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Chemistry

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Also known as: Retinoic acid, 302-79-4, All-trans-retinoic acid, Vitamin a acid, Trans-retinoic acid, Atra
Molecular Formula
C20H28O2
Molecular Weight
300.4  g/mol
InChI Key
SHGAZHPCJJPHSC-YCNIQYBTSA-N
FDA UNII
5688UTC01R

Tretinoin
An important regulator of GENE EXPRESSION during growth and development, and in NEOPLASMS. Tretinoin, also known as retinoic acid and derived from maternal VITAMIN A, is essential for normal GROWTH; and EMBRYONIC DEVELOPMENT. An excess of tretinoin can be teratogenic. It is used in the treatment of PSORIASIS; ACNE VULGARIS; and several other SKIN DISEASES. It has also been approved for use in promyelocytic leukemia (LEUKEMIA, PROMYELOCYTIC, ACUTE).
Tretinoin is a Retinoid.
1 2D Structure

Tretinoin

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
(2E,4E,6E,8E)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic acid
2.1.2 InChI
InChI=1S/C20H28O2/c1-15(8-6-9-16(2)14-19(21)22)11-12-18-17(3)10-7-13-20(18,4)5/h6,8-9,11-12,14H,7,10,13H2,1-5H3,(H,21,22)/b9-6+,12-11+,15-8+,16-14+
2.1.3 InChI Key
SHGAZHPCJJPHSC-YCNIQYBTSA-N
2.1.4 Canonical SMILES
CC1=C(C(CCC1)(C)C)C=CC(=CC=CC(=CC(=O)O)C)C
2.1.5 Isomeric SMILES
CC1=C(C(CCC1)(C)C)/C=C/C(=C/C=C/C(=C/C(=O)O)/C)/C
2.2 Other Identifiers
2.2.1 UNII
5688UTC01R
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Acid, All-trans-retinoic

2. Acid, Beta-all-trans-retinoic

3. Acid, Retinoic

4. Acid, Trans-retinoic

5. Acid, Vitamin A

6. All Trans Retinoic Acid

7. All-trans-retinoic Acid

8. Beta All Trans Retinoic Acid

9. Beta-all-trans-retinoic Acid

10. Potassium Salt, Tretinoin

11. Retin A

12. Retin-a

13. Retinoic Acid

14. Salt, Tretinoin Potassium

15. Salt, Tretinoin Sodium

16. Salt, Tretinoin Zinc

17. Sodium Salt, Tretinoin

18. Trans Retinoic Acid

19. Trans-retinoic Acid

20. Tretinoin Potassium Salt

21. Tretinoin Sodium Salt

22. Tretinoin Zinc Salt

23. Vesanoid

24. Vitamin A Acid

25. Zinc Salt, Tretinoin

2.3.2 Depositor-Supplied Synonyms

1. Retinoic Acid

2. 302-79-4

3. All-trans-retinoic Acid

4. Vitamin A Acid

5. Trans-retinoic Acid

6. Atra

7. Retin-a

8. Vesanoid

9. Aberel

10. Eudyna

11. Renova

12. Airol

13. All-trans Retinoic Acid

14. All-trans-vitamin A Acid

15. Dermairol

16. Aknoten

17. Aknefug

18. Cordes Vas

19. Epi-aberel

20. Tretinon

21. Tretin M

22. Retin A

23. Atralin

24. All-trans-vitamin A1 Acid

25. All-trans-tretinoin

26. Retionic Acid

27. All Trans Retinoic Acid

28. Vitamin A1 Acid, All-trans-

29. Retin-a Micro

30. Beta-retinoic Acid

31. All-(e)-retinoic Acid

32. Vitamin A Acid, All-trans-

33. (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic Acid

34. Retinoate

35. Retinoic Acid, All-trans-

36. Alltrans-retinoic Acid

37. Nsc-122758

38. Retacnyl

39. Vesnaroid

40. Ro 1-5488

41. Tretinoin, All-trans-

42. All Trans-retinoic Acid

43. Stieva-a

44. Tretinoine

45. Solage

46. All-trans-beta-retinoic Acid

47. Effederm

48. .beta.-retinoic Acid

49. Kerlocal

50. Oristar Rna

51. Retinoic Acid, All Trans

52. Tretinoin/all-trans Retinoic Acid

53. Aberela [norway]

54. Avitoin [norway]

55. Effederm [france]

56. A-acido (argentina)

57. 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic Acid

58. (all-e)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic Acid

59. Mls000028588

60. B-retinoic Acid

61. Tretinoine [inn-french]

62. Tretinoinum [inn-latin]

63. At-ra

64. Tretinoina [inn-spanish]

65. Tretinoino [inn-spanish]

66. Chembl38

67. (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-tetraenoic Acid

68. 2,4,6,8-nonatetraenoic Acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-e)-

69. Nsc122758

70. Atragen

71. Retinova

72. Smr000058245

73. (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2,4,6,8-tetraenoic Acid

74. Chebi:15367

75. 15-apo-beta-caroten-15-oic Acid

76. 5688utc01r

77. Tretinoin (tn)

78. Beta-ra

79. Acnavit [denmark]

80. Agn 100335

81. Rea

82. 9-cis-ra

83. Retin A (tn)

84. Ncgc00017280-10

85. Tretinoinum

86. Aberela

87. Acnavit

88. Avitoin

89. Betarretin

90. Tretinoina

91. Tretinoino

92. A-vitaminsyre

93. Mfcd00001551

94. All-trans-b-retinoic Acid

95. Dsstox_cid_1239

96. Cordes Vas [germany]

97. A-vitaminsyre [denmark]

98. 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexene-1-yl)-2,4,6,8-nonatetraenoic Acid (ecl)

99. Dsstox_rid_76031

100. Dsstox_gsid_21239

101. Trans-retinoate

102. Beta-retinoate

103. Tretinoine (french) (einecs)

104. Cis-retinoic Acid

105. Acide Retinoique (french) (dsl)

106. Refissa

107. Nexret

108. Vitamin A Acid, Trans-

109. Retisol-a

110. Acid A Vit (belgium, Netherlands)

111. 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)nona-2,4,6,8-tetraenoic Acid

112. 3,7-dimethyl-9-(2,6,6-trimethylcyclohexen-1-yl)nona-2e,4e,6e,8e-tetraenoic Acid

113. (11z)-retinoic Acid

114. (2e,4e,6e,8e)-3,7-dimethyl-9-(2,6,6-trimethyl-cyclohex-1-en-1-yl)nona-2,4,6,8-tetraenoic Acid

115. [3h]retinoic Acid

116. Renova (tn)

117. Ccris 3294

118. Avita (tn)

119. Hsdb 2169

120. Sr-01000000239

121. Einecs 206-129-0

122. Nsc 122758

123. Brn 2057223

124. Retinoicacid

125. Tretinoin (jan/usp/inn)

126. Retinoic Acid, Cis-9,trans-13-

127. Tretinion

128. Tnp00194

129. Unii-5688utc01r

130. Bml2-e05

131. Dtxsid7021239

132. 1cbr

133. [3h]tretinoin

134. [all-e]-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic Acid

135. Tretinoin [usan:usp:inn:ban]

136. Cas-302-79-4

137. Prestwick_424

138. All-(e)-retinoate

139. Tretinoine (french)

140. Altreno

141. Retinoic Acid, Cis-

142. (5e)-retinoic Acid

143. [3h]vitamin A Acid

144. 1n4h

145. Cpd000058245

146. Retinoic Acid All Trans

147. Tretinoin [inn]

148. Tretinoin [jan]

149. 6-s-trans-retinoic Acid

150. Tretinoin [hsdb]

151. Tretinoin [usan]

152. Vitamin-a-sa Currencyure

153. Opera_id_1055

154. Prestwick2_000257

155. Prestwick3_000257

156. Spectrum5_001746

157. Spectrum5_001933

158. Tretinoin [vandf]

159. Acide Retinoique (french)

160. Vesanoid (tn) (roche)

161. Tretinoin - Retinoic Acid

162. Bmse000562

163. Tretinoin [mart.]

164. Upcmld-dp097

165. R 2625

166. Renova (0.02% Cream)

167. Retinoic Acid [mi]

168. Schembl3145

169. Tretinoin [usp-rs]

170. Tretinoin [who-dd]

171. (9z,13z)-retinoic Acid

172. 3,7-dimethyl-9-(2,6,6-trimethylcyclohex-1-enyl)nona-2,4,6,8-all-trans-tetraenoic Acid

173. Altreno (0.05% Lotion)

174. Bidd:pxr0081

175. Lopac0_001061

176. Avita (0.025% Gel)

177. Bspbio_000074

178. Bspbio_001500

179. Retinoic Acid [inci]

180. Mls001076515

181. Mls002207234

182. Mls002222211

183. Mls002548861

184. Mls006010222

185. Bidd:gt0483

186. Spectrum1502016

187. 9-cis-retinoic Acid (9cra)

188. [3h]ra

189. Bpbio1_000082

190. Cid_444795

191. Gtpl2644

192. .beta.-all-trans-retinoic Acid

193. Tretinoin [orange Book]

194. Ziana Component Tretinoin

195. All-trans-retinoic Acid (atra)

196. Schembl19091395

197. Tretinoin [ep Monograph]

198. Bdbm31883

199. Hms502n05

200. Solage Component Tretinoin

201. Twyneo Component Tretinoin

202. Veltin Component Tretinoin

203. Tretinoin [usp Monograph]

204. Bcpp000036

205. Bdbm323588

206. Hms1361k22

207. Hms1568d16

208. Hms1791k22

209. Hms1921d14

210. Hms1989k22

211. Hms2089d20

212. Hms2092n11

213. Hms2095d16

214. Hms2236n03

215. Hms3259e11

216. Hms3263e04

217. Hms3402k22

218. Hms3411b09

219. Hms3675b09

220. Hms3712d16

221. Pharmakon1600-01502016

222. Retinoic Acid, All-trans- (8ci)

223. 124510-04-9

224. 2,4,6,8-nonatetraenoic Acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (2e,4e,6z,8e)-

225. Act00012

226. Bcp01405

227. Tretinoin Component Of Ziana

228. Tri-luma Component Tretinoin

229. Us10188615, At-ra

230. Tox21_110812

231. Tox21_202330

232. Tox21_300305

233. Tox21_501061

234. Tretinoin Component Of Solage

235. Tretinoin Component Of Twyneo

236. Tretinoin Component Of Veltin

237. All-trans Retinoic Acid (tretinoin)

238. Ccg-39912

239. Lmpr01090019

240. Nsc759631

241. S1653

242. Zinc12358651

243. Akos000280845

244. Tox21_110812_1

245. Ac-6824

246. Cs-1269

247. Db00755

248. Gs-3578

249. Lp01061

250. Nc00481

251. Nsc-759631

252. Sdccgsbi-0051031.p004

253. Tretinoin Component Of Tri-luma

254. Idi1_000903

255. Idi1_033970

256. Ncgc00017280-05

257. Ncgc00017280-06

258. Ncgc00017280-07

259. Ncgc00017280-08

260. Ncgc00017280-09

261. Ncgc00017280-12

262. Ncgc00017280-15

263. Ncgc00017280-16

264. Ncgc00017280-17

265. Ncgc00017280-18

266. Ncgc00017280-19

267. Ncgc00017280-20

268. Ncgc00017280-23

269. Ncgc00017280-38

270. Ncgc00021808-04

271. Ncgc00021808-05

272. Ncgc00021808-06

273. Ncgc00021808-07

274. Ncgc00021808-09

275. Ncgc00021808-11

276. Ncgc00021808-14

277. Ncgc00021808-15

278. Ncgc00254179-01

279. Ncgc00259879-01

280. Ncgc00261746-01

281. Bp-20401

282. Br164493

283. Hy-14649

284. Retinoic Acid, >=98% (hplc), Powder

285. Sbi-0051031.p003

286. Eu-0101061

287. Isotretinoin Impurity A [ep Impurity]

288. R0064

289. Sw203749-4

290. 02t794

291. C00777

292. D00094

293. Q29417

294. Ab00052318-15

295. Ab00052318-16

296. Ab00052318-17

297. Ab00052318_18

298. Ab00052318_19

299. A899883

300. L000833

301. Q-200610

302. Sr-01000000239-3

303. Sr-01000000239-4

304. Sr-01000000239-6

305. Sr-01000000239-7

306. Brd-k06926592-001-01-7

307. Brd-k71879491-001-15-0

308. Brd-k71879491-001-22-6

309. Sr-01000000239-12

310. Sr-01000000239-13

311. Sr-01000000239-14

312. Sr-01000000239-15

313. Wln: L6utj A1 B1u1y1&u2u1y1&u1vq C1 C1

314. Tretinoin, European Pharmacopoeia (ep) Reference Standard

315. Wln: L6utj A1 B1u1y1 & U2u1y1 & U1vq C1 C1

316. Tretinoin, United States Pharmacopeia (usp) Reference Standard

317. 3,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic Acid

318. Tretinoin, Pharmaceutical Secondary Standard; Certified Reference Material

319. (2e,4e)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexenyl)-2,4,6,8-nonatetraenoic Acid

320. (4e,6e,8e)-9-(2,6,6-trimethyl-1-cyclohexenyl)-3,7-dimethyl-2,4,6,8-nonatetraenoic Acid

321. (all-e)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate

322. 2,4,6,8-nonatetranoic Acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-

323. 2,6,8-nonatetranoic Acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-

324. 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoate

325. 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2e,4e,6e,8e,-nonatetraenoic Acid

326. All-trans-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic Acid

327. 2,4, 6,8-nonatetranoic Acid, 3,7-dimethyl-9-(2,6, 6-trimethyl-1-cyclohexen-1-yl)-, (2e, 4e, 6e, 8e)-

328. 2,4,6,8-nonatetraenoic Acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)--, (all Trans)-

329. 2,4,6,8-nonatetranoic Acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all Trans)-

330. 2,6,8-nonatetraenoic Acid, 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-, (all-e)-

331. 3,7-dimethyl-9-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2,4,6,8-nonatetraenoic Acid-, (all Trans)-

332. 97950-17-9

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 300.4 g/mol
Molecular Formula C20H28O2
XLogP36.3
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count2
Rotatable Bond Count5
Exact Mass300.208930132 g/mol
Monoisotopic Mass300.208930132 g/mol
Topological Polar Surface Area37.3 Ų
Heavy Atom Count22
Formal Charge0
Complexity567
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count4
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 12  
Drug NameAtralin
Drug LabelAtralin (tretinoin) Gel, 0.05% is a translucent to opaque, pale yellow gel containing 0.05% tretinoin, by weight for topical administration. Chemically, tretinoin is all-trans-retinoic acid, also known as (all-E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyc...
Active IngredientTretinoin
Dosage FormGel
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyDow Pharm

2 of 12  
Drug NameRenova
Drug LabelRENOVA (tretinoin cream) 0.02% contains the active ingredient tretinoin in a cream base. Tretinoin is a yellow- to light-orange crystalline powder having a characteristic floral odor. Tretinoin is soluble in dimethylsulfoxide, slightly soluble in p...
Active IngredientTretinoin
Dosage FormCream
RouteTopical
Strength0.05%; 0.02%
Market StatusPrescription
CompanyValeant Intl

3 of 12  
Drug NameRetin-a
PubMed HealthTretinoin
Drug ClassesAntiacne, Antineoplastic Agent, Dermatological Agent
Drug LabelRETIN-A Gel, Cream and Liquid, containing tretinoin are used for the topical treatment of acne vulgaris. RETIN-A Gel contains tretinoin (retinoic acid, vitamin A acid) in either of two strengths, 0.025% or 0.01% by weight, in a gel vehicle of butylat...
Active IngredientTretinoin
Dosage FormCream; Gel; Solution
RouteTopical
Strength0.05%; 0.1%; 0.025%; 0.01%
Market StatusPrescription
CompanyValeant Intl; Valeant Bermuda

4 of 12  
Drug NameRetin-a micro
PubMed HealthFluocinolone/Hydroquinone/Tretinoin (On the skin)
Drug ClassesCorticosteroid Combination, Dermatological Agent, Hypopigmentation Agent, Retinoid Combination
Drug LabelRetin-A Micro (tretinoin gel) microsphere, 0.1% and 0.04%, is a formulation containing 0.1% or 0.04%, by weight, tretinoin for topical treatment of acne vulgaris. This formulation uses patented methyl methacrylate/glycol dimethacrylate crosspolymer...
Active IngredientTretinoin
Dosage FormGel
RouteTopical
Strength0.1%; 0.04%
Market StatusPrescription
CompanyValeant Intl

5 of 12  
Drug NameTretinoin
PubMed HealthTretinoin
Drug ClassesAntiacne, Antineoplastic Agent, Dermatological Agent
Drug LabelTretinoin, USP is a retinoid that induces maturation of acute promyelocytic leukemia (APL) cells in culture. It is available in a 10 mg gelatin capsule for oral administration. Each capsule contains the following inactive ingredients: butylated hydro...
Active IngredientTretinoin
Dosage FormCream; Capsule; Gel
RouteOral; Topical
Strength0.05%; 0.1%; 0.025%; 0.0375%; 10mg; 0.01%; 0.04%; 0.075%
Market StatusPrescription
CompanyAnchen Pharms; Suneva Medcl; Spear Pharms; Barr Labs; Precision Dermat

6 of 12  
Drug NameTri-luma
Active Ingredienttretinoin; Fluocinolone acetonide; hydroquinone
Dosage FormCream
RouteTopical
Strength0.05%; 4%; 0.01%
Market StatusPrescription
CompanyGalderma Labs

7 of 12  
Drug NameAtralin
Drug LabelAtralin (tretinoin) Gel, 0.05% is a translucent to opaque, pale yellow gel containing 0.05% tretinoin, by weight for topical administration. Chemically, tretinoin is all-trans-retinoic acid, also known as (all-E)-3,7-dimethyl-9-(2,6,6-trimethyl-1-cyc...
Active IngredientTretinoin
Dosage FormGel
RouteTopical
Strength0.05%
Market StatusPrescription
CompanyDow Pharm

8 of 12  
Drug NameRenova
Drug LabelRENOVA (tretinoin cream) 0.02% contains the active ingredient tretinoin in a cream base. Tretinoin is a yellow- to light-orange crystalline powder having a characteristic floral odor. Tretinoin is soluble in dimethylsulfoxide, slightly soluble in p...
Active IngredientTretinoin
Dosage FormCream
RouteTopical
Strength0.05%; 0.02%
Market StatusPrescription
CompanyValeant Intl

9 of 12  
Drug NameRetin-a
PubMed HealthTretinoin
Drug ClassesAntiacne, Antineoplastic Agent, Dermatological Agent
Drug LabelRETIN-A Gel, Cream and Liquid, containing tretinoin are used for the topical treatment of acne vulgaris. RETIN-A Gel contains tretinoin (retinoic acid, vitamin A acid) in either of two strengths, 0.025% or 0.01% by weight, in a gel vehicle of butylat...
Active IngredientTretinoin
Dosage FormCream; Gel; Solution
RouteTopical
Strength0.05%; 0.1%; 0.025%; 0.01%
Market StatusPrescription
CompanyValeant Intl; Valeant Bermuda

10 of 12  
Drug NameRetin-a micro
PubMed HealthFluocinolone/Hydroquinone/Tretinoin (On the skin)
Drug ClassesCorticosteroid Combination, Dermatological Agent, Hypopigmentation Agent, Retinoid Combination
Drug LabelRetin-A Micro (tretinoin gel) microsphere, 0.1% and 0.04%, is a formulation containing 0.1% or 0.04%, by weight, tretinoin for topical treatment of acne vulgaris. This formulation uses patented methyl methacrylate/glycol dimethacrylate crosspolymer...
Active IngredientTretinoin
Dosage FormGel
RouteTopical
Strength0.1%; 0.04%
Market StatusPrescription
CompanyValeant Intl

11 of 12  
Drug NameTretinoin
PubMed HealthTretinoin
Drug ClassesAntiacne, Antineoplastic Agent, Dermatological Agent
Drug LabelTretinoin, USP is a retinoid that induces maturation of acute promyelocytic leukemia (APL) cells in culture. It is available in a 10 mg gelatin capsule for oral administration. Each capsule contains the following inactive ingredients: butylated hydro...
Active IngredientTretinoin
Dosage FormCream; Capsule; Gel
RouteOral; Topical
Strength0.05%; 0.1%; 0.025%; 0.0375%; 10mg; 0.01%; 0.04%; 0.075%
Market StatusPrescription
CompanyAnchen Pharms; Suneva Medcl; Spear Pharms; Barr Labs; Precision Dermat

12 of 12  
Drug NameTri-luma
Active Ingredienttretinoin; Fluocinolone acetonide; hydroquinone
Dosage FormCream
RouteTopical
Strength0.05%; 4%; 0.01%
Market StatusPrescription
CompanyGalderma Labs

4.2 Therapeutic Uses

Antineoplastic Agents Keratolytic Agents

National Library of Medicine's Medical Subject Headings. Tretinoin. Online file (MeSH, 2018). Available from, as of August 29, 2018: https://meshb.nlm.nih.gov/search


/CLINICAL TRIALS/ ClinicalTrials.gov is a registry and results database of publicly and privately supported clinical studies of human participants conducted around the world. The Web site is maintained by the National Library of Medicine (NLM) and the National Institutes of Health (NIH). Each ClinicalTrials.gov record presents summary information about a study protocol and includes the following: Disease or condition; Intervention (for example, the medical product, behavior, or procedure being studied); Title, description, and design of the study; Requirements for participation (eligibility criteria); Locations where the study is being conducted; Contact information for the study locations; and Links to relevant information on other health Web sites, such as NLM's MedlinePlus for patient health information and PubMed for citations and abstracts for scholarly articles in the field of medicine. trans-Retinoic acid is included in the database.

NIH/NLM; ClinicalTrials.Gov. Available from, as of August 29, 2018: https://clinicaltrials.gov/


Tretinoin gel and cream are indicated for topical application in the treatment of acne vulgaris. The safety and efficacy of the long-term use of this product in the treatment of other disorders have not been established. /Included in US product labeling; Tretinoin, topical/

NIH; DailyMed. Current Medication Information for Tretinoin Gel (Updated: January 3, 2018). Available from, as of September 13, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=4889c7f8-37d0-4f1a-9829-bca107806586


Tretinoin is used topically as a 0.05 or 0.1% cream for palliative therapy to improve dermatologic changes (e.g., fine wrinkling, mottled hyperpigmentation, roughness) associated with photodamage. /NOT included in US product labeling; Tretinoin, topical/

American Society of Health-System Pharmacists; Drug Information 2018. Bethesda, MD. 2018


For more Therapeutic Uses (Complete) data for all-trans-Retinoic acid (9 total), please visit the HSDB record page.


4.3 Drug Warning

/BOXED WARNING/ Experienced Physician and Institution. Patients with acute promyelocytic leukemia (APL) are at high risk in general and can have severe adverse reactions to tretinoin capsules. Tretinoin capsules should therefore be administered only to patients with APL under the strict supervision of a physician who is experienced in the management of patients with acute leukemia and in a facility with laboratory and supportive services sufficient to monitor drug tolerance and protect and maintain a patient compromised by drug toxicity, including respiratory compromise. Use of tretinoin capsules requires that the physician concludes that the possible benefit to the patient outweighs the following known adverse effects of the therapy. /Tretinoin, systemic/

NIH; DailyMed. Current Medication Information for Tretinoin Capsule (Updated: January 11, 2017). Available from, as of September 13, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9c4ae9d9-c2a0-4995-a27a-e3f0f0284db9


/BOXED WARNING/ Retinoic Acid-APL Syndrome. About 25% of patients with APL treated with tretinoin capsules have experienced a syndrome called the retinoic acid-APL (RA-APL) syndrome characterized by fever, dyspnea, acute respiratory distress, weight gain, radiographic pulmonary infiltrates, pleural and pericardial effusions, edema, and hepatic, renal, and multi-organ failure. This syndrome has occasionally been accompanied by impaired myocardial contractility and episodic hypotension. It has been observed with or without concomitant leukocytosis. Endotracheal intubation and mechanical ventilation have been required in some cases due to progressive hypoxemia, and several patients have expired with multi-organ failure. The syndrome generally occurs during the first month of treatment, with some cases reported following the first dose of tretinoin capsules. The management of the syndrome has not been defined rigorously, but high-dose steroids given at the first suspicion of the RA-APL syndrome appear to reduce morbidity and mortality. At the first signs suggestive of the syndrome (unexplained fever, dyspnea and/or weight gain, abnormal chest auscultatory findings or radiographic abnormalities), high-dose steroids (dexamethasone 10 mg intravenously administered every 12 hours for 3 days or until the resolution of symptoms) should be immediately initiated, irrespective of the leukocyte count. The majority of patients do not require termination of tretinoin capsules therapy during treatment of the RA-APL syndrome. However, in cases of moderate and severe RA-APL syndrome, temporary interruption of tretinoin capsules therapy should be considered. /Tretinoin, systemic/

NIH; DailyMed. Current Medication Information for Tretinoin Capsule (Updated: January 11, 2017). Available from, as of September 13, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9c4ae9d9-c2a0-4995-a27a-e3f0f0284db9


/BOXED WARNING/ During tretinoin capsules treatment about 40% of patients will develop rapidly evolving leukocytosis. Patients who present with high WBC at diagnosis (>5x10 9/L) have an increased risk of a further rapid increase in WBC counts. Rapidly evolving leukocytosis is associated with a higher risk of life-threatening complications. If signs and symptoms of the RA-APL syndrome are present together with leukocytosis, treatment with high-dose steroids should be initiated immediately. Some investigators routinely add chemotherapy to tretinoin capsules treatment in the case of patients presenting with a WBC count of >5x10 9/L or in the case of a rapid increase in WBC count for patients leukopenic at start of treatment, and have reported a lower incidence of the RA-APL syndrome. Consideration could be given to adding full-dose chemotherapy (including an anthracycline if not contraindicated) to the tretinoin capsules therapy on day 1 or 2 for patients presenting with a WBC count of >5x10 9/L, or immediately, for patients presenting with a WBC count of <5x10 9/L, if the WBC count reaches >/= 6x10(9)/L by day 5, or >/= 10x10(9)/L by day 10, or >/=15x10(9)/L by day 28. /Tretinoin, systemic/

NIH; DailyMed. Current Medication Information for Tretinoin Capsule (Updated: January 11, 2017). Available from, as of September 13, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9c4ae9d9-c2a0-4995-a27a-e3f0f0284db9


/BOXED WARNING/ Teratogenic Effects. Pregnancy Category D. There is a high risk that a severely deformed infant will result if tretinoin capsules are administered during pregnancy. If, nonetheless, it is determined that tretinoin capsules represent the best available treatment for a pregnant woman or a woman of childbearing potential, it must be assured that the patient has received full information and warnings of the risk to the fetus if she were to be pregnant and of the risk of possible contraception failure and has been instructed in the need to use two reliable forms of contraception simultaneously during therapy and for 1 month following discontinuation of therapy, and has acknowledged her understanding of the need for using dual contraception, unless abstinence is the chosen method. Within 1 week prior to the institution of tretinoin capsules therapy, the patient should have blood or urine collected for a serum or urine pregnancy test with a sensitivity of at least 50 mIU/mL. When possible, tretinoin capsules therapy should be delayed until a negative result from this test is obtained. When a delay is not possible, the patient should be placed on two reliable forms of contraception. Pregnancy testing and contraception counseling should be repeated monthly throughout the period of tretinoin capsules treatment. /Tretinoin, systemic/

NIH; DailyMed. Current Medication Information for Tretinoin Capsule (Updated: January 11, 2017). Available from, as of September 13, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9c4ae9d9-c2a0-4995-a27a-e3f0f0284db9


For more Drug Warnings (Complete) data for all-trans-Retinoic acid (44 total), please visit the HSDB record page.


4.4 Drug Indication

For the the induction of remission in patients with acute promyelocytic leukemia (APL), French-American-British (FAB) classification M3 (including the M3 variant); For the topical treatment of acne vulgaris, flat warts and other skin conditions (psoriasis, ichthyosis congenita, icthyosis vulgaris, lamellar icthyosis, keratosis palmaris et plantaris, epidermolytic hyperkeratosis, senile comedones, senile keratosis, keratosis follicularis (Darier's disease), and basal cell carcinomas.); For palliative therapy to improve fine wrinkling, mottled hyperpigmentation, roughness associated with photodamage. Tretinoin is also indicated in combination with [benzoyl peroxide] for the treatment of acne vulgaris in patients aged nine years and older.


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

Tretinoin, also known as all-trans-retinoic acid (ATRA), is a naturally occurring derivative of vitamin A (retinol). Retinoids such as tretinoin are important regulators of cell reproduction, proliferation, and differentiation and are used to treat acne and photodamaged skin and to manage keratinization disorders such as ichthyosis and keratosis follicularis. Tretinoin also represents the class of anticancer drugs called differentiating agents and is used in the treatment of acute promyelocytic leukemia (APL).


5.2 MeSH Pharmacological Classification

Keratolytic Agents

Agents that soften, separate, and cause desquamation of the cornified epithelium or horny layer of skin. They are used to expose mycelia of infecting fungi or to treat corns, warts, and certain other skin diseases. (See all compounds classified as Keratolytic Agents.)


Antineoplastic Agents

Substances that inhibit or prevent the proliferation of NEOPLASMS. (See all compounds classified as Antineoplastic Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
TRETINOIN
5.3.2 FDA UNII
5688UTC01R
5.3.3 Pharmacological Classes
Retinoids [CS]; Retinoid [EPC]
5.4 ATC Code

D10AD51

S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355


D - Dermatologicals

D10 - Anti-acne preparations

D10A - Anti-acne preparations for topical use

D10AD - Retinoids for topical use in acne

D10AD01 - Tretinoin


L - Antineoplastic and immunomodulating agents

L01 - Antineoplastic agents

L01X - Other antineoplastic agents

L01XF - Retinoids for cancer treatment

L01XF01 - Tretinoin


5.5 Absorption, Distribution and Excretion

Absorption

Tretinoin applied topically is typically between 1-31% absorbed. When formulated with [benzoyl peroxide], the extent of absorption was examined after 14 days of once-daily application of 1.9 g of the combination product. On Day 14, at steady-state, the mean Cmax for tretinoin and the metabolites 4-keto 13-cis RA and 13-cis RA were 0.15-0.19, 0.27-0.34, and 0.13-0.28 ng/mL, depending on the patient age group. The corresponding ranges for the mean AUC0-24 were 0.63-2.06, 2.39-2.89, and 0.96-1.99 ng\*h/mL.


/MILK/ It is not known whether topically applied tretinoin is excreted in human milk.

American Society of Health-System Pharmacists; Drug Information 2018. Bethesda, MD. 2018


Studies with radiolabeled drug have demonstrated that after the oral administration of 2.75 and 50 mg doses of tretinoin, greater than 90% of the radioactivity was recovered in the urine and feces. Based upon data from 3 subjects, approximately 63% of radioactivity was recovered in the urine within 72 hours and 31% appeared in the feces within 6 days.

NIH; DailyMed. Current Medication Information for Tretinoin Capsule (Updated: January 11, 2017). Available from, as of September 13, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9c4ae9d9-c2a0-4995-a27a-e3f0f0284db9


A single 45 mg/sq m (approximately 80 mg) oral dose to APL /acute promyelocytic leukemia/ patients resulted in a mean +/- SD peak tretinoin concentration of 347 +/- 266 ng/mL. Time to reach peak concentration was between 1 and 2 hours.

NIH; DailyMed. Current Medication Information for Tretinoin Capsule (Updated: January 11, 2017). Available from, as of September 13, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9c4ae9d9-c2a0-4995-a27a-e3f0f0284db9


The apparent volume of distribution of tretinoin has not been determined. Tretinoin is greater than 95% bound in plasma, predominately to albumin. Plasma protein binding remains constant over the concentration range of 10 to 500 ng/mL.

NIH; DailyMed. Current Medication Information for Tretinoin Capsule (Updated: January 11, 2017). Available from, as of September 13, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9c4ae9d9-c2a0-4995-a27a-e3f0f0284db9


For more Absorption, Distribution and Excretion (Complete) data for all-trans-Retinoic acid (12 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Hepatic


Evidence suggests that tretinoin induces its own metabolism. In patients with APL receiving 45 mg/sq m tretinoin daily, urinary excretion of 4-oxo trans retinoic acid glucuronide increased approximately tenfold over the course of 2-6 weeks of continuous therapy, suggesting that increased metabolism of tretinoin may be the primary mechanism leading to the decreased plasma drug concentrations observed during continued administration. Possible mechanisms for the increased clearance of tretinoin with continuous daily dosing of the drug include induction of CYP enzymes or oxidative cofactors and increased expression of cellular retinoic acid binding proteins. Increasing the dosage of tretinoin to compensate for the apparent autoinduction has not been shown to increase therapeutic response. Reduced plasma retinoid concentrations have been associated with relapse and clinical resistance, and some investigators suggest that the clinical failure of tretinoin may be related to a lack of sustained effective concentrations of the drug during prolonged treatment.

American Society of Health-System Pharmacists; Drug Information 2018. Bethesda, MD. 2018, p. 1392


Tretinoin metabolites have been identified in plasma and urine. Cytochrome P450 enzymes have been implicated in the oxidative metabolism of tretinoin. Metabolites include 13- cis retinoic acid, 4-oxo trans retinoic acid, 4-oxo cis retinoic acid, and 4-oxo trans retinoic acid glucuronide. In APL /acute promyelocytic leukemia/ patients, daily administration of a 45 mg/SQ m dose of tretinoin resulted in an approximately tenfold increase in the urinary excretion of 4-oxo trans retinoic acid glucuronide after 2 to 6 weeks of continuous dosing, when compared to baseline values.

NIH; DailyMed. Current Medication Information for Tretinoin Capsule (Updated: January 11, 2017). Available from, as of September 13, 2018: https://dailymed.nlm.nih.gov/dailymed/drugInfo.cfm?setid=9c4ae9d9-c2a0-4995-a27a-e3f0f0284db9


Ethanol fed rats showed enhanced microsomal retinoic acid metabolism (50%) accompanied by increased microsomal cytochrome P450 content (34%). The increased hepatic microsomal cytochrome P450 dependent metabolism of retinoic acid after chronic ethanol consumption may contribute to the accelerated catabolism of retinoic acid in vivo.

PMID:6803674 Sato M et al; Arch Biochem Biophys 213 (2): 557-64 (1982)


Following ip administration of high doses of 15-(14)C- and 10,11-(3)H-labeled retinoic acid to rats, 3 major metabolites were isolated from feces in microgram amounts by column, thin-layer and high-pressure liquid chromatography. Mass spectrometry provided identification as all-trans-4-oxoretinoic acid, all-trans-5'-hydroxy-retinoic acid and 7-trans-9-cis-11-trans-13-trans-5'-hydroxyretinoic acid.

PMID:863728 Hanni R et al; HELV CHIM ACTA 60 (3): 881 (1977)


For more Metabolism/Metabolites (Complete) data for all-trans-Retinoic acid (8 total), please visit the HSDB record page.


Tretinoin has known human metabolites that include 18-Hydroxyretinoic acid, 4-Hydroxyretinoic acid, 5,6-Epoxy-retinoic acid, and All-trans-retinoyl glucuronide.

Tretinoin is a known human metabolite of retinal.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560


5.7 Biological Half-Life

0.5-2 hours


In patients with APL /acute promyelocytic leukemia/ receiving tretinoin orally, a terminal elimination half-life of 0.5-2 hours has been reported following initial dosing.

American Society of Health-System Pharmacists; Drug Information 2018. Bethesda, MD. 2018, p. 1392


5.8 Mechanism of Action

Tretinoin binds to alpha, beta, and gamma retinoic acid receptors (RARs). RAR-alpha and RAR-beta have been associated with the development of acute promyelocytic leukemia and squamous cell cancers, respectively. RAR-gamma is associated with retinoid effects on mucocutaneous tissues and bone. Although the exact mechanism of action of tretinoin is unknown, current evidence suggests that the effectiveness of tretinoin in acne is due primarily to its ability to modify abnormal follicular keratinization. Comedones form in follicles with an excess of keratinized epithelial cells. Tretinoin promotes detachment of cornified cells and the enhanced shedding of corneocytes from the follicle. By increasing the mitotic activity of follicular epithelia, tretinoin also increases the turnover rate of thin, loosely-adherent corneocytes. Through these actions, the comedo contents are extruded and the formation of the microcomedo, the precursor lesion of acne vulgaris, is reduced. Tretinoin is not a cytolytic agent but instead induces cytodifferentiation and decreased proliferation of APL cells in culture and in vivo. When Tretinoin is given systemically to APL patients, tretinoin treatment produces an initial maturation of the primitive promyelocytes derived from the leukemic clone, followed by a repopulation of the bone marrow and peripheral blood by normal, polyclonal hematopoietic cells in patients achieving complete remission (CR). The exact mechanism of action of tretinoin in APL is unknown.


Although the precise mechanism(s) of action of tretinoin has not been fully elucidated, it is known that the drug is not a cytolytic agent. Tretinoin induces cellular differentiation and decreases the proliferation of acute promyelocytic leukemia (APL) cells. The PML/RAR-a fusion protein resulting from the chromosomal translocation appears to block myeloid differentiation at the promyelocyte stage, possibly by complexing and inactivating wild-type PML or by inhibiting the normal retinoic acid signaling pathway. In patients with APL who achieve a complete remission with tretinoin therapy, the drug causes an initial maturation of the primitive promyelocytes derived from the cellular leukemic clone followed by a repopulation of the bone marrow and peripheral blood by normal, polyclonal hematopoietic cells. Observations supporting cellular differentiation effects as a mechanism of tretinoin include the absence of bone marrow hypoplasia during induction, the appearance of immunophenotypically unique "intermediate cells" expressing both mature and immature cell surface antigens, and the presence of both Auer rods and the translocation in morphologically mature granulocytes until a late stage of induction. The mechanism by which the population of malignant cells is eliminated is not fully understood but appears to involve apoptosis (programmed cell death). Following induction therapy, the PML/RAR-a fusion protein can be detected in the majority of patients, suggesting that tretinoin alone does not eradicate the leukemic clone.

American Society of Health-System Pharmacists; Drug Information 2018. Bethesda, MD. 2018, p. 1391


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Italy
26th North American ISSX
Not Confirmed
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Olon S.p.A

Italy
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26th North American ISSX
Not Confirmed

Tretinoin

About the Company : We produce Active Pharmaceutical Ingredients (APIs) providing integrated full-service capabilities. Olon’s ability to develop and manufacture Active Pharmaceutical Ingredients (...

We produce Active Pharmaceutical Ingredients (APIs) providing integrated full-service capabilities. Olon’s ability to develop and manufacture Active Pharmaceutical Ingredients (APIs) in our network of facilities allows clients full access to integrated services resulting in faster production and delivery timelines, with one of the most extensive track records. We rely on synthetic and biological processes both for generic and contract development and the manufacturing market, in a full cGMPs environment, following ICH Q7 compliance.
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08

Siegfried AG

Switzerland
26th North American ISSX
Not Confirmed
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Siegfried AG

Switzerland
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26th North American ISSX
Not Confirmed

Tretinoin

About the Company : As an internationally renowned outsourcing partner, we offer products and tailor-made service packages that are seamlessly embedded in the value chain of our customers. Our pharmac...

As an internationally renowned outsourcing partner, we offer products and tailor-made service packages that are seamlessly embedded in the value chain of our customers. Our pharmaceutical industry partners benefit from a wide range of offers - from the development of active ingredients to development services for ready-made drugs, their approval and production to packaging and logistics. As a former fully integrated pharmaceutical company, Siegfried is now one of the few suppliers who can develop both active ingredients and ready-made drugs under one roof. This combination of experience and know-how is unique in the CDMO market.
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09

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

Tretinoin

About the Company : Sionc pharmaceuticals is specialized in manufacturing of complex and niche Active Pharmaceutical Ingredients in various therapeutic categories. Sionc has evolved as a reliable cont...

Sionc pharmaceuticals is specialized in manufacturing of complex and niche Active Pharmaceutical Ingredients in various therapeutic categories. Sionc has evolved as a reliable contributor in the generic drug industry for Regulatory markets with customer-centric approach since its inception in 2010. To Emerge as a Leading Global Pharmaceutical Company which creates value for all customers by offering excellence in product Quality Standard with committed service and be a significant contributor for global markets.
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10

26th North American ISSX
Not Confirmed
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26th North American ISSX
Not Confirmed

Tretinoin

About the Company : Srikem is a trusted source of Active Pharmaceutical Ingredients (APIs) for top pharmaceutical companies around the world. The company was founded in the year 1994 and our founder M...

Srikem is a trusted source of Active Pharmaceutical Ingredients (APIs) for top pharmaceutical companies around the world. The company was founded in the year 1994 and our founder Mr. Srinivasan has over 42 years of experience in this industry. We are an approved vendor for the top 10 pharmaceutical companies in India. Our plant is a multi-purpose unit handling operations involved in organic synthesis, which meets the standards prescribed by various agencies like FDA, Pollution Control Board, Health and Safety Authorities. We have a global presence in over 40 countries.
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27-Jan-2021
27-Aug-2024
KGS
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Average Price (USD/KGS)

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Total Quantity (KGS)

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Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

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DRUG PRODUCT COMPOSITIONS

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DOSAGE - CREAM;TOPICAL - 0.1%

USFDA APPLICATION NUMBER - 17340

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DOSAGE - CREAM;TOPICAL - 0.05%

USFDA APPLICATION NUMBER - 17522

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DOSAGE - GEL;TOPICAL - 0.025%

USFDA APPLICATION NUMBER - 17579

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DOSAGE - GEL;TOPICAL - 0.01%

USFDA APPLICATION NUMBER - 17955

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DOSAGE - CREAM;TOPICAL - 0.025%

USFDA APPLICATION NUMBER - 19049

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DOSAGE - GEL;TOPICAL - 0.04%

USFDA APPLICATION NUMBER - 20475

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DOSAGE - GEL;TOPICAL - 0.06%

USFDA APPLICATION NUMBER - 20475

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DOSAGE - GEL;TOPICAL - 0.08%

USFDA APPLICATION NUMBER - 20475

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DOSAGE - GEL;TOPICAL - 0.1%

USFDA APPLICATION NUMBER - 20475

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DOSAGE - CREAM;TOPICAL - 0.01%;4%;0.05%

USFDA APPLICATION NUMBER - 21112

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DOSAGE - GEL;TOPICAL - 0.05%

USFDA APPLICATION NUMBER - 22070

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DOSAGE - GEL;TOPICAL - 1.2%;0.025%

USFDA APPLICATION NUMBER - 50803

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