glimepiride   Click here for help

GtoPdb Ligand ID: 6820

Synonyms: Amaryl® | glimepride | HOE-490 | Sugral®
Approved drug
glimepiride is an approved drug (FDA (1995))
Compound class: Synthetic organic
Comment: Only approved by the EMA (2007) to be used in combination with pioglitazone (Tandemact®). Note that the PubChem CID listed above refers to the non-isomeric molecule. We show the isomeric form which corresponds to the structure held with the INN record for this compound.
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2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 9
Hydrogen bond donors 3
Rotatable bonds 11
Topological polar surface area 133.06
Molecular weight 490.22
XLogP 3.79
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES CCC1=C(C)CN(C1=O)C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)NC1CCC(CC1)C
Isomeric SMILES CCC1=C(C)CN(C1=O)C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)N[C@@H]1CC[C@H](CC1)C
InChI 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-
InChI Key WIGIZIANZCJQQY-RUCARUNLSA-N
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (1995))
IUPAC Name Click here for help
3-ethyl-4-methyl-2-oxo-N-(2-{4-[({[(1r,4r)-4-methylcyclohexyl]carbamoyl}amino)sulfonyl]phenyl}ethyl)-2,5-dihydro-1H-pyrrole-1-carboxamide
International Nonproprietary Names Click here for help
INN number INN
5718 glimepiride
Synonyms Click here for help
Amaryl® | glimepride | HOE-490 | Sugral®
Database Links Click here for help
CAS Registry No. 93479-97-1
ChEMBL Ligand CHEMBL1481
DrugBank Ligand DB00222
DrugCentral Ligand 1300
GtoPdb PubChem SID 178103426
PubChem CID 3476
Search Google for chemical match using the InChIKey WIGIZIANZCJQQY-RUCARUNLSA-N
Search Google for chemicals with the same backbone WIGIZIANZCJQQY
Search PubMed clinical trials glimepiride
Search PubMed titles glimepiride
Search PubMed titles/abstracts glimepiride
UniChem Compound Search for chemical match using the InChIKey WIGIZIANZCJQQY-RUCARUNLSA-N
UniChem Connectivity Search for chemical match using the InChIKey WIGIZIANZCJQQY-RUCARUNLSA-N
Wikipedia Glimepiride

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Tocris
Glimepiride (links to external site)
Cat. No. 2396