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ACTIVE PHARMA INGREDIENTS

36 API Suppliers, 22 USDMF, 5 CEP/COS, 8 JDMF, 40 KDMF, 10 NDC API, 6 Listed Suppliers, $ API Reference Price

36 API Suppliers
22 USDMF
5 CEP/COS
8 JDMF
40 KDMF
10 NDC API
6 Listed Suppliers
$ API Reference Price

INTERMEDIATES

1 Intermediates Suppliers

1 Intermediates Suppliers

FINISHED DOSAGE FORMULATIONS

138 FDF Dossiers, 79 FDA Orange Book, 2 Europe, 7 Canada, 27 South Africa, 23 Listed Dossiers

138 FDF Dossiers
79 FDA Orange Book
2 Europe
7 Canada
27 South Africa
23 Listed Dossiers

RELATED EXCIPIENT COMPANIES

4 SPI Pharma, 2 Seqens, 2 DKSH, 5 Faran Shimi Pharmaceutical, 1 Boai NKY Pharmaceuticals Ltd, 12 Gangwal Healthcare, 3 Nanjing Well Pharmaceutical, 1 ACG Worldwide, 5 Actylis, 1 Aeon Procare, 7 Anhui Sunhere Pharmaceutical Excipients Co.,Ltd, 24 BASF, 10 Corel Pharma Chem, 4 DFE Pharma, 1 Finar, 9 Gangwal Chemicals, 6 Ideal Cures Pvt Ltd, 4 Ingredion Pharma Solutions, 16 Kerry, 3 Kima Chemical, 6 Lonza Capsugel, 9 Microlex e.U, 1 Nanjing Bold Chemical, 2 Nomisma Healthcare, 2 Novo Excipients, 3 Pharmatrans-Sanaq, 5 Pluviaendo, 4 Prachin Chemical, 1 Qianhao Chemical (Hebei) Co., Ltd, 1 Qualicaps, 18 Roquette, 13 Seppic, 5 Shanghai Shenmei Pharmaceutical Technology Co., Ltd, 11 Sigachi Industries, 2 The Dow Chemical Company, 4 Vasa Pharmachem, 1 Vertellus

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2 US Medicaid Prescriptions, 9 Finished Drug Prices

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2 US Medicaid Prescriptions
9 Finished Drug Prices

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25 APIs, 2 FDF Dossiers

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25 APIs
2 FDF Dossiers

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2 Health Canada Patents

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2 Health Canada Patents

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Synopsis

ACTIVE PHARMA INGREDIENTS

API Suppliers

USDMF

CEP/COS

JDMF

EU WC

KDMF

NDC API

VMF

Listed Suppliers

API REF. PRICE (USD/KG)

$ 55

MARKET PLACE

API

FDF

1INTERMEDIATES

FINISHED DOSAGE FORMULATIONS

138

FDF Dossiers

FDA Orange Book

Europe

Canada

Australia

South Africa

Listed Dossiers

0 DRUGS IN DEVELOPMENT

DRUG PRODUCT COMPOSITIONS

REF. STANDARDS OR IMPURITIES

EDQM

USP

Others

PATENTS & EXCLUSIVITIES

US Patents

US Exclusivities

Health Canada Patents

DIGITAL CONTENT

Data Compilation #PharmaFlow

Stock Recap #PipelineProspector

Weekly News Recap #Phispers

News #PharmaBuzz

GLOBAL SALES INFORMATION

US Medicaid (USD)

8,313,194

Annual Reports (USD Million)

Finished Drug Prices

208 RELATED EXCIPIENT COMPANIES

354EXCIPIENTS BY APPLICATIONS

Chemistry

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Also known as: 51481-61-9, Tagamet, Acinil, Ulcedin, Eureceptor, Gastromet

Molecular Formula

C₁₀H₁₆N₆S

Molecular Weight

252.34 g/mol

InChI Key

AQIXAKUUQRKLND-UHFFFAOYSA-N

FDA UNII

80061L1WGD

A histamine congener, it competitively inhibits HISTAMINE binding to HISTAMINE H2 RECEPTORS. Cimetidine has a range of pharmacological actions. It inhibits GASTRIC ACID secretion, as well as PEPSIN and GASTRIN output.

Cimetidine is a Histamine-2 Receptor Antagonist. The mechanism of action of cimetidine is as a Histamine H2 Receptor Antagonist.

1 2D Structure

Cimetidine

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-cyano-2-methyl-3-[2-[(5-methyl-1H-imidazol-4-yl)methylsulfanyl]ethyl]guanidine

2.1.2 InChI

InChI=1S/C10H16N6S/c1-8-9(16-7-15-8)5-17-4-3-13-10(12-2)14-6-11/h7H,3-5H2,1-2H3,(H,15,16)(H2,12,13,14)

2.1.3 InChI Key

AQIXAKUUQRKLND-UHFFFAOYSA-N

2.1.4 Canonical SMILES

CC1=C(N=CN1)CSCCNC(=NC)NC#N

2.2 Other Identifiers

2.2.1 UNII

80061L1WGD

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Altramet

2. Biomet

3. Biomet400

4. Cimetidine Hcl

5. Cimetidine Hydrochloride

6. Eureceptor

7. Hcl, Cimetidine

8. Histodil

9. Hydrochloride, Cimetidine

10. N-cyano-n'-methyl-n''-(2-(((5-methyl-1h-imidazol-4-yl)methyl)thio)ethyl)guanidine

11. Sk And F 92334

12. Sk And F-92334

13. Sk And F92334

14. Skf 92334

15. Skf-92334

16. Skf92334

17. Tagamet

2.3.2 Depositor-Supplied Synonyms

1. 51481-61-9

2. Tagamet

3. Acinil

4. Ulcedin

5. Eureceptor

6. Gastromet

7. Dyspamet

8. Tametin

9. Ulcimet

10. Cimal

11. Ulcedine

12. Ulcomedina

13. Cimetag

14. Tratul

15. Skf-92334

16. Acibilin

17. Cimetum

18. Edalene

19. Ulcomet

20. Ulhys

21. Tagamet Hb

22. Tagamet Hb 200

23. Cimetidina

24. Cimetidinum

25. Valmagen

26. Brumetidina

27. N-cyano-n'-methyl-n''-[2-[[(4-methyl-1h-imidazol-5-yl)methyl]thio]ethyl]guanidine

28. Skf 92334

29. 1-cyano-2-methyl-3-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine

30. Stomedine

31. Aciloc

32. 2-cyano-1-methyl-3-(2-(((5-methylimidazol-4-yl)methyl)thio)ethyl)guanidine

33. 1-cyano-2-methyl-3-(2-(((5-methyl-4-imidazolyl)methyl)thio)ethyl)guanidine

34. Nsc-335308

35. Chebi:3699

36. N-cyano-n'-methyl-n''-(2-(((5-methyl-1h-imidazol-4-yl)methyl)thio)ethyl)guanidine

37. Chembl30

38. Metracin

39. Brumetadina

40. 2-cyano-1-methyl-3-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine

41. Mls000069791

42. 76181-71-0

43. Gastrobitan

44. Ulcestop

45. Ulcofalk

46. Evicer

47. Peptol

48. 80061l1wgd

49. 51481-61-9 (free)

50. Guanidine, N-cyano-n'-methyl-n''-(2-(((5-methyl-1h-imidazol-4-yl)methyl)thio)ethyl)-

51. Guanidine, N-cyano-n'-methyl-n''-[2-[[(5-methyl-1h-imidazol-4-yl)methyl]thio]ethyl]-

52. Guanidine, N-cyano-n'-methyl-n''-[2-[[(5-methyl-1h-imidazol-4-yl)methyl]thio]ethyl]-, (z)-

53. Nsc 335308

54. 2984-61-4

55. Ncgc00015240-06

56. Smr000038895

57. Cimetidine 100 Microg/ml In Acetonitrile

58. Dsstox_cid_329

59. 2-cyano-1-methyl-3-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]thio}ethyl)guanidine

60. Dsstox_rid_75517

61. Guanidine, N''-cyano-n-methyl-n'-(2-(((5-methyl-1h-imidazol-4-yl)methyl)thio)ethyl)-

62. N''-cyano-n-methyl-n'-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]thio}ethyl)guanidine

63. N-cyano-n'-methyl-n''-(2-([(5-methyl-1h-imidazol-4-yl)methyl]sulfanyl)ethyl)guanidine

64. Cimetidinum [inn-latin]

65. Dsstox_gsid_20329

66. Cimetidina [inn-spanish]

67. Drg-0150

68. (e)-2-cyano-1-methyl-3-(2-(((5-methyl-1h-imidazol-4-yl)methyl)thio)ethyl)guanidine

69. (z)-3-cyano-1-methyl-2-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine

70. 1-cyano-2-methyl-3-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine

71. 2-cyano-1-methyl-3-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine

72. Guanidine, N''-cyano-n-methyl-n'-[2-[[(5-methyl-1h-imidazol-4-yl)methyl]thio]ethyl]-

73. Tagamet (tn)

74. Ccris 3247

75. Equaline Acid Reducer

76. Hsdb 3917

77. Topcare Heartburn Relief

78. Sr-01000075260

79. Sr-05000001434

80. Fpf 1002

81. Einecs 257-232-2

82. Mfcd00133296

83. Cemitidine

84. Metidine

85. Unii-80061l1wgd

86. 1-cyano-2-methyl-3-(2-((5-methyl-1h-imidazol-4-yl)methylthio)ethyl)guanidine

87. 1-cyano-2-methyl-3-[2-[(5-methyl-1h-imidazol-4-yl)methylthio]ethyl]guanidine

88. Cimetidine,(s)

89. Prestwick_65

90. Cimetidine (tagamet)

91. Cimetidine [usan:usp:inn:ban:jan]

92. Cimetidine A

93. Spectrum_000495

94. Tocris-0902

95. Cimetidine [mi]

96. Opera_id_314

97. Cimetidine [inn]

98. Cimetidine [jan]

99. Prestwick3_000026

100. Spectrum2_000782

101. Spectrum3_001389

102. Spectrum4_000812

103. Spectrum5_001541

104. Cimetidine [hsdb]

105. Cimetidine [iarc]

106. Cimetidine [usan]

107. Lopac-c-4522

108. Cimetidine [vandf]

109. Upcmld-dp029

110. 2-cyano-1-methyl-3-[2-(5-methyl-1h-imidazol-4-yl-methylthio)ethyl]guanidine

111. C 4522

112. Cimetidine [mart.]

113. Schembl1093

114. Schembl1094

115. Skf-92334; Tagamet

116. Cimetidine [usp-rs]

117. Cimetidine [who-dd]

118. Cimetidine [who-ip]

119. Guanidine, N-cyano-n'-methyl-n''-(2-(((5-methyl-1h-imidazol-4-yl)methyl)thio) Ethyl)-

120. Lopac0_000293

121. Bspbio_000091

122. Bspbio_002978

123. Kbiogr_001323

124. Kbioss_000975

125. Us9138393, Cimetidine

126. Us9144538, Cimetidine

127. Mls001148596

128. Mls002153265

129. Mls002154178

130. Divk1c_000166

131. Spectrum1500684

132. Spbio_000884

133. Bpbio1_000101

134. Cimetidine (jp17/usp/inn)

135. Gtpl1231

136. Cimetidine [orange Book]

137. Dtxsid4020329

138. Schembl11282982

139. Upcmld-dp029:001

140. Bdbm22889

141. Cimetidine For System Suitability

142. Hms500i08

143. Kbio1_000166

144. Kbio2_000975

145. Kbio2_003543

146. Kbio2_006111

147. Kbio3_002198

148. Cimetidine [ep Monograph]

149. Cimetidine For Peak Identification

150. Ninds_000166

151. Bdbm181119

152. Cimetidine [usp Monograph]

153. Hms1921c14

154. Hms2089o03

155. Hms2092i14

156. Hms2095e13

157. Hms2232f16

158. Hms3259m15

159. Hms3260l08

160. Hms3267a03

161. Hms3369l10

162. Hms3414i17

163. Hms3651e21

164. Hms3678i17

165. Hms3712e13

166. Hms3750i05

167. Hms3884i12

168. Pharmakon1600-01500684

169. Cimetidine 1.0 Mg/ml In Methanol

170. Cimetidinum [who-ip Latin]

171. Ex-a1088

172. Tox21_110106

173. Tox21_201160

174. Tox21_500293

175. Bdbm50103595

176. Bdbm50403559

177. Ccg-40160

178. Nsc335308

179. Nsc757428

180. S1845

181. Stk528249

182. Zinc18115268

183. 1-cyano-2-methyl-3-[2-[[(5-methylimidazol-4-yl)methyl]thio]ethyl]guanidine

184. Akos005460997

185. Akos015900557

186. Akos015951369

187. Akos016003398

188. Akos016340377

189. Akos026749950

190. Akos032949548

191. Tox21_110106_1

192. Ab03708

193. Ac-8100

194. Ccg-204388

195. Ccg-220026

196. Ccg-221597

197. Db00501

198. Ks-5087

199. Lp00293

200. Nc00501

201. Nsc 757428

202. Nsc-757428

203. Sdccgsbi-0050281.p005

204. Idi1_000166

205. N''-cyano-n-methyl-n'-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine

206. N''-cyano-n-methyl-n'-[2-[(5-methyl-1h-imidazol-4-yl)methylthio]ethyl]guanidine

207. N-cyano-n'-methyl-[2-[[[5-methyl-1h-imidazol-4-yl]methyl]thio]ethyl]guanidine

208. Ncgc00015240-01

209. Ncgc00015240-02

210. Ncgc00015240-03

211. Ncgc00015240-04

212. Ncgc00015240-05

213. Ncgc00015240-07

214. Ncgc00024859-01

215. Ncgc00024859-02

216. Ncgc00024859-03

217. Ncgc00024859-04

218. Ncgc00024859-05

219. Ncgc00091439-01

220. Ncgc00091439-02

221. Ncgc00091439-03

222. Ncgc00091439-04

223. Ncgc00091439-05

224. Ncgc00091439-07

225. Ncgc00091439-10

226. Ncgc00185989-01

227. Ncgc00188961-01

228. Ncgc00258712-01

229. Ncgc00260978-01

230. Hy-14289

231. Nci60_002936

232. Sbi-0050281.p004

233. Db-051971

234. Eu-0100293

235. Ft-0602955

236. Sw196380-2

237. C06952

238. D00295

239. F16651

240. Ab00052157-03

241. Ab00052157_04

242. Ab00052157_05

243. 481c619

244. A828616

245. L000186

246. L003827

247. L013434

248. Q409492

249. Sr-05000001750

250. Q-200855

251. Q-200856

252. Sr-01000075260-1

253. Sr-01000075260-3

254. Sr-05000001434-1

255. Sr-05000001434-2

256. Sr-05000001750-1

257. Brd-k18618618-001-01-6

258. Brd-k34157611-001-04-6

259. Brd-k34157611-001-07-9

260. Z1259192068

261. Cimetidine, European Pharmacopoeia (ep) Reference Standard

262. Cimetidine, United States Pharmacopeia (usp) Reference Standard

263. 1-ethyl-2,3-dimethylimidazolium Tosylate, 98% [edimim] [tos]

264. 1-cyan-2-methyl-3-(2-{[(5-methylimidazol-4-yl)methyl]thio}ethyl)guanidin

265. Cimetidine, Pharmaceutical Secondary Standard; Certified Reference Material

266. N"-cyano-n-methyl-n'-[2-(5-methylimidazol-4-ylmethylthio)ethyl]-guanidine

267. N"-cyano-n-methyl-n'-[2-(5-methylimidazol-4-ylmethylthio)ethyl]guanidine

268. N-cyano-n'-methyl-n"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine

269. N-cyano-n'-methyl-n"-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]guanidine

270. N-cyano-n'-methyl-n"-[2-(5-methyl-4-imidazolylmethylthio)ethyl]guanidine

271. (z)-1-cyano-2-methyl-3-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine

272. (z)-n''-cyano-n-methyl-n'-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]sulfanyl}ethyl)guanidine

273. 2-chloro-5-(1-hydroxy-3-oxo-2,3-dihydro-1h-isoindol-1-yl)-benzenesulfonamide(cimetidine)

274. 2-cyano-1-methyl-3-(2-(((5-methylimidazol-4-yl)methyl)thio)ethyl)-guanidine

275. 2-methyl-8-phenethyl-imidazo[1,2-a]pyridine-3-carboxylic Acid Methyl Ester(cimetidine)

276. 2-methylamino-2-[2-(4-methyl-1h-5-imidazolylmethylsulfanyl)ethylamino]-(e)-1-imino Cyanide

277. 3-cyano-2-methyl-1-[2-[(5-methyl-1h-imidazol-4-yl)methylsulfanyl]ethyl]guanidine

278. 4-(((2-(((cyanoamino)(methylamino)methylene)amino)ethyl)thio)methyl)-5-methyl-1h-imidazole

279. Cimetidine For Peak Identification, European Pharmacopoeia (ep) Reference Standard

280. Cimetidine For System Suitability, European Pharmacopoeia (ep) Reference Standard

281. Guanidine, N-cyano-n'-methyl-n''-[2-[[5-methyl-1h-imidazol-4-yl)methyl]thio]ethyl]-

282. N''-cyano-n-methyl-n'-(2-((5-methyl-1h-imidazol-4-yl)-methylthio)ethyl)guanidine

283. N-cyano-n'-methyl-n"- [2-((5-methyl-4-imidazolyl)methylthio)ethyl]guanidine

284. N-cyano-n'-methyl-n"-[2-((4-methyl-5-imidazolyl) Methylthio)ethyl]guanidine

285. N-cyano-n'-methyl-n"-[2-((4-methyl-5-imidazolyl)- Methylthio)ethyl]guanidine

286. N-cyano-n'-methyl-n"-[2-((4-methyl-5-imidazolyl)-methylthio)ethyl]guanidine

287. N-cyano-n'-methyl-n"-[2-((4-methyl-5-imidazolyl)methyl-thio)ethyl]guanidine

288. N-cyano-n'-methyl-n"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl) Guanidine

289. N-cyano-n'-methyl-n"-[2-((5-methyl-4-imidazolyl)methylthio)-ethyl]guanidine

290. N-cyano-n'-methyl-n"-[2-((5-methyl-4-imidazolyl)methylthio)ethyl]-guanidine

291. N-cyano-n'-methyl-n"-[2-{(5-methyl-1h-imidazol-4-yl)methylthio}ethyl]guanidine

292. N-cyano-n'-methyl-n''-(2-([(5-methyl-1h-imidazol-4-yl)methyl]sulfanyl)ethyl)guanidine #

293. N-cyano-n'-methyl-n''-[2-[(5-methyl-1h-imidazol-4-yl)methyl]thio]ethyl]guanidine

294. N-cyano-n'-methyl-n''-[2-[[(5-methylimidazol-4-yl]methyl]thio]ethyl)guanidine

295. N-cyano-n'-methyl-n-"-[2-((4-methyl-5-imidazolyl)methylthio)ethyl]guanidine

296. N-methyl-n'-{2-[(5-methylimidazol-4-yl)-methylthio]-ethyl}-n"-cyanoguanidine

297. N-methyl-n-[2-(5-methyl-1h-4-imidazolylmethylsulfanyl)ethyl]-1-cyanoiminomethanediamine

298. N-methyl-n-[2-(5-methyl-1h-4-imidazolylmethylsulfanyl)ethyl]imino(-n-cyano)methanediaminem

299. N-tert-butyl-n''''''''-[4-(1h-imidazol-4-yl)-phenyl]-formamidine(cimetidine)

300. (cimetidine) N-methyl-n''''''''-[2-(5-methyl-1h-imidazol-4-ylmethylsulfanyl)-ethyl]-guanidine,cyanide

301. (cimetidine) N-methyl-n-[2-(5-methyl-1h-4-imidazolylmethylsulfanyl)ethyl]cyanoiminomethanediamine

302. (cimetidine)n-methyl-n-[2-(5-methyl-1h-4-imidazolylmethylsulfanyl)ethyl]cyanomethyliminomethanediamine

303. 2-methylamino-2-[2-(5-methyl-1h-4-imidazolylmethylsulfanyl)ethylamino]-(z)-1-imino Cyanide(cimetidine)

304. Guanidine,n-cyano-n'-methyl-n''-[2-[[(5-methyl-1h-imidazol-4-yl)methyl]thio]ethyl]-,(z)-

305. N''''''''''''''''''''''''''''''''-cyano-n-methyl-n''''''''''''''''-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]thio}ethyl)guanidine

306. N''''''''''''''''-cyano-n-methyl-n''''''''-({[(5-methyl-1h-imidazol-4-yl)methyl]thio}methyl)guanidine(cimetidine)

307. N''''''''''''''''-cyano-n-methyl-n''''''''-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]-lambda~4~-sulfanyl}ethyl)guanidine

308. N''''''''''''''''-cyano-n-methyl-n''''''''-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]thio}ethyl)guanidine

309. N''''''''''''''''-cyano-n-methyl-n''''''''-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]thio}ethyl)guanidine (cimetidine)

310. N''''''''''''''''-cyano-n-methyl-n''''''''-(2-{[(5-methyl-1h-imidazol-4-yl)methyl]thio}ethyl)guanidine(cimetidine)

311. N-cyano-n''''''''-methyl-n''''''''''''''''-(2-(((5-methyl-1h-imidazol-4-yl) Methyl)thio)ethyl)guanidine(cimetidine)

312. N-cyanomethyl-n''''''''-methyl-n''''''''''''''''-[2-(5-methyl-1h-imidazol-4-ylmethylsulfanyl)-ethyl]-guanidine ( Cimetidine)

313. N-methyl-n''''''''-[2-(5-methyl-1h-imidazol-4-ylmethylsulfanyl)-ethyl]-cyanoguanidine(cimetidine)

314. N-methyl-n''''''''-[2-(5-methyl-1h-imidazol-4-ylmethylsulfanyl)-ethyl]-n''''''''''''''''-cyano-guanidine

315. N-methyl-n''''''''-[2-(5-methyl-1h-imidazol-4-ylmethylsulfanyl)-ethyl]-n''''''''''''''''-cyano-guanidine(cimetidine)

316. N-methyl-n''''''''-cyano-n''''''''''''''''-[2-(5-methyl-1h-imidazol-4-ylmethylsulfanyl)-ethyl]-guanidine

317. N-methyl-n-[2-(5-methyl-1h-4-imidazolylmethylsulfanyl)ethyl]cyanoiminomethanediamine (cimetidine)

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₁₀H₁₆N₆S
Molecular Weight	252.34 g/mol
XLogP3	0.4
Hydrogen Bond Donor Count	3
Hydrogen Bond Acceptor Count	4
Rotatable Bond Count	7
Exact Mass	252.11571571 g/mol
Monoisotopic Mass	252.11571571 g/mol
Topological Polar Surface Area	114 Å²
Heavy Atom Count	17
Formal Charge	0
Complexity	296
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 4
Drug Name	Cimetidine
PubMed Health	Cimetidine
Drug Classes	Antiulcer, Gastric Acid Secretion Inhibitor
Drug Label	Cimetidine is a histamine H2-receptor antagonist. Chemically it is N"-cyano-N-methyl-N'-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]-ethyl]guanidine. Its structural formula is:Cimetidine contains an imidazole ring, and is chemically related to h
Active Ingredient	Cimetidine
Dosage Form	Tablet
Route	Oral
Strength	300mg; 200mg; 100mg; 800mg; 400mg
Market Status	Over the Counter; Prescription
Company	Ivax Sub Teva Pharms; Teva; Apotex; Perrigo; Contract Pharmacal; Pliva; Mylan; Dava Pharms

2 of 4
Drug Name	Tagamet hb
Active Ingredient	Cimetidine
Dosage Form	Tablet
Route	Oral
Strength	200mg
Market Status	Over the Counter
Company	Medtech Prods

3 of 4
Drug Name	Cimetidine
PubMed Health	Cimetidine
Drug Classes	Antiulcer, Gastric Acid Secretion Inhibitor
Drug Label	Cimetidine is a histamine H2-receptor antagonist. Chemically it is N"-cyano-N-methyl-N'-[2-[[(5-methyl-1H-imidazol-4-yl)methyl]thio]-ethyl]guanidine. Its structural formula is:Cimetidine contains an imidazole ring, and is chemically related to h
Active Ingredient	Cimetidine
Dosage Form	Tablet
Route	Oral
Strength	300mg; 200mg; 100mg; 800mg; 400mg
Market Status	Over the Counter; Prescription
Company	Ivax Sub Teva Pharms; Teva; Apotex; Perrigo; Contract Pharmacal; Pliva; Mylan; Dava Pharms

4 of 4
Drug Name	Tagamet hb
Active Ingredient	Cimetidine
Dosage Form	Tablet
Route	Oral
Strength	200mg
Market Status	Over the Counter
Company	Medtech Prods

4.2 Therapeutic Uses

Adjuvants, Immunologic; Analgesics, Non-Narcotic; Anti-Ulcer Agents; Enzyme Inhibitors; Histamine H2 Antagonists

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

IN MAN, A SINGLE DOSE (300 MG) WILL INHIBIT BASAL (FASTING) SECRETION AND ALSO SECRETION INDUCED BY SOLID, LIQ, OR PEPTONE MEALS, SHAM FEEDING, FUNDIC DISTENTION, PENTAGASTRIN, BETHANECHOL, INSULIN, AND CAFFEINE, AS WELL AS THE PHYSIOLOGICAL STIMULUS PROVIDED BY EATING. ... THIS SPECTRUM INCL THE CEPHALIC OR VAGAL PHASE.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 631

CIMETIDINE IS THE PREFERRED ALTERNATIVE FOR MANY PATIENTS WHO CANNOT OR WILL NOT TOLERATE AN INTENSIVE, PROLONGED ANTACID REGIMEN.

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 899

Cimetidine is a useful alternative to antacids in preventing aspiration pneumonitis during childbirth and elective surgical procedures. It is less useful than antacids during emergency surgery because of its slow onset of action. This drug had been given to prevent alkalosis in patients subjected to prolonged nasogastric aspiration, especially those secreting large amounts of acid, and to decrease ileostomy/jejunostomy output in the short bowel syndrome.

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 899

For more Therapeutic Uses (Complete) data for CIMETIDINE (21 total), please visit the HSDB record page.

4.3 Drug Warning

DESPITE POOR PENETRATION TO THE CNS, NEURAL DYSFUNCTION HAS BEEN ENCOUNTERED, PARTICULARLY WITH HIGH DOSES IN ELDERLY PATIENTS AND IN ASSOCIATION WITH IMPAIRED RENAL EXCRETION. THE EFFECTS INCL CONFUSION, SLURRED SPEECH, DELIRIUM, HALLUCINATIONS, AND COMA.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 631

IN SOME INSTANCES, WITHDRAWAL OF CIMETIDINE AFTER A PERIOD OF TREATMENT HAS BEEN FOLLOWED BY RELAPSES IN THE SYMPTOMS OF ULCER AND EVEN BY PERFORATION OF DUODENAL, ESOPHAGEAL, OR GASTRIC ULCERS.

Gilman, A. G., L. S. Goodman, and A. Gilman. (eds.). Goodman and Gilman's The Pharmacological Basis of Therapeutics. 6th ed. New York: Macmillan Publishing Co., Inc. 1980., p. 632

... CIMETIDINE IS INEFFECTIVE IN ACUTE OR ALCOHOLIC PANCREATITIS AND IT MAY ACTUALLY INCR AND PROLONG HYPERAMYLASEMIA.

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 899

... CLIN EXPERIENCE IN CHILDREN IS EXTREMELY LIMITED, AND THE BENEFIT/RISK RATIO SHOULD BE CONSIDERED CAREFULLY.

American Medical Association. AMA Drug Evaluations Annual 1991. Chicago, IL: American Medical Association, 1991., p. 771

For more Drug Warnings (Complete) data for CIMETIDINE (15 total), please visit the HSDB record page.

4.4 Drug Indication

Cimetidine is indicated to reduce gastric acid secretion and to treat the following disease states: duodenal ulcers, non-malignant gastric ulcers, gastroesophageal reflux disease, and pathological hypersecretion associated with Zollinger-Ellison Syndrome, systemic mastocytosis, and multiple endocrine adenomas. It is indicated for prophylaxis of recurrent gastric or duodenal ulcers, as adjunctive therapy in the management of cystic fibrosis in children, and to treat NSAID induced lesions and gastrointestinal symptoms.

5 Pharmacology and Biochemistry

5.1 Pharmacology

Cimetidine is a histamine H₂-receptor antagonist. It reduces basal and nocturnal gastric acid secretion and a reduction in gastric volume, acidity, and amount of gastric acid released in response to stimuli including food, caffeine, insulin, betazole, or pentagastrin. It is used to treat gastrointestinal disorders such as gastric or duodenal ulcer, gastroesophageal reflux disease, and pathological hypersecretory conditions. Cimetidine inhibits many of the isoenzymes of the hepatic CYP450 enzyme system. Other actions of Cimetidine include an increase in gastric bacterial flora such as nitrate-reducing organisms.

5.2 MeSH Pharmacological Classification

Cytochrome P-450 CYP1A2 Inhibitors

Drugs and compounds which inhibit or antagonize the biosynthesis or actions of CYTOCHROME P-450 CYP1A2. (See all compounds classified as Cytochrome P-450 CYP1A2 Inhibitors.)

Histamine H2 Antagonists

Drugs that selectively bind to but do not activate histamine H2 receptors, thereby blocking the actions of histamine. Their clinically most important action is the inhibition of acid secretion in the treatment of gastrointestinal ulcers. Smooth muscle may also be affected. Some drugs in this class have strong effects in the central nervous system, but these actions are not well understood. (See all compounds classified as Histamine H2 Antagonists.)

Anti-Ulcer Agents

Various agents with different action mechanisms used to treat or ameliorate PEPTIC ULCER or irritation of the gastrointestinal tract. This has included ANTIBIOTICS to treat HELICOBACTER INFECTIONS; HISTAMINE H2 ANTAGONISTS to reduce GASTRIC ACID secretion; and ANTACIDS for symptomatic relief. (See all compounds classified as Anti-Ulcer Agents.)

5.3 FDA Pharmacological Classification

5.3.1 Active Moiety

CIMETIDINE

5.3.2 FDA UNII

80061L1WGD

5.3.3 Pharmacological Classes

Histamine-2 Receptor Antagonist [EPC]; Histamine H2 Receptor Antagonists [MoA]

5.4 ATC Code

A - Alimentary tract and metabolism

A02 - Drugs for acid related disorders

A02B - Drugs for peptic ulcer and gastro-oesophageal reflux disease (gord)

A02BA - H2-receptor antagonists

A02BA01 - Cimetidine

5.5 Absorption, Distribution and Excretion

Absorption

Two peak plasma concentrations are often observed after oral administration of cimetidine, likely as a result of discontinuous absorption in the gastrointestinal tract. In healthy patients, the absolute bioavailability of cimetidine is approximately 60%; however, the bioavailability can be as high as 70% in patients with peptic ulcer disease. Overall, rates of bioavailability are much more variable in patients with peptic ulcer disease.

Route of Elimination

Cimetidine is excreted primarily in the urine.

Volume of Distribution

The volume of distribution of cimetidine is reported to be 1 L/kg.

Clearance

Cimetidine's reported systemic clearance value is approximately 500-600 ml/min.

About 15% of cimetidine is metabolized in the liver. Seventy percent is excreted unchanged in the urine, with fecal losses accounting for approximately 10%.

Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 434

Given orally, cimetidine and ranitidine are almost completely absorbed. Because of first-pass metabolism in the liver, the bioavailability is 50-60%. Both drugs are little bound to plasma proteins (10-20%).

Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 824

Both drugs are mainly excreted in urine - cimetidine up to 90% within 24 hr (50-75% unchanged) and ranitidine up to 60% within 24 hr (about 40% unchanged). The apparent volume of distribution is quite large, in the range of 1.5 l/kg bw, demonstrating that nearly all drug exists outside the intravascular space.

Haddad, L.M., Clinical Management of Poisoning and Drug Overdose. 2nd ed. Philadelphia, PA: W.B. Saunders Co., 1990., p. 824

Cimetidine is widely distributed throughout the body and is 15-20% bound to plasma proteins. Animal studies indicate that the drug crosses the placenta. Cimetidine is distributed into milk.

McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 2140

For more Absorption, Distribution and Excretion (Complete) data for CIMETIDINE (14 total), please visit the HSDB record page.

5.6 Metabolism/Metabolites

After intravenous administration of cimetidine, the majority of the parent drug (58-77%) is eliminated unchanged in the urine. Cimetidines primary metabolite is cimetidine sulfoxide and represents an estimated 10-15% of total elimination. Researchers have also identified a minor cimetidine metabolite with a hydroxylated methyl group on the imidazole ring which represents only 4% of total elimination. Both cytochrome P450 enzymes and flavin-containing monooxygenases are implicated in the metabolism of cimetidine, although it is unclear which specific enzymes are involved. Cimetidine is a well known enzyme inhibitor and may impair the metabolism of certain co-administered medications.

About 50% to 80% of an intravenous dose is excreted as unchanged drug; 40% of an oral dose is excreted unchanged in the urine in patients with peptic ulcer disease. Most of the remainder of the drug appears in the urine as 5-hydroxymethyl or sulfoxide metabolites.

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 900

Cimetidine is metabolized in the liver to sulfoxide and 5-hydroxymethyl derivatives, and possibly guanylurea, although this latter compound may result from in vitro degradation.

McEvoy G.K. (ed.). American Hospital Formulary Service-Drug Information 96. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 1996 (Plus Supplements)., p. 2140

5.7 Biological Half-Life

Cimetidine's half-life is estimated to be around 2 hours.

ELEVEN PATIENTS WITH ASCITIC CIRRHOSIS & ELEVEN PATIENTS WITHOUT LIVER DISEASE RECEIVED 200 MG OF CIMETIDINE ORALLY AND IV. NO DIFFERENCES WERE OBSERVED IN CIMETIDINE T/2 BETWEEN THE 2 GROUPS. CIMETIDINE CLEARANCE WAS DIMINISHED IN CIRRHOTIC PATIENTS (0.426 + OR - 0.138 VERSUS 0.649 + OR - 0.163 L/HR/KG).

PMID:6852412 ALBIN H ET AL; GASTROENTEROL CLIN BIOL 7 (3): 251-5 (1983)

The elimination half-life in man is 1.9 to 2.2 hours.

Ellenhorn, M.J. and D.G. Barceloux. Medical Toxicology - Diagnosis and Treatment of Human Poisoning. New York, NY: Elsevier Science Publishing Co., Inc. 1988., p. 434

The plasma elimination half-life is about 2 hours.

American Medical Association, Council on Drugs. AMA Drug Evaluations Annual 1994. Chicago, IL: American Medical Association, 1994., p. 900

The half-time for elimination of cimetidine ... is 2 to 3 hours ... .

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. 900

5.8 Mechanism of Action

Cimetidine binds to an H₂-receptor located on the basolateral membrane of the gastric parietal cell, blocking histamine effects. This competitive inhibition results in reduced gastric acid secretion and a reduction in gastric volume and acidity.

H2 antagonists inhibit gastric acid secretion elicited by histamine & other H2 agonists in a dose-dependent, competitive manner; the degree of inhibition parallels the concentration of the drug in plasma over a wide range. The H2 antagonists also inhibit acid secretion elicited by gastrin &, to a lesser extent, by muscarinic agonists. Importantly, these drugs inhibit basal (fasting) & nocturnal acid secretion & that stimulated by food, sham feeding, fundic distention, & various pharmacological agents; this property reflects the vital role of histamine in mediating the effects of diverse stimuli. The H2 antagonists reduce both the volume of gastric juice secreted & its H+ concentration. The output of pepsin, which is secreted by the chief cells of gastric glands (mainly under cholinergic control), generally falls in parallel with the reduction in volume of gastric juice. /H2 antagonists/

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. 899

Cimetidine blocks H2-receptors, which in part are responsible for the inflammatory response, in the cutaneous blood vessels of humans.

USP Convention. USPDI - Drug Information for the Health Care Professional. 16th ed. Volume I. Rockville, MD: U.S. Pharmaceutical Convention, Inc. 1996 (Plus updates)., p. 1612

The effects of cimetidine, omeprazole and atropine sulfate on the healing of acetic acid-induced gastric ulcers in rats with limited food intake time (9:00-10:00 am and 5:00-6:00 pm) were evaluated 15 days after the acid injection. Oral repeated admin of cimetidine (25-100 mg/kg twice daily) or omeprazole (10-50 mg/kg once daily) dose dependently accelerated ulcer healing. ... A single oral admin of omeprazole (50 mg/kg) or cimetidine (100 mg/kg) resulted in potent and long-lasting anti-acid secretory and gastrin-releasing actions. The degree and duration of anti-acid secretion by atropine sulfate were equal to those of cimetidine, but the elevation of gastrin release by atropine sulfate was weak and temporary. These results indicate that the gastric ulcers of rats with a limited food intake time are useful for evaluating the healing effects of cimetidine and omeprazole on gastric ulcers. In addition, the effects of both drugs may be related to the incr gastrin release rather than to the reduced acid secretion.

PMID:7843261 Ito M et al; Eur J Pharmacol 263 (3): 245-51 (1994)

Both KB-5492, a new anti-ulcer agent, and cimetidine, admin po at 25-200 mg/kg, dose-dependently prevented cysteamine (400 mg/kg, sc)-induced duodenal ulcers in rats with ED50 values of 63 and 40 mg/kg, respectively. Anti-ulcer doses of cimetidine, but not KB-5492, inhibited gastric acid hypersecretion induced by cysteamine (400 mg/kg, sc). In contrast, anti-ulcer doses of KB-5492, but not cimetidine, incr duodenal HC03- secretion in normal anesthetized rats. These findings suggest that KB-5492 prevents cysteamine-induced duodenal ulcers by stimulating duodenal HC03- secretion, whereas cimetidine does so by inhibiting cysteamine-induced gastric acid hypersecretion.

PMID:8022123 Morimoto Y et al; Jpn J Pharmacol 64 (3): 221-4 (1994)

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