:
3373:
3368:
3362:
3357:
3352:
3347:
3336:
3334:
3326:
3325:
3322:
3321:
3319:
3318:
3311:
3309:
3305:
3304:
3301:
3300:
3298:
3297:
3290:
3288:
3282:
3281:
3279:
3278:
3271:
3264:
3262:
3253:
3245:
3244:
3242:
3241:
3238:amphotericin B
3230:
3225:
3218:
3216:
3204:
3203:
3200:
3199:
3197:
3196:
3189:
3187:
3181:
3180:
3178:
3177:
3172:
3165:
3164:
3159:
3154:
3149:
3144:
3139:
3134:
3129:
3127:fosfluconazole
3124:
3117:
3116:
3111:
3106:
3099:
3097:
3091:
3090:
3088:
3087:
3083:
3082:
3077:
3072:
3067:
3062:
3057:
3052:
3047:
3042:
3037:
3032:
3027:
3022:
3017:
3012:
3007:
3002:
2997:
2992:
2987:
2980:
2978:
2969:
2953:
2942:
2936:
2935:
2919:
2918:
2911:
2904:
2896:
2890:
2889:
2875:
2874:External links
2872:
2869:
2868:
2848:"EU/3/18/2024"
2839:
2819:"EU/3/17/1901"
2810:
2780:
2750:
2720:
2691:
2666:
2639:(4): 583–590.
2623:
2602:
2553:
2538:(in Spanish).
2526:
2497:(9): 2217–20.
2477:
2428:
2389:(10): 4764–9.
2369:
2317:
2279:
2230:
2181:
2174:
2156:
2105:
2071:
2060:on 28 May 2009
2042:
2028:
2000:
1990:US 20050226924
1978:
1951:(3): 394–397.
1935:
1906:(5): 619–623.
1886:
1857:(2): 163–173.
1851:The Oncologist
1837:
1788:
1766:
1757:"Itraconazole"
1747:
1740:
1718:
1667:
1639:
1632:
1612:
1599:"Itraconazole"
1575:
1529:
1518:on 17 May 2018
1497:
1454:
1428:
1399:
1369:
1368:
1366:
1363:
1357:(FDA) and the
1343:
1340:
1322:chiral carbons
1309:
1306:
1290:P-glycoprotein
1288:, can inhibit
1286:clarithromycin
1273:
1270:
1222:
1219:
1217:
1214:
1212:
1211:
1210:
1209:
1204:
1199:
1194:
1183:
1174:
1165:
1160:
1155:
1150:
1145:
1140:
1135:
1130:
1123:
1118:
1115:
1113:
1112:
1109:
1106:
1100:
1095:
1092:
1085:
1080:
1075:
1074:abdominal pain
1072:
1067:
1061:
1053:
1052:
1049:
1043:
1023:
1020:
1009:
975:
972:
951:, where other
949:cryptococcosis
918:histoplasmosis
914:sporotrichosis
887:
884:
822:liver problems
799:histoplasmosis
766:
765:
754:
753:
751:
750:
747:
745:
742:
734:
733:
732:
729:
728:
726:
725:
722:
714:
713:
712:
709:
708:
705:
699:
698:
695:
689:
688:
683:
677:
676:
674:
673:
665:
663:
655:
654:
648:
642:
641:
638:
632:
626:
620:
614:
609:
603:
602:
598:
597:
587:
579:
578:
576:
575:
562:
560:
547:
546:
544:
543:
535:
533:
527:
526:
524:
523:
515:
513:
507:
506:
504:
503:
495:
493:
487:
486:
484:
483:
475:
473:
467:
466:
464:
463:
455:
453:
447:
446:
444:
443:
435:
433:
427:
426:
424:
423:
415:
413:
402:
401:
399:
398:
390:
388:
382:
381:
379:
378:
375:
367:
366:
365:
362:
361:
357:
356:
350:
344:
343:
340:
331:
330:
322:
316:
315:
304:
298:
297:
294:
288:
287:
284:
278:
277:
270:
269:
267:
266:
251:
238:
227:
213:
211:
205:
204:
200:
199:
197:
196:
183:
181:
175:
174:
154:
152:administration
146:
145:
143:
142:
140:
130:
128:
120:
119:
117:
116:
98:
96:
90:
89:
82:
76:
75:
68:
58:
57:
54:
50:
49:
46:
40:
39:
35:
34:
15:
9:
6:
4:
3:
2:
4941:
4930:
4927:
4925:
4922:
4920:
4917:
4915:
4912:
4910:
4907:
4905:
4902:
4900:
4897:
4895:
4892:
4890:
4887:
4885:
4882:
4880:
4877:
4875:
4872:
4870:
4867:
4865:
4862:
4861:
4859:
4849:
4839:
4838:
4835:
4822:
4819:
4817:
4814:
4812:
4809:
4807:
4804:
4802:
4799:
4797:
4794:
4792:
4789:
4787:
4784:
4782:
4779:
4777:
4774:
4772:
4769:
4767:
4764:
4762:
4759:
4757:
4754:
4752:
4749:
4747:
4744:
4742:
4739:
4737:
4734:
4732:
4729:
4727:
4724:
4722:
4719:
4717:
4714:
4712:
4709:
4707:
4704:
4702:
4699:
4697:
4694:
4693:
4691:
4687:
4681:
4678:
4676:
4673:
4671:
4668:
4666:
4663:
4661:
4658:
4656:
4653:
4651:
4648:
4646:
4643:
4641:
4638:
4636:
4633:
4631:
4630:Peradithiepin
4628:
4626:
4623:
4621:
4618:
4616:
4613:
4611:
4608:
4606:
4603:
4601:
4598:
4596:
4595:Meperathiepin
4593:
4591:
4588:
4586:
4583:
4581:
4578:
4576:
4573:
4571:
4570:Docloxythepin
4568:
4566:
4563:
4561:
4558:
4556:
4553:
4551:
4548:
4546:
4543:
4541:
4538:
4537:
4535:
4529:
4525:
4519:
4516:
4514:
4511:
4509:
4506:
4504:
4501:
4499:
4496:
4495:
4493:
4491:
4488:
4484:
4478:
4475:
4473:
4470:
4468:
4465:
4463:
4460:
4458:
4455:
4453:
4450:
4449:
4447:
4445:
4441:
4435:
4432:
4430:
4427:
4425:
4422:
4420:
4417:
4415:
4412:
4410:
4407:
4405:
4402:
4400:
4397:
4395:
4392:
4390:
4387:
4385:
4382:
4380:
4377:
4375:
4372:
4370:
4367:
4366:
4364:
4362:
4358:
4352:
4349:
4347:
4344:
4342:
4339:
4337:
4334:
4332:
4329:
4327:
4324:
4322:
4319:
4317:
4314:
4312:
4309:
4307:
4304:
4302:
4299:
4297:
4294:
4292:
4289:
4287:
4284:
4282:
4279:
4277:
4274:
4272:
4269:
4267:
4264:
4262:
4259:
4257:
4256:Diphenpipenol
4254:
4252:
4249:
4247:
4244:
4242:
4239:
4237:
4234:
4232:
4229:
4227:
4224:
4222:
4219:
4217:
4214:
4212:
4209:
4207:
4204:
4202:
4199:
4197:
4194:
4192:
4189:
4188:
4186:
4180:
4176:
4170:
4167:
4165:
4164:Trimetazidine
4162:
4160:
4157:
4155:
4152:
4150:
4147:
4145:
4142:
4140:
4137:
4135:
4132:
4130:
4127:
4125:
4122:
4120:
4117:
4115:
4112:
4110:
4107:
4105:
4102:
4100:
4097:
4095:
4092:
4090:
4087:
4085:
4082:
4080:
4077:
4075:
4072:
4070:
4067:
4066:
4064:
4062:
4058:
4052:
4049:
4047:
4044:
4042:
4039:
4037:
4034:
4032:
4029:
4027:
4024:
4022:
4019:
4017:
4014:
4012:
4009:
4007:
4006:Sonepiprazole
4004:
4002:
3999:
3997:
3994:
3992:
3989:
3987:
3984:
3982:
3979:
3977:
3974:
3972:
3969:
3967:
3964:
3962:
3959:
3957:
3954:
3952:
3949:
3947:
3944:
3942:
3939:
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:
3862:
3859:
3857:
3854:
3852:
3849:
3847:
3844:
3842:
3839:
3837:
3834:
3832:
3829:
3827:
3824:
3822:
3819:
3817:
3814:
3812:
3809:
3807:
3804:
3802:
3799:
3797:
3796:Ciprofloxacin
3794:
3792:
3789:
3787:
3784:
3782:
3779:
3777:
3774:
3772:
3769:
3767:
3764:
3762:
3759:
3757:
3754:
3753:
3751:
3749:
3745:
3739:
3736:
3734:
3731:
3729:
3726:
3724:
3721:
3719:
3716:
3714:
3711:
3710:
3708:
3700:
3696:
3689:
3684:
3682:
3677:
3675:
3670:
3669:
3666:
3650:
3648:
3645:
3644:
3642:
3639:
3636:
3633:
3631:
3628:
3627:
3623:
3617:
3614:
3612:
3609:
3607:
3603:
3600:
3598:
3595:
3593:
3590:
3588:
3585:
3583:
3580:
3578:
3575:
3573:
3570:
3569:
3566:
3563:
3561:
3558:
3556:
3553:
3551:
3548:
3546:
3543:
3541:
3538:
3536:
3533:
3531:
3528:
3526:
3523:
3521:
3518:
3516:
3513:
3511:
3508:
3506:
3503:
3501:
3498:
3496:
3493:
3491:
3488:
3486:
3483:
3481:
3478:
3476:
3475:chlorphenesin
3473:
3471:
3468:
3466:
3463:
3462:
3460:
3456:
3446:
3442:
3441:
3439:
3436:
3432:
3426:
3422:
3421:
3419:
3417:
3413:
3407:
3403:
3402:
3400:
3398:
3393:
3389:
3386:
3384:Intracellular
3382:
3372:
3371:ibrexafungerp
3369:
3366:
3363:
3361:
3358:
3356:
3353:
3351:
3348:
3346:
3345:anidulafungin
3342:
3341:echinocandins
3338:
3337:
3335:
3331:
3327:
3317:
3313:
3312:
3310:
3306:
3296:
3292:
3291:
3289:
3287:
3283:
3275:
3272:
3270:
3266:
3265:
3263:
3261:
3257:
3254:
3250:
3246:
3239:
3234:
3231:
3229:
3226:
3224:
3220:
3219:
3217:
3214:
3209:
3205:
3195:
3191:
3190:
3188:
3186:
3182:
3176:
3173:
3171:
3167:
3166:
3163:
3160:
3158:
3155:
3153:
3152:oteseconazole
3150:
3148:
3145:
3143:
3142:isavuconazole
3140:
3138:
3135:
3133:
3130:
3128:
3125:
3123:
3119:
3118:
3115:
3112:
3110:
3107:
3105:
3104:efinaconazole
3101:
3100:
3098:
3096:
3092:
3085:
3084:
3081:
3078:
3076:
3073:
3071:
3070:sertaconazole
3068:
3066:
3063:
3061:
3058:
3056:
3053:
3051:
3048:
3046:
3043:
3041:
3038:
3036:
3033:
3031:
3028:
3026:
3025:fenticonazole
3023:
3021:
3018:
3016:
3013:
3011:
3008:
3006:
3003:
3001:
2998:
2996:
2995:chlormidazole
2993:
2991:
2988:
2986:
2982:
2981:
2979:
2977:
2973:
2970:
2967:
2961:
2957:
2954:
2950:
2946:
2943:
2937:
2932:
2928:
2924:
2917:
2912:
2910:
2905:
2903:
2898:
2897:
2894:
2887:
2882:
2878:
2877:
2857:. 25 May 2018
2856:
2854:
2849:
2843:
2827:
2825:
2820:
2814:
2798:
2796:
2790:
2784:
2768:
2766:
2760:
2754:
2739:. 19 May 2016
2738:
2736:
2730:
2724:
2709:
2707:
2701:
2695:
2680:
2676:
2670:
2662:
2658:
2654:
2650:
2646:
2642:
2638:
2634:
2627:
2619:
2612:
2606:
2598:
2594:
2589:
2584:
2580:
2576:
2573:(4): 778–84.
2572:
2568:
2564:
2557:
2549:
2545:
2542:(6): 277–88.
2541:
2537:
2530:
2522:
2518:
2513:
2508:
2504:
2500:
2496:
2492:
2488:
2481:
2473:
2469:
2464:
2459:
2455:
2451:
2447:
2443:
2439:
2432:
2424:
2420:
2415:
2410:
2405:
2400:
2396:
2392:
2388:
2384:
2380:
2373:
2365:
2361:
2356:
2351:
2347:
2343:
2339:
2335:
2331:
2324:
2322:
2313:
2309:
2305:
2301:
2298:(4): 263–70.
2297:
2293:
2286:
2284:
2275:
2271:
2266:
2261:
2257:
2253:
2249:
2245:
2241:
2234:
2226:
2222:
2217:
2212:
2208:
2204:
2201:(4): 388–99.
2200:
2196:
2192:
2185:
2177:
2171:
2167:
2160:
2152:
2148:
2143:
2138:
2133:
2128:
2124:
2120:
2116:
2109:
2093:
2089:
2085:
2081:
2075:
2059:
2055:
2049:
2047:
2038:
2032:
2021:
2017:
2010:
2004:
1991:
1985:
1983:
1974:
1970:
1966:
1962:
1958:
1954:
1950:
1946:
1939:
1931:
1927:
1922:
1917:
1913:
1909:
1905:
1901:
1897:
1890:
1882:
1878:
1873:
1868:
1864:
1860:
1856:
1852:
1848:
1841:
1833:
1829:
1824:
1819:
1815:
1811:
1807:
1803:
1799:
1792:
1784:
1780:
1776:
1770:
1762:
1758:
1751:
1743:
1737:
1732:
1731:
1722:
1714:
1710:
1705:
1700:
1695:
1690:
1687:: 6875–6886.
1686:
1682:
1678:
1671:
1662:
1657:
1653:
1649:
1643:
1635:
1633:9783527607495
1629:
1625:
1624:
1616:
1600:
1594:
1592:
1590:
1588:
1586:
1584:
1582:
1580:
1571:
1567:
1563:
1559:
1555:
1551:
1547:
1543:
1536:
1534:
1514:
1507:
1501:
1493:
1489:
1485:
1481:
1477:
1473:
1469:
1465:
1458:
1442:
1438:
1432:
1417:
1413:
1409:
1403:
1387:
1383:
1377:
1375:
1370:
1362:
1360:
1356:
1352:
1347:
1335:
1331:
1329:
1328:
1323:
1314:
1305:
1303:
1298:
1295:
1291:
1287:
1283:
1279:
1269:
1266:
1262:
1259:
1255:
1251:
1247:
1242:
1240:
1236:
1232:
1228:
1208:
1205:
1203:
1200:
1198:
1195:
1193:
1190:
1189:
1187:
1184:
1182:
1178:
1175:
1173:
1169:
1166:
1164:
1161:
1159:
1156:
1154:
1151:
1149:
1146:
1144:
1141:
1139:
1136:
1134:
1131:
1128:
1125:
1124:
1122:
1110:
1107:
1105:
1101:
1099:
1096:
1093:
1090:
1087:yellow skin (
1086:
1084:
1081:
1079:
1076:
1073:
1071:
1068:
1066:
1063:
1062:
1060:
1058:
1050:
1048:
1044:
1041:
1037:
1036:
1035:
1033:
1029:
1019:
1017:
1013:
1005:
1001:
997:
992:
990:
986:
982:
971:
969:
965:
961:
956:
954:
950:
946:
942:
941:aspergillosis
937:
935:
931:
927:
923:
922:onychomycosis
919:
915:
911:
910:blastomycosis
907:
906:
901:
897:
893:
883:
881:
877:
872:
870:
865:
863:
859:
858:cell membrane
855:
851:
847:
846:breastfeeding
843:
839:
835:
831:
827:
826:heart failure
823:
819:
814:
812:
811:intravenously
808:
804:
800:
796:
792:
791:blastomycosis
788:
787:aspergillosis
784:
780:
776:
772:
762:
755:
746:
741:
740:
737:
730:
721:
720:
717:
710:
706:
704:
700:
696:
694:
693:Melting point
690:
687:
684:
682:
678:
671:
667:
666:
664:
661:
656:
649:
647:
643:
610:
608:
604:
599:
595:
591:
588:
586:
584:ECHA InfoCard
580:
572:
568:
567:DTXSID3023180
564:
563:
561:
552:
548:
541:
537:
536:
534:
532:
528:
521:
517:
516:
514:
512:
508:
501:
497:
496:
494:
492:
488:
481:
477:
476:
474:
472:
468:
461:
457:
456:
454:
452:
448:
441:
437:
436:
434:
432:
428:
421:
417:
416:
414:
407:
403:
396:
392:
391:
389:
387:
383:
374:
373:
370:
363:
358:
354:
351:
349:
345:
341:
339:
332:
328:
323:
321:
317:
313:
309:
306:Extensive in
305:
303:
299:
295:
293:
289:
285:
283:
279:
275:
271:
264:
252:
249:
239:
237:
228:
225:
215:
214:
212:
210:
206:
201:
193:
188:
185:
184:
182:
180:
176:
173:
169:
166:
162:
158:
155:
153:
147:
141:
132:
131:
129:
127:
121:
114:
109:
100:
99:
97:
95:
91:
87:
83:
81:
77:
73:
69:
67:
63:
59:
55:
51:
47:
45:
41:
38:Clinical data
36:
32:
27:
19:
4904:Orphan drugs
4874:Chloroarenes
4675:Trifluthepin
4645:Perphenazine
4625:Oxyprothepin
4620:Oxyclothepin
4580:Fluphenazine
4545:Clopenthixol
4414:Tandospirone
4041:Vortioxetine
4016:Tolpiprazole
3966:Posaconazole
3896:Lorpiprazole
3886:Ketoconazole
3881:Itraconazole
3880:
3836:Elopiprazole
3826:Dropropizine
3776:Aripiprazole
3597:tea tree oil
3582:lemon myrtle
3495:ethylparaben
3425:griseofulvin
3286:Benzylamines
3175:ravuconazole
3170:albaconazole
3162:voriconazole
3157:posaconazole
3147:itraconazole
3146:
3137:hexaconazole
3055:neticonazole
3045:luliconazole
3040:ketoconazole
3030:flutrimazole
3015:eberconazole
3005:clotrimazole
2990:butoconazole
2886:Itraconazole
2859:. Retrieved
2851:
2842:
2830:. Retrieved
2822:
2813:
2801:. Retrieved
2792:
2783:
2771:. Retrieved
2762:
2753:
2741:. Retrieved
2732:
2723:
2711:. Retrieved
2703:
2694:
2682:. Retrieved
2678:
2669:
2636:
2632:
2626:
2617:
2605:
2570:
2566:
2556:
2539:
2535:
2529:
2494:
2490:
2480:
2445:
2441:
2431:
2386:
2382:
2372:
2337:
2333:
2295:
2291:
2250:(1): 23–34.
2247:
2243:
2233:
2198:
2194:
2184:
2165:
2159:
2122:
2118:
2108:
2096:. Retrieved
2092:the original
2083:
2074:
2062:. Retrieved
2058:the original
2031:
2020:the original
2015:
2003:
1948:
1944:
1938:
1903:
1899:
1889:
1854:
1850:
1840:
1805:
1801:
1791:
1778:
1769:
1761:the original
1750:
1729:
1721:
1684:
1680:
1670:
1661:10665/325771
1651:
1642:
1622:
1615:
1603:. Retrieved
1545:
1541:
1520:. Retrieved
1513:the original
1500:
1467:
1463:
1457:
1445:. Retrieved
1440:
1431:
1419:. Retrieved
1411:
1402:
1390:. Retrieved
1385:
1348:
1345:
1326:
1319:
1299:
1278:cyclosporine
1275:
1254:angiogenesis
1243:
1224:
1216:Pharmacology
1129:(Cordarone);
1120:
1117:Interactions
1057:cyclodextrin
1054:
1032:voriconazole
1025:
1022:Side effects
996:cyclodextrin
993:
977:
957:
938:
903:
900:posaconazole
896:voriconazole
889:
886:Medical uses
873:
866:
818:side effects
815:
774:
771:Itraconazole
770:
769:
758:
335:Elimination
326:
209:Legal status
203:Legal status
113:Itraconazole
94:License data
23:Itraconazole
18:
4909:Piperazines
4771:Mirodenafil
4756:JNJ-7777120
4746:Hexocyclium
4711:Bucinnazine
4665:Thiothixene
4650:Pirenzepine
4635:Perathiepin
4575:Flupentixol
4565:Doclothepin
4560:Cyanothepin
4550:Clorotepine
4518:Ziprasidone
4508:Revospirone
4503:Perospirone
4490:piperazines
4467:Mirtazapine
4462:Delavirdine
4434:Zalospirone
4409:Revospirone
4321:Lidoflazine
4311:Hydroxyzine
4241:Clocinizine
4236:Cinnarizine
4169:Vesnarinone
4051:WAY-100,635
4046:WAY-100,135
4031:Vesnarinone
3951:Pardoprunox
3916:Mepiprazole
3871:Flibanserin
3856:Etoperidone
3846:Enpiprazole
3841:Eltoprazine
3831:EGIS-12,233
3806:Dapiprazole
3781:Batoprazine
3771:Antrafenine
3695:Piperazines
3637:from market
3616:pentamidine
3577:lemon grass
3535:taurolidine
3505:polynoxylin
3406:flucytosine
3350:caspofungin
3274:terbinafine
3260:Allylamines
3122:fluconazole
3114:terconazole
3109:fluconazole
3080:tioconazole
3075:sulconazole
3065:oxiconazole
3060:omoconazole
3035:isoconazole
3010:croconazole
2968:inhibitors)
2966:demethylase
2923:Antifungals
2244:Cancer Cell
2195:Cancer Cell
2098:16 December
1351:orphan drug
1197:ergometrine
1172:simvastatin
1143:nisoldipine
1094:yellow eyes
1028:fluconazole
945:candidiasis
905:Aspergillus
892:fluconazole
838:anaphylaxis
653: g·mol
590:100.123.596
540:ChEMBL22587
360:Identifiers
320:Metabolites
172:intravenous
168:suppository
80:MedlinePlus
53:Other names
44:Trade names
4884:Dioxolanes
4858:Categories
4806:Vardenafil
4796:Sildenafil
4786:Ranolazine
4726:Cinepazide
4610:Olanzapine
4600:Metitepine
4528:Tricyclics
4513:Tiospirone
4498:Lurasidone
4452:Atevirdine
4429:Umespirone
4424:Trimazosin
4389:Ipsapirone
4379:Eptapirone
4351:Vanoxerine
4326:Manidipine
4306:GBR-13,119
4301:GBR-13,098
4296:GBR-13,069
4291:GBR-12,935
4286:GBR-12,783
4266:Dotarizine
4221:Cetirizine
4206:BRL-15,572
4201:Amperozide
4144:Piberaline
4084:Bifeprunox
4079:Befuraline
4036:Vilazodone
4001:SB-399,885
3996:SB-357,134
3991:SB-271,046
3986:SB-258,585
3946:Oxypertine
3941:Niaprazine
3936:Nefazodone
3921:Naftopidil
3876:Fluprazine
3866:Fluanisone
3861:Flesinoxan
3791:BRL-15,572
3786:Bifeprunox
3766:Acaprazine
3733:Piperazine
3606:atovaquone
3587:orange oil
3550:tolnaftate
3545:tolciclate
3530:sulbentine
3500:haloprogin
3480:ciclopirox
3445:tavaborole
3437:inhibitors
3423:Systemic:
3404:Systemic:
3365:rezafungin
3360:micafungin
3355:cilofungin
3339:Systemic:
3333:inhibitors
3316:amorolfine
3295:butenafine
3252:inhibitors
3236:Systemic:
3213:ergosterol
3120:Systemic:
3050:miconazole
3000:climbazole
2985:bifonazole
2976:Imidazoles
2952:inhibitors
2949:Ergosterol
1605:8 December
1548:: 120441.
1421:22 October
1365:References
1292:, causing
1231:ergosterol
1202:ergotamine
1168:lovastatin
1163:lurasidone
1138:dofetilide
1127:amiodarone
1108:pale stool
953:antifungal
930:meningitis
862:metabolism
836:including
658:3D model (
646:Molar mass
520:CHEBI:6076
480:304NUG5GF4
451:ChemSpider
395:84625-61-6
386:CAS Number
369:IUPAC name
302:Metabolism
4801:Tadalafil
4781:Quipazine
4761:Lodenafil
4751:Indinavir
4741:EGIS-7625
4716:Cinepazet
4706:Azimilide
4615:Opipramol
4555:Clozapine
4540:Amoxapine
4472:ORG-12962
4457:Azaperone
4419:Tirilazad
4399:Prazitone
4394:Piribedil
4374:Dasatinib
4369:Buspirone
4341:Oxatomide
4331:Meclozine
4246:Cyclizine
4211:Buclizine
4196:Almitrine
4159:Sunifiram
4149:Piribedil
4129:Meclozine
4089:Buclizine
4021:Trazodone
3926:Naluzotan
3851:Ensaculin
3728:Midafotel
3647:Phase III
3635:Withdrawn
3592:patchouli
3540:ticlatone
3443:Topical:
3314:Topical:
3293:Topical:
3269:naftifine
3267:Topical:
3240:, hamycin
3228:natamycin
3221:Topical:
3194:abafungin
3192:Topical:
3185:Thiazoles
3168:Unknown:
3102:Topical:
3095:Triazoles
3020:econazole
2983:Topical:
2684:28 August
2679:Drugs.com
2536:Nutr Hosp
2064:10 August
1973:235608763
1570:232135660
1522:28 August
1386:Drugs.com
1308:Chemistry
1282:quinidine
1181:triazolam
1177:midazolam
1158:quinidine
1133:cisapride
1038:elevated
932:or other
880:sonidegib
842:pregnancy
681:Chirality
348:Excretion
337:half-life
150:Routes of
124:Pregnancy
72:Monograph
66:Drugs.com
4848:Medicine
4821:Zipeprol
4816:WY-46824
4811:VUF-6002
4640:Perazine
4590:Loxapine
4384:Gepirone
4316:JJC8-088
4281:DPI-3290
4216:BW373U86
4114:Imatinib
4109:Fipexide
4069:2C-B-BZP
4026:Urapidil
3981:S-15,535
3976:S-14,671
3971:S-14,506
3801:CSP-2503
3490:dimazole
3233:nystatin
3215:binding)
2941:membrane
2653:16415110
2472:21936514
2423:20176935
2364:21896639
2312:17432820
2274:23291299
2225:20385363
2151:21801420
1965:34160824
1930:23546045
1881:23340005
1832:21896639
1713:31692536
1650:(2019).
1562:33675927
1484:15242978
1153:pimozide
1111:headache
1089:jaundice
1070:vomiting
850:triazole
807:by mouth
777:, is an
761:(verify)
431:DrugBank
342:21 hours
179:ATC code
161:solution
157:By mouth
139: B3
126:category
108:DailyMed
4791:SA-4503
4276:DPI-287
4271:DPI-221
4251:DBL-583
4191:AD-1211
4154:RN-1747
4139:NSI-189
3761:3,4-CFP
3756:2C-B-PP
3611:dapsone
3223:hamycin
2597:8388198
2548:9477653
2521:8878612
2463:3307530
2414:2842052
2391:Bibcode
2355:3206167
2265:3548977
2216:4039177
2142:3161953
2125:: 333.
2086:. U.S.
2016:Janssen
1921:3636564
1872:3579600
1823:3206167
1704:6711563
1492:6941636
1361:(EMA).
1342:History
1148:alcohol
1098:itching
1078:fatigue
1012:blocker
816:Common
607:Formula
440:DB01167
406:PubChem
265:Rx-only
262:WARNING
234::
195:)
189: (
187:J02AC02
165:vaginal
110::
86:a692049
4834:Portal
4766:MK-212
4701:AP-238
4346:SNC-80
3906:Mefway
3630:WHO-EM
3458:Others
3308:Others
2960:Azoles
2861:15 May
2832:15 May
2803:15 May
2773:15 May
2743:15 May
2713:15 May
2661:189994
2659:
2651:
2595:
2588:187759
2585:
2546:
2519:
2512:163504
2509:
2470:
2460:
2421:
2411:
2362:
2352:
2310:
2272:
2262:
2223:
2213:
2172:
2149:
2139:
1996:
1971:
1963:
1928:
1918:
1879:
1869:
1830:
1820:
1738:
1711:
1701:
1630:
1568:
1560:
1490:
1482:
1447:15 May
1392:15 May
1284:, and
1065:nausea
966:, and
947:, and
920:, and
801:, and
716:SMILES
651:705.64
531:ChEMBL
500:D00350
353:Kidney
312:CYP3A4
259:
246:
236:â„ž-only
222:
106:
4776:PB-28
4731:CPD-1
4336:MT-45
4124:MDBZP
4011:TFMPP
3911:MeOPP
3738:PIPES
3723:HEPPS
2939:Wall/
2855:(EMA)
2826:(EMA)
2797:(FDA)
2793:U.S.
2767:(FDA)
2763:U.S.
2737:(FDA)
2733:U.S.
2708:(FDA)
2704:U.S.
2657:S2CID
2614:(PDF)
2023:(PDF)
2012:(PDF)
1969:S2CID
1566:S2CID
1516:(PDF)
1509:(PDF)
1488:S2CID
1441:(emc)
1265:VEGFR
1246:azole
1227:azole
1186:ergot
1104:urine
1102:dark
736:InChI
660:JSmol
511:ChEBI
460:49927
420:55283
308:liver
296:99.8%
4119:MBZP
4104:DBZP
3961:pFPP
3956:pCPP
3901:mCPP
3816:DMPP
3811:DCPP
2929:and
2863:2020
2834:2020
2805:2020
2775:2020
2745:2020
2715:2020
2686:2016
2649:PMID
2593:PMID
2544:PMID
2517:PMID
2468:PMID
2419:PMID
2360:PMID
2308:PMID
2270:PMID
2221:PMID
2170:ISBN
2147:PMID
2100:2019
2066:2006
1961:PMID
1926:PMID
1877:PMID
1828:PMID
1736:ISBN
1709:PMID
1628:ISBN
1607:2017
1558:PMID
1524:2016
1480:PMID
1449:2020
1423:2023
1394:2020
1252:and
1055:The
1004:cola
832:and
491:KEGG
471:UNII
276:data
62:AHFS
4094:BZP
3602:PCP
2931:J02
2927:D01
2641:doi
2583:PMC
2575:doi
2507:PMC
2499:doi
2458:PMC
2450:doi
2409:PMC
2399:doi
2387:107
2350:PMC
2342:doi
2300:doi
2260:PMC
2252:doi
2211:PMC
2203:doi
2137:PMC
2127:doi
1953:doi
1916:PMC
1908:doi
1867:PMC
1859:doi
1818:PMC
1810:doi
1699:PMC
1689:doi
1656:hdl
1550:doi
1546:599
1472:doi
1416:FDA
1327:cis
1179:or
1170:or
1030:or
1014:or
898:or
844:or
809:or
775:ITZ
556:EPA
410:CID
248:POM
192:WHO
163:),
56:ITZ
4860::
3643::
3604::
2850:.
2821:.
2791:.
2761:.
2731:.
2702:.
2677:.
2655:.
2647:.
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2616:.
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797:,
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624:Cl
621:38
615:35
255:US
242:UK
231:CA
224:S4
218:AU
170:,
159:,
135:AU
103:US
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