Ketoprofen
Title: Ketoprofen
CAS Registry Number: 22071-15-4
CAS Name: 3-Benzoyl-a-methylbenzeneacetic acid
Additional Names: m-benzoylhydratropic acid; 2-(3-benzoylphenyl)propionic acid
Manufacturers' Codes: RP-19583
Trademarks: 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)
Molecular Formula: C16H14O3
Molecular Weight: 254.28
Percent Composition: C 75.57%, H 5.55%, O 18.88%
Literature References: Prepn: D. Farge et al., ZA 6800524; eidem, US 3641127 (1968, 1972 both to Rhône-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).
Properties: Crystals from 6:20 benzene-petr ether, mp 94°. uv max (methanol): 255 nm (log e 4.33). Sol in ether, alc, acetone, chloroform, DMF, ethyl acetate. Slightly sol in water. LD50 orally in rats: 101 mg/kg (Ueno).
Melting point: mp 94°
Absorption maximum: uv max (methanol): 255 nm (log e 4.33)
Toxicity data: LD50 orally in rats: 101 mg/kg (Ueno)
 
Derivative Type: Lysine salt
CAS Registry Number: 57469-78-0
Trademarks: Artrosilene (Domp?
Molecular Formula: C16H14O3.C6H14N2O2
Molecular Weight: 400.47
Percent Composition: C 65.98%, H 7.05%, O 19.98%, N 7.00%
 
Derivative Type: (S)-(+)-Form tromethamine salt
CAS Registry Number: 156604-79-4
Additional Names: Dexketoprofen trometamol
Trademarks: Enantyum (Menarini); Keral (Menarini)
Molecular Formula: C16H14O3.C4H11NO3
Molecular Weight: 375.42
Percent Composition: C 63.99%, H 6.71%, O 25.57%, N 3.73%
Literature 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°. [a]D20 -5.2° (c = 1.47 in methanol).
Melting point: mp 104.8-105.1°
Optical Rotation: [a]D20 -5.2° (c = 1.47 in methanol)
 
Therap-Cat: Anti-inflammatory; analgesic.
Therap-Cat-Vet: Anti-inflammatory; analgesic.
Keywords: Analgesic (Non-Narcotic); Anti-inflammatory (Nonsteroidal); Arylpropionic Acid Derivatives.

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