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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

Approval Year

PubMed

PubMed

TitleDatePubMed
[Progress in studies on antidiabetic agents].
2001 Sep
Amaryl (glimepiride) in patients with type 2 diabetes mellitus.
2002
[Molecular mechanisms of insulin secretion].
2002 Dec
[Fear of the injection must not be an argument. Every second type 2 diabetic patient needs insulin].
2002 Dec 5
Immunoreactive insulin response to a single dose of glimepiride in lean type 2 diabetic subjects.
2002 Oct
[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
Glimepiride treatment and IGF-I in adolescents with type 1 diabetes: a prospective, randomized, double-blind, placebo-controlled study.
2003 Apr
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 Aug
Hormonal counterregulation and consecutive glimepiride serum concentrations during severe hypoglycaemia associated with glimepiride therapy.
2003 Dec
Glimepiride and serum adiponectin level in type 2 diabetic subjects: response to Nagasaka et al.
2003 Dec
Change in patients' body weight after 12 months of treatment with glimepiride or glibenclamide in Type 2 diabetes: a multicentre retrospective cohort study.
2003 Dec
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 Feb
Differential effects of sulphonylureas on the vasodilatory response evoked by K(ATP) channel openers.
2003 Feb
Impairment of myocardial protection in type 2 diabetic patients.
2003 Feb
Efficacy and safety profile of glimepiride in Mexican American Patients with type 2 diabetes mellitus: a randomized, placebo-controlled study.
2003 Jan
Effects of glimepiride on HbA(1c) and body weight in Type 2 diabetes: results of a 1.5-year follow-up study.
2003 Jul
Effect of glimepiride on serum adiponectin level in subjects with type 2 diabetes.
2003 Jul
Glimepiride reduces mononuclear activation of the redox-sensitive transcription factor nuclear factor-kappa B.
2003 Jul
Lispro insulin and metformin versus other combination in the diabetes mellitus type 2 management after secondary oral antidiabetic drug failure.
2003 Jun
Sulfonylureas and cardiovascular effects: from experimental data to clinical use. Available data in humans and clinical applications.
2003 Jun
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 Jun
Characteristics and time course of severe glimepiride- versus glibenclamide-induced hypoglycaemia.
2003 Jun
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 Jun 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 Jun 17
Glimepiride in type 2 diabetes mellitus: a review of the worldwide therapeutic experience.
2003 Mar
The mechanisms underlying the unique pharmacodynamics of nateglinide.
2003 Mar
[Differences between oral antidiabetics].
2003 Mar 20
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 Mar-Apr
Differential selectivity of insulin secretagogues: mechanisms, clinical implications, and drug interactions.
2003 Mar-Apr
Effects of sulfonylureas on K(ATP) channel-dependent vasodilation.
2003 Mar-Apr
Pitfalls in endosonographic imaging of suspected insulinomas: pancreatic nodules of unknown dignity.
2003 May
Study of glimepiride-b-cyclodextrin complex.
2003 Nov
Lichenoid drug eruption as a result of the recently released sulfonylurea glimepiride.
2003 Nov
The influence of glimepiride on the oxidative state of rats with streptozotocin-induced hyperglycemia.
2003 Nov
Efficacy of sulfonylureas with insulin in type 2 diabetes mellitus.
2003 Nov
Design of the cooperative study on glycemic control and complications in diabetes mellitus type 2: Veterans Affairs Diabetes Trial.
2003 Nov-Dec
A diabetic woman with worsening heart failure, hunger, and tremor.
2003 Oct
Risk of hypoglycaemia with oral antidiabetic agents in patients with Type 2 diabetes.
2003 Oct
Glimepiride pharmacokinetics in obese versus non-obese diabetic patients.
2004 Jan
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 Jan
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 Jan
Comparison of the effects of glimepiride and glibenclamide on adipose tissue tumour necrosis factor-alpha mRNA expression and cellularity.
2004 Jan
Long-acting sulfonylureas -- long-acting hypoglycaemia.
2004 Jan 19
Determination of glimepiride in human plasma by liquid chromatography-electrospray ionization tandem mass spectrometry.
2004 Jan 5
Prevention of weight gain in type 2 diabetes requiring insulin treatment.
2004 Mar
Patents
Name Type Language
GLIMEPIRIDE, CIS-
Common 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
GLIMEPIRIDE RELATED COMPOUND A
USP  
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 Sat Dec 16 08:00:55 GMT 2023 , Edited by admin on Sat Dec 16 08:00:55 GMT 2023
PRIMARY
RS_ITEM_NUM
1292314
Created by admin on Sat Dec 16 08:00:55 GMT 2023 , Edited by admin on Sat Dec 16 08:00:55 GMT 2023
PRIMARY
FDA UNII
24T6XIR2MZ
Created by admin on Sat Dec 16 08:00:55 GMT 2023 , Edited by admin on Sat Dec 16 08:00:55 GMT 2023
PRIMARY
PUBCHEM
3476
Created by admin on Sat Dec 16 08:00:55 GMT 2023 , Edited by admin on Sat Dec 16 08:00:55 GMT 2023
PRIMARY