456:
433:
699:(FDA) guidelines, despite demonstrating similar plasma retinoid levels as adapalene and tretinoin, which were classified as Category C drugs. Under the FDA's updated Pregnancy and Lactation Labeling Rule which eliminated the lettered pregnancy categories and came into effect in 2015, tazarotene was determined to be contraindicated in pregnancy. Because of the lack of pregnancy outcomes data for the drug, the determination was based on the teratogenic effects observed in rat and rabbit studies.
40:
824:
31:
715:
Adverse effects for tazarotene include skin irritation, such as redness, itchiness, and burning. In patients with psoriasis, these adverse effects can be mitigated by a combined treatment with either
1075:
2723:
94:
1500:
Tang-Liu DD, Matsumoto RM, Usansky JI (October 1999). "Clinical pharmacokinetics and drug metabolism of tazarotene: a novel topical treatment for acne and psoriasis".
900:
3126:
1919:
62:
3200:
539:
808:
for tazarotenic acid is 1.97 L/kg. Tazarotene is excreted from the body via feces and urine equally, and it has an elimination half-life of 16 to 18 hours.
1109:
2716:
1657:
1618:
1769:
1063:
525:
2251:
2709:
2351:
2295:
1863:
792:
More than 99% of tazarotenic acid, the active metabolite of tazarotene, in the blood binds to plasma proteins (the most predominant being
707:
Tazarotene is contraindicated for use in patients who are known to be or suspected of being pregnant. Tazarotene is a known teratogen.
1912:
559:
777:
567:
InChI=1S/C21H21NO2S/c1-4-24-20(23)16-7-9-17(22-14-16)8-5-15-6-10-19-18(13-15)21(2,3)11-12-25-19/h6-7,9-10,13-14H,4,11-12H2,1-3H3
3185:
210:
139:
695:
Before 2015, tazarotene was considered a
Category X drug (meaning its use was contraindicated during pregnancy) according to
2266:
1905:
875:. The anion from the reaction of the acetylene with base is then used to displace chlorine from Ethyl 6-chloronicotinate (
765:
3205:
3170:
3143:
2256:
1650:
1454:
Heath MS, Sahni DR, Curry ZA, Feldman SR (September 2018). "Pharmacokinetics of tazarotene and acitretin in psoriasis".
1134:
Kolli SS, Pecone D, Pona A, Cline A, Feldman SR (June 2019). "Topical
Retinoids in Acne Vulgaris: A Systematic Review".
1103:
1069:
696:
332:
2973:
2759:
3175:
2312:
1880:
1419:
Duvic M, Nagpal S, Asano AT, Chandraratna RA (August 1997). "Molecular mechanisms of tazarotene action in psoriasis".
412:
3180:
2281:
2246:
2344:
2271:
3091:
1097:
2073:
757:
1034:
723:. These effects tend to be mild to moderate, and increase in intensity as tazarotene concentration increases.
281:
3190:
2300:
1868:
1643:
860:
769:
80:
451:
2743:
797:
179:
3195:
2261:
272:
2690:
401:
3011:
2892:
817:
3006:
2337:
2276:
1614:
602:
189:
2957:
2116:
1225:
Stratigos AJ, Katsambas AD (2005). "The role of topical retinoids in the treatment of photoaging".
679:
Tazarotene can also be used for the treatment of photodamaged skin. It can reduce the clinical and
428:
227:
2544:
683:
signs of photodamaged skin. The therapy is more effective when used with the daily application of
3165:
2735:
1959:
1525:
1479:
1250:
1207:
1159:
852:
843:). Friedel-Crafts cyclization of the olefin with the equivalent of PPA then gives the thiopyran (
753:
716:
625:
2912:
2680:
1326:"Use of Topical Tazarotene for the Treatment of Acne Vulgaris in Pregnancy: A Literature Review"
3071:
3031:
3026:
3021:
2773:
3081:
3051:
2937:
2927:
2778:
2732:
2012:
1997:
1595:
1560:
1517:
1471:
1436:
1398:
1347:
1301:
1242:
1199:
1151:
951:
868:
381:
153:
52:
3001:
2922:
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2827:
2822:
2817:
2812:
2807:
3121:
3116:
3111:
3106:
3101:
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2832:
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2401:
2149:
2002:
1954:
1587:
1552:
1509:
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1388:
1378:
1337:
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1281:
1234:
1191:
1143:
941:
657:
610:
468:
236:
171:
2902:
2842:
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341:
848:
321:
455:
432:
39:
2484:
2474:
2459:
2396:
2391:
2381:
2306:
2131:
1992:
1874:
1393:
1367:"Retinoids in the treatment of skin aging: an overview of clinical efficacy and safety"
1366:
1342:
1325:
1296:
1269:
673:
668:, for the treatment of acne. This results in increased efficacy compared to tazarotene
1556:
1432:
3159:
3036:
2867:
2622:
2587:
2567:
2554:
2479:
2469:
2406:
2386:
2068:
2035:
1987:
1964:
1928:
1666:
1513:
1238:
1211:
1195:
970:
946:
929:
905:
637:
444:
1529:
1483:
1254:
1163:
823:
3016:
2978:
2882:
2862:
2857:
2764:
2670:
2650:
2572:
2534:
2524:
2504:
2489:
2416:
2174:
2121:
2111:
2106:
2063:
1969:
1949:
1932:
1764:
1753:
1670:
745:
720:
118:
113:
107:
102:
1467:
1005:
72:
1635:
261:
2897:
2852:
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2529:
2509:
2494:
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2446:
2436:
2426:
2210:
2194:
2179:
2087:
2082:
2077:
2053:
2045:
2020:
1979:
1817:
1812:
1737:
928:
Thielitz A, Abdel-Naser MB, Fluhr JW, Zouboulis CC, Gollnick H (December 2008).
672:. For psoriasis, a combination therapy of tazarotene and a mid- to high-potency
669:
661:
2701:
1147:
2996:
2847:
2660:
2655:
2539:
2519:
2499:
2360:
1941:
1840:
1779:
1774:
1732:
1706:
1625:
1383:
832:
773:
618:
501:
312:
123:
3127:
6-(N-ethyl-N-(5-isobutoxy-4-isopropyl-2-(E)-styrylphenyl)amino)nicotinic acid
1897:
831:
The formation of the ring system involves first alkylation of the anion from
3045:
2987:
2947:
2876:
2793:
2788:
2783:
2685:
2645:
2597:
2230:
2189:
2169:
2144:
2126:
2025:
1845:
1822:
1759:
1714:
1591:
1543:
Marks R (October 1998). "Pharmacokinetics and safety review of tazarotene".
761:
749:
684:
680:
653:
649:
645:
641:
621:
and photodamaged skin. It is a member of the acetylenic class of retinoids.
66:
1599:
1521:
1475:
1402:
1351:
1305:
1246:
1155:
955:
22:
1564:
1440:
1203:
2637:
2582:
2431:
2421:
2411:
2368:
2220:
2215:
2161:
2139:
1832:
1724:
1696:
1365:
Mukherjee S, Date A, Patravale V, Korting HC, Roeder A, Weindl G (2006).
781:
741:
737:
606:
292:
301:
3041:
2872:
2627:
2617:
2225:
2098:
2058:
2030:
793:
665:
247:
87:
30:
1286:
901:"Health product highlights 2021: Annexes of products approved in 2021"
820:, with selective affinity for retinoic acid receptors RARβ and RARγ.
624:
Tazarotene was approved for medical use in 1997 and is available as a
2592:
2514:
1578:
Menter A (August 2000). "Pharmacokinetics and safety of tazarotene".
392:
871:
in the presence of excess base to give the corresponding acetylene
361:
2577:
822:
736:
Tazarotene is selective for two types of retinoic acid receptors,
524:
515:
372:
816:
Acetylenic retinoid prodrug converted to the active metabolite,
614:
352:
2705:
2333:
1901:
1639:
2329:
1692:
1270:"A review of tazarotene in the treatment of photodamaged skin"
1182:
Foster RH, Brogden RN, Benfield P (May 1998). "Tazarotene".
417:
879:). This reaction affords the coupling product tazarotene (
148:
930:"Topical retinoids in acne--an evidence-based overview"
584:
969:
American
Society of Health-System Pharmacists, Inc.
636:
Tazarotene is most commonly used topically to treat
2956:
2742:
2636:
2606:
2553:
2445:
2367:
2239:
2203:
2160:
2097:
2044:
2011:
1978:
1940:
1831:
1805:
1798:
1746:
1723:
1705:
1685:
1678:
513:
500:
467:
462:
443:
411:
391:
371:
351:
331:
311:
291:
280:
271:
246:
226:
201:
188:
178:
170:
138:
133:
93:
79:
61:
51:
46:
764:expression and downregulating the expression of
744:. Like all retinoids, it affects the ability of
260:
1012:. American Society of Health-System Pharmacists
859:). Reaction of the enolate of that ketone with
676:is more effective than either treatment alone.
617:. Tazarotene is also used as a therapeutic for
235:
2744:
1035:"Arazlo (tazarotene) [package insert]"
2717:
2345:
1913:
1651:
1324:Han G, Wu JJ, Del Rosso JQ (September 2020).
867:as a transient intermediate. This eliminates
8:
1414:
1412:
1177:
1175:
1173:
609:. It is primarily used for the treatment of
21:
2958:
1495:
1493:
1129:
1127:
163:In general: ℞ (Prescription only)
2724:
2710:
2702:
2352:
2338:
2330:
1920:
1906:
1898:
1802:
1682:
1658:
1644:
1636:
1319:
1317:
1315:
454:
431:
320:
1392:
1382:
1341:
1295:
1285:
945:
547:O=C(OCC)c1ccc(nc1)C#Cc3ccc2SCCC(c2c3)(C)C
340:
1268:Ogden S, Samuel M, Griffiths CE (2008).
1029:
1027:
1006:"Tazarotene Monograph for Professionals"
1098:"Competitive Generic Therapy Approvals"
1000:
998:
996:
994:
992:
892:
804:) for tazarotene is 26.1 L/kg and the V
564:
544:
427:
300:
215:
2252:Clindamycin/adapalene/benzoyl peroxide
601:, among others, is a third-generation
445:
20:
400:
380:
71:
7:
2945:Retinoic acid metabolism inhibitors:
117:
106:
3201:Heterocyclic compounds with 2 rings
1064:"2022 First Generic Drug Approvals"
1044:. U.S. Food and Drug Administration
977:. U.S. National Library of Medicine
360:
251:
1112:from the original on June 29, 2023
1078:from the original on June 30, 2023
656:, tazarotene can be combined with
14:
1514:10.2165/00003088-199937040-00001
1239:10.2165/00003495-200565080-00003
1196:10.2165/00003495-199855050-00008
947:10.1111/j.1610-0387.2008.06741.x
778:epidermal growth factor receptor
485:
479:
38:
29:
660:or an oral antibiotic, such as
572:Key:OGQICQVSFDPSEI-UHFFFAOYSA-N
2749:Tooltip Retinoic acid receptor
1629:(1988, 1992 both to Allergan).
1456:Expert Opin Drug Metab Toxicol
494:
488:
473:
218:ethyl 6-pyridine-3-carboxylate
1:
3144:Receptor/signaling modulators
2983:-Retinoic acid (alitretinoin)
2769:-Retinoic acid (alitretinoin)
2267:Erythromycin/benzoyl peroxide
1557:10.1016/s0190-9622(98)70310-x
1468:10.1080/17425255.2018.1515198
1433:10.1016/S0190-9622(97)80396-9
1190:(5): 705–11, discussion 712.
766:keratinocyte transglutaminase
760:. It does so by upregulating
2257:Clindamycin/benzoyl peroxide
1104:Food and Drug Administration
1070:Food and Drug Administration
975:MedlinePlus Drug Information
835:with dimethylallyl bromide (
697:Food and Drug Administration
597:, sold under the brand name
2963:Tooltip Retinoid X receptor
16:Topical retinoid medication
3222:
3092:LE135 (RAR beta selective)
2992:-Retinoic acid (tretinoin)
2798:-Retinoic acid (tretinoin)
2282:Tretinoin/benzoyl peroxide
2247:Adapalene/benzoyl peroxide
1770:Calcipotriol/betamethasone
1148:10.1007/s40257-019-00423-z
463:Chemical and physical data
3135:
2290:
2272:Erythromycin/isotretinoin
1858:
1384:10.2147/ciia.2006.1.4.327
863:gives the enol phosphate
855:gives the methyl ketone (
839:) to give the thioether (
580:
555:
535:
206:
37:
28:
1667:Drugs used for psoriasis
1612:Prepn: Chandraratna RA,
1592:10.1067/mjd.2000.108321
1330:J Clin Aesthet Dermatol
861:diethyl chlorophosphate
770:ornithine decarboxylase
3186:Anti-acne preparations
2607:Vitamin A retinoids (C
828:
798:volume of distribution
2262:Clindamycin/tretinoin
1626:U.S. patent 5,089,509
827:Tazarotene synthesis:
826:
644:. Like other topical
3007:Docosahexaenoic acid
2277:Sulfacetamide/sulfur
934:J Dtsch Dermatol Ges
122:) (combination with
3206:Sulfur heterocycles
3171:Benzene derivatives
2117:Cyproterone acetate
851:in the presence of
732:Mechanism of action
25:
3176:Alkyne derivatives
2317:Never to phase III
1965:Blue light therapy
1960:8-Hydroxyquinoline
1931:-treating agents (
1885:Never to phase III
1580:J Am Acad Dermatol
1551:(4 Pt 2): S134–8.
1545:J Am Acad Dermatol
1502:Clin Pharmacokinet
1427:(2 Pt 3): S18–24.
1421:J Am Acad Dermatol
1136:Am J Clin Dermatol
853:aluminium chloride
847:). Acylation with
829:
717:mometasone furoate
626:generic medication
3181:Nicotinate esters
3153:
3152:
2733:Retinoid receptor
2699:
2698:
2691:Zuretinol acetate
2327:
2326:
2036:Red light therapy
2013:Anti-inflammatory
1895:
1894:
1854:
1853:
1794:
1793:
1586:(2 Pt 3): S31–5.
1371:Clin Interv Aging
1287:10.2147/cia.s1101
1274:Clin Interv Aging
1108:. June 29, 2023.
1074:. March 3, 2023.
869:diethyl phosphite
703:Contraindications
592:
591:
526:Interactive image
413:CompTox Dashboard
151:
3213:
3012:Fluorobexarotene
2964:
2960:
2893:Tazarotenic acid
2750:
2746:
2726:
2719:
2712:
2703:
2354:
2347:
2340:
2331:
2150:Ethinylestradiol
2003:Benzoyl peroxide
1955:Benzoyl peroxide
1922:
1915:
1908:
1899:
1803:
1683:
1660:
1653:
1646:
1637:
1630:
1628:
1622:
1621:
1617:
1610:
1604:
1603:
1575:
1569:
1568:
1540:
1534:
1533:
1497:
1488:
1487:
1451:
1445:
1444:
1416:
1407:
1406:
1396:
1386:
1362:
1356:
1355:
1345:
1321:
1310:
1309:
1299:
1289:
1265:
1259:
1258:
1222:
1216:
1215:
1179:
1168:
1167:
1131:
1122:
1121:
1119:
1117:
1094:
1088:
1087:
1085:
1083:
1060:
1054:
1053:
1051:
1049:
1039:
1031:
1022:
1021:
1019:
1017:
1002:
987:
986:
984:
982:
966:
960:
959:
949:
925:
919:
918:
916:
914:
909:. August 3, 2022
897:
818:tazarotenic acid
788:Pharmacokinetics
658:benzoyl peroxide
611:plaque psoriasis
588:
587:
528:
508:
496:
490:
487:
481:
475:
458:
447:
436:
435:
421:
419:
404:
384:
364:
344:
324:
304:
284:
264:
254:
253:
239:
193:
159:
150:
147:
121:
110:
75:
42:
33:
26:
24:
3221:
3220:
3216:
3215:
3214:
3212:
3211:
3210:
3156:
3155:
3154:
3149:
3131:
2962:
2952:
2748:
2738:
2730:
2700:
2695:
2632:
2610:
2602:
2560:
2549:
2452:
2441:
2374:
2363:
2358:
2328:
2323:
2322:
2307:Clinical trials
2286:
2235:
2199:
2156:
2093:
2040:
2007:
1974:
1936:
1926:
1896:
1891:
1890:
1875:Clinical trials
1850:
1827:
1790:
1742:
1719:
1701:
1674:
1664:
1634:
1633:
1624:
1619:
1613:
1611:
1607:
1577:
1576:
1572:
1542:
1541:
1537:
1499:
1498:
1491:
1453:
1452:
1448:
1418:
1417:
1410:
1364:
1363:
1359:
1323:
1322:
1313:
1267:
1266:
1262:
1224:
1223:
1219:
1181:
1180:
1171:
1133:
1132:
1125:
1115:
1113:
1096:
1095:
1091:
1081:
1079:
1062:
1061:
1057:
1047:
1045:
1037:
1033:
1032:
1025:
1015:
1013:
1004:
1003:
990:
980:
978:
968:
967:
963:
940:(12): 1023–31.
927:
926:
922:
912:
910:
899:
898:
894:
889:
849:acetyl chloride
814:
807:
803:
790:
734:
729:
713:
711:Adverse effects
705:
693:
634:
583:
581:
576:
573:
568:
563:
562:
551:
548:
543:
542:
531:
506:
493:
484:
478:
439:
415:
407:
387:
367:
347:
327:
307:
287:
267:
250:
242:
222:
219:
214:
213:
191:
180:Protein binding
172:Pharmacokinetic
166:
157:
129:
112:
82:
57:Tazorac, others
17:
12:
11:
5:
3219:
3217:
3209:
3208:
3203:
3198:
3193:
3191:Antipsoriatics
3188:
3183:
3178:
3173:
3168:
3158:
3157:
3151:
3150:
3148:
3147:
3140:
3136:
3133:
3132:
3130:
3129:
3124:
3119:
3114:
3109:
3104:
3099:
3094:
3089:
3084:
3079:
3074:
3069:
3064:
3055:
3054:
3049:
3039:
3034:
3029:
3024:
3019:
3014:
3009:
3004:
2999:
2994:
2985:
2976:
2967:
2965:
2954:
2953:
2951:
2950:
2941:
2940:
2935:
2930:
2925:
2920:
2915:
2906:
2905:
2900:
2895:
2890:
2885:
2880:
2870:
2865:
2860:
2855:
2850:
2845:
2840:
2835:
2830:
2825:
2820:
2815:
2810:
2805:
2800:
2791:
2786:
2781:
2776:
2771:
2762:
2753:
2751:
2740:
2739:
2731:
2729:
2728:
2721:
2714:
2706:
2697:
2696:
2694:
2693:
2688:
2683:
2678:
2673:
2668:
2663:
2658:
2653:
2648:
2642:
2640:
2638:Retinoid drugs
2634:
2633:
2631:
2630:
2625:
2620:
2614:
2612:
2608:
2604:
2603:
2601:
2600:
2595:
2590:
2585:
2580:
2575:
2570:
2564:
2562:
2558:
2555:Apocarotenoids
2551:
2550:
2548:
2547:
2542:
2537:
2532:
2527:
2522:
2517:
2512:
2507:
2502:
2497:
2492:
2487:
2485:Diadinoxanthin
2482:
2477:
2475:Citranaxanthin
2472:
2467:
2462:
2460:Antheraxanthin
2456:
2454:
2450:
2443:
2442:
2440:
2439:
2434:
2429:
2424:
2419:
2414:
2409:
2404:
2399:
2394:
2389:
2384:
2378:
2376:
2372:
2365:
2364:
2359:
2357:
2356:
2349:
2342:
2334:
2325:
2324:
2321:
2320:
2319:
2318:
2315:
2304:
2298:
2292:
2291:
2288:
2287:
2285:
2284:
2279:
2274:
2269:
2264:
2259:
2254:
2249:
2243:
2241:
2237:
2236:
2234:
2233:
2228:
2223:
2218:
2213:
2207:
2205:
2201:
2200:
2198:
2197:
2192:
2187:
2182:
2177:
2172:
2166:
2164:
2158:
2157:
2155:
2154:
2153:
2152:
2147:
2137:
2136:
2135:
2132:Spironolactone
2129:
2124:
2119:
2114:
2103:
2101:
2095:
2094:
2092:
2091:
2085:
2080:
2071:
2066:
2061:
2056:
2050:
2048:
2042:
2041:
2039:
2038:
2033:
2028:
2023:
2017:
2015:
2009:
2008:
2006:
2005:
2000:
1995:
1993:Salicylic acid
1990:
1984:
1982:
1976:
1975:
1973:
1972:
1967:
1962:
1957:
1952:
1946:
1944:
1938:
1937:
1927:
1925:
1924:
1917:
1910:
1902:
1893:
1892:
1889:
1888:
1887:
1886:
1883:
1872:
1866:
1860:
1859:
1856:
1855:
1852:
1851:
1849:
1848:
1843:
1837:
1835:
1829:
1828:
1826:
1825:
1820:
1815:
1809:
1807:
1800:
1796:
1795:
1792:
1791:
1789:
1788:
1783:
1777:
1772:
1767:
1756:
1750:
1748:
1744:
1743:
1741:
1740:
1735:
1729:
1727:
1721:
1720:
1718:
1717:
1711:
1709:
1703:
1702:
1700:
1699:
1689:
1687:
1680:
1676:
1675:
1665:
1663:
1662:
1655:
1648:
1640:
1632:
1631:
1605:
1570:
1535:
1489:
1462:(9): 919–927.
1446:
1408:
1357:
1336:(9): E59–E65.
1311:
1260:
1233:(8): 1061–72.
1217:
1169:
1142:(3): 345–365.
1123:
1089:
1055:
1023:
988:
961:
920:
891:
890:
888:
885:
813:
810:
805:
801:
789:
786:
780:, and various
733:
730:
728:
725:
712:
709:
704:
701:
692:
689:
674:corticosteroid
633:
630:
590:
589:
578:
577:
575:
574:
571:
569:
566:
558:
557:
556:
553:
552:
550:
549:
546:
538:
537:
536:
533:
532:
530:
529:
521:
519:
511:
510:
504:
498:
497:
491:
482:
476:
471:
465:
464:
460:
459:
449:
441:
440:
438:
437:
424:
422:
409:
408:
406:
405:
397:
395:
389:
388:
386:
385:
377:
375:
369:
368:
366:
365:
357:
355:
349:
348:
346:
345:
337:
335:
329:
328:
326:
325:
317:
315:
309:
308:
306:
305:
297:
295:
289:
288:
286:
285:
277:
275:
269:
268:
266:
265:
257:
255:
244:
243:
241:
240:
232:
230:
224:
223:
221:
220:
217:
209:
208:
207:
204:
203:
199:
198:
195:
186:
185:
182:
176:
175:
168:
167:
165:
164:
161:
144:
142:
136:
135:
131:
130:
128:
127:
99:
97:
91:
90:
85:
83:administration
77:
76:
69:
59:
58:
55:
49:
48:
44:
43:
35:
34:
15:
13:
10:
9:
6:
4:
3:
2:
3218:
3207:
3204:
3202:
3199:
3197:
3194:
3192:
3189:
3187:
3184:
3182:
3179:
3177:
3174:
3172:
3169:
3167:
3164:
3163:
3161:
3146:
3145:
3141:
3138:
3137:
3134:
3128:
3125:
3123:
3120:
3118:
3115:
3113:
3110:
3108:
3105:
3103:
3100:
3098:
3095:
3093:
3090:
3088:
3085:
3083:
3080:
3078:
3075:
3073:
3070:
3068:
3065:
3063:
3060:
3057:
3056:
3053:
3050:
3047:
3043:
3040:
3038:
3037:Retinoic acid
3035:
3033:
3030:
3028:
3025:
3023:
3020:
3018:
3015:
3013:
3010:
3008:
3005:
3003:
3000:
2998:
2995:
2993:
2991:
2986:
2984:
2982:
2977:
2975:
2972:
2969:
2968:
2966:
2961:
2955:
2949:
2946:
2943:
2942:
2939:
2936:
2934:
2931:
2929:
2926:
2924:
2921:
2919:
2916:
2914:
2911:
2908:
2907:
2904:
2901:
2899:
2896:
2894:
2891:
2889:
2886:
2884:
2881:
2878:
2874:
2871:
2869:
2868:Retinoic acid
2866:
2864:
2861:
2859:
2856:
2854:
2851:
2849:
2846:
2844:
2841:
2839:
2836:
2834:
2831:
2829:
2826:
2824:
2821:
2819:
2816:
2814:
2811:
2809:
2806:
2804:
2801:
2799:
2797:
2792:
2790:
2787:
2785:
2782:
2780:
2777:
2775:
2772:
2770:
2768:
2763:
2761:
2758:
2755:
2754:
2752:
2747:
2741:
2737:
2734:
2727:
2722:
2720:
2715:
2713:
2708:
2707:
2704:
2692:
2689:
2687:
2684:
2682:
2679:
2677:
2674:
2672:
2669:
2667:
2664:
2662:
2659:
2657:
2654:
2652:
2649:
2647:
2644:
2643:
2641:
2639:
2635:
2629:
2626:
2624:
2623:Retinoic acid
2621:
2619:
2616:
2615:
2613:
2605:
2599:
2596:
2594:
2591:
2589:
2588:Food orange 7
2586:
2584:
2581:
2579:
2576:
2574:
2571:
2569:
2568:Abscisic acid
2566:
2565:
2563:
2556:
2552:
2546:
2543:
2541:
2538:
2536:
2533:
2531:
2528:
2526:
2523:
2521:
2518:
2516:
2513:
2511:
2508:
2506:
2503:
2501:
2498:
2496:
2493:
2491:
2488:
2486:
2483:
2481:
2480:Cryptoxanthin
2478:
2476:
2473:
2471:
2470:Canthaxanthin
2468:
2466:
2463:
2461:
2458:
2457:
2455:
2448:
2444:
2438:
2435:
2433:
2430:
2428:
2425:
2423:
2420:
2418:
2415:
2413:
2410:
2408:
2405:
2403:
2400:
2398:
2395:
2393:
2390:
2388:
2385:
2383:
2380:
2379:
2377:
2370:
2366:
2362:
2355:
2350:
2348:
2343:
2341:
2336:
2335:
2332:
2316:
2314:
2311:
2310:
2308:
2305:
2302:
2299:
2297:
2294:
2293:
2289:
2283:
2280:
2278:
2275:
2273:
2270:
2268:
2265:
2263:
2260:
2258:
2255:
2253:
2250:
2248:
2245:
2244:
2242:
2238:
2232:
2229:
2227:
2224:
2222:
2219:
2217:
2214:
2212:
2209:
2208:
2206:
2202:
2196:
2193:
2191:
2188:
2186:
2183:
2181:
2178:
2176:
2173:
2171:
2168:
2167:
2165:
2163:
2159:
2151:
2148:
2146:
2143:
2142:
2141:
2138:
2133:
2130:
2128:
2125:
2123:
2120:
2118:
2115:
2113:
2110:
2109:
2108:
2107:Antiandrogens
2105:
2104:
2102:
2100:
2096:
2089:
2086:
2084:
2081:
2079:
2075:
2074:Tetracyclines
2072:
2070:
2069:Sulfacetamide
2067:
2065:
2062:
2060:
2057:
2055:
2052:
2051:
2049:
2047:
2043:
2037:
2034:
2032:
2029:
2027:
2024:
2022:
2019:
2018:
2016:
2014:
2010:
2004:
2001:
1999:
1996:
1994:
1991:
1989:
1988:Glycolic acid
1986:
1985:
1983:
1981:
1977:
1971:
1968:
1966:
1963:
1961:
1958:
1956:
1953:
1951:
1948:
1947:
1945:
1943:
1942:Antibacterial
1939:
1934:
1930:
1923:
1918:
1916:
1911:
1909:
1904:
1903:
1900:
1884:
1882:
1879:
1878:
1876:
1873:
1870:
1867:
1865:
1862:
1861:
1857:
1847:
1844:
1842:
1839:
1838:
1836:
1834:
1830:
1824:
1821:
1819:
1816:
1814:
1811:
1810:
1808:
1804:
1801:
1797:
1787:
1784:
1781:
1778:
1776:
1773:
1771:
1768:
1766:
1762:
1761:
1757:
1755:
1752:
1751:
1749:
1745:
1739:
1736:
1734:
1731:
1730:
1728:
1726:
1722:
1716:
1713:
1712:
1710:
1708:
1704:
1698:
1694:
1691:
1690:
1688:
1684:
1681:
1677:
1672:
1668:
1661:
1656:
1654:
1649:
1647:
1642:
1641:
1638:
1627:
1616:
1609:
1606:
1601:
1597:
1593:
1589:
1585:
1581:
1574:
1571:
1566:
1562:
1558:
1554:
1550:
1546:
1539:
1536:
1531:
1527:
1523:
1519:
1515:
1511:
1508:(4): 273–87.
1507:
1503:
1496:
1494:
1490:
1485:
1481:
1477:
1473:
1469:
1465:
1461:
1457:
1450:
1447:
1442:
1438:
1434:
1430:
1426:
1422:
1415:
1413:
1409:
1404:
1400:
1395:
1390:
1385:
1380:
1377:(4): 327–48.
1376:
1372:
1368:
1361:
1358:
1353:
1349:
1344:
1339:
1335:
1331:
1327:
1320:
1318:
1316:
1312:
1307:
1303:
1298:
1293:
1288:
1283:
1279:
1275:
1271:
1264:
1261:
1256:
1252:
1248:
1244:
1240:
1236:
1232:
1228:
1221:
1218:
1213:
1209:
1205:
1201:
1197:
1193:
1189:
1185:
1178:
1176:
1174:
1170:
1165:
1161:
1157:
1153:
1149:
1145:
1141:
1137:
1130:
1128:
1124:
1111:
1107:
1105:
1099:
1093:
1090:
1077:
1073:
1071:
1065:
1059:
1056:
1043:
1036:
1030:
1028:
1024:
1011:
1007:
1001:
999:
997:
995:
993:
989:
981:September 16,
976:
972:
965:
962:
957:
953:
948:
943:
939:
935:
931:
924:
921:
908:
907:
906:Health Canada
902:
896:
893:
886:
884:
882:
878:
874:
870:
866:
862:
858:
854:
850:
846:
842:
838:
834:
825:
821:
819:
811:
809:
799:
795:
787:
785:
783:
779:
775:
771:
767:
763:
759:
758:differentiate
755:
751:
747:
746:keratinocytes
743:
739:
731:
726:
724:
722:
718:
710:
708:
702:
700:
698:
690:
688:
686:
682:
677:
675:
671:
667:
663:
659:
655:
651:
647:
643:
639:
638:acne vulgaris
631:
629:
627:
622:
620:
616:
612:
608:
604:
600:
596:
586:
579:
570:
565:
561:
554:
545:
541:
534:
527:
523:
522:
520:
517:
512:
505:
503:
499:
472:
470:
466:
461:
457:
453:
450:
448:
446:ECHA InfoCard
442:
434:
430:
429:DTXSID5046691
426:
425:
423:
414:
410:
403:
399:
398:
396:
394:
390:
383:
379:
378:
376:
374:
370:
363:
359:
358:
356:
354:
350:
343:
339:
338:
336:
334:
330:
323:
319:
318:
316:
314:
310:
303:
299:
298:
296:
294:
290:
283:
279:
278:
276:
274:
270:
263:
259:
258:
256:
249:
245:
238:
234:
233:
231:
229:
225:
216:
212:
205:
200:
196:
194:
187:
183:
181:
177:
173:
169:
162:
155:
146:
145:
143:
141:
137:
132:
125:
120:
115:
109:
104:
101:
100:
98:
96:
92:
89:
86:
84:
78:
74:
70:
68:
64:
60:
56:
54:
50:
47:Clinical data
45:
41:
36:
32:
27:
19:
3196:Ethyl esters
3142:
3059:Antagonists:
3058:
3017:Isotretinoin
2989:
2980:
2970:
2944:
2910:Antagonists:
2909:
2887:
2883:Tamibarotene
2863:Palovarotene
2858:Isotretinoin
2795:
2766:
2756:
2675:
2671:Isotretinoin
2651:Alitretinoin
2573:Apocarotenal
2545:Zeinoxanthin
2535:Violaxanthin
2525:Rhodoxanthin
2505:Flavoxanthin
2490:Diatoxanthin
2447:Xanthophylls
2417:Neurosporene
2240:Combinations
2184:
2175:Isotretinoin
2122:Drospirenone
2112:Bicalutamide
2064:Erythromycin
1970:Tea tree oil
1950:Azelaic acid
1785:
1765:Calcipotriol
1758:
1754:Fumaric acid
1608:
1583:
1579:
1573:
1548:
1544:
1538:
1505:
1501:
1459:
1455:
1449:
1424:
1420:
1374:
1370:
1360:
1333:
1329:
1277:
1273:
1263:
1230:
1226:
1220:
1187:
1183:
1139:
1135:
1114:. Retrieved
1101:
1092:
1080:. Retrieved
1067:
1058:
1046:. Retrieved
1041:
1014:. Retrieved
1009:
979:. Retrieved
974:
971:"Tazarotene"
964:
937:
933:
923:
911:. Retrieved
904:
895:
880:
876:
872:
864:
856:
844:
840:
836:
830:
815:
791:
735:
727:Pharmacology
721:fluocinonide
714:
706:
694:
681:histological
678:
635:
632:Medical uses
623:
603:prescription
598:
594:
593:
582:
190:Elimination
140:Legal status
134:Legal status
18:
2898:Trifarotene
2853:Fenretinide
2666:Fenretinide
2530:Rubixanthin
2510:Fucoxanthin
2495:Dinoxanthin
2465:Astaxanthin
2437:Lycopersene
2427:Phytofluene
2361:Carotenoids
2303:from market
2211:Epristeride
2195:Trifarotene
2180:Motretinide
2088:Doxycycline
2083:Minocycline
2078:Lymecycline
2054:Clindamycin
2046:Antibiotics
2021:Niacinamide
1980:Keratolytic
1871:from market
1818:Methoxsalen
1813:Trioxysalen
1738:Methoxsalen
1733:Trioxysalen
1280:(1): 71–6.
754:proliferate
670:monotherapy
662:clindamycin
509: g·mol
452:100.115.380
382:CHEBI:32184
237:118292-40-3
202:Identifiers
53:Trade names
3160:Categories
2997:Bexarotene
2913:BMS-195614
2888:Tazarotene
2848:Etretinate
2736:modulators
2681:Temarotene
2676:Tazarotene
2661:Etretinate
2656:Bexarotene
2540:Zeaxanthin
2520:Neoxanthin
2500:Echinenone
2407:ζ-Carotene
2402:ε-Carotene
2397:δ-Carotene
2392:γ-Carotene
2387:β-Carotene
2382:α-Carotene
2185:Tazarotene
1841:Etretinate
1786:Tazarotene
1780:Tacalcitol
1775:Calcitriol
887:References
833:thiophenol
774:involucrin
648:, such as
595:Tazarotene
514:3D model (
502:Molar mass
402:ChEMBL1657
342:81BDR9Y8PS
313:ChemSpider
273:IUPHAR/BPS
228:CAS Number
211:IUPAC name
160:Schedule D
124:ulobetasol
23:Tazarotene
3166:Retinoids
3072:LG-100754
3046:vitamin A
3032:LG-100754
3027:LG-101506
3022:LG-100268
2971:Agonists:
2948:Liarozole
2877:vitamin A
2789:Adapalene
2784:Acitretin
2774:AC-261066
2757:Agonists:
2686:Tretinoin
2646:Acitretin
2598:Peridinin
2369:Carotenes
2313:Phase III
2301:Withdrawn
2231:Tioxolone
2190:Tretinoin
2170:Adapalene
2162:Retinoids
2145:Estradiol
2140:Estrogens
2127:Flutamide
2026:Ibuprofen
1881:Phase III
1869:Withdrawn
1846:Acitretin
1833:Retinoids
1823:Bergapten
1806:Psoralens
1760:vitamin D
1725:Psoralens
1715:Dithranol
1707:Antracens
1615:EP 284288
1212:261765064
1048:March 11,
1042:Drugs@FDA
1016:March 11,
1010:Drugs.com
913:March 25,
812:Synthesis
762:filaggrin
750:epidermis
691:Pregnancy
685:sunscreen
654:adapalene
650:tretinoin
646:retinoids
642:psoriasis
619:photoaged
192:half-life
81:Routes of
73:Monograph
67:Drugs.com
3139:See also
3082:UVI-3003
3052:SR-11237
2938:MM-11253
2928:ER-50891
2779:AC-55649
2583:Crocetin
2432:Torulene
2422:Phytoene
2412:Lycopene
2221:Pelretin
2216:Mesulfen
2099:Hormonal
1799:Systemic
1697:Coal tar
1623:; idem,
1600:10898827
1530:36445158
1522:10554045
1484:52070149
1476:30134735
1403:18046911
1352:33133344
1306:18488880
1255:24854629
1247:15907143
1164:59225325
1156:30674002
1116:June 29,
1110:Archived
1082:June 30,
1076:Archived
956:18479477
782:keratins
607:retinoid
605:topical
585:(verify)
293:DrugBank
197:19 Hours
95:ATC code
3042:Retinol
3002:CD 3254
2923:CD-2665
2918:BMS-493
2873:Retinol
2828:CD-2314
2823:CD-1530
2818:BMS-961
2813:BMS-753
2808:BMS-493
2628:Retinol
2618:Retinal
2593:Ionones
2226:Stridex
2059:Dapsone
2031:Aspirin
1679:Topical
1565:9777791
1441:9270552
1394:2699641
1343:7577328
1297:2544371
1204:9585866
796:). The
794:albumin
748:in the
666:dapsone
599:Tazorac
469:Formula
302:DB00799
248:PubChem
184:>99%
156: /
152::
116: (
114:D05AX55
111:)
105: (
103:D05AX05
88:Topical
3122:HX-711
3112:PA-452
3107:PA-451
3102:CD3254
3097:LE-540
3087:HX-603
3077:PA-452
3067:HX-630
3062:HX-531
2974:9CDHRA
2933:LE-135
2833:CD-437
2803:AM-580
2760:9CDHRA
2559:<40
2515:Lutein
2296:WHO-EM
1998:Sulfur
1864:WHO-EM
1620:
1598:
1563:
1528:
1520:
1482:
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1439:
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1162:
1154:
954:
540:SMILES
507:351.46
393:ChEMBL
362:D01132
158:
154:℞-only
3117:Rhein
2990:trans
2903:TTNPB
2843:EC 23
2838:Ch-55
2796:trans
2578:Bixin
2204:Other
1747:Other
1526:S2CID
1480:S2CID
1251:S2CID
1227:Drugs
1208:S2CID
1184:Drugs
1160:S2CID
1106:(FDA)
1102:U.S.
1072:(FDA)
1068:U.S.
1038:(PDF)
742:RAR-β
738:RAR-γ
560:InChI
516:JSmol
373:ChEBI
2988:all-
2794:all-
1929:Acne
1686:Tars
1596:PMID
1561:PMID
1518:PMID
1472:PMID
1437:PMID
1399:PMID
1348:PMID
1302:PMID
1243:PMID
1200:PMID
1152:PMID
1118:2023
1084:2023
1050:2021
1018:2021
983:2017
952:PMID
915:2024
756:and
740:and
652:and
640:and
615:acne
613:and
353:KEGG
333:UNII
322:5188
282:6952
262:5381
174:data
63:AHFS
2981:cis
2959:RXR
2767:cis
2745:RAR
1933:D10
1693:Tar
1671:D05
1588:doi
1553:doi
1510:doi
1464:doi
1429:doi
1389:PMC
1379:doi
1338:PMC
1292:PMC
1282:doi
1235:doi
1192:doi
1144:doi
942:doi
883:).
784:.
752:to
719:or
664:or
418:EPA
252:CID
119:WHO
108:WHO
3162::
2979:9-
2765:9-
2609:20
2557:(C
2451:40
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489:O
486:N
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474:C
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