indomethacin   

GtoPdb Ligand ID: 1909

Synonyms: Indocid® | Indocin®
indomethacin is an approved drug (FDA (1965))
Compound class: Synthetic organic
Comment: Indomethacin is a non-selective cyclooxygenase (COX) inhibitor belonging to the nonsteroidal anti-inflammatory drug (NSAID) family.
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2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 3
Hydrogen bond donors 1
Rotatable bonds 5
Topological polar surface area 68.53
Molecular weight 357.08
XLogP 3.42
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES COc1ccc2c(c1)c(CC(=O)O)c(n2C(=O)c1ccc(cc1)Cl)C
Isomeric SMILES COc1ccc2c(c1)c(CC(=O)O)c(n2C(=O)c1ccc(cc1)Cl)C
InChI InChI=1S/C19H16ClNO4/c1-11-15(10-18(22)23)16-9-14(25-2)7-8-17(16)21(11)19(24)12-3-5-13(20)6-4-12/h3-9H,10H2,1-2H3,(H,22,23)
InChI Key CGIGDMFJXJATDK-UHFFFAOYSA-N
Selectivity at GPCRs
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
DP2 receptor Hs Agonist Full agonist 6.1 – 7.7 pKi - 8,10
pKi 6.1 – 7.7 [8,10]
DP2 receptor Mm Agonist Full agonist 5.7 – 6.0 pKi - 2-3
pKi 5.7 – 6.0 [2-3]
Selectivity at nuclear hormone receptors
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Peroxisome proliferator-activated receptor-γ Hs Agonist Partial agonist 7.4 pKd - 1,5
pKd 7.4 [1,5]
Selectivity at enzymes
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
COX-1 Hs Inhibitor Inhibition 6.6 pIC50 - 4
pIC50 6.6 (IC50 2.6x10-7 M) [4]
COX-2 Hs Inhibitor Inhibition 5.6 pIC50 - 4
pIC50 5.6 (IC50 2.63x10-6 M) [4]
Selectivity at transporters
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Target Sp. Type Action Value Parameter Concentration range (M) Reference
Proton-coupled folate transporter Hs Inhibitor Inhibition 3.7 pIC50 - 7
pIC50 3.7 (IC50 2x10-4 M) [7]
Additional information and targets (data relate to human unless otherwise stated)
Description Data Reference
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