527:
504:
40:
31:
3200:
823:
group on the left aromatic ring to form griseophenone B. The halogenated species then undergoes a single phenolic oxidation in both rings forming the two oxygen diradical species. The right oxygen radical shifts alpha to the carbonyl via resonance allowing for a stereospecific radical coupling by the
795:
is the synthesis of the 14-carbon poly-β-keto chain by a type I iterative polyketide synthase (PKS) via iterative addition of 6 malonyl-CoA to an acyl-CoA starter unit. The 14-carbon poly-β-keto chain undergoes cyclization/aromatization, using cyclase/aromatase, respectively, through a
739:
given for 2 to 4 weeks is at least as effective as griseofulvin given for 6 to 8 weeks for treatment of
Trichophyton scalp infections. However, griseofulvin is more effective than terbinafine for treatment of Microsporum scalp infections.
769:
in keratin precursor cells and makes them resistant to fungal infections. The drug reaches its site of action only when hair or skin is replaced by the keratin-griseofulvin complex. Griseofulvin then enters the
850:
774:
through energy-dependent transport processes and binds to fungal microtubules. This alters the processing for mitosis and also underlying information for deposition of fungal cell walls.
189:
593:
2189:
3134:
1360:
KnasmĂĽller S, Parzefall W, Helma C, Kassie F, Ecker S, Schulte-Hermann R (September 1997). "Toxic effects of griseofulvin: disease models, mechanisms, and risk assessment".
1090:
Fleece D, Gaughan JP, Aronoff SC (November 2004). "Griseofulvin versus terbinafine in the treatment of tinea capitis: a meta-analysis of randomized, clinical trials".
2410:
2400:
2225:
2415:
3275:
134:
2182:
2395:
3064:
2175:
3230:
2265:
2435:
2240:
62:
3250:
3084:
607:
1184:"Studies in the biochemistry of micro-organisms: Griseofulvin, C(17)H(17)O(6)Cl, a metabolic product of Penicillium griseo-fulvum Dierckx"
2576:
2455:
2335:
829:
996:
965:
3059:
2756:
2696:
2844:
2450:
2365:
828:-methylated by SAM to generate dehydrogriseofulvin. Ultimately, a stereoselective reduction of the olefin on dehydrogriseofulvin by
2506:
824:
oxygen radical on the left ring forming a tetrahydrofuranone species. The newly formed grisan skeleton with a spiro center is then
885:
2133:
1417:
1309:
990:
718:
1273:
Birch A (1953). "Studies in relation to biosynthesis I. Some possible routes to derivatives of orcinol and phloroglucinol".
635:
InChI=1S/C17H17ClO6/c1-8-5-9(19)6-12(23-4)17(8)16(20)13-10(21-2)7-11(22-3)14(18)15(13)24-17/h6-8H,5H2,1-4H3/t8-,17+/m1/s1
652:
3255:
1074:
959:
932:
627:
3280:
2209:
2150:
2984:
849:
by Yokoo et al. 1979. The same team went on to find a similar effect on mice by a chemically unrelated substance,
819:(SAM) twice to yield griseophenone C. The griseophenone C is then halogenated at the activated site ortho to the
285:
174:
3245:
2666:
1900:
733:. It is ineffective topically. It is reserved for cases in which topical treatment with creams is ineffective.
1467:
3176:
522:
403:
2711:
2405:
2198:
483:
3265:
3190:
2486:
2481:
472:
3225:
1968:
1938:
1410:
1037:
910:
2969:
2516:
2355:
3270:
3094:
3009:
1833:
784:
713:
499:
1231:
Grove JF, Ismay D, Macmillan J, Mulholland TP, Rogers MA (1951). "The structure of griseofulvin".
2138:
2068:
1250:
Grove JF, MacMillan J, Mulholland TP, Rogers MA (1952). "762. Griseofulvin. Part IV. Structure".
120:
52:
2656:
2285:
2105:
1752:
980:
949:
452:
3240:
3235:
813:
677:
and scalp, as well as the skin when antifungal creams have not worked. It is taken by mouth.
666:
2501:
2491:
392:
3220:
2839:
2811:
2801:
2420:
1403:
797:
412:
264:
2496:
8:
2641:
2541:
2465:
2167:
1895:
1711:
1369:
1069:(in German) (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. p. 838.
327:
318:
127:
2835:
526:
503:
3114:
2869:
2670:
2201:
2058:
2028:
2023:
1208:
1183:
1159:
1134:
1115:
801:
681:
94:
692:, headache, trouble sleeping, and feeling tired. It is not recommended in people with
3260:
2819:
2526:
1919:
1381:
1342:
1305:
1213:
1164:
1107:
1070:
986:
955:
928:
215:
202:
86:
1119:
881:
72:
3104:
2824:
2706:
2636:
2521:
2511:
2425:
2275:
2063:
2013:
1373:
1334:
1282:
1255:
1203:
1195:
1154:
1150:
1146:
1099:
1045:
1019:
918:
539:
352:
225:
157:
147:
3204:
2781:
2676:
2556:
1645:
1635:
1325:
Harris CM, Roberson JS, Harris TM (August 1976). "Biosynthesis of griseofulvin".
730:
670:
256:
243:
233:
3129:
3049:
2919:
2776:
2631:
2596:
2255:
2144:
2075:
2018:
1988:
1973:
1741:
1630:
1377:
704:
may result in harm to the baby. Griseofulvin works by interfering with fungal
3214:
3069:
2944:
2829:
2791:
2686:
2651:
2586:
2385:
2345:
2245:
1978:
1874:
1848:
1655:
1607:
1573:
1528:
1498:
693:
674:
515:
252:
22:
1395:
3154:
3124:
3099:
3054:
2999:
2994:
2979:
2974:
2964:
2959:
2884:
2766:
2751:
2746:
2741:
2726:
2621:
2611:
2440:
2380:
2315:
2310:
2300:
2280:
2270:
2100:
2085:
1998:
1844:
1678:
1673:
1665:
1660:
1650:
1640:
1558:
1548:
1543:
1533:
1518:
1508:
1493:
1434:
1430:
1217:
1168:
1133:
Chen X, Jiang X, Yang M, González U, Lin X, Hua X, et al. (May 2016).
1111:
1103:
1042:
World Health
Organization model list of essential medicines: 21st list 2019
805:
771:
152:
142:
1385:
3139:
3109:
3089:
3039:
2914:
2909:
2894:
2864:
2691:
2646:
2606:
2601:
2551:
2546:
2531:
2370:
2330:
2235:
2119:
2080:
2038:
2008:
1909:
1853:
1789:
1777:
1625:
1617:
1612:
1583:
1578:
1568:
1563:
1538:
1513:
1346:
1259:
758:
736:
80:
1338:
1050:
372:
3119:
3079:
3024:
3014:
2954:
2939:
2924:
2904:
2879:
2874:
2854:
2849:
2806:
2796:
2761:
2736:
2716:
2681:
2660:
2616:
2591:
2375:
2340:
2325:
2320:
2289:
2250:
2230:
2109:
2090:
2053:
2048:
2033:
2003:
1983:
1948:
1868:
1863:
1858:
1819:
1798:
1763:
1716:
1553:
1503:
1488:
1452:
1426:
1010:
Beekman AM, Barrow RA (2014). "Fungal metabolites as pharmaceuticals".
923:
809:
569:
383:
1286:
1199:
3044:
3034:
3029:
3019:
3004:
2989:
2934:
2889:
2859:
2721:
2701:
2626:
2566:
2561:
2430:
2360:
2350:
2295:
2095:
2043:
1772:
1731:
1697:
1523:
1479:
701:
697:
338:
66:
1023:
2949:
2929:
2899:
2771:
2731:
2581:
2571:
2445:
1993:
1736:
1688:
1598:
689:
432:
363:
592:
39:
3159:
3144:
3074:
2536:
2260:
2114:
1726:
766:
762:
754:
705:
820:
685:
463:
30:
1359:
1249:
1463:
1302:
Medicinal
Natural Products: A Biosynthetic Approach (3rd ed.)
1230:
846:
583:
443:
248:
488:
1135:"Systemic antifungal therapy for tinea capitis in children"
423:
2197:
1036:
909:
711:
Griseofulvin was discovered in 1939 from the soil fungus
2210:
1064:
1054:. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
1181:
719:
845:
Griseofulvin is found to alter the bile metabolism of
791:
The first step in the biosynthesis of griseofulvin by
3188:
1353:
1132:
884:. The American Society of Health-System Pharmacists.
782:
It is produced industrially by fermenting the fungus
1324:
1182:
Oxford AE, Raistrick H, Simonart P (February 1939).
1089:
808:
intermediate. The benzophenone intermediate is then
673:(ringworm). This includes fungal infections of the
954:. Lippincott Williams & Wilkins. p. 631.
3212:
351:
913:(2009). Stuart MC, Kouimtzi M, Hill SR (eds.).
853:, in Yokoo et al. 1982 and Tsunoo et al. 1987.
326:
1003:
16:Antifungal medication used for dermatophytoses
3276:World Health Organization essential medicines
2183:
1425:
1411:
1009:
951:Disinfection, Sterilization, and Preservation
615:O=C2c3c(O21C(/OC)=C\C(=O)C1C)c(Cl)c(OC)cc3OC
301:)- 7-chloro- 2',4,6-trimethoxy- 6'-methyl- 3
2466:
1139:The Cochrane Database of Systematic Reviews
2517:Allopregnanedione (5α-dihydroprogesterone)
2190:
2176:
1418:
1404:
917:. World Health Organization. p. 149.
876:
874:
872:
870:
868:
866:
525:
502:
391:
38:
29:
1252:Journal of the Chemical Society (Resumed)
1207:
1158:
1049:
972:
922:
905:
903:
851:3,5-diethoxycarbonyl-1,4-dihydrocollidine
411:
2215:Tooltip Constitutive androstane receptor
1327:Journal of the American Chemical Society
1065:Mutschler E, Schäfer-Korting M (2001).
985:. Synapse Info Resources. p. 406.
863:
498:
371:
85:
3213:
2970:Pregnanedione (5β-dihydroprogesterone)
2356:Pregnanedione (5β-dihydroprogesterone)
1299:
1030:
999:from the original on 31 December 2013.
978:
968:from the original on 20 December 2016.
900:
516:
196:
3231:Benzofuran ethers at the benzene ring
2171:
1399:
1272:
1044:. Geneva: World Health Organization.
947:
888:from the original on 20 December 2016
729:Griseofulvin is used orally only for
700:. Use during or in the months before
471:
451:
209:
71:
156:
146:
3251:Halogen-containing natural products
748:
669:used to treat a number of types of
431:
342:
13:
14:
3292:
1304:. UK: John Wiley & Sons Ltd.
183:
105:
3198:
556:
550:
1901:thymidylate synthase inhibitors
1318:
1293:
1275:Australian Journal of Chemistry
1266:
1243:
1224:
1175:
1012:Australian Journal of Chemistry
777:
743:
724:
640:Key:DDUHZTYCFQRHIY-RBHXEPJQSA-N
2522:Allopregnanolone (brexanolone)
1362:Critical Reviews in Toxicology
1151:10.1002/14651858.CD004685.pub3
1126:
1083:
1058:
941:
559:
544:
1:
3177:Receptor/signaling modulators
3135:Tropanyl 3,5-dimethulbenzoate
2985:Pregnenolone 16α-carbonitrile
856:
835:
57:Gris-peg, Grifulvin V, others
680:Common side effects include
7:
2712:Dodecylbenzenesulfonic acid
2471:Tooltip Pregnane X receptor
2199:Xenobiotic-sensing receptor
238:Highly variable (25 to 70%)
10:
3297:
761:function, thus inhibiting
534:Chemical and physical data
3256:IARC Group 2B carcinogens
3168:
2464:
2208:
2128:
1969:bromochlorosalicylanilide
1961:
1939:Aminoacyl tRNA synthetase
1937:
1918:
1894:
1887:
1832:
1811:
1788:
1762:
1751:
1710:
1687:
1597:
1478:
1462:
1451:
1442:
1378:10.3109/10408449709078444
1038:World Health Organization
982:Handbook of Preservatives
911:World Health Organization
648:
623:
603:
581:
568:
538:
533:
514:
482:
462:
442:
422:
402:
382:
362:
337:
317:
281:
276:
263:
242:
232:
224:
173:
168:
133:
119:
93:
79:
61:
51:
46:
37:
28:
3095:Testosterone isocaproate
3010:Reverse triiodothyronine
915:WHO Model Formulary 2008
785:Penicillium griseofulvum
714:Penicillium griseofulvum
3281:Terpenes and terpenoids
2487:17α-Hydroxyprogesterone
2482:17α-Hydroxypregnenolone
1188:The Biochemical Journal
840:
309:-spiro ene]- 3,4'-dione
1753:Squalene monooxygenase
1590:Systemic: ketoconazole
1233:Chemistry and Industry
1104:10.1542/peds.2004-0428
832:affords griseofulvin.
3246:Disulfiram-like drugs
2226:6,7-Dimethylesculetin
1781:Systemic: terbinafine
1067:Arzneimittelwirkungen
979:Ash M, Ash I (2004).
667:antifungal medication
2813:Hypericum perforatum
2802:Hetacillin potassium
2069:Whitfield's ointment
1896:Pyrimidine analogues
1712:Polyene antimycotics
1370:Taylor & Francis
1260:10.1039/JR9520003977
817:-adenosyl methionine
2642:Cyproterone acetate
2542:Amlodipine besylate
1339:10.1021/ja00433a053
757:, interfering with
205:(Prescription only)
192:(Prescription only)
25:
3115:Thonzonium bromide
2870:Methylprednisolone
2671:prasterone sulfate
2155:Never to phase III
2059:tribromometacresol
2029:sodium thiosulfate
2024:selenium disulfide
1920:Mitotic inhibitors
1300:Dewick PM (2009).
1239:. London: 219–220.
802:aldol condensation
753:The drug binds to
682:allergic reactions
21:
3266:Resorcinol ethers
3186:
3185:
2820:Indinavir sulfate
2527:Alpha-Lipoic acid
2502:Δ-Androstenedione
2492:Δ-Androstenedione
2165:
2164:
1957:
1956:
1883:
1882:
1834:β-glucan synthase
1828:
1827:
1807:
1806:
1706:
1705:
1333:(17): 5380–5386.
1311:978-0-471-97478-9
1287:10.1071/ch9530360
1200:10.1042/bj0330240
992:978-1-890595-66-1
948:Block SS (2001).
660:
659:
594:Interactive image
484:CompTox Dashboard
213:
200:
187:
109:
3288:
3226:Aromatic ketones
3203:
3202:
3201:
3194:
3105:Thiamylal sodium
2840:Îł-linolenic acid
2836:α-Linolenic acid
2834:Linolenic acid:
2825:Lasalocid sodium
2815:(St John's wort)
2707:Docusate calcium
2637:Cyclophosphamide
2512:Allopregnanediol
2497:Δ-Androstenediol
2472:
2468:
2426:Ethinylestradiol
2276:Cyclophosphamide
2216:
2212:
2192:
2185:
2178:
2169:
2168:
2064:undecylenic acid
2014:potassium iodide
1892:
1891:
1760:
1759:
1476:
1475:
1460:
1459:
1449:
1448:
1420:
1413:
1406:
1397:
1396:
1390:
1389:
1357:
1351:
1350:
1322:
1316:
1315:
1297:
1291:
1290:
1270:
1264:
1263:
1247:
1241:
1240:
1228:
1222:
1221:
1211:
1179:
1173:
1172:
1162:
1130:
1124:
1123:
1098:(5): 1312–1315.
1087:
1081:
1080:
1062:
1056:
1055:
1053:
1034:
1028:
1027:
1007:
1001:
1000:
976:
970:
969:
945:
939:
938:
926:
907:
898:
897:
895:
893:
878:
749:Pharmacodynamics
656:
655:
596:
576:
561:
558:
552:
546:
529:
518:
507:
506:
492:
490:
475:
455:
435:
415:
395:
375:
355:
345:
344:
330:
268:
211:
208:
198:
195:
185:
182:
160:
150:
107:
104:
89:
75:
42:
33:
26:
24:
20:
3296:
3295:
3291:
3290:
3289:
3287:
3286:
3285:
3271:Spiro compounds
3211:
3210:
3209:
3199:
3197:
3189:
3187:
3182:
3164:
3065:Suberoylanilide
2782:Fluorometholone
2677:Dibunate sodium
2557:Aurothioglucose
2470:
2460:
2396:3,17β-Estradiol
2214:
2204:
2196:
2166:
2161:
2160:
2145:Clinical trials
2124:
1953:
1933:
1914:
1899:
1879:
1836:
1824:
1803:
1784:
1780:
1755:
1747:
1739:
1714:
1702:
1683:
1636:fosravuconazole
1593:
1469:
1468:lanosterol 14α-
1455:
1444:
1438:
1424:
1394:
1393:
1358:
1354:
1323:
1319:
1312:
1298:
1294:
1271:
1267:
1248:
1244:
1229:
1225:
1180:
1176:
1145:(5): CD004685.
1131:
1127:
1088:
1084:
1077:
1063:
1059:
1035:
1031:
1024:10.1071/ch13639
1008:
1004:
993:
977:
973:
962:
946:
942:
935:
908:
901:
891:
889:
880:
879:
864:
859:
843:
838:
793:P. griseofulvin
780:
751:
746:
731:dermatophytosis
727:
717:. It is on the
671:dermatophytoses
651:
649:
644:
641:
636:
631:
630:
619:
616:
611:
610:
599:
574:
564:
555:
549:
510:
486:
478:
458:
438:
418:
398:
378:
358:
341:
333:
313:
310:
289:
288:
266:
257:glucuronidation
234:Bioavailability
226:Pharmacokinetic
220:
164:
122:
115:
96:
17:
12:
11:
5:
3294:
3284:
3283:
3278:
3273:
3268:
3263:
3258:
3253:
3248:
3243:
3238:
3233:
3228:
3223:
3208:
3207:
3184:
3183:
3181:
3180:
3173:
3169:
3166:
3165:
3163:
3162:
3157:
3148:
3147:
3142:
3137:
3132:
3130:Troleandomycin
3127:
3122:
3117:
3112:
3107:
3102:
3097:
3092:
3087:
3082:
3077:
3072:
3067:
3062:
3057:
3052:
3050:Spironolactone
3047:
3042:
3037:
3032:
3027:
3022:
3017:
3012:
3007:
3002:
2997:
2992:
2987:
2982:
2977:
2972:
2967:
2962:
2957:
2952:
2947:
2942:
2937:
2932:
2927:
2922:
2920:Norelgestromin
2917:
2912:
2907:
2902:
2897:
2892:
2887:
2882:
2877:
2872:
2867:
2862:
2857:
2852:
2847:
2842:
2832:
2827:
2822:
2817:
2809:
2804:
2799:
2794:
2789:
2784:
2779:
2777:Flucloxacillin
2774:
2769:
2764:
2759:
2754:
2749:
2744:
2739:
2734:
2729:
2724:
2719:
2714:
2709:
2704:
2699:
2694:
2689:
2684:
2679:
2674:
2664:
2654:
2649:
2644:
2639:
2634:
2632:Corticosterone
2629:
2624:
2619:
2614:
2609:
2604:
2599:
2597:Chlorpromazine
2594:
2589:
2584:
2579:
2574:
2569:
2564:
2559:
2554:
2549:
2544:
2539:
2534:
2529:
2524:
2519:
2514:
2509:
2504:
2499:
2494:
2489:
2484:
2475:
2473:
2462:
2461:
2459:
2458:
2453:
2448:
2443:
2438:
2433:
2428:
2423:
2418:
2416:17-Androstanol
2413:
2411:3β-Androstanol
2408:
2406:3α-Androstenol
2403:
2401:3α-Androstanol
2398:
2389:
2388:
2383:
2378:
2373:
2368:
2363:
2358:
2353:
2348:
2343:
2338:
2333:
2328:
2323:
2318:
2313:
2308:
2303:
2298:
2293:
2283:
2278:
2273:
2268:
2263:
2258:
2256:Chlorpromazine
2253:
2248:
2243:
2238:
2233:
2228:
2219:
2217:
2206:
2205:
2195:
2194:
2187:
2180:
2172:
2163:
2162:
2159:
2158:
2157:
2156:
2153:
2142:
2136:
2130:
2129:
2126:
2125:
2123:
2122:
2117:
2112:
2103:
2098:
2093:
2088:
2083:
2078:
2076:citronella oil
2072:
2071:
2066:
2061:
2056:
2051:
2046:
2041:
2036:
2031:
2026:
2021:
2019:salicylic acid
2016:
2011:
2006:
2001:
1996:
1991:
1989:crystal violet
1986:
1981:
1976:
1974:chlorophetanol
1971:
1965:
1963:
1959:
1958:
1955:
1954:
1952:
1951:
1944:
1942:
1935:
1934:
1932:
1931:
1924:
1922:
1916:
1915:
1913:
1912:
1905:
1903:
1889:
1885:
1884:
1881:
1880:
1878:
1877:
1872:
1866:
1861:
1856:
1851:
1840:
1838:
1830:
1829:
1826:
1825:
1823:
1822:
1815:
1813:
1809:
1808:
1805:
1804:
1802:
1801:
1794:
1792:
1786:
1785:
1783:
1782:
1775:
1768:
1766:
1757:
1749:
1748:
1746:
1745:
1742:amphotericin B
1734:
1729:
1722:
1720:
1708:
1707:
1704:
1703:
1701:
1700:
1693:
1691:
1685:
1684:
1682:
1681:
1676:
1669:
1668:
1663:
1658:
1653:
1648:
1643:
1638:
1633:
1631:fosfluconazole
1628:
1621:
1620:
1615:
1610:
1603:
1601:
1595:
1594:
1592:
1591:
1587:
1586:
1581:
1576:
1571:
1566:
1561:
1556:
1551:
1546:
1541:
1536:
1531:
1526:
1521:
1516:
1511:
1506:
1501:
1496:
1491:
1484:
1482:
1473:
1457:
1446:
1440:
1439:
1423:
1422:
1415:
1408:
1400:
1392:
1391:
1352:
1317:
1310:
1292:
1265:
1242:
1223:
1194:(2): 240–248.
1174:
1125:
1082:
1075:
1057:
1029:
1018:(6): 827–843.
1002:
991:
971:
960:
940:
933:
899:
882:"Griseofulvin"
861:
860:
858:
855:
842:
839:
837:
834:
779:
776:
765:. It binds to
750:
747:
745:
742:
726:
723:
658:
657:
646:
645:
643:
642:
639:
637:
634:
626:
625:
624:
621:
620:
618:
617:
614:
606:
605:
604:
601:
600:
598:
597:
589:
587:
579:
578:
572:
566:
565:
562:
553:
547:
542:
536:
535:
531:
530:
520:
512:
511:
509:
508:
495:
493:
480:
479:
477:
476:
468:
466:
460:
459:
457:
456:
448:
446:
440:
439:
437:
436:
428:
426:
420:
419:
417:
416:
408:
406:
400:
399:
397:
396:
388:
386:
380:
379:
377:
376:
368:
366:
360:
359:
357:
356:
348:
346:
335:
334:
332:
331:
323:
321:
315:
314:
312:
311:
292:
284:
283:
282:
279:
278:
274:
273:
270:
261:
260:
246:
240:
239:
236:
230:
229:
222:
221:
219:
218:
206:
193:
179:
177:
171:
170:
166:
165:
163:
162:
139:
137:
131:
130:
125:
123:administration
117:
116:
114:
113:
111:
101:
99:
91:
90:
83:
77:
76:
69:
59:
58:
55:
49:
48:
44:
43:
35:
34:
15:
9:
6:
4:
3:
2:
3293:
3282:
3279:
3277:
3274:
3272:
3269:
3267:
3264:
3262:
3259:
3257:
3254:
3252:
3249:
3247:
3244:
3242:
3239:
3237:
3234:
3232:
3229:
3227:
3224:
3222:
3219:
3218:
3216:
3206:
3196:
3195:
3192:
3179:
3178:
3174:
3171:
3170:
3167:
3161:
3158:
3156:
3153:
3150:
3149:
3146:
3143:
3141:
3138:
3136:
3133:
3131:
3128:
3126:
3123:
3121:
3118:
3116:
3113:
3111:
3108:
3106:
3103:
3101:
3098:
3096:
3093:
3091:
3088:
3086:
3083:
3081:
3078:
3076:
3073:
3071:
3070:Sulfisoxazole
3068:
3066:
3063:
3061:
3058:
3056:
3053:
3051:
3048:
3046:
3043:
3041:
3038:
3036:
3033:
3031:
3028:
3026:
3023:
3021:
3018:
3016:
3013:
3011:
3008:
3006:
3003:
3001:
2998:
2996:
2993:
2991:
2988:
2986:
2983:
2981:
2978:
2976:
2973:
2971:
2968:
2966:
2963:
2961:
2958:
2956:
2953:
2951:
2948:
2946:
2945:Phenobarbital
2943:
2941:
2938:
2936:
2933:
2931:
2928:
2926:
2923:
2921:
2918:
2916:
2913:
2911:
2908:
2906:
2903:
2901:
2898:
2896:
2893:
2891:
2888:
2886:
2883:
2881:
2878:
2876:
2873:
2871:
2868:
2866:
2863:
2861:
2858:
2856:
2853:
2851:
2848:
2846:
2843:
2841:
2837:
2833:
2831:
2830:Levothyroxine
2828:
2826:
2823:
2821:
2818:
2816:
2814:
2810:
2808:
2805:
2803:
2800:
2798:
2795:
2793:
2792:Guggulsterone
2790:
2788:
2785:
2783:
2780:
2778:
2775:
2773:
2770:
2768:
2765:
2763:
2760:
2758:
2755:
2753:
2750:
2748:
2745:
2743:
2740:
2738:
2735:
2733:
2730:
2728:
2725:
2723:
2720:
2718:
2715:
2713:
2710:
2708:
2705:
2703:
2700:
2698:
2695:
2693:
2690:
2688:
2687:Dicloxacillin
2685:
2683:
2680:
2678:
2675:
2672:
2668:
2665:
2662:
2658:
2655:
2653:
2652:Dexamethasone
2650:
2648:
2645:
2643:
2640:
2638:
2635:
2633:
2630:
2628:
2625:
2623:
2620:
2618:
2615:
2613:
2610:
2608:
2605:
2603:
2600:
2598:
2595:
2593:
2590:
2588:
2587:Cephaloridine
2585:
2583:
2580:
2578:
2575:
2573:
2570:
2568:
2565:
2563:
2560:
2558:
2555:
2553:
2550:
2548:
2545:
2543:
2540:
2538:
2535:
2533:
2530:
2528:
2525:
2523:
2520:
2518:
2515:
2513:
2510:
2508:
2505:
2503:
2500:
2498:
2495:
2493:
2490:
2488:
2485:
2483:
2480:
2477:
2476:
2474:
2469:
2463:
2457:
2454:
2452:
2449:
2447:
2444:
2442:
2439:
2437:
2434:
2432:
2429:
2427:
2424:
2422:
2419:
2417:
2414:
2412:
2409:
2407:
2404:
2402:
2399:
2397:
2394:
2391:
2390:
2387:
2386:Valproic acid
2384:
2382:
2379:
2377:
2374:
2372:
2369:
2367:
2364:
2362:
2359:
2357:
2354:
2352:
2349:
2347:
2346:Phenobarbital
2344:
2342:
2339:
2337:
2334:
2332:
2329:
2327:
2324:
2322:
2319:
2317:
2314:
2312:
2309:
2307:
2304:
2302:
2299:
2297:
2294:
2291:
2287:
2284:
2282:
2279:
2277:
2274:
2272:
2269:
2267:
2264:
2262:
2259:
2257:
2254:
2252:
2249:
2247:
2246:Carbamazepine
2244:
2242:
2239:
2237:
2234:
2232:
2229:
2227:
2224:
2221:
2220:
2218:
2213:
2207:
2203:
2200:
2193:
2188:
2186:
2181:
2179:
2174:
2173:
2170:
2154:
2152:
2149:
2148:
2146:
2143:
2140:
2137:
2135:
2132:
2131:
2127:
2121:
2118:
2116:
2113:
2111:
2107:
2104:
2102:
2099:
2097:
2094:
2092:
2089:
2087:
2084:
2082:
2079:
2077:
2074:
2073:
2070:
2067:
2065:
2062:
2060:
2057:
2055:
2052:
2050:
2047:
2045:
2042:
2040:
2037:
2035:
2032:
2030:
2027:
2025:
2022:
2020:
2017:
2015:
2012:
2010:
2007:
2005:
2002:
2000:
1997:
1995:
1992:
1990:
1987:
1985:
1982:
1980:
1979:chlorphenesin
1977:
1975:
1972:
1970:
1967:
1966:
1964:
1960:
1950:
1946:
1945:
1943:
1940:
1936:
1930:
1926:
1925:
1923:
1921:
1917:
1911:
1907:
1906:
1904:
1902:
1897:
1893:
1890:
1888:Intracellular
1886:
1876:
1875:ibrexafungerp
1873:
1870:
1867:
1865:
1862:
1860:
1857:
1855:
1852:
1850:
1849:anidulafungin
1846:
1845:echinocandins
1842:
1841:
1839:
1835:
1831:
1821:
1817:
1816:
1814:
1810:
1800:
1796:
1795:
1793:
1791:
1787:
1779:
1776:
1774:
1770:
1769:
1767:
1765:
1761:
1758:
1754:
1750:
1743:
1738:
1735:
1733:
1730:
1728:
1724:
1723:
1721:
1718:
1713:
1709:
1699:
1695:
1694:
1692:
1690:
1686:
1680:
1677:
1675:
1671:
1670:
1667:
1664:
1662:
1659:
1657:
1656:oteseconazole
1654:
1652:
1649:
1647:
1646:isavuconazole
1644:
1642:
1639:
1637:
1634:
1632:
1629:
1627:
1623:
1622:
1619:
1616:
1614:
1611:
1609:
1608:efinaconazole
1605:
1604:
1602:
1600:
1596:
1589:
1588:
1585:
1582:
1580:
1577:
1575:
1574:sertaconazole
1572:
1570:
1567:
1565:
1562:
1560:
1557:
1555:
1552:
1550:
1547:
1545:
1542:
1540:
1537:
1535:
1532:
1530:
1529:fenticonazole
1527:
1525:
1522:
1520:
1517:
1515:
1512:
1510:
1507:
1505:
1502:
1500:
1499:chlormidazole
1497:
1495:
1492:
1490:
1486:
1485:
1483:
1481:
1477:
1474:
1471:
1465:
1461:
1458:
1454:
1450:
1447:
1441:
1436:
1432:
1428:
1421:
1416:
1414:
1409:
1407:
1402:
1401:
1398:
1387:
1383:
1379:
1375:
1371:
1367:
1363:
1356:
1348:
1344:
1340:
1336:
1332:
1328:
1321:
1313:
1307:
1303:
1296:
1288:
1284:
1280:
1276:
1269:
1261:
1257:
1253:
1246:
1238:
1234:
1227:
1219:
1215:
1210:
1205:
1201:
1197:
1193:
1189:
1185:
1178:
1170:
1166:
1161:
1156:
1152:
1148:
1144:
1140:
1136:
1129:
1121:
1117:
1113:
1109:
1105:
1101:
1097:
1093:
1086:
1078:
1076:3-8047-1763-2
1072:
1068:
1061:
1052:
1047:
1043:
1039:
1033:
1025:
1021:
1017:
1013:
1006:
998:
994:
988:
984:
983:
975:
967:
963:
961:9780683307405
957:
953:
952:
944:
936:
934:9789241547659
930:
925:
920:
916:
912:
906:
904:
887:
883:
877:
875:
873:
871:
869:
867:
862:
854:
852:
848:
833:
831:
827:
822:
818:
816:
811:
807:
803:
799:
794:
789:
787:
786:
775:
773:
768:
764:
760:
756:
741:
738:
734:
732:
722:
720:
716:
715:
709:
707:
703:
699:
695:
694:liver failure
691:
687:
683:
678:
676:
672:
668:
664:
654:
647:
638:
633:
632:
629:
622:
613:
612:
609:
602:
595:
591:
590:
588:
585:
580:
573:
571:
567:
543:
541:
537:
532:
528:
524:
521:
519:
517:ECHA InfoCard
513:
505:
501:
500:DTXSID8020674
497:
496:
494:
485:
481:
474:
470:
469:
467:
465:
461:
454:
450:
449:
447:
445:
441:
434:
430:
429:
427:
425:
421:
414:
410:
409:
407:
405:
401:
394:
390:
389:
387:
385:
381:
374:
370:
369:
367:
365:
361:
354:
350:
349:
347:
340:
336:
329:
325:
324:
322:
320:
316:
308:
304:
300:
296:
291:
290:
287:
280:
275:
271:
269:
262:
258:
254:
253:demethylation
250:
247:
245:
241:
237:
235:
231:
227:
223:
217:
207:
204:
194:
191:
181:
180:
178:
176:
172:
167:
159:
154:
149:
144:
141:
140:
138:
136:
132:
129:
126:
124:
118:
112:
103:
102:
100:
98:
92:
88:
84:
82:
78:
74:
70:
68:
64:
60:
56:
54:
50:
47:Clinical data
45:
41:
36:
32:
27:
19:
3241:Cyclohexenes
3236:Chloroarenes
3175:
3155:Ketoconazole
3152:Antagonists:
3151:
3125:Troglitazone
3100:Tetracycline
3055:Spiroxatrine
3000:Quingestrone
2995:Progesterone
2980:Pregnenolone
2975:Pregnanolone
2965:Pregnanediol
2960:Prednisolone
2885:Mifepristone
2812:
2787:Griseofulvin
2786:
2767:Fenbendazole
2752:Famprofazone
2747:Erythromycin
2742:Epothilone B
2727:Eburnamonine
2622:Clotrimazole
2612:Clofenvinfos
2547:Antimycotics
2478:
2441:Okadaic acid
2393:Antagonists:
2392:
2381:Troglitazone
2316:Mifepristone
2311:Methoxychlor
2306:Griseofulvin
2305:
2301:Ellagic acid
2281:Cypermethrin
2271:Clotrimazole
2222:
2101:tea tree oil
2086:lemon myrtle
1999:ethylparaben
1929:griseofulvin
1928:
1790:Benzylamines
1679:ravuconazole
1674:albaconazole
1666:voriconazole
1661:posaconazole
1651:itraconazole
1641:hexaconazole
1559:neticonazole
1549:luliconazole
1544:ketoconazole
1534:flutrimazole
1519:eberconazole
1509:clotrimazole
1494:butoconazole
1365:
1361:
1355:
1330:
1326:
1320:
1301:
1295:
1278:
1274:
1268:
1251:
1245:
1236:
1232:
1226:
1191:
1187:
1177:
1142:
1138:
1128:
1095:
1091:
1085:
1066:
1060:
1051:10665/325771
1041:
1032:
1015:
1011:
1005:
981:
974:
950:
943:
914:
890:. Retrieved
844:
825:
814:
806:benzophenone
804:to form the
792:
790:
783:
781:
778:Biosynthesis
772:dermatophyte
752:
744:Pharmacology
735:
728:
725:Medical uses
712:
710:
679:
663:Griseofulvin
662:
661:
650:
306:
302:
298:
294:
265:Elimination
175:Legal status
169:Legal status
23:Griseofulvin
18:
3221:Antifungals
3140:Zafirlukast
3110:Thiothixene
3090:Terconazole
3040:Simvastatin
2915:Nisoldipine
2910:Nilvadipine
2895:Nicardipine
2865:Metacycline
2692:Dimercaprol
2647:Demecolcine
2607:Clindamycin
2602:Ciglitazone
2552:Artemisinin
2532:Ambrisentan
2436:Nigramide J
2371:Telmisartan
2331:Nicardipine
2241:Benfuracarb
2236:Artemisinin
2141:from market
2120:pentamidine
2081:lemon grass
2039:taurolidine
2009:polynoxylin
1910:flucytosine
1854:caspofungin
1778:terbinafine
1764:Allylamines
1626:fluconazole
1618:terconazole
1613:fluconazole
1584:tioconazole
1579:sulconazole
1569:oxiconazole
1564:omoconazole
1539:isoconazole
1514:croconazole
1472:inhibitors)
1470:demethylase
1427:Antifungals
1372:: 495–537.
924:10665/44053
759:microtubule
737:Terbinafine
577: g·mol
523:100.004.335
453:CHEBI:27779
277:Identifiers
81:MedlinePlus
53:Trade names
3215:Categories
3120:Tianeptine
3085:Tenylidone
3080:Tacrolimus
3025:Rimexolone
3015:Rifampicin
2955:Plicamycin
2940:Paclitaxel
2925:Omeprazole
2905:Nifedipine
2880:Mevastatin
2875:Metyrapone
2855:Lovastatin
2850:Loratadine
2807:Hyperforin
2797:Haloprogin
2762:Felodipine
2737:Enzacamene
2717:Dronabinol
2682:Diclazuril
2661:prasterone
2617:Chloroxine
2592:Cephradine
2562:Bile acids
2376:Tolnaftate
2341:Permethrin
2326:Nevirapine
2321:Nefazodone
2290:prasterone
2251:Carvedilol
2231:Amiodarone
2202:modulators
2110:atovaquone
2091:orange oil
2054:tolnaftate
2049:tolciclate
2034:sulbentine
2004:haloprogin
1984:ciclopirox
1949:tavaborole
1941:inhibitors
1927:Systemic:
1908:Systemic:
1869:rezafungin
1864:micafungin
1859:cilofungin
1843:Systemic:
1837:inhibitors
1820:amorolfine
1799:butenafine
1756:inhibitors
1740:Systemic:
1717:ergosterol
1624:Systemic:
1554:miconazole
1504:climbazole
1489:bifonazole
1480:Imidazoles
1456:inhibitors
1453:Ergosterol
1281:(4): 360.
1092:Pediatrics
892:8 December
857:References
836:Toxicology
810:methylated
582:3D model (
570:Molar mass
413:32HRV3E3D5
384:ChemSpider
319:CAS Number
286:IUPAC name
272:9–21 hours
244:Metabolism
3045:Sirolimus
3035:Ritonavir
3030:Riodipine
3020:Rifaximin
3005:Reserpine
2990:Proadifen
2935:Oxatomide
2890:Nafcillin
2860:Meclizine
2722:Droxidopa
2702:Docetaxel
2627:Colforsin
2577:Bumecaine
2567:Bithionol
2479:Agonists:
2456:T-0901317
2431:Meclizine
2361:Reserpine
2351:Phenytoin
2336:Octicizer
2296:Efavirenz
2223:Agonists:
2151:Phase III
2139:Withdrawn
2096:patchouli
2044:ticlatone
1947:Topical:
1818:Topical:
1797:Topical:
1773:naftifine
1771:Topical:
1744:, hamycin
1732:natamycin
1725:Topical:
1698:abafungin
1696:Topical:
1689:Thiazoles
1672:Unknown:
1606:Topical:
1599:Triazoles
1524:econazole
1487:Topical:
702:pregnancy
698:porphyria
473:ChEMBL562
267:half-life
121:Routes of
95:Pregnancy
73:Monograph
67:Drugs.com
3261:Mutagens
3205:Medicine
3172:See also
3060:SR-12813
2950:Piperine
2930:Orlistat
2900:Nicotine
2772:Fentanyl
2757:Febantel
2732:Ecopipam
2697:Dinaline
2582:Cafestol
2572:Bosentan
2446:PK-11195
1994:dimazole
1737:nystatin
1719:binding)
1445:membrane
1254:: 3977.
1218:16746904
1169:27169520
1120:34976866
1112:15520113
1040:(2019).
997:Archived
966:Archived
886:Archived
690:diarrhea
653:(verify)
364:DrugBank
328:126-07-8
135:ATC code
128:By mouth
97:category
3160:Sesamin
3145:Zeranol
3075:Suramin
2845:LOE-908
2537:AMI-193
2451:S-07662
2366:TCPOBOP
2261:Chrysin
2115:dapsone
1727:hamycin
1386:9347226
1209:1264363
1160:8691867
798:Claisen
767:keratin
763:mitosis
755:tubulin
706:mitosis
540:Formula
373:DB00400
339:PubChem
155: (
153:D01BA01
151:)
145: (
143:D01AA08
110: D
87:a682295
3191:Portal
2667:DHEA-S
2507:AA-861
2134:WHO-EM
1962:Others
1812:Others
1464:Azoles
1384:
1347:956563
1345:
1308:
1216:
1206:
1167:
1157:
1118:
1110:
1073:
989:
958:
931:
821:phenol
686:nausea
665:is an
608:SMILES
575:352.77
464:ChEMBL
433:D00209
393:389934
353:441140
216:â„ž-only
214:
201:
188:
2266:CITCO
1443:Wall/
1368:(5).
1116:S2CID
830:NADPH
675:nails
628:InChI
584:JSmol
444:ChEBI
249:Liver
2838:and
2657:DHEA
2421:AITC
2286:DHEA
1433:and
1382:PMID
1343:PMID
1306:ISBN
1214:PMID
1165:PMID
1143:2016
1108:PMID
1071:ISBN
987:ISBN
956:ISBN
929:ISBN
894:2016
847:mice
841:Mice
812:via
800:and
424:KEGG
404:UNII
255:and
228:data
63:AHFS
2467:PXR
2211:CAR
2106:PCP
1435:J02
1431:D01
1374:doi
1335:doi
1283:doi
1256:doi
1204:PMC
1196:doi
1155:PMC
1147:doi
1100:doi
1096:114
1046:hdl
1020:doi
919:hdl
696:or
489:EPA
343:CID
305:,4'
297:,6'
203:POM
158:WHO
148:WHO
3217::
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688:,
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184:AU
106:AU
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