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

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    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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    DOSAGE - TABLET;ORAL - 1MG

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