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.
IUPHAR Pharmacology Education Project (PEP) logo

View more information in the IUPHAR Pharmacology Education Project: indomethacin

2D Structure
Click here for structure editor
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
References
1. Ferry G, Bruneau V, Beauverger P, Goussard M, Rodriguez M, Lamamy V, Dromaint S, Canet E, Galizzi JP, Boutin JA. (2001)
Binding of prostaglandins to human PPARgamma: tool assessment and new natural ligands.
Eur. J. Pharmacol., 417 (1-2): 77-89. [PMID:11301062]
2. Hata AN, Lybrand TP, Breyer RM. (2005)
Identification of determinants of ligand binding affinity and selectivity in the prostaglandin D2 receptor CRTH2.
J Biol Chem, 280: 32442-32451. [PMID:16030019]
3. Hata AN, Zent R, Breyer MD, Breyer RM. (2003)
Expression and molecular pharmacology of the mouse CRTH2 receptor.
J. Pharmacol. Exp. Ther., 306 (2): 463-70. [PMID:12721327]
4. Kassab SE, Khedr MA, Ali HI, Abdalla MM. (2017)
Discovery of new indomethacin-based analogs with potentially selective cyclooxygenase-2 inhibition and observed diminishing to PGE2 activities.
Eur J Med Chem, 141: 306-321. [PMID:29031075]
5. Lehmann JM, Lenhard JM, Oliver BB, Ringold GM, Kliewer SA. (1997)
Peroxisome proliferator-activated receptors alpha and gamma are activated by indomethacin and other non-steroidal anti-inflammatory drugs.
J. Biol. Chem., 272 (6): 3406-10. [PMID:9013583]
6. Matsuura K, Shiraishi H, Hara A, Sato K, Deyashiki Y, Ninomiya M, Sakai S. (1998)
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]
7. Qiu A, Jansen M, Sakaris A, Min SH, Chattopadhyay S, Tsai E, Sandoval C, Zhao R, Akabas MH, Goldman ID. (2006)
Identification of an intestinal folate transporter and the molecular basis for hereditary folate malabsorption.
Cell, 127 (5): 917-28. [PMID:17129779]
8. Sawyer N, Cauchon E, Chateauneuf A, Cruz RP, Nicholson DW, Metters KM, O'Neill GP, Gervais FG. (2002)
Molecular pharmacology of the human prostaglandin D2 receptor, CRTH2.
Br. J. Pharmacol., 137 (8): 1163-72. [PMID:12466225]
9. Skarydová L, Zivná L, Xiong G, Maser E, Wsól V. (2009)
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]