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Chemistry

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Also known as: 93479-97-1, Amaryl, Glimepirid, Amarel, Glimepirida, Glimepiridum
Molecular Formula
C24H34N4O5S
Molecular Weight
490.6  g/mol
InChI Key
WIGIZIANZCJQQY-UHFFFAOYSA-N
FDA UNII
24T6XIR2MZ

Glimepiride
Glimepiride is a long-acting, third-generation sulfonylurea with hypoglycemic activity. Compared to other generations of sulfonylurea compounds, glimepiride is very potent and has a longer duration of action. This agent is metabolized by CYP2C9 and shows peroxisome proliferator-activated receptor gamma (PPARgamma) agonistic activity.
Glimepiride is a Sulfonylurea.
1 2D Structure

Glimepiride

2 Identification
2.1 Computed Descriptors
2.1.1 IUPAC Name
4-ethyl-3-methyl-N-[2-[4-[(4-methylcyclohexyl)carbamoylsulfamoyl]phenyl]ethyl]-5-oxo-2H-pyrrole-1-carboxamide
2.1.2 InChI
InChI=1S/C24H34N4O5S/c1-4-21-17(3)15-28(22(21)29)24(31)25-14-13-18-7-11-20(12-8-18)34(32,33)27-23(30)26-19-9-5-16(2)6-10-19/h7-8,11-12,16,19H,4-6,9-10,13-15H2,1-3H3,(H,25,31)(H2,26,27,30)
2.1.3 InChI Key
WIGIZIANZCJQQY-UHFFFAOYSA-N
2.1.4 Canonical SMILES
CCC1=C(CN(C1=O)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCC(CC3)C)C
2.2 Other Identifiers
2.2.1 UNII
24T6XIR2MZ
2.3 Synonyms
2.3.1 MeSH Synonyms

1. 1-(4-(2-(3-ethyl-4-methyl-2-oxo-3-pyrrolinecarboxamido)ethyl)phenylsulfonyl)-3-(4-methylcyclohexyl)urea

2. Amarel

3. Amaryl

4. Glymepiride

5. Hoe 490

6. Hoe-490

7. Roname

2.3.2 Depositor-Supplied Synonyms

1. 93479-97-1

2. Amaryl

3. Glimepirid

4. Amarel

5. Glimepirida

6. Glimepiridum

7. Hoe-490

8. Glimepride

9. Hoe 490

10. Cis-glimepiride

11. 684286-46-2

12. Glimepiride, Cis-

13. Glimperide

14. Glimepiride Impurity A

15. 4-ethyl-3-methyl-n-[2-[4-[(4-methylcyclohexyl)carbamoylsulfamoyl]phenyl]ethyl]-5-oxo-2h-pyrrole-1-carboxamide

16. Chebi:5383

17. 1-((p-(2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)ethyl)phenyl)sulfonyl)-3-(trans-4-methylcyclohexyl)urea

18. Endial

19. Nsc-759809

20. 24t6xir2mz

21. 6ky687524k

22. 261361-60-8

23. Ncgc00016960-03

24. Glimepiridum [latin]

25. Roname

26. Glimepirida [spanish]

27. Cas-93479-97-1

28. Glista Od

29. Dsstox_cid_20675

30. Dsstox_rid_79534

31. Dsstox_gsid_40675

32. 1h-pyrrole-1-carboxamide, 3-ethyl-2,5-dihydro-4-methyl-n-(2-(4-(((((4-methylcyclohexyl)amino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-oxo-, Trans-

33. 3-ethyl-4-methyl-n-[2-(4-{[(trans-4-methylcyclohexyl)carbamoyl]sulfamoyl}phenyl)ethyl]-2-oxo-2,5-dihydro-1h-pyrrole-1-carboxamide

34. Glymepirid

35. Glorion

36. Glemax

37. Glimer

38. Solosa

39. 3-ethyl-4-methyl-n-[2-(4-{[(cis-4-methylcyclohexyl)carbamoyl]sulfamoyl}phenyl)ethyl]-2-oxo-2,5-dihydro-1h-pyrrole-1-carboxamide

40. Smr000466368

41. Amaryl (tn)

42. Ccris 7083

43. Sr-05000001508

44. Unii-24t6xir2mz

45. Brn 5365754

46. Gimepiride

47. Vitamine

48. Niddaryl

49. Sugral

50. Hoe490

51. Unii-6ky687524k

52. Glimepiride,(s)

53. 1-[[4-[2-[[(3-ethyl-4-methyl-2-oxo-2,3-dihydro-1h-pyrrol-1-yl)carbonyl]amino]ethyl]phenyl]sulphonyl]-3-(cis-4-methylcyclohexyl)urea (cis-glimepiride)

54. 3-ethyl-4-methyl-n-[2-[4-[(4-methylcyclohexyl)carbamoylsulfamoyl]phenyl]ethyl]-2-oxo-5h-pyrrole-1-carboxamide

55. Glimepiride [usan:usp:inn:ban]

56. Amaryl, Glista Od

57. Glimepiride- Bio-x

58. Mfcd00878417

59. Cpd000466368

60. Glimepiride [mi]

61. Prestwick0_000651

62. Prestwick1_000651

63. Prestwick2_000651

64. Prestwick3_000651

65. Glimepiride [inn]

66. Glimepiride [jan]

67. Glimepiride [usan]

68. Glimepiride [vandf]

69. Chembl1481

70. Glimepiride [mart.]

71. Oprea1_382896

72. Schembl16084

73. Schembl16086

74. Bspbio_000681

75. Glimepiride [usp-rs]

76. Glimepiride [who-dd]

77. Glimepiride Cis-isomer

78. Mls000759495

79. Mls001076674

80. Mls001401419

81. Mls003915622

82. Mls006011260

83. Spbio_002602

84. Glimepiride [ema Epar]

85. Bpbio1_000751

86. Chembl149223

87. Gtpl6820

88. Schembl8738802

89. Glimepiride (jp17/usp/inn)

90. Dtxsid5040675

91. Schembl14371714

92. Schembl14965363

93. Chebi:92609

94. Dtxsid20861130

95. Glimepiride [orange Book]

96. Glimepiride For System Suitability

97. Glimepiride [ep Monograph]

98. Glimepiride [usp Impurity]

99. Hms1570c03

100. Hms2052l03

101. Hms2090k18

102. Hms2097c03

103. Hms2235l07

104. Hms3269a09

105. Hms3372o07

106. Hms3394l03

107. Hms3413k06

108. Hms3654f17

109. Hms3677k06

110. Hms3714c03

111. Pharmakon1600-01504915

112. Zinc537791

113. Glimepiride [usp Monograph]

114. Bcp05331

115. Duetact Component Glimepiride

116. Hy-b0104

117. Tox21_110713

118. Ac-476

119. Bdbm50237590

120. Nsc759809

121. Nsc813217

122. S1344

123. Stl451059

124. Stl453194

125. Glimepiride Related Compound A

126. Akos015894919

127. Akos015969663

128. Glimepiride, >=98% (hplc), Solid

129. Tox21_110713_1

130. Zinc100001976

131. Zinc100070954

132. Ab07644

133. Bcp9000728

134. Ccg-101156

135. Cs-1844

136. Db00222

137. Glimepiride Component Of Duetact

138. Ks-5238

139. Nc00406

140. Nsc 759809

141. Nsc-813217

142. Ncgc00016960-01

143. Ncgc00016960-02

144. Ncgc00016960-04

145. Ncgc00016960-05

146. Ncgc00016960-07

147. Ncgc00161404-01

148. Ncgc00161404-02

149. Ncgc00181757-01

150. Ncgc00371061-02

151. Ncgc00371061-06

152. 1-{[4-(2-{[(3-ethyl-4-methyl-2-oxo-2,5-dihydro-1h-pyrrol-1-yl)carbonyl]amino}ethyl)phenyl]sulfonyl}-3-(trans-4-methylcyclohexyl)urea

153. 1h-pyrrole-1-carboxamide, 2,5-dihydro-3-ethyl-4-methyl-n-(2-(4-(((((4-methylcyclohexyl)amino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-oxo-, Trans-

154. 3-ethyl-4-methyl-n-(4-(n-((1r,4r)-4-methylcyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-oxo-2,5-dihydro

155. Bg164507

156. Smr001550123

157. Glimepiride 100 Microg/ml In Acetonitrile

158. Ab00513874

159. Cs-0165191

160. Ft-0626713

161. Ft-0668978

162. G0395

163. Glimepiride Impurity A [ep Impurity]

164. Sw196369-4

165. C07669

166. D00593

167. Glimepiride Related Compound A [usp-rs]

168. Ab00513874-06

169. Ab00513874-08

170. Ab00513874-09

171. Ab00513874_10

172. Ab00513874_11

173. 479g971

174. A844609

175. A899888

176. Q425027

177. Q-201158

178. Sr-05000001508-1

179. Sr-05000001508-2

180. Sr-05000001508-3

181. Brd-k34776109-001-03-4

182. Brd-k42693031-001-01-8

183. Glimepiride Related Compound A [usp Impurity]

184. Q27253874

185. Glimepiride, British Pharmacopoeia (bp) Reference Standard

186. Glimepiride, European Pharmacopoeia (ep) Reference Standard

187. 3-ethyl-4-methyl-n-(4-(n-((1r,4r)-4-methylcyclohexylcarbamoyl)

188. Glimepiride, United States Pharmacopeia (usp) Reference Standard

189. Sulfamoyl)phenethyl)-2-oxo-2,5-dihydro-1h-pyrrole-1-carboxamide

190. Glimepiride For System Suitability, European Pharmacopoeia (ep) Reference Standard

191. 1-((4-(2-(((3-ethyl-4-methyl-2-oxo-2,3-dihydro-1h-pyrrol-1-yl)carbonyl)amino)ethyl)phenyl)sulfonyl)-3-(cis-4-methylcyclohexyl)urea

192. 1h-pyrrole-1-carboxamide, 3-ethyl-2,5-dihydro-4-methyl-n-(2-(4-(((((cis-4-methylcyclohexyl)amino)carbonyl)amino)sulfonyl)phenyl)ethyl)-2-oxo-

193. 1h-pyrrole-1-carboxamide, 3-ethyl-2,5-dihydro-4-methyl-n-[2-[4-[[[[(trans- 4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-

194. 3-ethyl-2,5-dihydro-4-methyl-n-[2-[4-[[[[(4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1h-pyrrole-1-carboxamide

195. 3-ethyl-2,5-dihydro-4-methyl-n-[2-[4-[[[[(trans-4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1h-pyrrole-1-carboxamide

196. 3-ethyl-4-methyl-2-oxo-n-(2-{4-[({[(1r,4r)-4-methylcyclohexyl]carbamoyl}amino)sulfonyl]phenyl}ethyl)-2,5-dihydro-1h-pyrrole-1-carboxamide

197. 3-ethyl-4-methyl-n-(4-(n-(((1r,4r)-4-methylcyclohexyl)carbamoyl)sulfamoyl)phenethyl)-2-oxo-2,5-dihydro-1h-pyrrole-1-carboxamide

198. 3-ethyl-4-methyl-n-(4-(n-(((1s,4s)-4-methylcyclohexyl)carbamoyl)sulfamoyl)phenethyl)-2-oxo-2,5-dihydro-1h-pyrrole-1-carboxamide? (glimepiride Impurity Pound(c)

199. 3-ethyl-4-methyl-n-(4-(n-((1r,4r)-4-methylcyclohexylcarbamoyl)sulfamoyl)phenethyl)-2-oxo-2,5-dihydro-1h-pyrrole-1-carboxamide

200. 3-ethyl-4-methyl-n-(4-(n-((rel-(1r,4r)-4-methylcyclohexyl)carbamoyl)sulfamoyl)phenethyl)-2-oxo-2,5-dihydro-1h-pyrrole-1-carboxamide

201. 3-ethyl-4-methyl-n-(4-(n-((trans-4-methylcyclohexyl)carbamoyl)sulfamoyl)phenethyl)-2-oxo-2,5-dihydro-1h-pyrrole-1-carboxamide

202. 3-ethyl-4-methyl-n-[2-(4-{[(4-methylcyclohexyl)carbamoyl]sulfamoyl}phenyl)ethyl]-2-oxo-2,5-dihydro-1h-pyrrole-1-carboxamide

203. 3-ethyl-4-methyl-n-[2-(4-{[(cis-4-methylcyclohexyl)carbamoyl]sulfamoyl}phenyl)ethyl]-2-oxo-2,5-dihydro-1h-pyrrole-1-car

204. 3-ethyl-4-methyl-n-[2-[4-[[3-(4-methylcyclohexyl)ureido]sulfonyl]phenyl]ethyl]-2-oxo-2,5-dihydro-1h-pyrrole-1-carboxamide

205. 3-ethyl-4-methyl-n-{2-[4-({[(4-methylcyclohexyl)carbamoyl]amino}sulfonyl)phenyl]ethyl}-2-oxo-2,5-dihydro-1h-pyrrole-1-carboxamide

206. N'-{[4-(2-{[(3-ethyl-4-methyl-2-oxo-2,5-dihydro-1h-pyrrol-1-yl)carbonyl]amino}ethyl)phenyl]sulfonyl}-n-(4-methylcyclohexyl)carbamimidic Acid

207. N-(4-ethyl-3-methyl-5-oxo-2h-pyrrol-1-yl)-3-[4-[(4-methylcyclohexyl)carbamoylsulfamoyl]phenyl]propanamide;glimepiride

208. N-[4-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido)-ethyl]-benzenesulfonyl]-n'-4-methylcyclohexylurea

209. Trans-1-(4-(2-(3-ethyl-4-me-2-oxo-2,5-dihydro-1h-pyrrole-1-carboxamido)ethyl)phenylsulfonyl)-3-(4-methylcyclohexyl)urea

210. Trans-3-ethyl-2,5-dihydro-4-methyl-n-[2-[4-[[[[(4-methyl Cyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1h-pyrrole-1-carboxamide

211. Trans-3-ethyl-2,5-dihydro-4-methyl-n-[2-[4-[[[[(4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1h-pyrrole-1-carboxamide

212. Trans-3-ethyl-2,5-dihydro-4-methyl-n-[2-[4-[[[[trans-4-methylcyclohexyl)amino]carbonyl]amino]sulfonyl]phenyl]ethyl]-2-oxo-1h-pyrrole-1-carboxyamide

2.4 Create Date
2004-09-16
3 Chemical and Physical Properties
Molecular Weight 490.6 g/mol
Molecular Formula C24H34N4O5S
XLogP33.9
Hydrogen Bond Donor Count3
Hydrogen Bond Acceptor Count5
Rotatable Bond Count7
Exact Mass490.22499137 g/mol
Monoisotopic Mass490.22499137 g/mol
Topological Polar Surface Area133 Ų
Heavy Atom Count34
Formal Charge0
Complexity895
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 4  
Drug NameAmaryl
PubMed HealthGlimepiride (By mouth)
Drug ClassesHypoglycemic
Drug LabelAMARYL is an oral sulfonylurea that contains the active ingredient glimepiride. Chemically, glimepiride is identified as 1-[[p-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) ethyl]phenyl]sulfonyl]-3-(trans-4-methylcyclohexyl)urea (C24H34N4O5S)...
Active IngredientGlimepiride
Dosage FormTablet
RouteOral
Strength4mg; 2mg; 1mg
Market StatusPrescription
CompanySanofi Aventis Us

2 of 4  
Drug NameGlimepiride
PubMed HealthGlimepiride (By mouth)
Drug ClassesHypoglycemic
Drug LabelGlimepiride Tablets, USP are an oral blood-glucose-lowering drug of the sulfonylurea class. Glimepiride, USP is a white to yellowish-white, crystalline, odorless to practically odorless powder formulated into tablets of 1-mg, 2-mg, and 4-mg strengths...
Active IngredientGlimepiride
Dosage FormTablet
RouteOral
Strength1mg; 8mg; 4mg; 6mg; 2mg; 3mg
Market StatusPrescription
CompanyActavis Labs Fl; Teva; Accord Hlthcare; Aurobindo Pharma; Invagen Pharms; Hikma Pharms; Indoco Remedies; Micro Labs Ltd India; Vintage; Dr Reddys Labs; Carlsbad; Mylan

3 of 4  
Drug NameAmaryl
PubMed HealthGlimepiride (By mouth)
Drug ClassesHypoglycemic
Drug LabelAMARYL is an oral sulfonylurea that contains the active ingredient glimepiride. Chemically, glimepiride is identified as 1-[[p-[2-(3-ethyl-4-methyl-2-oxo-3-pyrroline-1-carboxamido) ethyl]phenyl]sulfonyl]-3-(trans-4-methylcyclohexyl)urea (C24H34N4O5S)...
Active IngredientGlimepiride
Dosage FormTablet
RouteOral
Strength4mg; 2mg; 1mg
Market StatusPrescription
CompanySanofi Aventis Us

4 of 4  
Drug NameGlimepiride
PubMed HealthGlimepiride (By mouth)
Drug ClassesHypoglycemic
Drug LabelGlimepiride Tablets, USP are an oral blood-glucose-lowering drug of the sulfonylurea class. Glimepiride, USP is a white to yellowish-white, crystalline, odorless to practically odorless powder formulated into tablets of 1-mg, 2-mg, and 4-mg strengths...
Active IngredientGlimepiride
Dosage FormTablet
RouteOral
Strength1mg; 8mg; 4mg; 6mg; 2mg; 3mg
Market StatusPrescription
CompanyActavis Labs Fl; Teva; Accord Hlthcare; Aurobindo Pharma; Invagen Pharms; Hikma Pharms; Indoco Remedies; Micro Labs Ltd India; Vintage; Dr Reddys Labs; Carlsbad; Mylan

4.2 Drug Indication

Glimepiride is indicated for the management of type 2 diabetes in adults as an adjunct to diet and exercise to improve glycemic control as monotherapy. It may also be indicated for use in combination with metformin or insulin to lower blood glucose in patients with type 2 diabetes whose high blood sugar levels cannot be controlled by diet and exercise in conjunction with an oral hypoglycemic (a drug used to lower blood sugar levels) agent alone.


5 Pharmacology and Biochemistry
5.1 Pharmacology

Glimepiride stimulates the secretion of insulin granules from the pancreatic beta cells and improves the sensitivity of peripheral tissues to insulin to increase peripheral glucose uptake, thus reducing plasma blood glucose levels and glycated hemoglobin (HbA1C) levels. A multi-center, randomized, placebo-controlled clinical trial evaluated the efficacy of glimepiride (18 mg) as monotherapy titrated over 10 weeks compared with placebo in T2DM subjects who were not controlled by diet alone. In this study, there was a reduction in fasting plasma glucose (FPG) by 46 mg/dL, post-prandial glucose (PPG) by 72 mg/dL, and HbA1c by 1.4% more than the placebo. In another randomized study comprising of patients with T2DM receiving either placebo or one of the three doses (1, 4, or 8 mg) of glimepiride during a 14-week study period, all glimepiride regimens significantly reduced FPG, PPG, and HbA1c values (P < 0.001) compared to placebo by the end of the study period. The 4- and 8-mg doses of glimepiride were more effective than the 1-mg dose; however, the 4-mg dose provided a nearly maximal antihyperglycemic effect.


5.2 MeSH Pharmacological Classification

Hypoglycemic Agents

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


Immunosuppressive Agents

Agents that suppress immune function by one of several mechanisms of action. Classical cytotoxic immunosuppressants act by inhibiting DNA synthesis. Others may act through activation of T-CELLS or by inhibiting the activation of HELPER CELLS. While immunosuppression has been brought about in the past primarily to prevent rejection of transplanted organs, new applications involving mediation of the effects of INTERLEUKINS and other CYTOKINES are emerging. (See all compounds classified as Immunosuppressive Agents.)


Anti-Arrhythmia Agents

Agents used for the treatment or prevention of cardiac arrhythmias. They may affect the polarization-repolarization phase of the action potential, its excitability or refractoriness, or impulse conduction or membrane responsiveness within cardiac fibers. Anti-arrhythmia agents are often classed into four main groups according to their mechanism of action: sodium channel blockade, beta-adrenergic blockade, repolarization prolongation, or calcium channel blockade. (See all compounds classified as Anti-Arrhythmia Agents.)


5.3 FDA Pharmacological Classification
5.3.1 Active Moiety
GLIMEPIRIDE
5.3.2 FDA UNII
6KY687524K
5.3.3 Pharmacological Classes
Sulfonylurea [EPC]; Sulfonylurea Compounds [CS]
5.4 ATC Code

A10BB12

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

A10BB12 - Glimepiride


5.5 Absorption, Distribution and Excretion

Absorption

Glimepiride is completely absorbed after oral administration within 1 hour of administration with a linear pharmacokinetics profile. Following administration of a single oral dose of glimepiride in healthy subjects and with multiple oral doses with type 2 diabetes, the peak plasma concentrations (Cmax) were reached after 2 to 3 hours post-dose. Accumulation does not occur after multiple doses. When glimepiride was given with meals, the time to reach Cmax was increased by 12% while the mean and AUC (area under the curve) were decreased by 8 to 9%, respectively. In a pharmacokinetic study of Japanese patients with T2DM, Cmax value in once-daily dose was higher than those in twice-daily doses. The absolute bioavailability of glimepiride is reported to be complete following oral administration.


Route of Elimination

Following oral administration of glimepiride in healthy male subjects, approximately 60% of the total radioactivity was recovered in the urine in 7 days, with M1 and M2 accounting for 80-90% of the total radioactivity recovered in the urine. The ratio of M1 to M2 was approximately 3:2 in two subjects and 4:1 in one subject. Approximately 40% of the total radioactivity was recovered in feces where M1 and M2 accounted for about 70% of the radioactivity and a ratio of M1 to M2 being 1:3. No parent drug was recovered from urine or feces.


Volume of Distribution

Following intravenous dosing in healthy subjects, the volume of distribution was 8.8 L (113 mL/kg).


Clearance

A single-dose, crossover, dose-proportionality (1, 2, 4, and 8 mg) study in normal subjects and from a single- and multiple-dose, parallel, dose proportionality (4 and 8 mg) study in patients with type 2 diabetes (T2D) were performed. In these studies, the total body clearance was 52.1 +/- 16.0 mL/min, 48.5 +/- 29.3 mL/min in patients with T2D given a single oral dose, and 52.7 +/- 40.3 mL/min in patients with T2D given multiple oral doses. Following intravenous dosing in healthy subjects, the total body clearance was 47.8 mL/min.


5.6 Metabolism/Metabolites

Glimepiride is reported to undergo hepatic metabolism. Following either an intravenous or oral dose, glimepiride undergoes oxidative biotransformation mediated by CYP2C9 enzyme to form a major metabolite, cyclohexyl hydroxymethyl derivative (M1), that is pharmacologically active. M1 can be further metabolized to the inactive metabolite carboxyl derivative (M2) by one or several cytosolic enzymes. M1 retained approximately one third of the pharmacologic activity of its parent in an animal model, with a half-life of 3-6 hours. However, whether the glucose-lowering effect of M1 is clinically significant is not clear.


Glimepiride has known human metabolites that include Cyclohexylhydroymethylglimepiride.

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


5.7 Biological Half-Life

The elimination half-life of glimepiride is approximately 5 to 8 hours, which can increase up to 9 hours following multiple doses.


5.8 Mechanism of Action

ATP-sensitive potassium channels on pancreatic beta cells that are gated by intracellular ATP and ADP. The hetero-octomeric complex of the channel is composed of four pore-forming Kir6.2 subunits and four regulatory sulfonylurea receptor (SUR) subunits. Alternative splicing allows the formation of channels composed of varying subunit isoforms expressed at different concentrations in different tissues. In pancreatic beta cells, ATP-sensitive potassium channels play a role as essential metabolic sensors and regulators that couple membrane excitability with glucose-stimulated insulin secretion (GSIS). When there is a decrease in the ATP:ADP ratio, the channels are activated and open, leading to K+ efflux from the cell, membrane hyperpolarization, and suppression of insulin secretion. In contrast, increased uptake of glucose into the cell leads to elevated intracellular ATP:ADP ratio, leading to the closure of channels and membrane depolarization. Depolarization leads to activation and opening of the voltage-dependent Ca2+ channels and consequently an influx of calcium ions into the cell. Elevated intracellular calcium levels causes the contraction of the filaments of actomyosin responsible for the exocytosis of insulin granules stored in vesicles. Glimepiride blocks the ATP-sensitive potassium channel by binding non-specifically to the B sites of both sulfonylurea receptor-1 (SUR1) and sulfonylurea receptor-2A (SUR2A) subunits as well as the A site of SUR1 subunit of the channel to promote insulin secretion from the beta cell.


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S.A.","supplierCountry":"GREECE","foreign_port":"ATHENS","customer":"ACTAVIS PHARMA DEVELOPMENT CENTRE PRIVATE LIMITED","customerCountry":"INDIA","quantity":"0.05","actualQuantity":"50","unit":"GMS","unitRateFc":"0.3","totalValueFC":"39.8","currency":"EUR","unitRateINR":"66.2","date":"21-May-2024","totalValueINR":"3308.32","totalValueInUsd":"39.8","indian_port":"Madras Air","hs_no":"29319090","bill_no":"3585477","productDescription":"API","marketType":"REGULATED MARKET","country":"GREECE","selfForZScoreResived":"Pharma Grade","supplierPort":"ATHENS","supplierAddress":"28 OCTOVRIOU STREET 1123 51 AG. VARVARA, GREECE","customerAddress":"210 - 210A, GALLERIA, HIRANANDANI"}]
01-Jan-2021
31-Aug-2024
KGS
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Average Price (USD/KGS)

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Total Quantity (KGS)

Total Value (USD)

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

API Imports and Exports

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(USD/KGS)
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DOSAGE - TABLET;ORAL - 1MG

USFDA APPLICATION NUMBER - 20496

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DOSAGE - TABLET;ORAL - 2MG

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DOSAGE - TABLET;ORAL - 4MG

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