irbesartan   Click here for help

GtoPdb Ligand ID: 589

Synonyms: Aprovel® | Avapro® | Karvea® | SR 47436
Approved drug
irbesartan is an approved drug (EMA & FDA (1997))
Compound class: Synthetic organic
Comment: Irbesartan is an angiotensin receptor antagonist.
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 7
Topological polar surface area 87.13
Molecular weight 428.23
XLogP 6.06
No. Lipinski's rules broken 1
SMILES / InChI / InChIKey
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Canonical SMILES CCCCC1=NC2(C(=O)N1Cc1ccc(cc1)c1ccccc1c1n[nH]nn1)CCCC2
Isomeric SMILES CCCCC1=NC2(C(=O)N1Cc1ccc(cc1)c1ccccc1c1n[nH]nn1)CCCC2
InChI InChI=1S/C25H28N6O/c1-2-3-10-22-26-25(15-6-7-16-25)24(32)31(22)17-18-11-13-19(14-12-18)20-8-4-5-9-21(20)23-27-29-30-28-23/h4-5,8-9,11-14H,2-3,6-7,10,15-17H2,1H3,(H,27,28,29,30)
InChI Key YOSHYTLCDANDAN-UHFFFAOYSA-N
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
AT1 receptor Primary target of this compound Hs Antagonist Antagonist 8.7 – 8.8 pIC50 - 2
pIC50 8.7 – 8.8 (IC50 1.99x10-9 – 1.58x10-9 M) [2]
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Sodium/bile acid and sulphated solute cotransporter 1 Hs Inhibitor Inhibition 4.9 pKi - 1
pKi 4.9 (Ki 1.19x10-5 M) [1]