U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C24H34N4O5S
Molecular Weight 490.6176
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of GLIMEPIRIDE

SMILES

CCC1=C(C)CN(C1=O)C(=NCCc2ccc(cc2)S(=O)(=O)NC(=N[C@@]3([H])CC[C@]([H])(C)CC3)O)O

InChI

InChIKey=WIGIZIANZCJQQY-RUCARUNLSA-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 490.6176
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
Curator's Comment:: Description was created based on several sources, including https://www.accessdata.fda.gov/drugsatfda_docs/label/2009/020496s021lbl.pdf

Glimepiride, like glyburide and glipizide, is a "second-generation" sulfonylurea agents. Glimepiride is used with diet to lower blood glucose by increasing the secretion of insulin from pancreas and increasing the sensitivity of peripheral tissues to insulin. The mechanism of action of glimepiride in lowering blood glucose appears to be dependent on stimulating the release of insulin from functioning pancreatic beta cells, and increasing sensitivity of peripheral tissues to insulin. Glimepiride likely binds to ATP-sensitive potassium channel receptors on the pancreatic cell surface, reducing potassium conductance and causing depolarization of the membrane. Membrane depolarization stimulates calcium ion influx through voltage-sensitive calcium channels. This increase in intracellular calcium ion concentration induces the secretion of insulin. Glimepiride is used for concomitant use with insulin for the treatment of noninsulin-dependent (type 2) diabetes mellitus. Glimepiride`s original trade name is Amaryl.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AMARYL

Approved Use

AMARYL is indicated as an adjunct to diet and exercise to improve glycemic control in adults with type 2 diabetes mellitus

Launch Date

9.1972803E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
74.05 μg/L
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GLIMEPIRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
551 ng/mL
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GLIMEPIRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
646.98 μg × h/L
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GLIMEPIRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
4.08 h
2 mg single, oral
dose: 2 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GLIMEPIRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
5.3 h
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GLIMEPIRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
0.5%
8 mg single, oral
dose: 8 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
GLIMEPIRIDE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: UNKNOWN
food status: UNKNOWN
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Other InhibitorOther SubstrateOther Inducer







Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes [Inhibition 100 uM]
yes [Inhibition 100 uM]
yes [Inhibition 100 uM]
yes [Inhibition 100 uM]
yes [Inhibition 100 uM]
yes [Inhibition 100 uM]
Drug as victim

Drug as victim

Tox targets
PubMed

PubMed

TitleDatePubMed
Effectiveness of nateglinide on in vitro insulin secretion from rat pancreatic islets desensitized to sulfonylureas.
2001
Glucose-dependent and glucose-sensitizing insulinotropic effect of nateglinide: comparison to sulfonylureas and repaglinide.
2001
[Progress in studies on antidiabetic agents].
2001 Sep
Amaryl (glimepiride) in patients with type 2 diabetes mellitus.
2002
Haemodynamic and metabolic effects of low daily dose sulphonylureas in diabetic dog hearts.
2002
[Differential type 2 diabetes therapy based on pathophysiological aspects].
2002 Aug
[Molecular mechanisms of insulin secretion].
2002 Dec
Sulfonylurea stimulation of insulin secretion.
2002 Dec
Efficacy of glimepiride for the treatment of diabetes occurring during glucocorticoid therapy.
2002 Dec
Acute effect of glimepiride on insulin-stimulated glucose metabolism in glucose-tolerant insulin-resistant offspring of patients with type 2 diabetes.
2002 Nov
Dynamics of plasma membrane microdomains and cross-talk to the insulin signalling cascade.
2002 Oct 30
Effects of insulin and sulphonylureas on insulin-like growth factor-I levels in streptozotocin-induced diabetic rats.
2002 Oct-Dec
[Glimepiride].
2002 Sep
Glimepiride improves both first and second phases of insulin secretion in type 2 diabetes.
2002 Sep
[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
Differential effects of sulphonylureas on the vasodilatory response evoked by K(ATP) channel openers.
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
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
Efficacy of sulfonylureas with insulin in type 2 diabetes mellitus.
2003 Nov
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

Sample Use Guides

The usual starting dose of AMARYL as initial therapy is 1-2 mg once daily, administered with breakfast or the first main meal. Those patients who may be more sensitive to hypoglycemic drugs should be started at 1 mg once daily, and should be titrated carefully.
Route of Administration: Oral
Therapeutic concentrations of glimepiride (10 uM) block three types of recombinant KATP channel ± Kir6.2/SUR1, Kir6.2/SUR2A and Kir6.2/SUR2B (corresponding to the b-cell, cardiac and smooth muscle types of KATP channel)
Substance Class Chemical
Created
by admin
on Fri Jun 25 21:03:45 UTC 2021
Edited
by admin
on Fri Jun 25 21:03:45 UTC 2021
Record UNII
6KY687524K
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
GLIMEPIRIDE
EMA EPAR   EP   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP   USP-RS   VANDF   WHO-DD  
USAN   INN  
Official Name English
GLIMEPIRIDE [ORANGE BOOK]
Common Name English
AMARYL
Brand Name English
GLIMEPIRIDE [USP-RS]
Common Name English
GLIMEPIRIDE [MI]
Common Name English
GLIMEPIRIDE [EP MONOGRAPH]
Common Name English
HOE 490
Code English
NSC-759809
Code English
DUETACT COMPONENT GLIMEPIRIDE
Common Name English
GLIMEPIRIDE [USP MONOGRAPH]
Common Name English
GLIMEPIRIDE [MART.]
Common Name English
GLIMEPIRIDE [INN]
Common Name English
GLIMEPIRIDE [VANDF]
Common Name English
GLIMEPIRIDE [WHO-DD]
Common Name English
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-
Common Name English
GLIMEPIRIDE [USAN]
Common Name English
GLIMEPIRIDE [USP]
Common Name English
GLIMEPIRIDE [JAN]
Common Name English
GLIMEPIRIDE COMPONENT OF DUETACT
Common Name English
GLIMEPIRIDE [EMA EPAR]
Common Name English
1-((P-(2-(3-ETHYL-4-METHYL-2-OXO-3-PYRROLINE-1-CARBOXAMIDO)ETHYL)PHENYL)SULFONYL)-3-(TRANS-4-METHYLCYCLOHEXYL)UREA
Common Name English
Classification Tree Code System Code
NDF-RT N0000008054
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
LIVERTOX 459
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
NDF-RT N0000008054
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
WHO-VATC QA10BD06
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
NDF-RT N0000008054
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
WHO-VATC QA10BB12
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
NCI_THESAURUS C97936
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
WHO-ATC A10BB12
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
WHO-ATC A10BD06
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
WHO-ATC A10BD04
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
NDF-RT N0000175608
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
WHO-VATC QA10BD04
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
Code System Code Type Description
ChEMBL
CHEMBL1481
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
NCI_THESAURUS
C29073
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
RXCUI
25789
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY RxNorm
WIKIPEDIA
GLIMEPIRIDE
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
MERCK INDEX
M5745
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY Merck Index
CAS
93479-97-1
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
LACTMED
Glimepiride
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
FDA UNII
6KY687524K
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
EVMPD
SUB07925MIG
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
INN
5718
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
DRUG BANK
DB00222
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
IUPHAR
6820
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
MESH
C057619
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
USP_CATALOG
1292303
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY USP-RS
EPA CompTox
93479-97-1
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
DRUG CENTRAL
1300
Created by admin on Fri Jun 25 21:03:45 UTC 2021 , Edited by admin on Fri Jun 25 21:03:45 UTC 2021
PRIMARY
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