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

Details

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

SHOW SMILES / InChI
Structure of GLIMEPIRIDE

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-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 490.616
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
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
[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
Sulfonylurea stimulation of insulin secretion.
2002 Dec
Efficacy of glimepiride for the treatment of diabetes occurring during glucocorticoid therapy.
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
Effects of insulin and sulphonylureas on insulin-like growth factor-I levels in streptozotocin-induced diabetic rats.
2002 Oct-Dec
[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
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
Plasma adiponectin plays an important role in improving insulin resistance with glimepiride in elderly type 2 diabetic subjects.
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
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
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 Wed Jul 05 23:19:49 UTC 2023
Edited
by admin
on Wed Jul 05 23:19:49 UTC 2023
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 [WHO-DD]
Common 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
GLIMEPIRIDE [USP IMPURITY]
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
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 [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 Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
LIVERTOX 459
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
NDF-RT N0000008054
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
WHO-VATC QA10BD06
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
NDF-RT N0000008054
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
WHO-VATC QA10BB12
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
NCI_THESAURUS C97936
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
WHO-ATC A10BB12
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
WHO-ATC A10BD06
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
WHO-ATC A10BD04
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
NDF-RT N0000175608
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
WHO-VATC QA10BD04
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
Code System Code Type Description
ChEMBL
CHEMBL1481
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY
NCI_THESAURUS
C29073
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY
RXCUI
25789
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY RxNorm
WIKIPEDIA
GLIMEPIRIDE
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY
RS_ITEM_NUM
1292303
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY
MERCK INDEX
M5745
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY Merck Index
CAS
93479-97-1
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY
LACTMED
Glimepiride
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY
FDA UNII
6KY687524K
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY
CHEBI
5383
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY
SMS_ID
100000085456
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY
EVMPD
SUB07925MIG
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY
INN
5718
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY
DRUG BANK
DB00222
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY
NSC
759809
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY
IUPHAR
6820
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY
DAILYMED
6KY687524K
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY
MESH
C057619
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY
EPA CompTox
DTXSID5040675
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY
USAN
EE-37
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY
DRUG CENTRAL
1300
Created by admin on Wed Jul 05 23:19:49 UTC 2023 , Edited by admin on Wed Jul 05 23:19:49 UTC 2023
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
USP
BINDER->LIGAND
BINDING
TARGET -> INHIBITOR
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
Related Record Type Details
METABOLITE LESS ACTIVE -> PARENT
URINE
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY
Name Property Type Amount Referenced Substance Defining Parameters References
Volume of Distribution PHARMACOKINETIC
Biological Half-life PHARMACOKINETIC