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Details

Stereochemistry ACHIRAL
Molecular Formula C24H34N4O5S
Molecular Weight 490.616
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLIMEPIRIDE, CIS-

SMILES

CCC1=C(C)CN(C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)N[C@@H]3CC[C@H](C)CC3)C1=O

InChI

InChIKey=WIGIZIANZCJQQY-UWUNEBHHSA-N
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)/t16-,19+

HIDE SMILES / InChI

Molecular Formula C24H34N4O5S
Molecular Weight 490.616
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

Approval Year

PubMed

PubMed

TitleDatePubMed
Prevention of weight gain in type 2 diabetes requiring insulin treatment.
2004-03
Long-acting sulfonylureas -- long-acting hypoglycaemia.
2004-01-19
Determination of glimepiride in human plasma by liquid chromatography-electrospray ionization tandem mass spectrometry.
2004-01-05
Glimepiride pharmacokinetics in obese versus non-obese diabetic patients.
2004-01
Protective actions of gliclazide on high insulin-enhanced neutrophil-endothelial cell interactions through inhibition of mitogen activated protein kinase and protein kinase C pathways.
2004-01
The influence of glimepiride on the binding kinetics of insulin with its skeletal muscle and liver receptors in rats with short term and prolonged hyperglycemia induced by streptozotocin.
2004-01
Comparison of the effects of glimepiride and glibenclamide on adipose tissue tumour necrosis factor-alpha mRNA expression and cellularity.
2004-01
Hormonal counterregulation and consecutive glimepiride serum concentrations during severe hypoglycaemia associated with glimepiride therapy.
2003-12
Glimepiride and serum adiponectin level in type 2 diabetic subjects: response to Nagasaka et al.
2003-12
Change in patients' body weight after 12 months of treatment with glimepiride or glibenclamide in Type 2 diabetes: a multicentre retrospective cohort study.
2003-12
Study of glimepiride-b-cyclodextrin complex.
2003-11
Lichenoid drug eruption as a result of the recently released sulfonylurea glimepiride.
2003-11
The influence of glimepiride on the oxidative state of rats with streptozotocin-induced hyperglycemia.
2003-11
Efficacy of sulfonylureas with insulin in type 2 diabetes mellitus.
2003-11
Design of the cooperative study on glycemic control and complications in diabetes mellitus type 2: Veterans Affairs Diabetes Trial.
2003-10-30
A diabetic woman with worsening heart failure, hunger, and tremor.
2003-10
Risk of hypoglycaemia with oral antidiabetic agents in patients with Type 2 diabetes.
2003-10
Prospective multicentre trial comparing the efficacy of, and compliance with, glimepiride or acarbose treatment in patients with type 2 diabetes not controlled with diet alone.
2003-08
Effects of glimepiride on HbA(1c) and body weight in Type 2 diabetes: results of a 1.5-year follow-up study.
2003-07
Effect of glimepiride on serum adiponectin level in subjects with type 2 diabetes.
2003-07
Glimepiride reduces mononuclear activation of the redox-sensitive transcription factor nuclear factor-kappa B.
2003-07
Summaries for patients. A comparison of three insulin regimens (morning glargine, bedtime glargine, or bedtime neutral protamine Hagedorn) in addition to a pill for treating type 2 diabetes.
2003-06-17
Glimepiride combined with morning insulin glargine, bedtime neutral protamine hagedorn insulin, or bedtime insulin glargine in patients with type 2 diabetes. A randomized, controlled trial.
2003-06-17
Lispro insulin and metformin versus other combination in the diabetes mellitus type 2 management after secondary oral antidiabetic drug failure.
2003-06
Sulfonylureas and cardiovascular effects: from experimental data to clinical use. Available data in humans and clinical applications.
2003-06
Comparison of the micro- and macro-vascular effects of glimepiride and gliclazide in metformin-treated patients with Type 2 diabetes: a double-blind, crossover study.
2003-06
Characteristics and time course of severe glimepiride- versus glibenclamide-induced hypoglycaemia.
2003-06
Pitfalls in endosonographic imaging of suspected insulinomas: pancreatic nodules of unknown dignity.
2003-05
Combined bedtime insulin--daytime sulphonylurea regimen compared with two different daily insulin regimens in type 2 diabetes: effects on HbA1c and hypoglycaemia rate--a randomised trial.
2003-04-04
Glimepiride treatment and IGF-I in adolescents with type 1 diabetes: a prospective, randomized, double-blind, placebo-controlled study.
2003-04
[Differences between oral antidiabetics].
2003-03-20
Differential selectivity of insulin secretagogues: mechanisms, clinical implications, and drug interactions.
2003-03-08
Effects of sulfonylureas on K(ATP) channel-dependent vasodilation.
2003-03-08
Glimepiride in type 2 diabetes mellitus: a review of the worldwide therapeutic experience.
2003-03
The mechanisms underlying the unique pharmacodynamics of nateglinide.
2003-03
Comparison between repaglinide and glimepiride in patients with type 2 diabetes mellitus: a one-year, randomized, double-blind assessment of metabolic parameters and cardiovascular risk factors.
2003-02
Differential effects of sulphonylureas on the vasodilatory response evoked by K(ATP) channel openers.
2003-02
Impairment of myocardial protection in type 2 diabetic patients.
2003-02
Efficacy and safety profile of glimepiride in Mexican American Patients with type 2 diabetes mellitus: a randomized, placebo-controlled study.
2003-01
[Glimepiride in daily practice].
2003
[A 50-year history of new drugs in Japan-the development and progress of anti-diabetic drugs and the epidemiological aspects of diabetes mellitus].
2003
A flaw in the use of sulfonylurea screening to diagnose sulfonylurea overdosages.
2003
Inadvertent sulfonylurea overdosage and hypoglycemia in an elderly woman: failure of serum hypoglycemia screening.
2003
[Glimepiride--an oral antidiabetic agent].
2003
[Sulfonylurea receptors and their interaction with glimepiride].
2003
[Fear of the injection must not be an argument. Every second type 2 diabetic patient needs insulin].
2002-12-05
[Molecular mechanisms of insulin secretion].
2002-12
Immunoreactive insulin response to a single dose of glimepiride in lean type 2 diabetic subjects.
2002-10
Amaryl (glimepiride) in patients with type 2 diabetes mellitus.
2002
[Progress in studies on antidiabetic agents].
2001-09
Patents
Substance Class Chemical
Created
by admin
on Mon Mar 31 21:49:23 GMT 2025
Edited
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on Mon Mar 31 21:49:23 GMT 2025
Record UNII
24T6XIR2MZ
Record Status Validated (UNII)
Record Version
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Name Type Language
GLIMEPIRIDE, CIS-
Common Name English
GLIMEPIRIDE RELATED COMPOUND A
USP  
Preferred Name English
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
Systematic Name English
GLIMEPIRIDE CIS-ISOMER
Common Name English
GLIMEPIRIDE IMPURITY A [EP IMPURITY]
Common Name English
GLIMEPIRIDE RELATED COMPOUND A [USP IMPURITY]
Common Name English
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-
Systematic Name English
GLIMEPIRIDE RELATED COMPOUND A [USP-RS]
Common Name English
Code System Code Type Description
CAS
684286-46-2
Created by admin on Mon Mar 31 21:49:23 GMT 2025 , Edited by admin on Mon Mar 31 21:49:23 GMT 2025
PRIMARY
RS_ITEM_NUM
1292314
Created by admin on Mon Mar 31 21:49:23 GMT 2025 , Edited by admin on Mon Mar 31 21:49:23 GMT 2025
PRIMARY
FDA UNII
24T6XIR2MZ
Created by admin on Mon Mar 31 21:49:23 GMT 2025 , Edited by admin on Mon Mar 31 21:49:23 GMT 2025
PRIMARY
PUBCHEM
3476
Created by admin on Mon Mar 31 21:49:23 GMT 2025 , Edited by admin on Mon Mar 31 21:49:23 GMT 2025
PRIMARY
Related Record Type Details
PARENT -> IMPURITY