5305. Ketoprofen

Nomenclature

CAS number: 22071-15-4
3-Benzoyl-α-methylbenzeneacetic acid; m-benzoylhydratropic acid; 2-(3-benzoylphenyl)propionic acid; RP-19583; Alreumat (Bayer); Alrheumun (Bayer); Capisten (Kissei); Epatec (Nissan); Fastum (Menarini); Iso-K (San Carlo); Ketofen (Fort Dodge); Ketopron (Alcon); Menamin (RPR); Meprofen (AGIPS); Orudis (RPR); Oruvail (RPR); Profenid (RPR); Toprec (RPR); Toprek (RPR).
C16H14O3; mol wt 254.28.
C 75.57%, H 5.55%, O 18.88%.

Description and references

Prepn: D. Farge et al., ZA 6800524; eidem, US 3641127 (1968, 1972 both to Rhne-Poulenc); G. A. Pinna et al., Farmaco Ed. Sci. 35, 684 (1980). Resolution of isomers: S. Rendic et al., Chimia 29, 170 (1975). Enantioselective synthesis and absolute configuration of (+)-form: G. Comisso et al., Gazz. Chim. Ital. 110, 123 (1980). Pharmacology of enantiomers: P. J. Hayball et al., Chirality 4, 484 (1992). HPLC determn in plasma: R. Lovlin et al., J. Chromatogr. B 679, 196 (1996). Toxicity data: K. Ueno et al., J. Med. Chem. 19, 941 (1976). Comprehensive description: G. G. Liversidge, Anal. Profiles Drug Subs. 10, 443-471 (1981). Review of pharmacokinetics: F. Jamali, D. R. Brocks, Clin. Pharmacokinet. 19, 197-217 (1990); of clinical experience: E. M. Veys, Scand. J. Rheumatol. Suppl. 90, 3-44 (1991).

Chemical structure

Properties

Crystals from 6:20 benzene-petr ether, mp 94°. uv max (methanol): 255 nm (log ε 4.33). Sol in ether, alc, acetone, chloroform, DMF, ethyl acetate. Slightly sol in water. LD50 orally in rats: 101 mg/kg (Ueno).

Derivative

Lysine salt.

Nomenclature

CAS number: 57469-78-0
Artrosilene (Dompé).
C16H14O3.C6H14N2O2; mol wt 400.47.
C 65.98%, H 7.05%, O 19.98%, N 7.00%.

Derivative

(S)-(+)-Form tromethamine salt.

Nomenclature

CAS number: 156604-79-4
Dexketoprofen trometamol; Enantyum (Menarini); Keral (Menarini).
C16H14O3.C4H11NO3; mol wt 375.42.
C 63.99%, H 6.71%, O 25.57%, N 3.73%.

Description and references

Prepn: G. Carganico et al., WO 9411332 (1994 to Menarini). Clinical trial: C. Gay et al., Clin. Drug Invest. 11, 320 (1996).

Properties

White crystalline solid from ethanol-ethyl acetate, mp 104.8-105.1°. [α]D20 5.2° (c = 1.47 in methanol).

Therapeutic Category

Anti-inflammatory; analgesic.

Therapeutic Category (Veterinary)

Anti-inflammatory; analgesic.

Keywords

Anti-inflammatory (Nonsteroidal); Arylpropionic Acid Derivatives; Analgesic; Non-opioids; Acetic/Propionic Acid Derivatives