indomethacin   Click here for help

GtoPdb Ligand ID: 1909

Synonyms: Indocid® | Indocin®
Approved drug PDB Ligand Immunopharmacology Ligand
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
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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
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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)
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Discovery of new indomethacin-based analogs with potentially selective cyclooxygenase-2 inhibition and observed diminishing to PGE2 activities.
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Peroxisome proliferator-activated receptors alpha and gamma are activated by indomethacin and other non-steroidal anti-inflammatory drugs.
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Identification of a principal mRNA species for human 3alpha-hydroxysteroid dehydrogenase isoform (AKR1C3) that exhibits high prostaglandin D2 11-ketoreductase activity.
J Biochem, 124 (5): 940-6. [PMID:9792917]
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Identification of an intestinal folate transporter and the molecular basis for hereditary folate malabsorption.
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Molecular pharmacology of the human prostaglandin D2 receptor, CRTH2.
Br J Pharmacol, 137 (8): 1163-72. [PMID:12466225]
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AKR1C3 as a potential target for the inhibitory effect of dietary flavonoids.
Chem Biol Interact, 178 (1-3): 138-44. [PMID:19007764]
10. Sugimoto H, Shichijo M, Okano M, Bacon KB. (2005)
CRTH2-specific binding characteristics of [3H]ramatroban and its effects on PGD2-, 15-deoxy-Delta12, 14-PGJ2- and indomethacin-induced agonist responses.
Eur J Pharmacol, 524 (1-3): 30-7. [PMID:16256979]