glipizide   Click here for help

GtoPdb Ligand ID: 6821

Synonyms: CP-28720 | Glucotrol® | K-4024
Approved drug
glipizide is an approved drug (FDA (1984))
Compound class: Synthetic organic
Comment: A sulfonylurea family drug inhibiting sulfonylurea receptor 1 (ABCC8)/Kir6.2 (KCNJ11).
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View more information in the IUPHAR Pharmacology Education Project: glipizide

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 10
Topological polar surface area 138.53
Molecular weight 445.18
XLogP 2.26
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 Cc1ncc(nc1)C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)NC1CCCCC1
Isomeric SMILES Cc1ncc(nc1)C(=O)NCCc1ccc(cc1)S(=O)(=O)NC(=O)NC1CCCCC1
InChI InChI=1S/C21H27N5O4S/c1-15-13-24-19(14-23-15)20(27)22-12-11-16-7-9-18(10-8-16)31(29,30)26-21(28)25-17-5-3-2-4-6-17/h7-10,13-14,17H,2-6,11-12H2,1H3,(H,22,27)(H2,25,26,28)
InChI Key ZJJXGWJIGJFDTL-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Use as an adjunct to diet for the control of hyperglycemia caused by diabetes mellitus type 2, where dietary control has failed. Only approved by the EMA (2007) to be used in combination with pioglitazone (tandemact).
Mechanism Of Action and Pharmacodynamic Effects Click here for help
A sulfonylurea which stimulates insulin sectetion by pancreatic β cells. The sulfonyurea drugs appear to bind sulfonylurea receptors and it has been shown experimentally that tritiated glibenclamide can be used to pull out a 140 kDa protein identified as SUR1 (now known as ABCC8) [3]. SUR2 (ABCC9) has also been identified [1]. However, this is not the full mechanism of action and the functional channel has been characterised as a hetero-octamer formed by four SUR and four Kir6.2 subunits, with the Kir6.2 subunits forming the core ion pore and the SUR subunits providing the regulatory properties [2]. Co-expression of Kir6.2 with SUR1, reconstitutes the ATP-dependent K+ conductivity inhibited by the sulfonyureas [1].