glimepiride

Also known as 3-ethyl-4-methyl-N-[2-(4-{[(trans-4-methylcyclohexyl)carbamoyl]sulfamoyl}phenyl)ethyl]-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide, 3-ethyl-4-methyl-N-[4-(N-{[(1r,4r)-4-methylcyclohexyl]carbamoyl}sulfamoyl)phenethyl]-2-oxo-2,5-dihydro-1H-pyrrole-1-carboxamide

Glimepiride is an antidiabetic medication within the sulfonylurea class, primarily prescribed for the management of type 2 diabetes. It is regarded as a second-line option compared to metformin, due to metformin's well-established safety and efficacy. Use of glimepiride is recommended in conjunction with lifestyle modifications such as diet and exercise. It is taken by mouth, reaching a peak effect within three hours and lasting for about a day.

In the Vinony graph

Within Vinony's link graph, glimepiride is referenced by 680 other articles, and connects out to metformin, valproic acid and anti-diabetic medication.

It is catalogued under topics including Benzenesulfonylureas, Drugboxes which contain changes to verified fields and Drugboxes which contain changes to watched fields.

Its subject is documented across 29 Wikipedia language editions.

Chemical data

Formula: C24H34N4O5S
Molecular weight: 490.6 g/mol
IUPAC name: 4-ethyl-3-methyl-N-[2-[4-[(4-methylcyclohexyl)carbamoylsulfamoyl]phenyl]ethyl]-5-oxo-2H-pyrrole-1-carboxamide
SMILES: CCC1=C(CN(C1=O)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCC(CC3)C)C
InChIKey: WIGIZIANZCJQQY-UHFFFAOYSA-N
XLogP: 3.9
Polar surface area: 133 Å²
H-bond donors: 3
H-bond acceptors: 5
Formal charge: 0

via PubChem

Drug data · ChEMBL

Max clinical phase: Approved
Molecule type: Small molecule
First approval: 1995
Admin. routes: oral
Indications: diabetes mellitus, MODY, hypertension, atherosclerosis

via ChEMBL · EBI

Research

1,852 papers

Pioglitazone hydrochloride/glimepiride.Drugs of today (Barcelona, Spain : 1998) · 2007
Glimepiride pharmacokinetics in overdose.Clinical toxicology (Philadelphia, Pa.) · 2022
Glimepiride. A review of its use in the management of type 2 diabetes mellitus.Drugs · 1998
[Glimepiride--an oral antidiabetic agent].Medicinski arhiv · 2003
Clinical profile of glimepiride.Diabetes research and clinical practice · 1995

via PubMed

Wikidata facts

Mass: 490.22499118799993

Show 7 more facts

chemical formula: C₂₄H₃₄N₄O₅S
has characteristic: bitterness
canonical SMILES: CCC1=C(CN(C1=O)C(=O)NCCC2=CC=C(C=C2)S(=O)(=O)NC(=O)NC3CCC(CC3)C)C
isomeric SMILES: CCC1=C(C)CN(C(=O)NCCc2ccc(cc2)S(=O)(=O)NC(=O)N[C@H]2CC[C@H](C)CC2)C1=O
defined daily dose: 2
subject has role: immunosuppressive drug
Commons category: Glimepiride

Sources (3)

via Wikidata · CC0

~6 min read

Encyclopedic overview

7 sections

Contents

Medical uses
Contraindications
Adverse effects
Interactions
Mechanism of action
Pharmacokinetics
References

{{drugbox | Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 412761821 | image = Glimepiride.svg | image_class = skin-invert-image | width = 300 | alt = | image2 = Glimepiride ball-and-stick model from xtal 1997.png | image_class2 = bg-transparent

Excerpted from Wikipedia’s “glimepiride” article, available under the CC BY-SA 4.0 licence.