5798. Mefenamic Acid

Nomenclature

CAS number: 61-68-7
2-[(2,3-Dimethylphenyl)amino]benzoic acid; N-(2,3-xylyl)anthranilic acid; CI-473; INF-3355; Lysalgo (SIT); Mefenacid (Streuli); Parkemed (Parke-Davis); Ponalar (Parke-Davis); Ponstan (Pfizer); Ponstel (Warner-Lambert); Ponstyl (Parke-Davis); Pontal (Parke-Davis).
C15H15NO2; mol wt 241.29.
C 74.67%, H 6.27%, N 5.80%, O 13.26%.

Description and references

Prepn: BE 605302; R. A. Scherrer, US 3138636 (1961, 1964 both to Parke-Davis). Pharmacology: C. V. Winder et al., J. Pharmacol. Exp. Ther. 138, 405 (1962); C. V. Winder et al., Arthritis Rheum. 12, 472 (1969); and toxicology: Mokhort, Korkhova, Farmakol. Toksikol. (Kiev) 1968, 85, C.A. 71, 29080c (1969); U. Jahn, R. W. Adrian, Arzneim.-Forsch. 19, 36 (1969). Crystal structure: J. F. McConnell, F. Z. Company, Cryst. Struct. Commun. 5, 861 (1976). Clinical trial in primary dysmenorrhea: P. W. Budoff, J. Am. Med. Assoc. 241, 2713 (1979). HPLC determn in human plasma: I. Niopas, K. Mamzoridi, J. Chromatogr. B 656, 447 (1994).

Chemical structure

Properties

Crystals, mp 230-231° (effervescence). pKa 4.2. uv max (0.lN NaOH): 285, 340 nm. Soly in H2O, pH 7.1 (g/100 ml): 0.0041 (25°); 0.008 (37°). Soluble in solns of alkali hydroxides; sparingly sol in ether, chloroform; slightly sol in ethanol. LD50 orally in mice, rats: 630, 790 mg/kg (Jahn, Adrian).

Derivative

Sodium salt.
C15H14NNaO2; mol wt 263.27.
C 68.43%, H 5.36%, N 5.32%, Na 8.73%, O 12.15%.

Properties

White powder. Soly in H2O: >5 g/100 ml. LD50 in mice (mg/kg): 600 orally; 150 i.p. (Mokhort, Korkhova).

Therapeutic Category

Anti-inflammatory; analgesic.

Keywords

Anti-inflammatory (Nonsteroidal); Aminoarylcarboxylic Acid Derivatives