GCZ

N-[(3aR,6aS)-hexahydrocyclopenta[c]pyrrol-2(1H)-ylcarbamoyl]-4-methylbenzenesulfonamide

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Chemical Component Summary
Name	N-[(3aR,6aS)-hexahydrocyclopenta[c]pyrrol-2(1H)-ylcarbamoyl]-4-methylbenzenesulfonamide
Synonyms	gliclazide
Identifiers	1-[(3aR,6aS)-3,3a,4,5,6,6a-hexahydro-1H-cyclopenta[c]pyrrol-2-yl]-3-(4-methylphenyl)sulfonyl-urea
Formula	C₁₅ H₂₁ N₃ O₃ S
Molecular Weight	323.411
Type	NON-POLYMER
Isomeric SMILES	Cc1ccc(cc1)S(=O)(=O)NC(=O)NN2C[C@H]3CCC[C@H]3C2
InChI	InChI=1S/C15H21N3O3S/c1-11-5-7-14(8-6-11)22(20,21)17-15(19)16-18-9-12-3-2-4-13(12)10-18/h5-8,12-13H,2-4,9-10H2,1H3,(H2,16,17,19)/t12-,13+
InChIKey	BOVGTQGAOIONJV-BETUJISGSA-N

Chemical Details
Formal Charge	0
Atom Count	43
Chiral Atom Count	2
Bond Count	45
Aromatic Bond Count	6

Drug Info: DrugBank

DrugBank ID	DB01120 ?
Name	Gliclazide
Groups	approved
Description	Gliclazide is an oral antihyperglycemic agent used for the treatment of non-insulin-dependent diabetes mellitus (NIDDM). It has been classified differently according to its drug properties in which based on its chemical structure, gliclazide is considered a first-generation sulfonylurea due to the structural presence of a sulfonamide group able to release a proton and the presence of one aromatic group.[A39546] On the other hand, based on the pharmacological efficacy, gliclazide is considered a second-generation sulfonylurea which presents a higher potency and a shorter half-life.[T238, T360] Gliclazide belongs to the sulfonylurea class of insulin secretagogues, which act by stimulating β cells of the pancreas to release insulin. Sulfonylureas increase both basal insulin secretion and meal-stimulated insulin release. Medications in this class differ in their dose, rate of absorption, duration of action, route of elimination and binding site on their target pancreatic β cell receptor. Sulfonylureas also increase peripheral glucose utilization, decrease hepatic gluconeogenesis and may increase the number and sensitivity of insulin receptors. Sulfonylureas are associated with weight gain, though less so than insulin. Due to their mechanism of action, sulfonylureas may cause hypoglycemia and require consistent food intake to decrease this risk. The risk of hypoglycemia is increased in elderly, debilitated and malnourished individuals. Gliclazide has been shown to decrease fasting plasma glucose, postprandial blood glucose and glycosolated hemoglobin (HbA1c) levels (reflective of the last 8-10 weeks of glucose control). Gliclazide is extensively metabolized by the liver; its metabolites are excreted in both urine (60-70%) and feces (10-20%).
Synonyms	1-(hexahydrocyclopenta(c)pyrrol-2(1H)-yl)-3-(p-tolylsulfonyl)urea Gliclazidum Gliclazide Gliclazida 1-(3-azabicyclo(3.3.0)oct-3-yl)-3-(p-tolylsulfonyl)urea
Brand Names	Mylan-gliclazide Mr Ag-gliclazide Mr Mint-gliclazide Mr Jamp Gliclazide-MR PMS-gliclazide Gliclazide-80 Sandoz Gliclazide Mr Ava-gliclazide Mylan-gliclazide Diamicron Mr Diamicron Nu-gliclazide Glic Apo-gliclazide Mr Gliclazide Gliclazide -tab 80mg Apo-gliclazide Gliclazide Mr Sandoz Gliclazide Teva-gliclazide Taro-gliclazide Mr
Indication	For the treatment of NIDDM in conjunction with diet and exercise.
Categories	Alimentary Tract and Metabolism Amides Benzene Derivatives Benzenesulfonamides Blood Glucose Lowering Agents Cytochrome P-450 CYP2C19 Substrates Cytochrome P-450 CYP2C9 Substrates Cytochrome P-450 Substrates Drugs Used in Diabetes Genito Urinary System and Sex Hormones Gynecological Antiinfectives and Antiseptics Hypoglycemia-Associated Agents Insulin Secretagogues Oral Hypoglycemics Sulfonamides Sulfones Sulfonylureas Sulfur Compounds
ATC-Code	A10BB09 G01AE10
CAS number	21187-98-4

Drug Targets

Name	Target Sequence	Pharmacological Action	Actions
ATP-binding cassette sub-family C member 8	MPLAFCGSENHSAAYRVDQGVLNNGCFVDALNVVPHVFLLFITFPILFIG...	unknown	binder
Vascular endothelial growth factor A	MNFLLSWVHWSLALLLYLHHAKWSQAAPMAEGGGQNHHEVVKFMDVYQRS...	unknown	other/unknown
Cytochrome P450 2C9	MDSLVVLVLCLSCLLLLSLWRQSSGRGKLPPGPTPLPVIGNILQIGIKDI...	unknown	substrate
Cytochrome P450 2C19	MDPFVVLVLCLSCLLLLSIWRQSSGRGKLPPGPTPLPVIGNILQIDIKDV...	unknown	substrate
Serum albumin	MKWVTFISLLFLFSSAYSRGVFRRDAHKSEVAHRFKDLGEENFKALVLIA...	unknown

Drug Info/Drug Targets: DrugBank 3.0: a comprehensive resource for 'omics' research on drugs. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS. Nucleic Acids Res. 2011 Jan; 39 (Database issue):D1035-41. | PMID:21059682