mefenamic acid   Click here for help

GtoPdb Ligand ID: 2593

Synonyms: CI-473 | CN-35355 | INF-3355 | Ponstan® | Ponstel®
Approved drug PDB Ligand Immunopharmacology Ligand
mefenamic acid is an approved drug (FDA (1967))
Compound class: Synthetic organic
Comment: Mefenamic acid is an anthranilic acid derivative (or fenamate) class NSAID drug.
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View more information in the IUPHAR Pharmacology Education Project: mefenamic acid

2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 3
Hydrogen bond donors 2
Rotatable bonds 3
Topological polar surface area 49.33
Molecular weight 241.11
XLogP 3.94
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
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Canonical SMILES OC(=O)c1ccccc1Nc1cccc(c1C)C
Isomeric SMILES OC(=O)c1ccccc1Nc1cccc(c1C)C
InChI InChI=1S/C15H15NO2/c1-10-6-5-9-13(11(10)2)16-14-8-4-3-7-12(14)15(17)18/h3-9,16H,1-2H3,(H,17,18)
InChI Key HYYBABOKPJLUIN-UHFFFAOYSA-N
References
1. Abbott GW, Butler MH, Bendahhou S, Dalakas MC, Ptacek LJ, Goldstein SA. (2001)
MiRP2 forms potassium channels in skeletal muscle with Kv3.4 and is associated with periodic paralysis.
Cell, 104 (2): 217-31. [PMID:11207363]
2. Heinrich DM, Flanagan JU, Jamieson SM, Silva S, Rigoreau LJ, Trivier E, Raynham T, Turnbull AP, Denny WA. (2013)
Synthesis and structure-activity relationships for 1-(4-(piperidin-1-ylsulfonyl)phenyl)pyrrolidin-2-ones as novel non-carboxylate inhibitors of the aldo-keto reductase enzyme AKR1C3.
Eur J Med Chem, 62: 738-44. [PMID:23454516]
3. Klose C, Straub I, Riehle M, Ranta F, Krautwurst D, Ullrich S, Meyerhof W, Harteneck C. (2011)
Fenamates as TRP channel blockers: mefenamic acid selectively blocks TRPM3.
Br. J. Pharmacol., 162 (8): 1757-69. [PMID:21198543]