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1-[(2-Chlorophenyl)diphenylmethyl]imidazole

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ACTIVE PHARMA INGREDIENTS

34 API Suppliers, 12 USDMF, 5 CEP/COS, 1 JDMF, 4 EU WC, 21 NDC API, 1 VMF, 22 Listed Suppliers, $ API Reference Price

34 API Suppliers
12 USDMF
5 CEP/COS
1 JDMF
4 EU WC
21 NDC API
1 VMF
22 Listed Suppliers
$ API Reference Price

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1 Intermediates Suppliers

1 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

241 FDF Dossiers, 43 FDA Orange Book, 28 Europe, 31 Canada, 10 Australia, 51 South Africa, 78 Listed Dossiers

241 FDF Dossiers
43 FDA Orange Book
28 Europe
31 Canada
10 Australia
51 South Africa
78 Listed Dossiers

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1 Evonik, 8 SPI Pharma, 1 Seqens, 8 DKSH, 2 Jai Radhe Sales, 2 Nippon Fine Chemical, 1 Boai NKY Pharmaceuticals Ltd, 8 Gangwal Healthcare, 11 Nanjing Well Pharmaceutical, 7 Actylis, 1 Aeon Procare, 6 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd, 33 BASF, 1 BioSpectra, 1 Clariant, 6 Corel Pharma Chem, 3 DFE Pharma, 3 Finar, 12 Gangwal Chemicals, 1 Ideal Cures Pvt Ltd, 1 Ingredion Pharma Solutions, 10 Kerry, 3 Lubrizol Life Science Health, 14 Microlex e.U, 1 Nanjing Bold Chemical, 1 Novo Excipients, 2 Pharmatrans-Sanaq, 6 Pluviaendo, 3 Prachin Chemical, 13 Roquette, 15 Seppic, 3 Shanghai Shenmei Pharmaceutical Technology Co., Ltd, 9 Sigachi Industries, 1 Ulanqab Kema New Material, 1 Valens Pharmachem, 3 Vasa Pharmachem

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42 APIs, 8 FDF Dossiers

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4 EDQM , 1 USP , 17 Others

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Synopsis

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EU WC

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Listed Suppliers

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241

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Chemistry

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Also known as: 23593-75-1, Lotrimin, Canesten, Mycelex, Clotrimazol, Mycosporin

Molecular Formula

C₂₂H₁₇ClN₂

Molecular Weight

344.8 g/mol

InChI Key

VNFPBHJOKIVQEB-UHFFFAOYSA-N

FDA UNII

G07GZ97H65

An imidazole derivative with a broad spectrum of antimycotic activity. It inhibits biosynthesis of the sterol ergostol, an important component of fungal CELL MEMBRANES. Its action leads to increased membrane permeability and apparent disruption of enzyme systems bound to the membrane.

Clotrimazole is an Azole Antifungal.

1 2D Structure

Clotrimazole

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[(2-chlorophenyl)-diphenylmethyl]imidazole

2.1.2 InChI

InChI=1S/C22H17ClN2/c23-21-14-8-7-13-20(21)22(25-16-15-24-17-25,18-9-3-1-4-10-18)19-11-5-2-6-12-19/h1-17H

2.1.3 InChI Key

VNFPBHJOKIVQEB-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=C(C=C1)C(C2=CC=CC=C2)(C3=CC=CC=C3Cl)N4C=CN=C4

2.2 Other Identifiers

2.2.1 UNII

G07GZ97H65

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Bay B 5097

2. Canesten

3. Fb B 5097

4. Kanesten

5. Klotrimazole

6. Lotrimin

7. Mycelex

2.3.2 Depositor-Supplied Synonyms

1. 23593-75-1

2. Lotrimin

3. Canesten

4. Mycelex

5. Clotrimazol

6. Mycosporin

7. Empecid

8. Mykosporin

9. Gyne Lotrimin

10. Chlotrimazole

11. Trimysten

12. Gyne-lotrimin

13. 1-(o-chlorotrityl)imidazole

14. Mycelex G

15. Rimazole

16. Mycelex 7

17. Tibatin

18. Gynix

19. Mono-baycuten

20. Lotrimin Af Cream

21. Mycelex Troches

22. Lotrimin Af Solution

23. Mycelex Otc

24. Canestine

25. Pedisafe

26. Veltrim

27. Lotrimin Af

28. Trivagizole 3

29. Desamix F

30. Mycelex-g

31. Bay B 5097

32. Fem Care

33. Gyne-lotrimin 3

34. Mycelex-7

35. Clotrimazolum

36. Monobaycuten

37. (chlorotrityl)imidazole

38. 1-((2-chlorophenyl)diphenylmethyl)-1h-imidazole

39. Canifug

40. Bay 5097

41. Lotrimax

42. Lotrimin Af Jock-itch Cream

43. Mycelax

44. Mycofug

45. Mycelex-7 Combination Pack

46. Gyne-lotrimin Combination Pack

47. 1-(o-chloro-alpha,alpha-diphenylbenzyl)imidazole

48. Gyne-lotrimin 3 Combination Pack

49. Bay-b 5097

50. 1-[(2-chlorophenyl)-diphenylmethyl]imidazole

51. 1h-imidazole, 1-[(2-chlorophenyl)diphenylmethyl]-

52. Fb 5097

53. Lotrimin (tn)

54. Mycelex (tn)

55. 1-(o-chlorophenyldiphenylmethyl)imidazole

56. (2-chlorophenyl)diphenyl-1-imidazolylmethane

57. Trivagizole

58. Diphenyl(2-chlorophenyl)(1-imidazolyl)methane

59. Diphenyl-(2-chlorophenyl)-1-imidazolylmethane

60. 1-(alpha-(2-chlorophenyl)benzhydryl)imidazole

61. Nsc 257473

62. 1-[(2-chlorophenyl)diphenylmethyl]-1h-imidazole

63. 1-[(2-chlorophenyl)(diphenyl)methyl]-1h-imidazole

64. Mycelex: Mycosporinrimazole

65. Bay B 9057

66. Prestwick_120

67. Bis-phenyl-(2-chlorophenyl)(1-imidazoyl)methane

68. Gnf-pf-3499

69. 1h-imidazole, 1-((2-chlorophenyl)diphenylmethyl)-

70. Methane, Bis-phenyl-(2-chlorophenyl)-1-imidazolyl-

71. Bisphenyl-(2-chlorphenyl)-1-imidazolyl-methan

72. Lopac-c-6019

73. Nsc257473

74. Chembl104

75. Nsc-257473

76. 1-(2-chlorotrityl)imidazole

77. Mls000028502

78. Chebi:3764

79. 1-[(2-chlorophenyl)-diphenyl-methyl]imidazole

80. G07gz97h65

81. Bay-5097

82. Svt-15652

83. 1-(o-chloro-.alpha.,.alpha.-diphenylbenzyl)imidazole

84. Ncgc00015251-02

85. Clotrimaderm

86. Canestene

87. Clomatin

88. Cutistad

89. Esparol

90. Smr000058306

91. Stiemazol

92. Nalbix

93. Femcare

94. Lotrimin Lotion

95. Canesten Cream

96. Cas-23593-75-1

97. Clotrimazole 100 Microg/ml In Acetonitrile

98. Gino-lotremine

99. Lotrimin Cream

100. Mycelex Cream

101. Myclo Solution

102. Mycelex Solution

103. Myclo Cream

104. Dsstox_cid_9871

105. Myclo-gyne

106. Pan-fungex

107. Canesten Solution

108. Lotrimin Solution

109. Neo-zol Cream

110. Bis-phenyl-(2-chlorophenyl)-1-imidazoyl)methane

111. Dsstox_rid_78827

112. Mycelex Twin Pack

113. Dsstox_gsid_29871

114. Lotrimin Af Lotion

115. Clotrimazol [inn-spanish]

116. Clotrimazolum [inn-latin]

117. Myclo Spray Solution

118. Clotrimeizol

119. Jidesheng

120. Canesten 1-day Therapy

121. Canesten 3-day Therapy

122. Canesten 6-day Therapy

123. Drg-0072

124. B 5097

125. Ccris 6245

126. Canesten 1-day Cream Combi-pak

127. Hsdb 3266

128. Canesten Combi-pak 1-day Therapy

129. Canesten Combi-pak 3-day Therapy

130. Sr-01000075771

131. Einecs 245-764-8

132. Brn 0622318

133. Chlortrimazole

134. Clortrimazole

135. Otomax

136. Unii-g07gz97h65

137. 1-((o-chloro-phenyl)diphenylmethyl)imidazole

138. Gyne-lotrimin3

139. Bis-fenil-(2-clorofenil)-1-imidazolil-metano

140. Clotrimaderm Cream

141. Clotrimazole,(s)

142. Mfcd00057220

143. Bis-fenil-(2-clorofenil)-1-imidazolil-metano [italian]

144. Bisphenyl-(2-chlorphenyl)-1-imidazolyl-methan [german]

145. Clotrimazole Crystalline

146. Clotrimazole [usan:usp:inn:ban:jan]

147. Spectrum_001343

148. Cpd000058306

149. Clotrimazole (canesten)

150. Prestwick0_000267

151. Prestwick1_000267

152. Prestwick2_000267

153. Prestwick3_000267

154. Spectrum2_000128

155. Spectrum3_000359

156. Spectrum4_000295

157. Spectrum5_000781

158. Clotrimazole [mi]

159. Clotrimazole [inn]

160. Clotrimazole [jan]

161. C 6019

162. Clotrimazole [usan]

163. Ncimech_000609

164. Cid_2812

165. Schembl3850

166. Clotrimazole [vandf]

167. Bidd:pxr0036

168. Lopac0_000315

169. Bspbio_000114

170. Bspbio_002057

171. Clotrimazole [mart.]

172. Kbiogr_000850

173. Kbioss_001823

174. 5-23-04-00291 (beilstein Handbook Reference)

175. Mls000758243

176. Mls001423972

177. Bidd:gt0450

178. Clotrimazole [usp-rs]

179. Clotrimazole [who-dd]

180. Divk1c_000665

181. Spectrum1500200

182. Bay B5097

183. Bayb 5097

184. Imidazole, 1-(o-chloro-alpha,alpha-diphenylbenzyl)-

185. Spbio_000176

186. Spbio_002333

187. Bpbio1_000126

188. Gtpl2330

189. Component Of Otomax (salt/mix)

190. Dtxsid7029871

191. Gyne-lotrimin3 Combination Pack

192. Bdbm31774

193. Clotrimazole (jp17/usp/inn)

194. Hms502b07

195. Kbio1_000665

196. Kbio2_001823

197. Kbio2_004391

198. Kbio2_006959

199. Kbio3_001277

200. Clotrimazole [green Book]

201. Imidazole, 1-(o-chloro-.alpha.,.alpha.-diphenylbenzyl)-

202. Component Of Lotrimax (salt/mix)

203. Ninds_000665

204. Clotrimazole [ep Impurity]

205. Clotrimazole [orange Book]

206. Hms1568f16

207. Hms1920o21

208. Hms2051e11

209. Hms2091g10

210. Hms2095f16

211. Hms2235e20

212. Hms3260p12

213. Hms3369i03

214. Hms3393e11

215. Hms3655i09

216. Hms3712f16

217. Pharmakon1600-01500200

218. Clotrimazole [ep Monograph]

219. Clotrimazole [usp Impurity]

220. Imidazole,.alpha.-diphenylbenzyl)-

221. Bcp02150

222. Clotrimazole For Peak Identification

223. Zinc3807804

224. Clotrimazole [usp Monograph]

225. Tox21_110111

226. Tox21_300415

227. Tox21_500315

228. Ccg-35563

229. Nsc756700

230. S1606

231. Stk700023

232. Akos005607024

233. Lotrisone Component Clotrimazole

234. Tox21_110111_1

235. Cs-1926

236. Db00257

237. Lp00315

238. Nc00035

239. Nsc-756700

240. Sb17418

241. Sdccgsbi-0050303.p005

242. Clotrimazole 100 Microg/ml In Methanol

243. Idi1_000665

244. Mrf-0000070

245. Qtl1_000024

246. Ncgc00015251-01

247. Ncgc00015251-03

248. Ncgc00015251-04

249. Ncgc00015251-05

250. Ncgc00015251-06

251. Ncgc00015251-07

252. Ncgc00015251-08

253. Ncgc00015251-09

254. Ncgc00015251-10

255. Ncgc00015251-11

256. Ncgc00015251-12

257. Ncgc00015251-13

258. Ncgc00015251-14

259. Ncgc00015251-27

260. Ncgc00093761-01

261. Ncgc00093761-02

262. Ncgc00093761-03

263. Ncgc00093761-04

264. Ncgc00093761-05

265. Ncgc00093761-06

266. Ncgc00254538-01

267. Ncgc00261000-01

268. 1-(o-chloro-a,a-diphenylbenzyl)imidazole

269. As-13816

270. Clotrimazole Component Of Lotrisone

271. Hy-10882

272. 1-(2-chloro-?,?-diphenylbenzyl)imidazole

273. Sbi-0050303.p004

274. Db-046195

275. 1-[(2-chlorophenyl)diphenylmethyl]imidazole

276. Ab00051951

277. Eu-0100315

278. Ft-0603193

279. Sw196431-5

280. C06922

281. D00282

282. 1-(.alpha.-(2-chlorophenyl)benzhydryl)imidazole

283. 1-[(2-chlorophenyl)-di(phenyl)methyl]imidazole

284. Ab00051951-14

285. Ab00051951_15

286. Ab00051951_16

287. Clotrimazole, Vetranal(tm), Analytical Standard

288. 593c751

289. A816789

290. Q413546

291. 1h-imidazole, 1-[(2-chlorophenyl)-diphenylmethyl]

292. Sr-01000075771-1

293. Sr-01000075771-6

294. Sr-01000075771-8

295. W-107394

296. 1-[(2-chloro-phenyl)-diphenyl-methyl]-1h-imidazole

297. Brd-k15916496-001-14-7

298. Sr-01000075771-10

299. 3acdfdf8-38e3-4368-85d0-bdf8ae1e6591

300. Clotrimazole, British Pharmacopoeia (bp) Reference Standard

301. Clotrimazole, European Pharmacopoeia (ep) Reference Standard

302. Clotrimazole, United States Pharmacopeia (usp) Reference Standard

303. 1-(o-chlorotrityl)imidazole;1-(o-chloro-alpha,alpha-diphenylbenzyl)imidazole

304. Clotrimazole For Peak Identification, European Pharmacopoeia (ep) Reference Standard

305. Clotrimazole, Pharmaceutical Secondary Standard; Certified Reference Material

306. 117829-71-7

2.4 Create Date

2005-03-25

3 Chemical and Physical Properties

Molecular Formula	C₂₂H₁₇ClN₂
Molecular Weight	344.8 g/mol
XLogP3	5
Hydrogen Bond Donor Count	0
Hydrogen Bond Acceptor Count	1
Rotatable Bond Count	4
Exact Mass	344.1080262 g/mol
Monoisotopic Mass	344.1080262 g/mol
Topological Polar Surface Area	17.8 Å²
Heavy Atom Count	25
Formal Charge	0
Complexity	396
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 20
Drug Name	Clotrimazole
PubMed Health	Clotrimazole
Drug Classes	Antifungal, Imidazole
Drug Label	Each Clotrimazole Troche (clotrimazole lozenges) USP contains 10 mg clotrimazole [1-(o-chloro-,-diphenylbenzyl) imidazole], a synthetic antifungal agent, for topical use in the mouth.Structural Formula:The troche dosage form is a large, slowly di...
Active Ingredient	Clotrimazole
Dosage Form	Cream; Solution; Troche/lozenge
Route	Topical; Vaginal; Oral
Strength	1%; 10mg
Market Status	Over the Counter; Prescription
Company	Fougera Pharms; Glenmark Pharms; Paddock; Actavis Mid Atlantic; Teva; Taro; Roxane

2 of 20
Drug Name	Gyne-lotrimin
PubMed Health	Clotrimazole
Drug Classes	Antifungal, Imidazole
Active Ingredient	Clotrimazole
Dosage Form	Tablet; Cream
Route	Vaginal
Strength	1%; 100mg
Market Status	Over the Counter
Company	Schering Plough

3 of 20
Drug Name	Gyne-lotrimin 3
PubMed Health	Clotrimazole (Topical route)
Drug Classes	Antifungal, Imidazole
Active Ingredient	Clotrimazole
Dosage Form	Tablet; Cream
Route	Vaginal
Strength	200mg; 2%
Market Status	Over the Counter
Company	Schering Plough

4 of 20
Drug Name	Gyne-lotrimin 3 combination pack
PubMed Health	Clotrimazole
Drug Classes	Antifungal, Imidazole
Active Ingredient	Clotrimazole
Dosage Form	Cream, tablet
Route	Topical, vaginal
Strength	1%,200mg
Market Status	Over the Counter
Company	Schering Plough

5 of 20
Drug Name	Gyne-lotrimin combination pack
PubMed Health	Clotrimazole (Vaginal)
Drug Classes	Antifungal
Active Ingredient	Clotrimazole
Dosage Form	Cream, tablet
Route	Topical, vaginal
Strength	1%,100mg
Market Status	Over the Counter
Company	Schering Plough

6 of 20
Drug Name	Lotrimin af
Active Ingredient	Clotrimazole
Dosage Form	Cream; Lotion; Solution
Route	topical
Strength	1%
Market Status	Over the Counter
Company	Schering Plough

7 of 20
Drug Name	Mycelex
Active Ingredient	Clotrimazole
Dosage Form	Solution
Route	topical
Strength	1%
Market Status	Over the Counter
Company	Bayer Hlthcare

8 of 20
Drug Name	Mycelex-7
Active Ingredient	Clotrimazole
Dosage Form	Tablet; Cream
Route	Vaginal
Strength	1%; 100mg
Market Status	Over the Counter
Company	Bayer

9 of 20
Drug Name	Mycelex-7 combination pack
Active Ingredient	Clotrimazole
Dosage Form	Cream, tablet
Route	Topical, vaginal
Strength	1%,100mg
Market Status	Over the Counter
Company	Bayer

10 of 20
Drug Name	Trivagizole 3
Active Ingredient	Clotrimazole
Dosage Form	Cream
Route	Vaginal
Strength	2%
Market Status	Over the Counter
Company	Taro

11 of 20
Drug Name	Clotrimazole
PubMed Health	Clotrimazole
Drug Classes	Antifungal, Imidazole
Drug Label	Each Clotrimazole Troche (clotrimazole lozenges) USP contains 10 mg clotrimazole [1-(o-chloro-,-diphenylbenzyl) imidazole], a synthetic antifungal agent, for topical use in the mouth.Structural Formula:The troche dosage form is a large, slowly di...
Active Ingredient	Clotrimazole
Dosage Form	Cream; Solution; Troche/lozenge
Route	Topical; Vaginal; Oral
Strength	1%; 10mg
Market Status	Over the Counter; Prescription
Company	Fougera Pharms; Glenmark Pharms; Paddock; Actavis Mid Atlantic; Teva; Taro; Roxane

12 of 20
Drug Name	Gyne-lotrimin
PubMed Health	Clotrimazole
Drug Classes	Antifungal, Imidazole
Active Ingredient	Clotrimazole
Dosage Form	Tablet; Cream
Route	Vaginal
Strength	1%; 100mg
Market Status	Over the Counter
Company	Schering Plough

13 of 20
Drug Name	Gyne-lotrimin 3
PubMed Health	Clotrimazole (Topical route)
Drug Classes	Antifungal, Imidazole
Active Ingredient	Clotrimazole
Dosage Form	Tablet; Cream
Route	Vaginal
Strength	200mg; 2%
Market Status	Over the Counter
Company	Schering Plough

14 of 20
Drug Name	Gyne-lotrimin 3 combination pack
PubMed Health	Clotrimazole
Drug Classes	Antifungal, Imidazole
Active Ingredient	Clotrimazole
Dosage Form	Cream, tablet
Route	Topical, vaginal
Strength	1%,200mg
Market Status	Over the Counter
Company	Schering Plough

15 of 20
Drug Name	Gyne-lotrimin combination pack
PubMed Health	Clotrimazole (Vaginal)
Drug Classes	Antifungal
Active Ingredient	Clotrimazole
Dosage Form	Cream, tablet
Route	Topical, vaginal
Strength	1%,100mg
Market Status	Over the Counter
Company	Schering Plough

16 of 20
Drug Name	Lotrimin af
Active Ingredient	Clotrimazole
Dosage Form	Cream; Lotion; Solution
Route	topical
Strength	1%
Market Status	Over the Counter
Company	Schering Plough

17 of 20
Drug Name	Mycelex
Active Ingredient	Clotrimazole
Dosage Form	Solution
Route	topical
Strength	1%
Market Status	Over the Counter
Company	Bayer Hlthcare

18 of 20
Drug Name	Mycelex-7
Active Ingredient	Clotrimazole
Dosage Form	Tablet; Cream
Route	Vaginal
Strength	1%; 100mg
Market Status	Over the Counter
Company	Bayer

19 of 20
Drug Name	Mycelex-7 combination pack
Active Ingredient	Clotrimazole
Dosage Form	Cream, tablet
Route	Topical, vaginal
Strength	1%,100mg
Market Status	Over the Counter
Company	Bayer

20 of 20
Drug Name	Trivagizole 3
Active Ingredient	Clotrimazole
Dosage Form	Cream
Route	Vaginal
Strength	2%
Market Status	Over the Counter
Company	Taro

4.2 Therapeutic Uses

Anti-Infective Agents, Local; Antifungal Agents; Growth Inhibitors

National Library of Medicine's Medical Subject Headings online file (MeSH, 1999)

CLOTRIMAZOLE IS A CHLORINATED IMIDAZOLE DERIVATIVE THAT IS USED TO TREAT TOPICAL FUNGAL, DERMATOPHYTE, & YEAST INFECTIONS. WHILE CLOTRIMAZOLE HAS MARKED IN VITRO ACTIVITY AGAINST MANY FUNGI, IT IS OF LITTLE VALUE IN TREATMENT OF SYSTEMIC MYCOSES.

Miller, R. R., and D. J. Greenblatt. Handbook of Drug Therapy. New York: Elsevier North Holland, 1979., p. 166

VAGINAL: 1 TABLET (100 MG) IS INSERTED DAILY FOR 1 WK FOR CANDIDAL VAGINITIS. TOPICAL: SUFFICIENT CREAM OR SOLN IS APPLIED TWICE DAILY TO SKIN INFECTED WITH CANDIDA ALBICANS, TRICOPHYTON, OR MICROSPORUM SPECIES. 2 WK OF THERAPY IS USUALLY SUFFICIENT.

Miller, R. R., and D. J. Greenblatt. Handbook of Drug Therapy. New York: Elsevier North Holland, 1979., p. 167

CLOTRIMAZOLE HAS BEEN USED INVESTIGATIONALLY FOR ORAL TREATMENT OF MUCOCUTANEOUS CANDIDIASIS.

Miller, R. R., and D. J. Greenblatt. Handbook of Drug Therapy. New York: Elsevier North Holland, 1979., p. 167

For more Therapeutic Uses (Complete) data for CLOTRIMAZOLE (12 total), please visit the HSDB record page.

4.3 Drug Warning

PREPN OF CLOTRIMAZOLE ARE NOT INTENDED FOR OPHTHALMIC USE & SHOULD BE USED WITH CAUTION AROUND EYES.

American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 1424

Clotrimazole lozenges should not be used for the treatment of systemic myotic infections.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 2102

Clotrimazole Vaginal tablets ... single-dose therapy is not recommended for the treatment of severe vulvovaginal candidiasis.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 2102

To achieve maximum theraputic effect of clotrimazole when the drug is administered orally as a lozenge, the lozenge must be dissolved slowly in the mouth. Therefore, patients receiving clotrimazole lozenges must be of such age and physical and/or mental condition that they can comprehend and follow administration instruction. Liver function tests should be conducted periodically during oral therapy with clotrimazole lozenges, especially in patients with preexisting hepatic impairment.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 2102

Clotrimazole topical cream, lotion, and solution should be used during the first trimester of pregnancy only when the drug is considered essential to the welfare of the patient. Since it is not known whether clotrimazole is distributed into milk, the drug should be used with caution in nursing women.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 2103

4.4 Drug Indication

**Topical preparations** Clotrimazole topical cream is indicated for the topical treatment of the following dermal infections,: Tinea pedis, tinea cruris, and tinea corporis due to _Trichophyton rubrum_, _Trichophyton mentagrophytes_, _Epidermophyton floccosum_ Candidiasis due to _Candida albicans_ Tinea versicolor due to _Malassezia furfur_ Diaper rash infected by _Candida albicans_ In some preparations, clotrimazole may be combined with betamethasone dipropionate, a corticosteroid. **Oral preparations** The oral troche preparation is indicated for the local treatment of oropharyngeal candidiasis. It is also indicated as a prophylactic drug to reduce the incidence of oropharyngeal candidiasis in patients immunocompromised by conditions such as chemotherapy, radiotherapy, or steroid therapy utilized in the treatment of leukemia, solid tumors, or renal transplantation. Troche preparations are not indicated for the treatment of any systemic mycoses.

FDA Label

5 Pharmacology and Biochemistry

5.1 Pharmacology

Clotrimazole is a broad-spectrum antifungal agent that inhibits the growth of pathogenic yeasts by changing the permeability of cell membranes. The action of clotrimazole is fungistatic at concentrations of drug up to 20 mcg/mL and may be fungicidal _in vitro_ against Candida albicans and other species of the genus Candida at higher concentrations. Unfortunately, resistance to clotrimazole, which was rare in the past, is now common in various patient populations. Clotrimazole is generally considered to be a fungistatic, and not a fungicidal drug, although this contrast is not absolute, as clotrimazole shows fungicidal properties at higher concentrations.

5.2 MeSH Pharmacological Classification

14-alpha Demethylase Inhibitors

Compounds that specifically inhibit STEROL 14-DEMETHYLASE. A variety of azole-derived ANTIFUNGAL AGENTS act through this mechanism. (See all compounds classified as 14-alpha Demethylase Inhibitors.)

Anti-Infective Agents, Local

Substances used on humans and other animals that destroy harmful microorganisms or inhibit their activity. They are distinguished from DISINFECTANTS, which are used on inanimate objects. (See all compounds classified as Anti-Infective Agents, Local.)

Antifungal Agents

Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

CLOTRIMAZOLE

5.3.2 FDA UNII

G07GZ97H65

5.3.3 Pharmacological Classes

Azoles [CS]; Azole Antifungal [EPC]

5.4 ATC Code

G01AF02

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

A - Alimentary tract and metabolism

A01 - Stomatological preparations

A01A - Stomatological preparations

A01AB - Antiinfectives and antiseptics for local oral treatment

A01AB18 - Clotrimazole

D - Dermatologicals

D01 - Antifungals for dermatological use

D01A - Antifungals for topical use

D01AC - Imidazole and triazole derivatives

D01AC01 - Clotrimazole

G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics

G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

G01AF - Imidazole derivatives

G01AF02 - Clotrimazole

5.5 Absorption, Distribution and Excretion

Absorption

Because clotrimazole is generally not significantly absorbed, drug interactions are not a major issue with its use.

Route of Elimination

Mainly hepatic.

Volume of Distribution

The topical form is minimally absorbed in the serum and tissues. Clotrimazole is a lipophilic drug, and has been shown to be secreted in breastmilk in animal studies. There are limited data available regarding the volume of distribution following oral troche administration.

GIVEN ORALLY OR IV WAS ABSORBED, DISTRIBUTED, ELIMINATED READILY. EXCRETED AS INACTIVE METABOLITE IN BILE, LITTLE IN URINE.

DUHM B ET AL; POSTGRAD MED J (SUPPL) 500 (1): 13-16 (1974)

Absorption of clotrimazol is less than 0.5% after application to the intact skin: from the vagina, it is 3 to 10%. Fungicidal concentrations remain in the vagina for as long as 3 days after application of the drug. The small amount absorbed is metabolized in the liver and excreted in bile. In adults, an oral dose of 200 mg per day will give rise to plasma concentrations of 0.2 to 0.35 ug/ml.

Gilman, A.G., T.W. Rall, A.S. Nies and P. Taylor (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 8th ed. New York, NY. Pergamon Press, 1990., p. 1176

Only very small amounts of clotrimazole appear to be absorbed systemically following topical application to the skin. Following application to the skin, highest concentrations of clotrimazole are present in the stratum corneum; lower drug concentrations occur in the stratum spinosum and the papillary and reticular dermis. Small amounts of clotrimazole are absorbed systemically when the drug is administered intravaginally. Following intravaginal administration of radiolabeled clotrimazole in patients with normal or inflamed vaginal mucosa, peak serum concentrations of clotrimazole 24 hours after insertion of a single 100 mg tablet of the drug are 0.03 ug/ml and peak serum concentrations 24 hours after administration of a cream containing 50 mg of the drug are 0.01 ug/ml. About 3-10% of an intravaginal dose of the drug reaches systemic circulation, principally as metabolites.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 2101

Clotrimazole is absorbed from the gastrointestinal tract ... and excreted in the feces and urine. When applied topically clotrimazole penetrates the epidermis but there is little if any systemic absorption. Slight absorption has been reported following the administration of vaginal tablets.

Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 721

5.6 Metabolism/Metabolites

Hepatic (metabolized to inactive metabolites).

Clotrimazole ... is metabolized in the liver to inactive compounds ... .

Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 721

The effect of the antifungal imidazole compound, clotrimazole, on the metabolism of benzo[a]pyrene was studied in cultured keratinocytes prepared from BALB/c mouse epidermis. Varying concentrations of clotrimazole added to the cultured keratinocytes resulted in a dose dependent inhibition of the activities of the microsomal cytochrome p450 dependent monooxygenases aryl hydrocarbon hydroxylase and 7-ethoxycoumarin O-deethylase. The major organic solvent soluble metabolites of benzo(a)pyrene identified in the cultured cells were trans-7,8-dihydro-7,8-dihydroxybenzo(a)pyrene, 9-hydroxybenzo(a)pyrene, and 3-hydroxybenzo(a)pyrene, although small amounts of trans-4,5-dihydro-4,5-dihydroxybenzo(a)pyrene, benzo(a)pyrene-quinones, and trans-9,10-dihydroxybenzo(a)pyrene were also present. The major organic solvent extractable metabolites of benzo(a)pyrene found in the extracellular culture medium were primarily the diols with smaller quantities of phenols and quinones. The major water soluble metabolites of benzo(a)pyrene present both intracellularly and extracellularly were glucuronide conjugates of 3-hydroxybenzo(a)pyrene, 9-hydroxybenzo(a)pyrene, and benzo(a)pyrene-3,6-dione and to a lesser extent sulfate conjugates (primarily of the trans-7,8-dihydro-7,8- dihydroxybenzo(a)pyrene). Clotrimazole inhibited the generation of organic solvent soluble and water soluble conjugates in a dose dependent manner. The in vitro metabolism of benzo(a)pyrene by microsomes prepared from control and benz(a)anthracene induced cultured keratinocytes was also inhibited by clotrimazole with greater inhibitory effect on benz(a)anthracene induced keratinocytes especially with respect to the formation of diols and quinones. The enzyme mediated covalent binding of benzo(a)pyrene to mouse keratinocyte DNA and protein was also substantially diminished by clotrimazole in a dose dependent fashion. These results indicate that clotrimazole, a widely used drug for the management of a variety of superficial dermatophyte infections of the skin, is a potent inhibitor of cytochrome p450 dependent transformation of polycyclic aromatic hydrocarbons in cultured murine keratinocytes. This system offers a convenient approach for studies as inhibitors of carcinogen metabolism in the epidermis.

PMID:3755152 Das M et al; J Invest Dermatol 87 (1): 4-10 (1986)

5.7 Biological Half-Life

Clotrimazole was given by mouth in a dose of 1.5 g to 7 healthy subjects and 47 patients and peak blood concentrations of up to 1 ug/ml were detected microbiologically at 2 or 4 hours. The half-life was between 3.5 and 5.5 hours.

Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 721

Clotrimazole was absorbed from the gastrointestinal tract and had a biological half-life of about 4 hours. Liver and kidney dysfunction had little influence on serum concentrations or half-life.

Reynolds, J.E.F., Prasad, A.B. (eds.) Martindale-The Extra Pharmacopoeia. 28th ed. London: The Pharmaceutical Press, 1982., p. 721

5.8 Mechanism of Action

Clotrimazole acts primarily by damaging the permeability barrier in the cell membrane of fungi. Clotrimazole causes inhibition of ergosterol biosynthesis, an essential constituent of fungal cell membranes. If ergosterol synthesis is either completely or partially inhibited, the cell is no longer able to construct an intact and functional cell membrane,. Because ergosterol directly promotes the growth of fungal cells in a hormonelike fashion, rapid onset of the above events leads to dose-dependent inhibition of fungal growth. Though decreased ergosterol, due to the inhibition of lanosterol 14-demethylase (also known as _CYP51_) is accepted to be primarily responsible for the antimycotic properties of clotrimazole, this drug also shows other pharmacological effects. These include the inhibition of sarcoplasmic reticulum Ca2+ATPase, depletion of intracellular calcium, and blocking of calciumdependent potassium channels and voltagedependent calcium channels. The action of clotrimazole on these targets accounts for other effects of this drug that are separate from its antimycotic activities.

Clotrimazole exerts its antifungal activity by altering cell membrane permeability, apparently by binding with phospholipids in the fungal cell membrane. In contrast to polyene antibiotics (eg, amphotericin B), the action of clotrimazole is less dependent on the sterol content of the cell membrane. As a result of alteration of permeability, the cell membrane is unable to function as a selective barrier, and potassium and other cellular constituents are lost.

McEvoy, G.K. (ed.). American Hospital Formulary Service - Drug Information 92. Bethesda, MD: American Society of Hospital Pharmacists, Inc., 1992 (Plus Supplements 1992)., p. 2101

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Number of Transactions

Total Quantity (KGS)

Total Value (USD)

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

API Imports and Exports

Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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1-[(2-Chlorophenyl)diphenylmethyl]imidazole

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CHEMISTRY

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ACTIVE PHARMA INGREDIENTS

34 API Suppliers

12 USDMF

5 CEP/COS

1 JDMF

4 EU WC

21 NDC API

1 VMF

22 Listed Suppliers

$ API Reference Price

INTERMEDIATES

1 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

241 FDF Dossiers

43 FDA Orange Book

28 Europe

31 Canada

10 Australia

51 South Africa

78 Listed Dossiers

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2 Jai Radhe Sales

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11 Nanjing Well Pharmaceutical

7 Actylis

1 Aeon Procare

6 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd

33 BASF

1 BioSpectra

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6 Corel Pharma Chem

3 DFE Pharma

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9 Sigachi Industries

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3 Vasa Pharmachem

EXCIPIENTS BY APPLICATIONS

51 Topical

36 Solubilizers

35 Fillers, Diluents & Binders

30 Thickeners and Stabilizers

25 Direct Compression

20 Emulsifying Agents

20 Coating Systems & Additives

20 Parenteral

18 Granulation

17 Lubricants & Glidants

17 Co-Processed Excipients

17 Disintegrants & Superdisintegrants

14 Surfactant & Foaming Agents

14 Film Formers & Plasticizers

11 Controlled & Modified Release

9 Rheology Modifiers