538:
515:
51:
42:
3211:
834:
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
806:
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
750:
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.
780:
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
861:
785:
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.
200:
604:
2200:
3145:
1371:
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".
1101:
Fleece D, Gaughan JP, Aronoff SC (November 2004). "Griseofulvin versus terbinafine in the treatment of tinea capitis: a meta-analysis of randomized, clinical trials".
2421:
2411:
2236:
2426:
3286:
145:
2193:
2406:
3075:
2186:
3241:
2276:
2446:
2251:
73:
3261:
3095:
618:
1195:"Studies in the biochemistry of micro-organisms: Griseofulvin, C(17)H(17)O(6)Cl, a metabolic product of Penicillium griseo-fulvum Dierckx"
2587:
2466:
2346:
840:
1007:
976:
3070:
2767:
2707:
2855:
2461:
2376:
839:-methylated by SAM to generate dehydrogriseofulvin. Ultimately, a stereoselective reduction of the olefin on dehydrogriseofulvin by
2517:
835:
oxygen radical on the left ring forming a tetrahydrofuranone species. The newly formed grisan skeleton with a spiro center is then
896:
2144:
1428:
1320:
1001:
729:
1284:
Birch A (1953). "Studies in relation to biosynthesis I. Some possible routes to derivatives of orcinol and phloroglucinol".
646:
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
663:
3266:
1085:
970:
943:
638:
3291:
2220:
2161:
2995:
860:
by Yokoo et al. 1979. The same team went on to find a similar effect on mice by a chemically unrelated substance,
830:(SAM) twice to yield griseophenone C. The griseophenone C is then halogenated at the activated site ortho to the
296:
185:
3256:
2677:
1911:
744:. It is ineffective topically. It is reserved for cases in which topical treatment with creams is ineffective.
1478:
3187:
533:
414:
2722:
2416:
2209:
494:
3276:
3201:
2497:
2492:
483:
3236:
1979:
1949:
1421:
1048:
921:
2980:
2527:
2366:
3281:
3105:
3020:
1844:
795:
724:
510:
17:
1242:
Grove JF, Ismay D, Macmillan J, Mulholland TP, Rogers MA (1951). "The structure of griseofulvin".
2149:
2079:
1261:
Grove JF, MacMillan J, Mulholland TP, Rogers MA (1952). "762. Griseofulvin. Part IV. Structure".
131:
63:
2667:
2296:
2116:
1763:
991:
960:
463:
3251:
3246:
824:
688:
and scalp, as well as the skin when antifungal creams have not worked. It is taken by mouth.
677:
2512:
2502:
403:
3231:
2850:
2822:
2812:
2431:
1414:
808:
423:
275:
2507:
8:
2652:
2552:
2476:
2178:
1906:
1722:
1380:
1080:(in German) (8 ed.). Stuttgart: Wissenschaftliche Verlagsgesellschaft. p. 838.
338:
329:
138:
2846:
537:
514:
3125:
2880:
2681:
2212:
2069:
2039:
2034:
1219:
1194:
1170:
1145:
1126:
812:
692:
105:
703:, headache, trouble sleeping, and feeling tired. It is not recommended in people with
3271:
2830:
2537:
1930:
1392:
1353:
1316:
1224:
1175:
1118:
1081:
997:
966:
939:
226:
213:
97:
1130:
892:
83:
3115:
2835:
2717:
2647:
2532:
2522:
2436:
2286:
2074:
2024:
1384:
1345:
1293:
1266:
1214:
1206:
1165:
1161:
1157:
1110:
1056:
1030:
929:
550:
363:
236:
168:
158:
3215:
2792:
2687:
2567:
1656:
1646:
1336:
Harris CM, Roberson JS, Harris TM (August 1976). "Biosynthesis of griseofulvin".
741:
681:
267:
254:
244:
3140:
3060:
2930:
2787:
2642:
2607:
2266:
2155:
2086:
2029:
1999:
1984:
1752:
1641:
1388:
715:
may result in harm to the baby. Griseofulvin works by interfering with fungal
3225:
3080:
2955:
2840:
2802:
2697:
2662:
2597:
2396:
2356:
2256:
1989:
1885:
1859:
1666:
1618:
1584:
1539:
1509:
704:
685:
526:
263:
33:
1406:
3165:
3135:
3110:
3065:
3010:
3005:
2990:
2985:
2975:
2970:
2895:
2777:
2762:
2757:
2752:
2737:
2632:
2622:
2451:
2391:
2326:
2321:
2311:
2291:
2281:
2111:
2096:
2009:
1855:
1689:
1684:
1676:
1671:
1661:
1651:
1569:
1559:
1554:
1544:
1529:
1519:
1504:
1445:
1441:
1228:
1179:
1144:
Chen X, Jiang X, Yang M, González U, Lin X, Hua X, et al. (May 2016).
1122:
1114:
1053:
World Health
Organization model list of essential medicines: 21st list 2019
816:
782:
163:
153:
1396:
3150:
3120:
3100:
3050:
2925:
2920:
2905:
2875:
2702:
2657:
2617:
2612:
2562:
2557:
2542:
2381:
2341:
2246:
2130:
2091:
2049:
2019:
1920:
1864:
1800:
1788:
1636:
1628:
1623:
1594:
1589:
1579:
1574:
1549:
1524:
1357:
1270:
769:
747:
91:
1349:
1061:
383:
3130:
3090:
3035:
3025:
2965:
2950:
2935:
2915:
2890:
2885:
2865:
2860:
2817:
2807:
2772:
2747:
2727:
2692:
2671:
2627:
2602:
2386:
2351:
2336:
2331:
2300:
2261:
2241:
2120:
2101:
2064:
2059:
2044:
2014:
1994:
1959:
1879:
1874:
1869:
1830:
1809:
1774:
1727:
1564:
1514:
1499:
1463:
1437:
1021:
Beekman AM, Barrow RA (2014). "Fungal metabolites as pharmaceuticals".
934:
820:
580:
394:
1297:
1210:
3055:
3045:
3040:
3030:
3015:
3000:
2945:
2900:
2870:
2732:
2712:
2637:
2577:
2572:
2441:
2371:
2361:
2306:
2106:
2054:
1783:
1742:
1708:
1534:
1490:
712:
708:
349:
77:
1034:
2960:
2940:
2910:
2782:
2742:
2592:
2582:
2456:
2004:
1747:
1699:
1609:
700:
443:
374:
603:
50:
3170:
3155:
3085:
2547:
2271:
2125:
1737:
777:
773:
765:
716:
831:
696:
474:
41:
1370:
1260:
1474:
1313:
Medicinal
Natural Products: A Biosynthetic Approach (3rd ed.)
1241:
857:
594:
454:
259:
499:
1146:"Systemic antifungal therapy for tinea capitis in children"
434:
2208:
1047:
920:
722:
Griseofulvin was discovered in 1939 from the soil fungus
2221:
1075:
1065:. WHO/MVP/EMP/IAU/2019.06. License: CC BY-NC-SA 3.0 IGO.
1192:
730:
856:
Griseofulvin is found to alter the bile metabolism of
802:
The first step in the biosynthesis of griseofulvin by
3199:
1364:
1143:
895:. The American Society of Health-System Pharmacists.
793:
It is produced industrially by fermenting the fungus
1335:
1193:
Oxford AE, Raistrick H, Simonart P (February 1939).
1100:
819:
intermediate. The benzophenone intermediate is then
684:(ringworm). This includes fungal infections of the
965:. Lippincott Williams & Wilkins. p. 631.
3223:
362:
924:(2009). Stuart MC, Kouimtzi M, Hill SR (eds.).
864:, in Yokoo et al. 1982 and Tsunoo et al. 1987.
337:
1014:
27:Antifungal medication used for dermatophytoses
3287:World Health Organization essential medicines
2194:
1436:
1422:
1020:
962:Disinfection, Sterilization, and Preservation
626:O=C2c3c(O21C(/OC)=C\C(=O)C1C)c(Cl)c(OC)cc3OC
312:)- 7-chloro- 2',4,6-trimethoxy- 6'-methyl- 3
2477:
1150:The Cochrane Database of Systematic Reviews
2528:Allopregnanedione (5α-dihydroprogesterone)
2201:
2187:
1429:
1415:
928:. World Health Organization. p. 149.
887:
885:
883:
881:
879:
877:
536:
513:
402:
49:
40:
1263:Journal of the Chemical Society (Resumed)
1218:
1169:
1060:
983:
933:
916:
914:
862:3,5-diethoxycarbonyl-1,4-dihydrocollidine
422:
2226:Tooltip Constitutive androstane receptor
1338:Journal of the American Chemical Society
1076:Mutschler E, Schäfer-Korting M (2001).
996:. Synapse Info Resources. p. 406.
874:
509:
382:
96:
14:
3224:
2981:Pregnanedione (5β-dihydroprogesterone)
2367:Pregnanedione (5β-dihydroprogesterone)
1310:
1041:
1010:from the original on 31 December 2013.
989:
979:from the original on 20 December 2016.
911:
527:
207:
3242:Benzofuran ethers at the benzene ring
2182:
1410:
1283:
1055:. Geneva: World Health Organization.
958:
899:from the original on 20 December 2016
740:Griseofulvin is used orally only for
711:. Use during or in the months before
482:
462:
220:
82:
167:
157:
3262:Halogen-containing natural products
759:
680:used to treat a number of types of
442:
353:
24:
25:
3303:
1315:. UK: John Wiley & Sons Ltd.
194:
116:
3209:
567:
561:
1912:thymidylate synthase inhibitors
1329:
1304:
1286:Australian Journal of Chemistry
1277:
1254:
1235:
1186:
1023:Australian Journal of Chemistry
788:
754:
735:
651:Key:DDUHZTYCFQRHIY-RBHXEPJQSA-N
2533:Allopregnanolone (brexanolone)
1373:Critical Reviews in Toxicology
1162:10.1002/14651858.CD004685.pub3
1137:
1094:
1069:
952:
570:
555:
13:
1:
3188:Receptor/signaling modulators
3146:Tropanyl 3,5-dimethulbenzoate
2996:Pregnenolone 16α-carbonitrile
867:
846:
68:Gris-peg, Grifulvin V, others
691:Common side effects include
7:
2723:Dodecylbenzenesulfonic acid
2482:Tooltip Pregnane X receptor
2210:Xenobiotic-sensing receptor
249:Highly variable (25 to 70%)
10:
3308:
772:function, thus inhibiting
545:Chemical and physical data
3267:IARC Group 2B carcinogens
3179:
2475:
2219:
2139:
1980:bromochlorosalicylanilide
1972:
1950:Aminoacyl tRNA synthetase
1948:
1929:
1905:
1898:
1843:
1822:
1799:
1773:
1762:
1721:
1698:
1608:
1489:
1473:
1462:
1453:
1389:10.3109/10408449709078444
1049:World Health Organization
993:Handbook of Preservatives
922:World Health Organization
659:
634:
614:
592:
579:
549:
544:
525:
493:
473:
453:
433:
413:
393:
373:
348:
328:
292:
287:
274:
253:
243:
235:
184:
179:
144:
130:
104:
90:
72:
62:
57:
48:
39:
3106:Testosterone isocaproate
3021:Reverse triiodothyronine
926:WHO Model Formulary 2008
796:Penicillium griseofulvum
725:Penicillium griseofulvum
3292:Terpenes and terpenoids
2498:17α-Hydroxyprogesterone
2493:17α-Hydroxypregnenolone
1199:The Biochemical Journal
851:
320:-spiro ene]- 3,4'-dione
1764:Squalene monooxygenase
1601:Systemic: ketoconazole
1244:Chemistry and Industry
1115:10.1542/peds.2004-0428
843:affords griseofulvin.
3257:Disulfiram-like drugs
2237:6,7-Dimethylesculetin
1792:Systemic: terbinafine
1078:Arzneimittelwirkungen
990:Ash M, Ash I (2004).
678:antifungal medication
2824:Hypericum perforatum
2813:Hetacillin potassium
2080:Whitfield's ointment
1907:Pyrimidine analogues
1723:Polyene antimycotics
1381:Taylor & Francis
1271:10.1039/JR9520003977
828:-adenosyl methionine
2653:Cyproterone acetate
2553:Amlodipine besylate
1350:10.1021/ja00433a053
768:, interfering with
216:(Prescription only)
203:(Prescription only)
36:
3126:Thonzonium bromide
2881:Methylprednisolone
2682:prasterone sulfate
2166:Never to phase III
2070:tribromometacresol
2040:sodium thiosulfate
2035:selenium disulfide
1931:Mitotic inhibitors
1311:Dewick PM (2009).
1250:. London: 219–220.
813:aldol condensation
764:The drug binds to
693:allergic reactions
32:
3277:Resorcinol ethers
3197:
3196:
2831:Indinavir sulfate
2538:Alpha-Lipoic acid
2513:Δ-Androstenedione
2503:Δ-Androstenedione
2176:
2175:
1968:
1967:
1894:
1893:
1845:β-glucan synthase
1839:
1838:
1818:
1817:
1717:
1716:
1344:(17): 5380–5386.
1322:978-0-471-97478-9
1298:10.1071/ch9530360
1211:10.1042/bj0330240
1003:978-1-890595-66-1
959:Block SS (2001).
671:
670:
605:Interactive image
495:CompTox Dashboard
224:
211:
198:
120:
16:(Redirected from
3299:
3237:Aromatic ketones
3214:
3213:
3212:
3205:
3116:Thiamylal sodium
2851:Îł-linolenic acid
2847:α-Linolenic acid
2845:Linolenic acid:
2836:Lasalocid sodium
2826:(St John's wort)
2718:Docusate calcium
2648:Cyclophosphamide
2523:Allopregnanediol
2508:Δ-Androstenediol
2483:
2479:
2437:Ethinylestradiol
2287:Cyclophosphamide
2227:
2223:
2203:
2196:
2189:
2180:
2179:
2075:undecylenic acid
2025:potassium iodide
1903:
1902:
1771:
1770:
1487:
1486:
1471:
1470:
1460:
1459:
1431:
1424:
1417:
1408:
1407:
1401:
1400:
1368:
1362:
1361:
1333:
1327:
1326:
1308:
1302:
1301:
1281:
1275:
1274:
1258:
1252:
1251:
1239:
1233:
1232:
1222:
1190:
1184:
1183:
1173:
1141:
1135:
1134:
1109:(5): 1312–1315.
1098:
1092:
1091:
1073:
1067:
1066:
1064:
1045:
1039:
1038:
1018:
1012:
1011:
987:
981:
980:
956:
950:
949:
937:
918:
909:
908:
906:
904:
889:
760:Pharmacodynamics
667:
666:
607:
587:
572:
569:
563:
557:
540:
529:
518:
517:
503:
501:
486:
466:
446:
426:
406:
386:
366:
356:
355:
341:
279:
222:
219:
209:
206:
196:
193:
171:
161:
118:
115:
100:
86:
53:
44:
37:
35:
31:
21:
3307:
3306:
3302:
3301:
3300:
3298:
3297:
3296:
3282:Spiro compounds
3222:
3221:
3220:
3210:
3208:
3200:
3198:
3193:
3175:
3076:Suberoylanilide
2793:Fluorometholone
2688:Dibunate sodium
2568:Aurothioglucose
2481:
2471:
2407:3,17β-Estradiol
2225:
2215:
2207:
2177:
2172:
2171:
2156:Clinical trials
2135:
1964:
1944:
1925:
1910:
1890:
1847:
1835:
1814:
1795:
1791:
1766:
1758:
1750:
1725:
1713:
1694:
1647:fosravuconazole
1604:
1480:
1479:lanosterol 14α-
1466:
1455:
1449:
1435:
1405:
1404:
1369:
1365:
1334:
1330:
1323:
1309:
1305:
1282:
1278:
1259:
1255:
1240:
1236:
1191:
1187:
1156:(5): CD004685.
1142:
1138:
1099:
1095:
1088:
1074:
1070:
1046:
1042:
1035:10.1071/ch13639
1019:
1015:
1004:
988:
984:
973:
957:
953:
946:
919:
912:
902:
900:
891:
890:
875:
870:
854:
849:
804:P. griseofulvin
791:
762:
757:
742:dermatophytosis
738:
728:. It is on the
682:dermatophytoses
662:
660:
655:
652:
647:
642:
641:
630:
627:
622:
621:
610:
585:
575:
566:
560:
521:
497:
489:
469:
449:
429:
409:
389:
369:
352:
344:
324:
321:
300:
299:
277:
268:glucuronidation
245:Bioavailability
237:Pharmacokinetic
231:
175:
133:
126:
107:
28:
23:
22:
15:
12:
11:
5:
3305:
3295:
3294:
3289:
3284:
3279:
3274:
3269:
3264:
3259:
3254:
3249:
3244:
3239:
3234:
3219:
3218:
3195:
3194:
3192:
3191:
3184:
3180:
3177:
3176:
3174:
3173:
3168:
3159:
3158:
3153:
3148:
3143:
3141:Troleandomycin
3138:
3133:
3128:
3123:
3118:
3113:
3108:
3103:
3098:
3093:
3088:
3083:
3078:
3073:
3068:
3063:
3061:Spironolactone
3058:
3053:
3048:
3043:
3038:
3033:
3028:
3023:
3018:
3013:
3008:
3003:
2998:
2993:
2988:
2983:
2978:
2973:
2968:
2963:
2958:
2953:
2948:
2943:
2938:
2933:
2931:Norelgestromin
2928:
2923:
2918:
2913:
2908:
2903:
2898:
2893:
2888:
2883:
2878:
2873:
2868:
2863:
2858:
2853:
2843:
2838:
2833:
2828:
2820:
2815:
2810:
2805:
2800:
2795:
2790:
2788:Flucloxacillin
2785:
2780:
2775:
2770:
2765:
2760:
2755:
2750:
2745:
2740:
2735:
2730:
2725:
2720:
2715:
2710:
2705:
2700:
2695:
2690:
2685:
2675:
2665:
2660:
2655:
2650:
2645:
2643:Corticosterone
2640:
2635:
2630:
2625:
2620:
2615:
2610:
2608:Chlorpromazine
2605:
2600:
2595:
2590:
2585:
2580:
2575:
2570:
2565:
2560:
2555:
2550:
2545:
2540:
2535:
2530:
2525:
2520:
2515:
2510:
2505:
2500:
2495:
2486:
2484:
2473:
2472:
2470:
2469:
2464:
2459:
2454:
2449:
2444:
2439:
2434:
2429:
2427:17-Androstanol
2424:
2422:3β-Androstanol
2419:
2417:3α-Androstenol
2414:
2412:3α-Androstanol
2409:
2400:
2399:
2394:
2389:
2384:
2379:
2374:
2369:
2364:
2359:
2354:
2349:
2344:
2339:
2334:
2329:
2324:
2319:
2314:
2309:
2304:
2294:
2289:
2284:
2279:
2274:
2269:
2267:Chlorpromazine
2264:
2259:
2254:
2249:
2244:
2239:
2230:
2228:
2217:
2216:
2206:
2205:
2198:
2191:
2183:
2174:
2173:
2170:
2169:
2168:
2167:
2164:
2153:
2147:
2141:
2140:
2137:
2136:
2134:
2133:
2128:
2123:
2114:
2109:
2104:
2099:
2094:
2089:
2087:citronella oil
2083:
2082:
2077:
2072:
2067:
2062:
2057:
2052:
2047:
2042:
2037:
2032:
2030:salicylic acid
2027:
2022:
2017:
2012:
2007:
2002:
2000:crystal violet
1997:
1992:
1987:
1985:chlorophetanol
1982:
1976:
1974:
1970:
1969:
1966:
1965:
1963:
1962:
1955:
1953:
1946:
1945:
1943:
1942:
1935:
1933:
1927:
1926:
1924:
1923:
1916:
1914:
1900:
1896:
1895:
1892:
1891:
1889:
1888:
1883:
1877:
1872:
1867:
1862:
1851:
1849:
1841:
1840:
1837:
1836:
1834:
1833:
1826:
1824:
1820:
1819:
1816:
1815:
1813:
1812:
1805:
1803:
1797:
1796:
1794:
1793:
1786:
1779:
1777:
1768:
1760:
1759:
1757:
1756:
1753:amphotericin B
1745:
1740:
1733:
1731:
1719:
1718:
1715:
1714:
1712:
1711:
1704:
1702:
1696:
1695:
1693:
1692:
1687:
1680:
1679:
1674:
1669:
1664:
1659:
1654:
1649:
1644:
1642:fosfluconazole
1639:
1632:
1631:
1626:
1621:
1614:
1612:
1606:
1605:
1603:
1602:
1598:
1597:
1592:
1587:
1582:
1577:
1572:
1567:
1562:
1557:
1552:
1547:
1542:
1537:
1532:
1527:
1522:
1517:
1512:
1507:
1502:
1495:
1493:
1484:
1468:
1457:
1451:
1450:
1434:
1433:
1426:
1419:
1411:
1403:
1402:
1363:
1328:
1321:
1303:
1276:
1253:
1234:
1205:(2): 240–248.
1185:
1136:
1093:
1086:
1068:
1040:
1029:(6): 827–843.
1013:
1002:
982:
971:
951:
944:
910:
893:"Griseofulvin"
872:
871:
869:
866:
853:
850:
848:
845:
790:
787:
776:. It binds to
761:
758:
756:
753:
737:
734:
669:
668:
657:
656:
654:
653:
650:
648:
645:
637:
636:
635:
632:
631:
629:
628:
625:
617:
616:
615:
612:
611:
609:
608:
600:
598:
590:
589:
583:
577:
576:
573:
564:
558:
553:
547:
546:
542:
541:
531:
523:
522:
520:
519:
506:
504:
491:
490:
488:
487:
479:
477:
471:
470:
468:
467:
459:
457:
451:
450:
448:
447:
439:
437:
431:
430:
428:
427:
419:
417:
411:
410:
408:
407:
399:
397:
391:
390:
388:
387:
379:
377:
371:
370:
368:
367:
359:
357:
346:
345:
343:
342:
334:
332:
326:
325:
323:
322:
303:
295:
294:
293:
290:
289:
285:
284:
281:
272:
271:
257:
251:
250:
247:
241:
240:
233:
232:
230:
229:
217:
204:
190:
188:
182:
181:
177:
176:
174:
173:
150:
148:
142:
141:
136:
134:administration
128:
127:
125:
124:
122:
112:
110:
102:
101:
94:
88:
87:
80:
70:
69:
66:
60:
59:
55:
54:
46:
45:
26:
9:
6:
4:
3:
2:
3304:
3293:
3290:
3288:
3285:
3283:
3280:
3278:
3275:
3273:
3270:
3268:
3265:
3263:
3260:
3258:
3255:
3253:
3250:
3248:
3245:
3243:
3240:
3238:
3235:
3233:
3230:
3229:
3227:
3217:
3207:
3206:
3203:
3190:
3189:
3185:
3182:
3181:
3178:
3172:
3169:
3167:
3164:
3161:
3160:
3157:
3154:
3152:
3149:
3147:
3144:
3142:
3139:
3137:
3134:
3132:
3129:
3127:
3124:
3122:
3119:
3117:
3114:
3112:
3109:
3107:
3104:
3102:
3099:
3097:
3094:
3092:
3089:
3087:
3084:
3082:
3081:Sulfisoxazole
3079:
3077:
3074:
3072:
3069:
3067:
3064:
3062:
3059:
3057:
3054:
3052:
3049:
3047:
3044:
3042:
3039:
3037:
3034:
3032:
3029:
3027:
3024:
3022:
3019:
3017:
3014:
3012:
3009:
3007:
3004:
3002:
2999:
2997:
2994:
2992:
2989:
2987:
2984:
2982:
2979:
2977:
2974:
2972:
2969:
2967:
2964:
2962:
2959:
2957:
2956:Phenobarbital
2954:
2952:
2949:
2947:
2944:
2942:
2939:
2937:
2934:
2932:
2929:
2927:
2924:
2922:
2919:
2917:
2914:
2912:
2909:
2907:
2904:
2902:
2899:
2897:
2894:
2892:
2889:
2887:
2884:
2882:
2879:
2877:
2874:
2872:
2869:
2867:
2864:
2862:
2859:
2857:
2854:
2852:
2848:
2844:
2842:
2841:Levothyroxine
2839:
2837:
2834:
2832:
2829:
2827:
2825:
2821:
2819:
2816:
2814:
2811:
2809:
2806:
2804:
2803:Guggulsterone
2801:
2799:
2796:
2794:
2791:
2789:
2786:
2784:
2781:
2779:
2776:
2774:
2771:
2769:
2766:
2764:
2761:
2759:
2756:
2754:
2751:
2749:
2746:
2744:
2741:
2739:
2736:
2734:
2731:
2729:
2726:
2724:
2721:
2719:
2716:
2714:
2711:
2709:
2706:
2704:
2701:
2699:
2698:Dicloxacillin
2696:
2694:
2691:
2689:
2686:
2683:
2679:
2676:
2673:
2669:
2666:
2664:
2663:Dexamethasone
2661:
2659:
2656:
2654:
2651:
2649:
2646:
2644:
2641:
2639:
2636:
2634:
2631:
2629:
2626:
2624:
2621:
2619:
2616:
2614:
2611:
2609:
2606:
2604:
2601:
2599:
2598:Cephaloridine
2596:
2594:
2591:
2589:
2586:
2584:
2581:
2579:
2576:
2574:
2571:
2569:
2566:
2564:
2561:
2559:
2556:
2554:
2551:
2549:
2546:
2544:
2541:
2539:
2536:
2534:
2531:
2529:
2526:
2524:
2521:
2519:
2516:
2514:
2511:
2509:
2506:
2504:
2501:
2499:
2496:
2494:
2491:
2488:
2487:
2485:
2480:
2474:
2468:
2465:
2463:
2460:
2458:
2455:
2453:
2450:
2448:
2445:
2443:
2440:
2438:
2435:
2433:
2430:
2428:
2425:
2423:
2420:
2418:
2415:
2413:
2410:
2408:
2405:
2402:
2401:
2398:
2397:Valproic acid
2395:
2393:
2390:
2388:
2385:
2383:
2380:
2378:
2375:
2373:
2370:
2368:
2365:
2363:
2360:
2358:
2357:Phenobarbital
2355:
2353:
2350:
2348:
2345:
2343:
2340:
2338:
2335:
2333:
2330:
2328:
2325:
2323:
2320:
2318:
2315:
2313:
2310:
2308:
2305:
2302:
2298:
2295:
2293:
2290:
2288:
2285:
2283:
2280:
2278:
2275:
2273:
2270:
2268:
2265:
2263:
2260:
2258:
2257:Carbamazepine
2255:
2253:
2250:
2248:
2245:
2243:
2240:
2238:
2235:
2232:
2231:
2229:
2224:
2218:
2214:
2211:
2204:
2199:
2197:
2192:
2190:
2185:
2184:
2181:
2165:
2163:
2160:
2159:
2157:
2154:
2151:
2148:
2146:
2143:
2142:
2138:
2132:
2129:
2127:
2124:
2122:
2118:
2115:
2113:
2110:
2108:
2105:
2103:
2100:
2098:
2095:
2093:
2090:
2088:
2085:
2084:
2081:
2078:
2076:
2073:
2071:
2068:
2066:
2063:
2061:
2058:
2056:
2053:
2051:
2048:
2046:
2043:
2041:
2038:
2036:
2033:
2031:
2028:
2026:
2023:
2021:
2018:
2016:
2013:
2011:
2008:
2006:
2003:
2001:
1998:
1996:
1993:
1991:
1990:chlorphenesin
1988:
1986:
1983:
1981:
1978:
1977:
1975:
1971:
1961:
1957:
1956:
1954:
1951:
1947:
1941:
1937:
1936:
1934:
1932:
1928:
1922:
1918:
1917:
1915:
1913:
1908:
1904:
1901:
1899:Intracellular
1897:
1887:
1886:ibrexafungerp
1884:
1881:
1878:
1876:
1873:
1871:
1868:
1866:
1863:
1861:
1860:anidulafungin
1857:
1856:echinocandins
1853:
1852:
1850:
1846:
1842:
1832:
1828:
1827:
1825:
1821:
1811:
1807:
1806:
1804:
1802:
1798:
1790:
1787:
1785:
1781:
1780:
1778:
1776:
1772:
1769:
1765:
1761:
1754:
1749:
1746:
1744:
1741:
1739:
1735:
1734:
1732:
1729:
1724:
1720:
1710:
1706:
1705:
1703:
1701:
1697:
1691:
1688:
1686:
1682:
1681:
1678:
1675:
1673:
1670:
1668:
1667:oteseconazole
1665:
1663:
1660:
1658:
1657:isavuconazole
1655:
1653:
1650:
1648:
1645:
1643:
1640:
1638:
1634:
1633:
1630:
1627:
1625:
1622:
1620:
1619:efinaconazole
1616:
1615:
1613:
1611:
1607:
1600:
1599:
1596:
1593:
1591:
1588:
1586:
1585:sertaconazole
1583:
1581:
1578:
1576:
1573:
1571:
1568:
1566:
1563:
1561:
1558:
1556:
1553:
1551:
1548:
1546:
1543:
1541:
1540:fenticonazole
1538:
1536:
1533:
1531:
1528:
1526:
1523:
1521:
1518:
1516:
1513:
1511:
1510:chlormidazole
1508:
1506:
1503:
1501:
1497:
1496:
1494:
1492:
1488:
1485:
1482:
1476:
1472:
1469:
1465:
1461:
1458:
1452:
1447:
1443:
1439:
1432:
1427:
1425:
1420:
1418:
1413:
1412:
1409:
1398:
1394:
1390:
1386:
1382:
1378:
1374:
1367:
1359:
1355:
1351:
1347:
1343:
1339:
1332:
1324:
1318:
1314:
1307:
1299:
1295:
1291:
1287:
1280:
1272:
1268:
1264:
1257:
1249:
1245:
1238:
1230:
1226:
1221:
1216:
1212:
1208:
1204:
1200:
1196:
1189:
1181:
1177:
1172:
1167:
1163:
1159:
1155:
1151:
1147:
1140:
1132:
1128:
1124:
1120:
1116:
1112:
1108:
1104:
1097:
1089:
1087:3-8047-1763-2
1083:
1079:
1072:
1063:
1058:
1054:
1050:
1044:
1036:
1032:
1028:
1024:
1017:
1009:
1005:
999:
995:
994:
986:
978:
974:
972:9780683307405
968:
964:
963:
955:
947:
945:9789241547659
941:
936:
931:
927:
923:
917:
915:
898:
894:
888:
886:
884:
882:
880:
878:
873:
865:
863:
859:
844:
842:
838:
833:
829:
827:
822:
818:
814:
810:
805:
800:
798:
797:
786:
784:
779:
775:
771:
767:
752:
749:
745:
743:
733:
731:
727:
726:
720:
718:
714:
710:
706:
705:liver failure
702:
698:
694:
689:
687:
683:
679:
675:
665:
658:
649:
644:
643:
640:
633:
624:
623:
620:
613:
606:
602:
601:
599:
596:
591:
584:
582:
578:
554:
552:
548:
543:
539:
535:
532:
530:
528:ECHA InfoCard
524:
516:
512:
511:DTXSID8020674
508:
507:
505:
496:
492:
485:
481:
480:
478:
476:
472:
465:
461:
460:
458:
456:
452:
445:
441:
440:
438:
436:
432:
425:
421:
420:
418:
416:
412:
405:
401:
400:
398:
396:
392:
385:
381:
380:
378:
376:
372:
365:
361:
360:
358:
351:
347:
340:
336:
335:
333:
331:
327:
319:
315:
311:
307:
302:
301:
298:
291:
286:
282:
280:
273:
269:
265:
264:demethylation
261:
258:
256:
252:
248:
246:
242:
238:
234:
228:
218:
215:
205:
202:
192:
191:
189:
187:
183:
178:
170:
165:
160:
155:
152:
151:
149:
147:
143:
140:
137:
135:
129:
123:
114:
113:
111:
109:
103:
99:
95:
93:
89:
85:
81:
79:
75:
71:
67:
65:
61:
58:Clinical data
56:
52:
47:
43:
38:
30:
19:
3252:Cyclohexenes
3247:Chloroarenes
3186:
3166:Ketoconazole
3163:Antagonists:
3162:
3136:Troglitazone
3111:Tetracycline
3066:Spiroxatrine
3011:Quingestrone
3006:Progesterone
2991:Pregnenolone
2986:Pregnanolone
2976:Pregnanediol
2971:Prednisolone
2896:Mifepristone
2823:
2798:Griseofulvin
2797:
2778:Fenbendazole
2763:Famprofazone
2758:Erythromycin
2753:Epothilone B
2738:Eburnamonine
2633:Clotrimazole
2623:Clofenvinfos
2558:Antimycotics
2489:
2452:Okadaic acid
2404:Antagonists:
2403:
2392:Troglitazone
2327:Mifepristone
2322:Methoxychlor
2317:Griseofulvin
2316:
2312:Ellagic acid
2292:Cypermethrin
2282:Clotrimazole
2233:
2112:tea tree oil
2097:lemon myrtle
2010:ethylparaben
1940:griseofulvin
1939:
1801:Benzylamines
1690:ravuconazole
1685:albaconazole
1677:voriconazole
1672:posaconazole
1662:itraconazole
1652:hexaconazole
1570:neticonazole
1560:luliconazole
1555:ketoconazole
1545:flutrimazole
1530:eberconazole
1520:clotrimazole
1505:butoconazole
1376:
1372:
1366:
1341:
1337:
1331:
1312:
1306:
1289:
1285:
1279:
1262:
1256:
1247:
1243:
1237:
1202:
1198:
1188:
1153:
1149:
1139:
1106:
1102:
1096:
1077:
1071:
1062:10665/325771
1052:
1043:
1026:
1022:
1016:
992:
985:
961:
954:
925:
901:. Retrieved
855:
836:
825:
817:benzophenone
815:to form the
803:
801:
794:
792:
789:Biosynthesis
783:dermatophyte
763:
755:Pharmacology
746:
739:
736:Medical uses
723:
721:
690:
674:Griseofulvin
673:
672:
661:
317:
313:
309:
305:
276:Elimination
186:Legal status
180:Legal status
34:Griseofulvin
29:
3232:Antifungals
3151:Zafirlukast
3121:Thiothixene
3101:Terconazole
3051:Simvastatin
2926:Nisoldipine
2921:Nilvadipine
2906:Nicardipine
2876:Metacycline
2703:Dimercaprol
2658:Demecolcine
2618:Clindamycin
2613:Ciglitazone
2563:Artemisinin
2543:Ambrisentan
2447:Nigramide J
2382:Telmisartan
2342:Nicardipine
2252:Benfuracarb
2247:Artemisinin
2152:from market
2131:pentamidine
2092:lemon grass
2050:taurolidine
2020:polynoxylin
1921:flucytosine
1865:caspofungin
1789:terbinafine
1775:Allylamines
1637:fluconazole
1629:terconazole
1624:fluconazole
1595:tioconazole
1590:sulconazole
1580:oxiconazole
1575:omoconazole
1550:isoconazole
1525:croconazole
1483:inhibitors)
1481:demethylase
1438:Antifungals
1383:: 495–537.
935:10665/44053
770:microtubule
748:Terbinafine
588: g·mol
534:100.004.335
464:CHEBI:27779
288:Identifiers
92:MedlinePlus
64:Trade names
3226:Categories
3131:Tianeptine
3096:Tenylidone
3091:Tacrolimus
3036:Rimexolone
3026:Rifampicin
2966:Plicamycin
2951:Paclitaxel
2936:Omeprazole
2916:Nifedipine
2891:Mevastatin
2886:Metyrapone
2866:Lovastatin
2861:Loratadine
2818:Hyperforin
2808:Haloprogin
2773:Felodipine
2748:Enzacamene
2728:Dronabinol
2693:Diclazuril
2672:prasterone
2628:Chloroxine
2603:Cephradine
2573:Bile acids
2387:Tolnaftate
2352:Permethrin
2337:Nevirapine
2332:Nefazodone
2301:prasterone
2262:Carvedilol
2242:Amiodarone
2213:modulators
2121:atovaquone
2102:orange oil
2065:tolnaftate
2060:tolciclate
2045:sulbentine
2015:haloprogin
1995:ciclopirox
1960:tavaborole
1952:inhibitors
1938:Systemic:
1919:Systemic:
1880:rezafungin
1875:micafungin
1870:cilofungin
1854:Systemic:
1848:inhibitors
1831:amorolfine
1810:butenafine
1767:inhibitors
1751:Systemic:
1728:ergosterol
1635:Systemic:
1565:miconazole
1515:climbazole
1500:bifonazole
1491:Imidazoles
1467:inhibitors
1464:Ergosterol
1292:(4): 360.
1103:Pediatrics
903:8 December
868:References
847:Toxicology
821:methylated
593:3D model (
581:Molar mass
424:32HRV3E3D5
395:ChemSpider
330:CAS Number
297:IUPAC name
283:9–21 hours
255:Metabolism
3056:Sirolimus
3046:Ritonavir
3041:Riodipine
3031:Rifaximin
3016:Reserpine
3001:Proadifen
2946:Oxatomide
2901:Nafcillin
2871:Meclizine
2733:Droxidopa
2713:Docetaxel
2638:Colforsin
2588:Bumecaine
2578:Bithionol
2490:Agonists:
2467:T-0901317
2442:Meclizine
2372:Reserpine
2362:Phenytoin
2347:Octicizer
2307:Efavirenz
2234:Agonists:
2162:Phase III
2150:Withdrawn
2107:patchouli
2055:ticlatone
1958:Topical:
1829:Topical:
1808:Topical:
1784:naftifine
1782:Topical:
1755:, hamycin
1743:natamycin
1736:Topical:
1709:abafungin
1707:Topical:
1700:Thiazoles
1683:Unknown:
1617:Topical:
1610:Triazoles
1535:econazole
1498:Topical:
713:pregnancy
709:porphyria
484:ChEMBL562
278:half-life
132:Routes of
106:Pregnancy
84:Monograph
78:Drugs.com
3272:Mutagens
3216:Medicine
3183:See also
3071:SR-12813
2961:Piperine
2941:Orlistat
2911:Nicotine
2783:Fentanyl
2768:Febantel
2743:Ecopipam
2708:Dinaline
2593:Cafestol
2583:Bosentan
2457:PK-11195
2005:dimazole
1748:nystatin
1730:binding)
1456:membrane
1265:: 3977.
1229:16746904
1180:27169520
1131:34976866
1123:15520113
1051:(2019).
1008:Archived
977:Archived
897:Archived
701:diarrhea
664:(verify)
375:DrugBank
339:126-07-8
146:ATC code
139:By mouth
108:category
18:Xuanjing
3171:Sesamin
3156:Zeranol
3086:Suramin
2856:LOE-908
2548:AMI-193
2462:S-07662
2377:TCPOBOP
2272:Chrysin
2126:dapsone
1738:hamycin
1397:9347226
1220:1264363
1171:8691867
809:Claisen
778:keratin
774:mitosis
766:tubulin
717:mitosis
551:Formula
384:DB00400
350:PubChem
166: (
164:D01BA01
162:)
156: (
154:D01AA08
121: D
98:a682295
3202:Portal
2678:DHEA-S
2518:AA-861
2145:WHO-EM
1973:Others
1823:Others
1475:Azoles
1395:
1358:956563
1356:
1319:
1227:
1217:
1178:
1168:
1129:
1121:
1084:
1000:
969:
942:
832:phenol
697:nausea
676:is an
619:SMILES
586:352.77
475:ChEMBL
444:D00209
404:389934
364:441140
227:â„ž-only
225:
212:
199:
2277:CITCO
1454:Wall/
1379:(5).
1127:S2CID
841:NADPH
686:nails
639:InChI
595:JSmol
455:ChEBI
260:Liver
2849:and
2668:DHEA
2432:AITC
2297:DHEA
1444:and
1393:PMID
1354:PMID
1317:ISBN
1225:PMID
1176:PMID
1154:2016
1119:PMID
1082:ISBN
998:ISBN
967:ISBN
940:ISBN
905:2016
858:mice
852:Mice
823:via
811:and
435:KEGG
415:UNII
266:and
239:data
74:AHFS
2478:PXR
2222:CAR
2117:PCP
1446:J02
1442:D01
1385:doi
1346:doi
1294:doi
1267:doi
1215:PMC
1207:doi
1166:PMC
1158:doi
1111:doi
1107:114
1057:hdl
1031:doi
930:hdl
707:or
500:EPA
354:CID
316:,4'
308:,6'
214:POM
169:WHO
159:WHO
3228::
2158::
2119::
1391:.
1377:27
1375:.
1352:.
1342:98
1340:.
1288:.
1248:11
1246:.
1223:.
1213:.
1203:33
1201:.
1197:.
1174:.
1164:.
1152:.
1148:.
1125:.
1117:.
1105:.
1027:67
1025:.
1006:.
975:.
938:.
913:^
876:^
799:.
732:.
719:.
699:,
695:,
568:Cl
565:17
559:17
304:(2
221:US
208:UK
201:S4
195:AU
117:AU
3204::
2684:)
2680:(
2674:)
2670:(
2303:)
2299:(
2202:e
2195:t
2188:v
1909:/
1882:)
1858:(
1726:(
1477:(
1448:)
1440:(
1430:e
1423:t
1416:v
1399:.
1387::
1360:.
1348::
1325:.
1300:.
1296::
1290:6
1273:.
1269::
1231:.
1209::
1182:.
1160::
1133:.
1113::
1090:.
1059::
1037:.
1033::
948:.
932::
907:.
837:O
826:S
597:)
574:6
571:O
562:H
556:C
502:)
498:(
318:H
314:H
310:R
306:S
270:)
262:(
223::
210::
197::
172:)
119::
76:/
20:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
