azilsartan medoxomil   Click here for help

GtoPdb Ligand ID: 6900

Synonyms: Edarbi® | TAK 491
Approved drug
azilsartan medoxomil is an approved drug (EMA & FDA (2011))
Compound class: Synthetic organic
Comment: Azilsartan medoxomil is metabolised into the active form azilsartan. The azilsartan ligand page (accessed via the link above) contains more details of the drug's clinical use and mechanistic action.
The marketed brand, Edarbi®, contains azilsartan medoxomil potassium (PubChem CID 23699544).
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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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Click here for structure editor
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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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 6
Hydrogen bond donors 1
Rotatable bonds 10
Topological polar surface area 155.59
Molecular weight 568.16
XLogP 6.16
No. Lipinski's rules broken 1

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES CCOc1nc2c(n1Cc1ccc(cc1)c1ccccc1c1[nH]oc(=O)n1)c(ccc2)C(=O)OCc1oc(=O)oc1C
Isomeric SMILES CCOc1nc2c(n1Cc1ccc(cc1)c1ccccc1c1[nH]oc(=O)n1)c(ccc2)C(=O)OCc1oc(=O)oc1C
InChI InChI=1S/C30H24N4O8/c1-3-38-28-31-23-10-6-9-22(27(35)39-16-24-17(2)40-30(37)41-24)25(23)34(28)15-18-11-13-19(14-12-18)20-7-4-5-8-21(20)26-32-29(36)42-33-26/h4-14H,3,15-16H2,1-2H3,(H,32,33,36)
InChI Key QJFSABGVXDWMIW-UHFFFAOYSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (EMA & FDA (2011))
Is prodrug? Yes
Active form azilsartan
IUPAC Name Click here for help
(5-methyl-2-oxo-1,3-dioxol-4-yl)methyl 2-ethoxy-3-[[4-[2-(5-oxo-2H-1,2,4-oxadiazol-3-yl)phenyl]phenyl]methyl]benzimidazole-4-carboxylate
International Nonproprietary Names Click here for help
INN number INN
8874 azilsartan medoxomil
Synonyms Click here for help
Edarbi® | TAK 491
Database Links Click here for help
CAS Registry No. 863031-21-4 (source: Scifinder)
ChEMBL Ligand CHEMBL2028661
DrugBank Ligand DB08822
DrugCentral Ligand 4322, 4322
GtoPdb PubChem SID 178103482
PubChem CID 135409642
Search Google for chemical match using the InChIKey QJFSABGVXDWMIW-UHFFFAOYSA-N
Search Google for chemicals with the same backbone QJFSABGVXDWMIW
Search PubMed clinical trials azilsartan medoxomil
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Search PubMed titles/abstracts azilsartan medoxomil
UniChem Compound Search for chemical match using the InChIKey QJFSABGVXDWMIW-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey QJFSABGVXDWMIW-UHFFFAOYSA-N
Wikipedia Azilsartan