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2D Structure
Also known as: Glibenclamide, 10238-21-8, Glybenclamide, Glynase, Diabeta, Micronase
Molecular Formula
C23H28ClN3O5S
Molecular Weight
494.0  g/mol
InChI Key
ZNNLBTZKUZBEKO-UHFFFAOYSA-N
FDA UNII
SX6K58TVWC

An antidiabetic sulfonylurea derivative with actions like those of chlorpropamide
Glyburide is a Sulfonylurea.
1 2D Structure

2D Structure

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
5-chloro-N-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamide
2.1.2 InChI
InChI=1S/C23H28ClN3O5S/c1-32-21-12-9-17(24)15-20(21)22(28)25-14-13-16-7-10-19(11-8-16)33(30,31)27-23(29)26-18-5-3-2-4-6-18/h7-12,15,18H,2-6,13-14H2,1H3,(H,25,28)(H2,26,27,29)
2.1.3 InChI Key
ZNNLBTZKUZBEKO-UHFFFAOYSA-N
2.1.4 Canonical SMILES
COC1=C(C=C(C=C1)Cl)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCCCC3
2.2 Other Identifiers
2.2.1 UNII
SX6K58TVWC
2.3 Synonyms
2.3.1 MeSH Synonyms

1. Daonil

2. Diabeta

3. Euglucon 5

4. Euglucon N

5. Glibenclamide

6. Glybenclamide

7. Hb 419

8. Hb 420

9. Hb-419

10. Hb-420

11. Hb419

12. Hb420

13. Maninil

14. Micronase

15. Neogluconin

2.3.2 Depositor-Supplied Synonyms

1. Glibenclamide

2. 10238-21-8

3. Glybenclamide

4. Glynase

5. Diabeta

6. Micronase

7. Daonil

8. Euglucon

9. Maninil

10. Glybenzcyclamide

11. Semi-daonil

12. Apo-glibenclamide

13. Euglucon 5

14. Azuglucon

15. Bastiverit

16. Benclamin

17. Betanase

18. Duraglucon

19. Euglucan

20. Euglykon

21. Glibenil

22. Glucolon

23. Orabetic

24. Prodiabet

25. Renabetic

26. Yuglucon

27. Dibelet

28. Gilemal

29. Glibens

30. Glibil

31. Glimel

32. Glimide

33. Humedia

34. Libanil

35. Suraben

36. Tiabet

37. Adiab

38. Melix

39. Pira

40. Med-glionil

41. Glibenclamidum

42. Glibenclamida

43. Hb 419

44. Glibenclamidum [inn-latin]

45. Glibenclamida [inn-spanish]

46. 5-chloro-n-(4-(n-(cyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-methoxybenzamide

47. Glyburide (glibenclamide)

48. Hb-419

49. Ur 606

50. Cirara

51. 1-((p-(2-(5-chloro-o-anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexylurea

52. 1-(p-(2-(5-chloro-2-methoxybenzamido)ethyl)benzenesulfonyl)-3-cyclohexylurea

53. Neogluconin

54. 5-chloro-n-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamide

55. 5-chloro-n-(2-(4-((((cyclohexylamino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-methoxybenzamide

56. Glibenclamide [inn]

57. U 26452

58. Gewaglucon

59. Glibenbeta

60. Glidiabet

61. Glucobene

62. Glucohexal

63. Glucoremed

64. Hexaglucon

65. Lederglib

66. Lisaglucon

67. Normoglucon

68. Praeciglucon

69. Calabren

70. Cytagon

71. Euclamin

72. Glamide

73. Glibesyn

74. Glibetic

75. Gliboral

76. Glisulin

77. Glitisol

78. Glubate

79. Glucomid

80. Glucoven

81. Glycomin

82. Miglucan

83. Debtan

84. Gliban

85. Gliben

86. Glibet

87. Glicem

88. Gluben

89. Glyben

90. Nadib

91. Sugril

92. Sx6k58tvwc

93. Chembl472

94. Novo-glyburide

95. Nsc-759618

96. Glibenclamid Al

97. 5-chloro-n-[4-(cyclohexylureidosulfonyl)phenethyl]-2-methoxybenzamide

98. Gen-glybe

99. Norglicem 5

100. Betanese 5

101. N-(4-(2-(5-chloro-2-methoxybenzamido)ethyl)phenylsulfonyl)-n'-cyclohexylurea

102. Glibenclamid Fabra

103. 5-chloro-n-[2-(4-{[(cyclohexylcarbamoyl)amino]sulfonyl}phenyl)ethyl]-2-methoxybenzamide

104. Benzamide, 5-chloro-n-(2-(4-((((cyclohexylamino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-methoxy-

105. Mls000069721

106. Chebi:5441

107. Glibenclamid Basics

108. Glibenclamid-cophar

109. Glibenclamid Heumann

110. Semi-euglucon

111. Glibenclamid Genericon

112. Hemi-daonil

113. U-26452

114. Glibenclamid-ratiopharm

115. U-26,452

116. 5-chloro-n-(2-{4-[(cyclohexylcarbamoyl)sulfamoyl]phenyl}ethyl)-2-methoxybenzamide

117. Urea, 1-(p-(2-(5-chloro-2-methoxybenzamido)ethyl)benzenesulfonyl)-3-cyclohexyl-

118. Benzamide, 5-chloro-n-[2-[4-[[[(cyclohexylamino)carbonyl]amino]sulfonyl]phenyl]ethyl]-2-methoxy-

119. Glyburide [usan]

120. Ncgc00015467-11

121. Abbenclamide

122. Diabiphage

123. Glibadone

124. Smr000058229

125. Semi-gliben-puren N

126. Gbn 5

127. Cas-10238-21-8

128. Glibenclamid Riker M.

129. Glyburide (micronized)

130. Urea, 1-((p-(2-(chloro-o-anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexyl-

131. Dsstox_cid_17237

132. Dsstox_rid_79313

133. Dsstox_gsid_37237

134. U-26,45

135. Micronized Glyburide

136. Glycron

137. 1-[[p-[2-(5-chloro-o-anisamido)ethyl]phenyl]sulfonyl]-3-cyclohexylurea

138. 5-chloro-n-(2-{4-[n-(n-cyclohexylcarbamoyl)sulfamoyl]phenyl}ethyl)-2-methoxybenzamide

139. 5-chloro-n-(4-(n-(cyclohexylcarbamoyl)sulfamoyl)-phenethyl)-2-methoxybenzamide

140. Glyburide (usp)

141. Micronase (tn)

142. 1-{4-[2-(5-chloro-2-methoxybenzamido)ethyl]benzenesulfonyl}-3-cyclohexylurea;1-{4-[2-(5-chloro-2-methoxybenzamido)ethyl]benzenesulfonyl}-3-cyclohexylurea

143. Diabeta (tn)

144. Glynase (tn)

145. Sr-01000000196

146. Glyburide [usan:usp]

147. Einecs 233-570-6

148. Unii-sx6k58tvwc

149. Brn 2230085

150. Amglidia

151. Delmide

152. 5-chloro-n-(4-[n-(cyclohexylcarbamoyl)sulfamoyl]phenethyl)-2-methoxybenzamide

153. Glibenclamide,(s)

154. Gbm

155. Prestwick_569

156. Glibenclamide B.p.

157. Glyburide (diabeta)

158. Mfcd00056625

159. Rp-1127

160. Spectrum_000250

161. Tocris-0911

162. Glibenclamide - Bio-x

163. Glybenzcyclamide, 99%

164. Glibenclamide; Glyburide

165. Opera_id_801

166. Glyburide [mi]

167. Prestwick0_000316

168. Prestwick1_000316

169. Prestwick2_000316

170. Prestwick3_000316

171. Spectrum2_001816

172. Spectrum3_001327

173. Spectrum4_001199

174. Spectrum5_001631

175. Glyburide [vandf]

176. Lopac-g-0639

177. Probes1_000431

178. Probes2_000378

179. Upcmld-dp006

180. G 0639

181. Glibenclamide [jan]

182. N-p-[2-(5-chloro-2-methoxybenzamido)ethyl]benzenesulfonyl-n'-cyclohexylurea

183. Glyburide [usp-rs]

184. Glyburide [who-ip]

185. Glibenclamide (jp17/inn)

186. N-(4-(beta-(2-methoxy-5-chlorbenzamido)-aethyl)-benzolsulfonyl)-n'-cyclohexyl-harnstoff

187. Cbiol_001790

188. Lopac0_000499

189. Oprea1_764617

190. Schembl22009

191. Bspbio_000312

192. Bspbio_001351

193. Bspbio_003053

194. Kbiogr_000071

195. Kbiogr_001897

196. Kbioss_000071

197. Kbioss_000730

198. Mls001077262

199. Bidd:gt0239

200. Divk1c_000481

201. Glibenclamide [mart.]

202. Spectrum2300229

203. Spbio_001831

204. Spbio_002531

205. Glibenclamide [who-dd]

206. Glibenclamide [who-ip]

207. Bpbio1_000344

208. Gtpl2414

209. Glyburide [orange Book]

210. Dtxsid0037237

211. Upcmld-dp006:001

212. Hms501i03

213. Kbio1_000481

214. Kbio2_000071

215. Kbio2_000730

216. Kbio2_002639

217. Kbio2_003298

218. Kbio2_005207

219. Kbio2_005866

220. Kbio3_000141

221. Kbio3_000142

222. Kbio3_002273

223. Glyburide [usp Monograph]

224. Glybenclamide, >=99% (hplc)

225. Ninds_000481

226. Bio1_000076

227. Bio1_000565

228. Bio1_001054

229. Bio2_000071

230. Bio2_000551

231. Hms1361d13

232. Hms1568p14

233. Hms1791d13

234. Hms1922l08

235. Hms1989d13

236. Hms2089l06

237. Hms2093p04

238. Hms2095p14

239. Hms3259o12

240. Hms3261d19

241. Hms3267a15

242. Hms3402d13

243. Hms3411f16

244. Hms3428d15

245. Hms3651e17

246. Hms3675f16

247. Hms3712p14

248. Pharmakon1600-02300229

249. Zinc537805

250. Bcp05327

251. Glibenclamide [ep Monograph]

252. Glibenclamide For Peak Identification

253. Tox21_110158

254. Tox21_300758

255. Tox21_500499

256. Bdbm50012957

257. Ccg-39618

258. Glucovance Component Glyburide

259. Hd 419

260. Nsc759618

261. Nsc813214

262. Stk362992

263. Glibenclamidum [who-ip Latin]

264. Glyburide - Cas 10238-21-8

265. Akos001487495

266. Tox21_110158_1

267. Bcp9000729

268. Cs-1075

269. Db01016

270. Ks-5326

271. Lp00499

272. Nc00566

273. Nsc 759618

274. Nsc-813214

275. Sb17414

276. Sdccgsbi-0050483.p004

277. Glyburide Component Of Glucovance

278. Idi1_000481

279. Idi1_033821

280. Glibenclamide 1.0 Mg/ml In Acetonitrile

281. Ncgc00015467-01

282. Ncgc00015467-02

283. Ncgc00015467-03

284. Ncgc00015467-04

285. Ncgc00015467-05

286. Ncgc00015467-06

287. Ncgc00015467-07

288. Ncgc00015467-08

289. Ncgc00015467-09

290. Ncgc00015467-10

291. Ncgc00015467-12

292. Ncgc00015467-13

293. Ncgc00015467-14

294. Ncgc00015467-15

295. Ncgc00015467-16

296. Ncgc00015467-17

297. Ncgc00015467-18

298. Ncgc00015467-20

299. Ncgc00015467-21

300. Ncgc00015467-36

301. Ncgc00015467-37

302. Ncgc00016689-01

303. Ncgc00023447-02

304. Ncgc00023447-04

305. Ncgc00023447-05

306. Ncgc00023447-06

307. Ncgc00023447-07

308. Ncgc00023447-08

309. Ncgc00023447-09

310. Ncgc00023447-10

311. Ncgc00023447-11

312. Ncgc00023447-12

313. Ncgc00254662-01

314. Ncgc00261184-01

315. Bg166164

316. Hy-15206

317. Sbi-0050483.p003

318. Glyburide, Meets Usp Testing Specifications

319. Ab00051949

320. Eu-0100499

321. Ft-0601608

322. G-150

323. G0382

324. Glibenclamide 100 Microg/ml In Acetonitrile

325. S1716

326. Sw195828-5

327. A19539

328. C07022

329. D00336

330. D81733

331. M01823

332. Ab00051949-16

333. Ab00051949-17

334. Ab00051949_18

335. Ab00051949_19

336. Q420626

337. Sr-01000000196-2

338. Sr-01000000196-4

339. Sr-01000000196-5

340. Sr-01000000196-6

341. Sr-01000000196-8

342. W-108874

343. Brd-k36927236-001-06-0

344. Brd-k36927236-001-17-7

345. Z277540138

346. Glybenclamide, European Pharmacopoeia (ep) Reference Standard

347. Glyburide, United States Pharmacopeia (usp) Reference Standard

348. 1-((p-(2-(5-chloro-o-anisamido)ethyl)phenyl)sulfonyl)-3-cyclohexyl Urea

349. 5-chloro-n-[4-(3-cyclohexylureidosulfonyl)phenethyl]-2-methoxybenzamide

350. 5-chloro-n-[2-[4-(cyclohexylcarbamoylsulfamoyl)phenyl]ethyl]-2-methoxybenzamide.

351. 5-chloro-n-[4-({[(cyclohexylamino)carbonyl]amino}sulfonyl)phenethyl]-2-methoxybenzamide

352. Glibenclamide For Peak Identification, European Pharmacopoeia (ep) Reference Standard

353. Glyburide (glibenclamide), Pharmaceutical Secondary Standard; Certified Reference Material

354. N-(4-(.beta.-(2-methoxy-5-chlorbenzamido)-aethyl)-benzolsulfonyl)-n'-cyclohexyl-harnstoff

355. N1-[4-({[(cyclohexylamino)carbonyl]amino}sulfonyl)phenethyl]-5-chloro-2-methoxybenzamide

356. 5-chloro-n-(2-[4-(([(cyclohexylamino)carbonyl]amino)sulfonyl)phenyl]ethyl)-2-methoxybenzamide #

357. 5-chloro-n-[2-[4-[[[(cyclohexylamino)carbonyl]-amino]sulfonyl]phenyl]-ethyl]-2-methoxybenzamide

358. 5-chloro-n-[2-[4-[[[(cylcohexylamino)carbonyl]amino]sulphonyl]phenyl]ethyl]-2-methoxybenzamide

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 494.0 g/mol
Molecular Formula C23H28ClN3O5S
XLogP34.8
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count8
Exact Mass493.1438199 g/mol
Monoisotopic Mass493.1438199 g/mol
Topological Polar Surface Area122 Ų
Heavy Atom Count33
Formal Charge0
Complexity746
Isotope Atom Count0
Defined Atom Stereocenter Count0
Undefined Atom Stereocenter Count0
Defined Bond Stereocenter Count0
Undefined Bond Stereocenter Count0
Covalently Bonded Unit Count1
4 Drug and Medication Information
4.1 Drug Information
1 of 8  
Drug NameDiabeta
PubMed HealthGlyburide (By mouth)
Drug ClassesHypoglycemic
Drug LabelDiaeta (glyburide) is an oral blood-glucose-lowering drug of the sulfonylurea class. It is a white, crystalline compound, formulated as tablets of 1.25 mg, 2.5 mg, and 5 mg strengths for oral administration. Diaeta tablets USP contain the activ...
Active IngredientGlyburide
Dosage FormTablet
RouteOral
Strength2.5mg; 5mg; 1.25mg
Market StatusPrescription
CompanySanofi Aventis Us

2 of 8  
Drug NameGlyburide
Active IngredientGlyburide
Dosage FormTablet
RouteOral
Strength1.5mg; 4.5mg; 6mg; 3mg
Market StatusPrescription
CompanyTeva; Hikma; Dava Pharms; Mylan

3 of 8  
Drug NameGlyburide
PubMed HealthGlyburide (By mouth)
Drug ClassesHypoglycemic
Drug LabelGlyburide tablets USP contain glyburide, which is an oral blood-glucose-lowering drug of the sulfonylurea class. Glyburide is a white, crystalline compound. The chemical name for glyburide is 1-[[p-[2-(5-chloro-o-anisamido)ethyl]phenyl]-sulfonyl]-3-c...
Active IngredientGlyburide
Dosage FormTablet
RouteOral
Strength2.5mg; 1.25mg; 5mg
Market StatusPrescription
CompanyCorepharma; Teva; Aurobindo Pharma; Heritage Pharms

4 of 8  
Drug NameGlynase
Drug LabelGLYNASE PresTab Tablets contain micronized (smaller particle size) glyburide, which is an oral blood-glucose-lowering drug of the sulfonylurea class. Glyburide is a white, crystalline compound, formulated as GLYNASE PresTab Tablets of 1.5, 3, and 6 m...
Active IngredientGlyburide
Dosage FormTablet
RouteOral
Strength1.5mg; 6mg; 3mg
Market StatusPrescription
CompanyPharmacia And Upjohn

5 of 8  
Drug NameGlyburide
PubMed HealthGlyburide (By mouth)
Drug ClassesHypoglycemic
Drug LabelGlyburide tablets USP contain glyburide, which is an oral blood-glucose-lowering drug of the sulfonylurea class. Glyburide is a white, crystalline compound. The chemical name for glyburide is 1-[[p-[2-(5-chloro-o-anisamido)ethyl]phenyl]-sulfonyl]-3-c...
Active IngredientGlyburide
Dosage FormTablet
RouteOral
Strength2.5mg; 1.25mg; 5mg
Market StatusPrescription
CompanyCorepharma; Teva; Aurobindo Pharma; Heritage Pharms

6 of 8  
Drug NameGlynase
Drug LabelGLYNASE PresTab Tablets contain micronized (smaller particle size) glyburide, which is an oral blood-glucose-lowering drug of the sulfonylurea class. Glyburide is a white, crystalline compound, formulated as GLYNASE PresTab Tablets of 1.5, 3, and 6 m...
Active IngredientGlyburide
Dosage FormTablet
RouteOral
Strength1.5mg; 6mg; 3mg
Market StatusPrescription
CompanyPharmacia And Upjohn

7 of 8  
Drug NameDiabeta
PubMed HealthGlyburide (By mouth)
Drug ClassesHypoglycemic
Drug LabelDiaeta (glyburide) is an oral blood-glucose-lowering drug of the sulfonylurea class. It is a white, crystalline compound, formulated as tablets of 1.25 mg, 2.5 mg, and 5 mg strengths for oral administration. Diaeta tablets USP contain the activ...
Active IngredientGlyburide
Dosage FormTablet
RouteOral
Strength2.5mg; 5mg; 1.25mg
Market StatusPrescription
CompanySanofi Aventis Us

8 of 8  
Drug NameGlyburide
Active IngredientGlyburide
Dosage FormTablet
RouteOral
Strength1.5mg; 4.5mg; 6mg; 3mg
Market StatusPrescription
CompanyTeva; Hikma; Dava Pharms; Mylan

4.2 Drug Indication

Glyburide is indicated alone or as part of combination product with metformin, as an adjunct to diet and exercise, to improve glycemic control in adults with type 2 diabetes mellitus.


Amglidia is indicated for the treatment of neonatal diabetes mellitus, for use in newborns, infants and children.

Sulphonylureas like Amglidia have been shown to be effective in patients with mutations in the genes coding for the -cell ATP-sensitive potassium channel and chromosome 6q24-related transient neonatal diabetes mellitus.


Treatment of neonatal diabetes mellitus


Treatment of large hemispheric infarction


5 Pharmacology and Biochemistry
5.1 Pharmacology

Glyburide is a second generation sulfonylurea that stimulates insulin secretion through the closure of ATP-sensitive potassium channels on beta cells, raising intracellular potassium and calcium ion concentrations. Glibenclamide has a long duration of action as it is given once daily, and a wide therapeutic index as patients are started at doses as low as 0.75mg but that can increase as high as 10mg or more. Patients taking glyburide should be cautioned regarding an increased risk of cardiovascular mortality as seen with tolbutamide, another sulfonylurea.


5.2 MeSH Pharmacological Classification

Hypoglycemic Agents

Substances which lower blood glucose levels. (See all compounds classified as Hypoglycemic Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
GLYBURIDE
5.3.2 FDA UNII
SX6K58TVWC
5.3.3 Pharmacological Classes
Sulfonylurea [EPC]; Sulfonylurea Compounds [CS]
5.4 ATC Code

A10BB01


A10BB01

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

A10 - Drugs used in diabetes

A10B - Blood glucose lowering drugs, excl. insulins

A10BB - Sulfonylureas

A10BB01 - Glibenclamide


5.5 Absorption, Distribution and Excretion

Absorption

Elderly patients taking glyburide reached a Cmax of 211-315ng/mL with a Tmax of 0.9-1.0h, while younger patients reached a Cmax of 144-302ng/mL with a Tmax of 1.3-3.0h. Patients taking glyburide have and AUC of 348ng*h/mL.


Route of Elimination

Unlike other sulfonylureas, glyburide is 50% excreted in the urine and 50% in the feces. Glyburide is mainly excreted as the metabolite 4-trans-hydroxyglyburide.


Volume of Distribution

Elderly patients have a volume of distribution of 19.3-52.6L, while younger patients have a volume of distribution of 21.5-49.3L.


Clearance

Elderly patients have a clearance of 2.70-3.55L/h, while younger patients have a clearance of 2.47-4.11L/h.


5.6 Metabolism/Metabolites

Glyburide is metabolized mainly by CYP3A4, followed by CYP2C9, CYP2C19, CYP3A7, and CYP3A5. These enzymes metabolize glyburide to 4-trans-hydroxycyclohexyl glyburide (M1), 4-cis-hydroxycyclohexyl glyburide (M2a), 3-cis-hydroxycyclohexyl glyburide (M2b), 3-trans-hydroxycyclohexyl glyburide (M3), 2-trans-hydroxycyclohexyl glyburide (M4), and ethylhydroxycyclohexyl glyburide (M5). The M1 and M2b metabolites are considered active, along with the parent molecule.


Glyburide has known human metabolites that include 2-trans-hydroxycyclohexyl glyburide, 3-cis-Hydroxycyclohexyl glyburide, 3-trans-Hydroxycyclohexyl glyburide, and 4-cis-hydroxycyclohexyl glyburide.

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


5.7 Biological Half-Life

Elderly patients have a terminal elimination half life of 4.0-13.4h, while younger patients have a terminal elimination half life of 4.0-13.9h.


5.8 Mechanism of Action

Glyburide belongs to a class of drugs known as sulfonylureas. These drugs act by closing ATP-sensitive potassium channels on pancreatic beta cells. The ATP-sensitive potassium channels on beta cells are known as sulfonylurea receptor 1 (SUR1). Under low glucose concentrations, SUR1 remains open, allowing for potassium ion efflux to create a -70mV membrane potential. Normally SUR1 closes in response to high glucose concentrations, the membrane potential of the cells becomes less negative, the cell depolarizes, voltage gated calcium channels open, calcium ions enter the cell, and the increased intracellular calcium concentration stimulates the release of insulin containing granules. Glyburide bypasses this process by forcing SUR1 closed and stimulating increased insulin secretion.