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Prestwick3_000493
Also known as: 73590-58-6, Losec, Prilosec, Esomeprazole, Antra, Omeprazon
Molecular Formula
C17H19N3O3S
Molecular Weight
345.4  g/mol
InChI Key
SUBDBMMJDZJVOS-UHFFFAOYSA-N
FDA UNII
KG60484QX9

A 4-methoxy-3,5-dimethylpyridyl, 5-methoxybenzimidazole derivative of timoprazole that is used in the therapy of STOMACH ULCERS and ZOLLINGER-ELLISON SYNDROME. The drug inhibits an H(+)-K(+)-EXCHANGING ATPASE which is found in GASTRIC PARIETAL CELLS.
Omeprazole is a Proton Pump Inhibitor. The mechanism of action of omeprazole is as a Proton Pump Inhibitor, and Cytochrome P450 2C19 Inhibitor.
1 2D Structure

Prestwick3_000493

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1H-benzimidazole
2.1.2 InChI
InChI=1S/C17H19N3O3S/c1-10-8-18-15(11(2)16(10)23-4)9-24(21)17-19-13-6-5-12(22-3)7-14(13)20-17/h5-8H,9H2,1-4H3,(H,19,20)
2.1.3 InChI Key
SUBDBMMJDZJVOS-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CC1=CN=C(C(=C1OC)C)CS(=O)C2=NC3=C(N2)C=C(C=C3)OC
2.2 Other Identifiers
2.2.1 UNII
KG60484QX9
2.3 Synonyms
2.3.1 MeSH Synonyms

1. H 168 68

2. H 168-68

3. H 16868

4. Magnesium, Omeprazole

5. Omeprazole Magnesium

6. Omeprazole Sodium

7. Prilosec

8. Sodium, Omeprazole

2.3.2 Depositor-Supplied Synonyms

1. 73590-58-6

2. Losec

3. Prilosec

4. Esomeprazole

5. Antra

6. Omeprazon

7. Audazol

8. Omapren

9. Omepral

10. Parizac

11. Zegerid

12. Mopral

13. Miol

14. Belmazol

15. Ceprandal

16. Dizprazol

17. Dudencer

18. Emeproton

19. Epirazole

20. Gastrimut

21. Gastroloc

22. Gibancer

23. Indurgan

24. Inhibitron

25. Inhipump

26. Logastric

27. Pepticum

28. Peptilcer

29. Prazidec

30. Sanamidol

31. Secrepina

32. Ulcometion

33. Mepral

34. Miracid

35. Omeprol

36. Omezol

37. Omisec

38. Omizac

39. Ompanyt

40. Ozoken

41. Prysma

42. Ramezol

43. Ulceral

44. Ulcesep

45. Ulcozol

46. Zefxon

47. Zoltum

48. Desec

49. Elgam

50. Lomac

51. Ulsen

52. Ultop

53. Zimor

54. Ocid

55. Omed

56. Omid

57. Omep

58. Demeprazol

59. Nopramin

60. Omeprazol

61. Omezolan

62. Paprazol

63. Pepticus

64. Prazentol

65. Prazolit

66. Procelac

67. Regulacid

68. Danlox

69. Erbolin

70. Lensor

71. Morecon

72. Nilsec

73. Olexin

74. Omegast

75. Omesek

76. Ortanol

77. Osiren

78. Proclor

79. Result

80. Ulcsep

81. Victrix

82. Zepral

83. Exter

84. Gasec

85. Ulzol

86. Omebeta 20

87. Tedec Ulceral

88. Aulcer

89. Antra Mups

90. Omerprazole

91. Omez

92. 119141-88-7

93. Omepradex

94. Omeprazolum

95. H 168/68

96. Gastrogard

97. Nuclosina

98. Omesec

99. Omeprazole-d3

100. Mfcd00083192

101. Prestwick_808

102. 5-methoxy-2-(((4-methoxy-3,5-dimethyl-2-pyridyl)methyl)sulfinyl)benzimidazole

103. 6-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1h-benzo[d]imidazole

104. H-168/68

105. Omz

106. Chebi:77260

107. 119141-89-8

108. 6-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1h-benzimidazole

109. 1h-benzimidazole, 5-methoxy-2-(((4-methoxy-3,5-dimethyl-2-pyridinyl)methyl)sulfinyl)-

110. Aisi'aomeilazuona Esomeprazole Sodium

111. Nsc-751450

112. Nsc-759192

113. Chembl1503

114. Nexiam

115. Esomeprazole Sodium Salt

116. 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methanesulfinyl]-1h-1,3-benzodiazole

117. 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1h-benzimidazole

118. 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1h-benzimidazole

119. Mls000069373

120. Kg60484qx9

121. 73590-58-6 (free Form)

122. Omeprazol [inn-spanish]

123. Omeprazolum [inn-latin]

124. Ncgc00016925-06

125. Esomperazole

126. Smr000058847

127. Emilok

128. Cas-73590-58-6

129. Dsstox_cid_1080

130. 2-({[3,5-dimethyl-4-(methyloxy)pyridin-2-yl]methyl}sulfinyl)-5-(methyloxy)-1h-benzimidazole

131. 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methane]sulfinyl}-1h-1,3-benzodiazole

132. Dsstox_rid_75929

133. Dsstox_gsid_21080

134. ( -)-omeprazole

135. (r)-5-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1h-benzo[d]imidazole

136. Omeprazone

137. Omeprazen

138. Omeprazole Delayed-release

139. Omeprazole Pellets

140. 5-methoxy-2-(((4-methoxy-3,5-dimethylpyridin-2-yl)methyl)sulfinyl)-1h-benzo[d]imidazole

141. 5-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl)-1h-benzo[d]imidazole

142. 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridyl)methylsulfinyl]-1h-benzimidazole

143. 5-methoxy-2-[(4-methoxy-3,5-dimethyl-pyridin-2-yl)methylsulfinyl]-3h-benzoimidazole

144. 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]benzimidazole

145. Prilosec (tn)

146. (+-)-omeprazole

147. Ccris 7099

148. Hsdb 3575

149. Sr-01000003003

150. Unii-kg60484qx9

151. Omeprazole-d6

152. Omeprazole, Solid

153. 5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-1h-benzimidazole

154. Agi-010

155. Omeprazole,(s)

156. Omeprazole Solution

157. Omeprazole-[d3]

158. (rs)-6-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl) Methylsulfinyl)-1h-benzo(d)imidazole

159. (rs)-6-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl) Methylsulfinyl)-1h-benzo[d]imidazole

160. 326602-80-6

161. Omeprazole S-isomer

162. 2-(((3,5-dimethyl-4-methoxy-2-pyridyl)methyl)sulfinyl)-5-methoxy-1h-benzimidazole

163. Omeprazole - Bio-x

164. Dm-3458

165. Omeprazole [usan:usp:inn:ban:jan]

166. Omeprazole-13c,d3

167. Omeprazole (prilosec)

168. Omeprazole [mi]

169. Omeprazole [inn]

170. Omeprazole [jan]

171. Maybridge4_002645

172. Opera_id_1863

173. Prestwick0_000493

174. Prestwick1_000493

175. Prestwick2_000493

176. Prestwick3_000493

177. (.+/-.)-omeprazole

178. Omeprazole [hsdb]

179. Omeprazole [usan]

180. O0359

181. Omeprazole [vandf]

182. Upcmld-dp075

183. Cid_4594

184. Omeprazole [mart.]

185. Schembl1191

186. Omeprazole [usp-rs]

187. Omeprazole [who-dd]

188. H 16868

189. Bspbio_000385

190. Mls001076112

191. Mls001424148

192. Mls006010400

193. Mls006011759

194. Bidd:gt0189

195. Spbio_002306

196. Bpbio1_000425

197. Gtpl4279

198. Omeprazole (jp17/usp/inn)

199. Omeprazole [green Book]

200. Dtxsid6021080

201. Omeprazole [orange Book]

202. Schembl11995456

203. Upcmld-dp075:001

204. Chebi:91766

205. Omeprazole [usp Impurity]

206. Hms1528i05

207. Hms1569d07

208. Hms2052g17

209. Hms2090e16

210. Hms2090f11

211. Hms2096d07

212. Hms2232b21

213. Hms3269d17

214. Hms3394g17

215. Hms3413j07

216. Hms3651a11

217. Hms3677j07

218. Hms3713d07

219. Omeprazole [usp Monograph]

220. Pharmakon1600-01505693

221. Zegerid Component Omeprazole

222. Amy30573

223. Bcp05852

224. Bcp13592

225. Bcp21299

226. Hy-b0113

227. Yosprala Component Omeprazole

228. 2,3,5-trimethylpyridine/omeprazole

229. Tox21_110686

230. Tox21_200509

231. Ac-401

232. Bbl028172

233. Bdbm50103597

234. Bdbm50241343

235. Dl-462

236. Mfcd23135254

237. Nsc751450

238. Nsc759192

239. S1389

240. Stk623746

241. Akos005066653

242. Akos015895343

243. Omeprazole Component Of Zegerid

244. Tox21_110686_1

245. Ac-4676

246. Ccg-101130

247. Ccg-213517

248. Cs-1868

249. Db00338

250. Hs-0055

251. Nc00380

252. Nsc 751450

253. Nsc 759192

254. Omeprazole Component Of Yosprala

255. (s)-5-methoxy-2-[(4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl]-3h-benzoimidazole

256. Idi1_032523

257. Ncgc00016925-01

258. Ncgc00016925-02

259. Ncgc00016925-03

260. Ncgc00016925-04

261. Ncgc00016925-05

262. Ncgc00016925-07

263. Ncgc00016925-08

264. Ncgc00016925-10

265. Ncgc00016925-11

266. Ncgc00021522-03

267. Ncgc00021522-04

268. Ncgc00021522-05

269. Ncgc00258063-01

270. Omeprazole, Analytical Reference Material

271. Bo164173

272. Sy009746

273. Sy077145

274. Sbi-0206896.p001

275. Ft-0601585

276. Ft-0652860

277. Ft-0653294

278. Ft-0673283

279. Ft-0689771

280. H 199

281. Sw196942-4

282. A19447

283. C07324

284. D00455

285. 141o887

286. A837865

287. A892647

288. A937349

289. Q422210

290. Sr-01000003003-4

291. Sr-01000003003-7

292. Sr-01000003003-8

293. 5-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl)

294. Brd-a55962179-001-04-9

295. Brd-a55962179-001-08-0

296. Brd-a55962179-001-20-5

297. Brd-a88691025-001-07-4

298. F0001-2386

299. Z1672902589

300. Omeprazole, British Pharmacopoeia (bp) Reference Standard

301. Omeprazole, European Pharmacopoeia (ep) Reference Standard

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

303. 2-(3-methoxy-2,4-dimethylbenzylsulfinyl)-6-methoxy-1h-benzo[d]imidazole

304. 5-methoxy-2-((s)-((4-methoxy-3,5-dimethyl-2- Pyridinyl)methyl)sulfinyl)-

305. Omeprazole, Pharmaceutical Secondary Standard; Certified Reference Material

306. (+)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]-sulfinyl]-1h-benzimidazole

307. (-)-5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]-sulfinyl]-1h-benzimidazole

308. (rs)-5-methoxy-2-(4-methoxy-3,5-dimethyl-2-pyridylmethylsulphinyl)benzimidazole

309. 1h-benzimidazole,5-methoxy-2-[(r)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-

310. 5-methoxy 2-[[(4-methoxy-3,5-dimethyl-2-pyrdinyl)-methyl]sulfinyl]-1h-benzimidazole

311. 5-methoxy 2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1 H-benzimidazole

312. 5-methoxy 2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1h-benzimidazole

313. 5-methoxy-2-(2-(4-methoxy-3,5-dimethylpyridin-2-yl)ethylsulfinyl)-1h-benzo[d]imidazole

314. 5-methoxy-2-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethanesulfinyl)-1h-benzoimidazole

315. 5-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl- 1h-benzimidazole

316. 5-methoxy-2-[[(3,5-dimethyl-4-methoxy-2-pyridyl)methyl]sulfinyl]-1h-benzimidazole

317. 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulphinyl]-1h-benzimidazole

318. 5-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridyl)methyl]sulfinyl]-benzimidazole

319. 5-methoxy-2-[[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulphinyl]1h-benzimidazole

320. 6-methoxy-2-(((4-methoxy-3,5-dimethyl Pyridin-2-yl)methyl)sulfinyl)-1h-benzo[d]imidazole

321. 6-methoxy-2-((4-methoxy-3,5-dimethylpyridin-2-yl)methylsulfinyl)-1h-benzo[d]imidazole

322. 6-methoxy-2-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methylsulfinyl]-1h-benzimidazole

323. 6-methoxy-2-[(4-methoxy-3,5-dimethyl-pyridin-2-yl)methylsulfinyl]-1h-benzimidazole

324. 6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1h-benzimidazole

325. 6-methoxy-2-[[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-1h-benzimidazole

326. 6-methoxy-2-[[(4-methoxy-3,5dimethyl-2-pyridinyl)-methyl]sulfinyl]-1h-benzimidazole

327. 6-methoxy-2-[[(4-methoxy3,5-dimethyl-2-pyridinyl)-methyl]sulfinyl]-1h-benzimidazole

328. 6-methoxy-2-[[(4methoxy-3,5-dimethyl2-pyridinyl)methyl]sulfinyl]-1h-benzimidazole

329. Omeprazole For Peak Identification, European Pharmacopoeia (ep) Reference Standard

330. Omeprazole Solution, 1.0 Mg/ml In Methanol, Ampule Of 1 Ml, Certified Reference Material

331. (omeprazole)5-methoxy-2-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethanesulfinyl)-1h-benzoimidazole

332. 1h-benzimidazole,6-methoxy-2-[(r)-[(4-methoxy-3,5-dimethyl-2-pyridinyl)methyl]sulfinyl]-

333. 5-methoxy-2-(((4-methoxy-3,5,-dimethyl-2-pyridinyl)-methyl)sulphinyl)-1h-benzimidazole

334. 5-methoxy-2-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethanesulfinyl)-1h-benzoimidazole (omeprazole)

335. 5-methoxy-2-(4-methoxy-3,5-dimethyl-pyridin-2-ylmethanesulfinyl)-1h-benzoimidazole(omeprazole)

2.4 Create Date
2005-03-25
3 Chemical and Physical Properties
Molecular Weight 345.4 g/mol
Molecular Formula C17H19N3O3S
XLogP32.2
Hydrogen Bond Donor Count1
Hydrogen Bond Acceptor Count6
Rotatable Bond Count5
Exact Mass345.11471265 g/mol
Monoisotopic Mass345.11471265 g/mol
Topological Polar Surface Area96.3 Ų
Heavy Atom Count24
Formal Charge0
Complexity453
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count1
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 14  
Drug NameNexium
PubMed HealthEsomeprazole
Drug ClassesGastric Acid Secretion Inhibitor, Gastrointestinal Agent
Active IngredientEsomeprazole magnesium
Dosage FormCapsule, delayed rel pellets; For suspension, delayed release
RouteOral
Strengtheq 5mg base/packet; eq 20mg base/packet; eq 20mg base; eq 40mg base; eq 10mg base/packet; eq 40mg base/packet; eq 2.5mg base/packet
Market StatusPrescription
CompanyAstrazeneca

2 of 14  
Drug NameNexium iv
PubMed HealthOmeprazole (By mouth)
Drug ClassesGastric Acid Secretion Inhibitor
Drug LabelThe active ingredient in Omeprazole Delayed-Release Capsules is a substituted benzimidazole, 5-methoxy-2-[[(4-methoxy-3, 5-dimethyl-2-pyridinyl) methyl] sulfinyl]-1H-benzimidazole, a compound that inhibits gastric acid secretion. Its empirical formul...
Active IngredientEsomeprazole sodium
Dosage FormInjectable
RouteIntravenous
Strengtheq 20mg base/vial; eq 40mg base/vial
Market StatusPrescription
CompanyAstrazeneca

3 of 14  
Drug NameOmeprazole
PubMed HealthOmeprazole (By mouth)
Drug ClassesGastric Acid Secretion Inhibitor
Drug Label11 DESCRIPTIONThe active ingredient in PRILOSEC (omeprazole) Delayed-Release Capsules is a substituted benzimidazole, 5-methoxy-2-[[(4-methoxy-3, 5-dimethyl-2-pyridinyl) methyl] sulfinyl]-1H-benzimidazole, a compound that inhibits gastric acid secret...
Active IngredientOmeprazole
Dosage FormCapsule, delayed rel pellets; Tablet, delayed release
Routeoral; Oral
Strength10mg; 40mg; 20mg
Market StatusTentative Approval; Over the Counter; Prescription
CompanyActavis Labs Fl; Apotex; Sandoz; Kremers Urban Pharms; Zydus Pharms Usa; Dr Reddys Labs; Dexcel Pharma; Mylan; Impax Labs

4 of 14  
Drug NameOmeprazole magnesium
PubMed HealthOmeprazole/Sodium Bicarbonate (By mouth)
Drug ClassesGastric Acid Secretion Inhibitor
Drug Label11 DESCRIPTIONThe active ingredient in PRILOSEC (omeprazole) Delayed-Release Capsules is a substituted benzimidazole, 5-methoxy-2-[[(4-methoxy-3, 5-dimethyl-2-pyridinyl) methyl] sulfinyl]-1H-benzimidazole, a compound that inhibits gastric acid secret...
Active IngredientOmeprazole magnesium
Dosage FormCapsule, delayed release
RouteOral
Strengtheq 20mg base
Market StatusOver the Counter
CompanyDr Reddys Labs

5 of 14  
Drug NamePrilosec
Active IngredientOmeprazole magnesium; Omeprazole
Dosage FormCapsule, delayed rel pellets; For suspension, delayed release
RouteOral
Strengtheq 10mg base/packet; 10mg; 40mg; 20mg; eq 2.5mg base/packet
Market StatusPrescription
CompanyAstrazeneca

6 of 14  
Drug NamePrilosec otc
Active IngredientOmeprazole magnesium
Dosage FormTablet, delayed release
RouteOral
Strengtheq 20mg base
Market StatusOver the Counter
CompanyAstrazeneca

7 of 14  
Drug NameZegerid
Active Ingredientsodium bicarbonate; Omeprazole
Dosage FormCapsule; For suspension
RouteOral
Strength20mg/packet; 1.1gm; 40mg/packet; 1.68gm/packet; 40mg; 20mg
Market StatusPrescription
CompanySantarus

8 of 14  
Drug NameNexium
PubMed HealthEsomeprazole
Drug ClassesGastric Acid Secretion Inhibitor, Gastrointestinal Agent
Active IngredientEsomeprazole magnesium
Dosage FormCapsule, delayed rel pellets; For suspension, delayed release
RouteOral
Strengtheq 5mg base/packet; eq 20mg base/packet; eq 20mg base; eq 40mg base; eq 10mg base/packet; eq 40mg base/packet; eq 2.5mg base/packet
Market StatusPrescription
CompanyAstrazeneca

9 of 14  
Drug NameNexium iv
PubMed HealthOmeprazole (By mouth)
Drug ClassesGastric Acid Secretion Inhibitor
Drug LabelThe active ingredient in Omeprazole Delayed-Release Capsules is a substituted benzimidazole, 5-methoxy-2-[[(4-methoxy-3, 5-dimethyl-2-pyridinyl) methyl] sulfinyl]-1H-benzimidazole, a compound that inhibits gastric acid secretion. Its empirical formul...
Active IngredientEsomeprazole sodium
Dosage FormInjectable
RouteIntravenous
Strengtheq 20mg base/vial; eq 40mg base/vial
Market StatusPrescription
CompanyAstrazeneca

10 of 14  
Drug NameOmeprazole
PubMed HealthOmeprazole (By mouth)
Drug ClassesGastric Acid Secretion Inhibitor
Drug Label11 DESCRIPTIONThe active ingredient in PRILOSEC (omeprazole) Delayed-Release Capsules is a substituted benzimidazole, 5-methoxy-2-[[(4-methoxy-3, 5-dimethyl-2-pyridinyl) methyl] sulfinyl]-1H-benzimidazole, a compound that inhibits gastric acid secret...
Active IngredientOmeprazole
Dosage FormCapsule, delayed rel pellets; Tablet, delayed release
Routeoral; Oral
Strength10mg; 40mg; 20mg
Market StatusTentative Approval; Over the Counter; Prescription
CompanyActavis Labs Fl; Apotex; Sandoz; Kremers Urban Pharms; Zydus Pharms Usa; Dr Reddys Labs; Dexcel Pharma; Mylan; Impax Labs

11 of 14  
Drug NameOmeprazole magnesium
PubMed HealthOmeprazole/Sodium Bicarbonate (By mouth)
Drug ClassesGastric Acid Secretion Inhibitor
Drug Label11 DESCRIPTIONThe active ingredient in PRILOSEC (omeprazole) Delayed-Release Capsules is a substituted benzimidazole, 5-methoxy-2-[[(4-methoxy-3, 5-dimethyl-2-pyridinyl) methyl] sulfinyl]-1H-benzimidazole, a compound that inhibits gastric acid secret...
Active IngredientOmeprazole magnesium
Dosage FormCapsule, delayed release
RouteOral
Strengtheq 20mg base
Market StatusOver the Counter
CompanyDr Reddys Labs

12 of 14  
Drug NamePrilosec
Active IngredientOmeprazole magnesium; Omeprazole
Dosage FormCapsule, delayed rel pellets; For suspension, delayed release
RouteOral
Strengtheq 10mg base/packet; 10mg; 40mg; 20mg; eq 2.5mg base/packet
Market StatusPrescription
CompanyAstrazeneca

13 of 14  
Drug NamePrilosec otc
Active IngredientOmeprazole magnesium
Dosage FormTablet, delayed release
RouteOral
Strengtheq 20mg base
Market StatusOver the Counter
CompanyAstrazeneca

14 of 14  
Drug NameZegerid
Active Ingredientsodium bicarbonate; Omeprazole
Dosage FormCapsule; For suspension
RouteOral
Strength20mg/packet; 1.1gm; 40mg/packet; 1.68gm/packet; 40mg; 20mg
Market StatusPrescription
CompanySantarus

4.2 Therapeutic Uses

Anti-Ulcer Agents; Enzyme Inhibitors

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


Omeprazole is indicated for the treatment of a complex of symptoms which may be caused by any of the conditions where a reduction of gastric acid secretion is required (e.g., duodenal ulcer, gastric ulcer, nonsteroidal anti-inflammatory drugs associated gastric and duodenal ulcer, reflux esophagitis, gastroesophageal reflex disease) or when no identifiable organic cause is found (i.e., functional dyspepsia). /Included in US product labeling/

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2131


Omeprazole is indicated for the treatment of heartburn and other symptoms associated with gastroesophageal reflux disease. Omeprazole is indicated for the short-term treatment of erosive esophagitis (associated with gastroesophageal reflux disease) that has been diagnosed by endoscopy. Omeprazole also is indicated to maintain healing of erosive esophagitis. /Included in US product labeling/

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2131


Omeprazole is indicated for the long-term treatment of pathologic gastric hypersecretion associated with Zollinger-Ellison syndrome (alone or as part of multiple endocrine neoplasia Type-1), systemic mastocytosis, and multiple endocrine adenoma. /Included in US product labeling/

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2131


For more Therapeutic Uses (Complete) data for OMEPRAZOLE (8 total), please visit the HSDB record page.


4.3 Drug Warning

Pregnancy risk category: C /RISK CANNOT BE RULED OUT. Adequate, well controlled human studies are lacking, and animal studies have shown risk to the fetus or are lacking as well. There is a chance of fetal harm if the drug is given during pregnancy; but the potential benefits may outweigh the potential risk./

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2132


No information is available on the relationship of age to the effects of omeprazole in geriatric patients. However, a somewhat decreased rate of elimination and increased bioavailability are more likely to occur in geriatric patients taking omeprazole.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2132


Omeprazole generally is well tolerated. The most frequent adverse effects associated with omeprazole therapy involve the GI tract (e.g., diarrhea, nausea, constipation, abdominal pain, vomiting) and the CNS (e.g., headache, dizziness).

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 2839


Diarrhea, abdominal pain, nausea, vomiting, constipation, flatulence, and acid regurgitation are the most frequent adverse GI effects of omeprazole, occurring in about 1-5% of patients. Dysphagia, abdominal swelling, anorexia, irritable colon, fecal discoloration, pancreatitis (sometimes fatal), esophageal candidiasis, mucosal atrophy of the tongue, taste perversion, and dry mouth have been reported occasionally but in many cases were not directly attributed to the drug. Benign gastric fundic polyps have been reported rarely and appear to resolve upon discontinuation of omeprazole therapy.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 2840


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


4.4 Drug Indication

Omeprazole, according to the FDA label is a proton pump inhibitor (PPI) used for the following purposes: Treatment of active duodenal ulcer in adults Eradication of Helicobacter pylori to reduce the risk of duodenal ulcer recurrence in adults Treatment of active benign gastric ulcer in adults Treatment of symptomatic gastroesophageal reflux disease (GERD) in patients 1 year of age and older Treatment of erosive esophagitis (EE) due to acid-mediated GERD in patients 1 month of age and older Maintenance of healing of EE due to acid-mediated GERD in patients 1 year of age and older Pathologic hypersecretory conditions in adults


FDA Label


5 Pharmacology and Biochemistry
5.1 Pharmacology

**Effects on gastric acid secretion** This drug decreases gastric acid secretion. After oral administration, the onset of the antisecretory effect of omeprazole is usually achieved within one hour, with the maximum effect occurring by 2 hours after administration. The inhibitory effect of omeprazole on acid secretion increases with repeated once-daily dosing, reaching a plateau after four days. **Effects on serum gastrin** In studies of 200 or more patients, serum gastrin levels increased during the first 1-2 weeks of daily administration of therapeutic doses of omeprazole. This occurred in a parallel fashion with the inhibition of acid secretion. No further increase in serum gastrin occurred with continued omeprazole administration. Increased gastrin causes enterochromaffin-like cell hyperplasia and increased serum Chromogranin A (CgA) levels. The increased CgA levels may lead to false positive results in diagnostic studies for neuroendocrine tumors. **Enterochromaffin-like (ECL) cell effects** Human gastric biopsy samples have been obtained from more than 3000 pediatric and adult patients treated with omeprazole in long-term clinical studies. The incidence of enterochromaffin-like cell hyperplasia in these studies increased with time; however, no case of ECL cell carcinoids, dysplasia, or neoplasia have been identified in these patients. These studies, however, are of insufficient in power and duration to draw conclusions on the possible influence of long-term administration of omeprazole in the development of any premalignant or malignant conditions. **Other effects** Systemic effects of omeprazole in the central nervous system, cardiovascular and respiratory systems have not been found to date. Omeprazole, given in oral doses of 30 or 40 mg for 2-4 weeks, showed no effect on thyroid function, carbohydrate metabolism, or circulating levels of parathyroid hormone, cortisol, estradiol, testosterone, prolactin, cholecystokinin or secretin.


5.2 MeSH Pharmacological Classification

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.)


Proton Pump Inhibitors

Compounds that inhibit H(+)-K(+)-EXCHANGING ATPASE. They are used as ANTI-ULCER AGENTS and sometimes in place of HISTAMINE H2 ANTAGONISTS for GASTROESOPHAGEAL REFLUX. (See all compounds classified as Proton Pump Inhibitors.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
OMEPRAZOLE
5.3.2 FDA UNII
KG60484QX9
5.3.3 Pharmacological Classes
Cytochrome P450 2C19 Inhibitors [MoA]; Proton Pump Inhibitor [EPC]; Proton Pump Inhibitors [MoA]; Alkalinizing Activity [MoA]; Cytochrome P450 2C19 Inhibitors [MoA]
5.4 ATC Code

A02BC01

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

A02 - Drugs for acid related disorders

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

A02BC - Proton pump inhibitors

A02BC01 - Omeprazole


A - Alimentary tract and metabolism

A02 - Drugs for acid related disorders

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

A02BC - Proton pump inhibitors

A02BC05 - Esomeprazole


5.5 Absorption, Distribution and Excretion

Absorption

Omeprazole delayed-release capsules contain an enteric-coated granule formulation of omeprazole (because omeprazole is acid-labile), so that absorption of omeprazole begins only after the granules exit the stomach. Absorption of omeprazole occurs rapidly, with peak plasma concentrations of omeprazole achieved within 0.5-3.5 hours. Absolute bioavailability (compared with intravenous administration) is approximately 30-40% at doses of 20-40 mg, largely due to pre-systemic metabolism. The bioavailability of omeprazole increases slightly upon repeated administration of omeprazole delayed-release capsules.


Route of Elimination

After a single dose oral dose of a buffered solution of omeprazole, negligible (if any) amounts of unchanged drug were excreted in urine. Most of the dose (about 77%) was eliminated in urine as at least six different metabolites. Two metabolites were identified as _hydroxyomeprazole_ and the corresponding _carboxylic acid_. The remainder of the dose was found in the feces. This suggests significant biliary excretion of omeprazole metabolites. Three metabolites have been identified in the plasma, the _sulfide_ and _sulfone_ derivatives of omeprazole, and _hydroxyomeprazole_. These metabolites possess minimal or no antisecretory activity.


Volume of Distribution

Approximately 0.3 L/kg, corresponding to the volume of extracellular water.


Clearance

Healthy subject (delayed release capsule), total body clearance 500 - 600 mL/min Geriatric plasma clearance: 250 mL/min Hepatic impairment plasma clearance: 70 mL/min


Absorption: rapid. Distribution: Distributed in tissue, particularly gastric parietal cells.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2132


Elimination: Renal 72 to 80%. Fecal 18 to 23%. In dialysis - Not readily dialyzable, because of extensive protein binding.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2132


To clarify the in vivo first-pass metabolism of omeprazole, the pharmacokinetics were examined after oral, intraduodenal, intraportal venous, and intravenous administration at various doses to rats. Extraction ratios in the liver and intestinal tract were determined from the areas under the concentration-time curve (AUC) for intraportal venous and intravenous administration and from those for intraduodenal and intraportal venous administration, respectively. Assuming that the drug was absorbed from the gastrointestinal tract completely, the hepatic and intestinal extraction ratios were 0.80, 0.63, and 0.59 at doses of 2.5, 5, and 10 mg/kg and 0.70 and 0.73 at doses of 5 and 10 mg/kg, respectively. The bioavailability of orally administered omeprazole was 6.4, 9.6, and 12.6% at the doses of l0, 20, and 40 mg/kg, respectively. There were no differences in the distribution volume of steady state, total clearance, or elimination half-life at any doses. In addition, the AUC value after oral administration (20 mg/kg) in rats acutely intoxicated with CC(14) was 2.4 times larger than that in the control. These findings suggest that omeprazole undergoes a first-pass metabolism in the intestinal mucosa and/or lumen, as well as in the liver, and that the major contribution to the dose-dependent increase in bioavailability is a saturation of the first-pass metabolism in the liver.

PMID:7983597 Watanabe K et al; J Pharm Sci 83 (8): 1131-4 (1994)


Omeprazole is distributed into human milk; following oral administration of omeprazole 20 mg in one lactating women, concentrations of the drug were measured in breast milk.

McEvoy, G.K. (ed.). American Hospital Formulary Service- Drug Information 2004. Bethesda, MD: American Society of Health-System Pharmacists, Inc. 2004 (Plus Supplements)., p. 2841


For more Absorption, Distribution and Excretion (Complete) data for OMEPRAZOLE (6 total), please visit the HSDB record page.


5.6 Metabolism/Metabolites

Omeprazole is heavily metabolized in the liver by the cytochrome P450 (CYP) enzyme system. The main part of its metabolism depends on the polymorphically expressed CYP2C19, which is responsible for the formation of _hydroxyomeprazole_, the major metabolite found in plasma. The remaining part depends on CYP3A4, responsible for the formation of _omeprazole sulphone_.


The in vitro metabolism of omeprazole was studied in human liver microsomes in order to define the metabolic pathways and identify the cytochrome P450 (CYP) isoforms responsible for the formation of the major omeprazole metabolites. 2 The four major metabolites identified in vitro, in tentative order of importance, were hydroxyomeprazole, omeprazole sulphone, 5-O-desmethylomeprazole, and an unidentified compound termed metabolite X. Omeprazole pyridone was also detected but could not be quantitated. Incubation of hydroxyomeprazole and omeprazole sulphone with human microsomes resulted in both cases in formation of the hydroxysulphone. The kinetics of formation of the four primary metabolites studied were biphasic suggesting the involvement of multiple CYP isoforms in each case. Further studies used substrate concentrations at which the high affinity activities predominated. 3 Formation of the major metabolite, hydroxyomeprazole, was significantly correlated with S-mephenytoin hydroxylase and with benzo[a]pyrene metabolism and CYP3A content. Inhibition studies with isoform selective inhibitors also indicated a dominant role of S-mephenytoin hydroxylase with some CYP3A contribution in the formation of hydroxyomeprazole. Correlation and inhibition data for the sulphone and metabolite X were consistent with a predominant role of the CYP3A subfamily in formation of these metabolites. Formation of 5-O-desmethylomeprazole was inhibited by both R, S-mephenytoin and quinidine, indicating that both S-mephenytoin hydroxylase and CYP2D6 may mediate this reaction in human liver microsomes and in vivo. The Vmax/Km (indicator of intrinsic clearance in vivo) for hydroxyomeprazole was four times greater than that for omeprazole sulphone. Consistent with findings in vivo, the results predict that omeprazole clearance in vivo would be reduced in poor metabolisers of mephenytoin due to reduction in the dominant partial metabolic clearance to hydroxyomeprazole.

PMID:12959268 Full text: https://www.ncbi.nlm.nih.gov/pmc/articles/PMC1364656 Andersson T et al; Br J Clin Pharmacol 36 (6): 521-30 (1993)


Omeprazole has known human metabolites that include 3-Hydroxyomeprazole, 5'-O-Desmethyl omeprazole, 5-Hydroxyomeprazole, and Omeprazole sulfone.

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


5.7 Biological Half-Life

0.5-1 hour (healthy subjects, delayed-release capsule) Approximately 3 hours (hepatic impairment)


Plasma - Normal hepatic function - 30 minutes to 1 hour. Chronic hepatic disease - 3 hours.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2132


5.8 Mechanism of Action

Hydrochloric acid (HCl) secretion into the gastric lumen is a process regulated mainly by the H(+)/K(+)-ATPase of the proton pump, expressed in high quantities by the parietal cells of the stomach. ATPase is an enzyme on the parietal cell membrane that facilitates hydrogen and potassium exchange through the cell, which normally results in the extrusion of potassium and formation of HCl (gastric acid). Omeprazole is a member of a class of antisecretory compounds, the substituted _benzimidazoles_, that stop gastric acid secretion by selective inhibition of the _H+/K+ ATPase_ enzyme system. Proton-pump inhibitors such as omeprazole bind covalently to cysteine residues via disulfide bridges on the alpha subunit of the _H+/K+ ATPase_ pump, inhibiting gastric acid secretion for up to 36 hours. This antisecretory effect is dose-related and leads to the inhibition of both basal and stimulated acid secretion, regardless of the stimulus. **Mechanism of H. pylori eradication** Peptic ulcer disease (PUD) is frequently associated with _Helicobacter pylori_ bacterial infection (NSAIDs). The treatment of H. pylori infection may include the addition of omeprazole or other proton pump inhibitors as part of the treatment regimen,. _H. pylori_ replicates most effectively at a neutral pH. Acid inhibition in H. pylori eradication therapy, including proton-pump inhibitors such as omeprazole, raises gastric pH, discouraging the growth of H.pylori. It is generally believed that proton pump inhibitors inhibit the _urease_ enzyme, which increases the pathogenesis of H. pylori in gastric-acid related conditions.


Omeprazole is a selective and irreversible proton pump inhibitor. Omeprazole suppresses gastric acid secretion by specific inhibition of the hydrogen-potassium adenosinetriphosphatase (H+, K+-ATPase) enzyme system found at the secretory surface of parietal cells. It inhibits the final transport of hydrogen ions (via exchange with potassium ions) into the gastric lumen. Since the H+/K+ ATPase enzyme system is regarded as the acid (proton) pump of the gastric mucosa, omeprazole is known as a gastric acid pump inhibitor. Omeprazole inhibits both basal and stimulated acid secretion irrespective of the stimulus.

Thomson.Micromedex. Drug Information for the Health Care Professional. 24th ed. Volume 1. Plus Updates. Content Reviewed by the United States Pharmacopeial Convention, Inc. Greenwood Village, CO. 2004., p. 2132


After oral administration, the onset of the antisecretory effect of omeprazole occurs within one hour, with the maximum effect occurring within two hours. Inhibition of secretion is about 50% of maximum at 24 hours and the duration of inhibition lasts up to 72 hours. The antisecretory effect thus lasts far longer than would be expected from the very short (less than one hour) plasma half-life, apparently due to prolonged binding to the parietal H + /K + ATPase enzyme. When the drug is discontinued, secretory activity returns gradually, over 3 to 5 days. The inhibitory effect of omeprazole on acid secretion increases with repeated once-daily dosing, reaching a plateau after four days.

Physicians Desk Reference. 58th ed. Thomson PDR. Montvale, NJ 2004., p. 634


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