6417. Naproxen

Nomenclature

CAS number: 22204-53-1
(αS)-6-Methoxy-α-methyl-2-naphthaleneacetic acid; d-2-(6-methoxy-2-naphthyl)propionic acid; MNPA; RS-3540; Bonyl (Erco); Dysmenalgit (Krewel); Equiproxen (Syntex); Floginax (Lifepharma); Laraflex (Lagap); Laser (Tosi); Malexin (BASF); Naixan (Tanabe); Napren (Nycomed); Naprius (Magis); Naprosyn (Syntex); Naprosyne (Syntex); Naprux (Andromaco); Naxen (Syntex); Nycopren (Nycomed); Pranoxen (Napp); Prexan (Lafare); Proxen (Syntex); Proxine (Del Saz & Filippini); Veradol (Schering AG); Xenar (Alfa).
C14H14O3; mol wt 230.26.
C 73.03%, H 6.13%, O 20.85%.

Description and references

Nonsteroidal anti-inflammatory. Prepn: J. H. Fried, I. T. Harrison, ZA 6707597; eidem, US 3904682; eidem, US 4009197 (1968, 1975, 1977 all to Syntex); I. T. Harrison et al., J. Med. Chem. 13, 203 (1970). Pharmacology: Roszkowski et al., J. Pharmacol. Exp. Ther. 179, 114 (1971). Activity may be due to the ability to inhibit prostaglandin biosynthesis. Mode of action studies: Tomlinson et al., Biochem. Biophys. Res. Commun. 46, 552 (1972). Metabolism: Runkel et al., J. Pharm. Sci. 61, 703 (1972). HPLC determn in plasma and serum: P. J. Streete, J. Chromatogr. 495, 179 (1989). Stereoselective synthesis: K. T. Wan, M. E. Davis, Nature 370, 449 (1994). Clinical studies: Katona et al., Clin. Trials J. 8, 3 (1972); Runkel, Chem. Pharm. Bull. 20, 1457 (1972). Review: Arzneim.-Forsch. 25, 278-332 (1975). Review of pharmacology and therapeutic efficacy: R. N. Brogden et al., Drugs 18, 241-277 (1979). Comprehensive description: F. J. Al-Shammary et al., Anal. Profiles Drug Subs. Excip. 21, 345-373 (1992).

Chemical structure

Properties

Crystals from acetone-hexane, mp 152-154°. [α]D +66° (in chloroform). Sol in 25 parts ethanol (96%), 20 parts methanol, 15 parts chloroform, 40 parts ether. Practically insol in water. LD50 in mice (mg/kg): 435 i.v.; 1234 orally; in rats (mg/kg): 575 i.p.; 534 orally (Roszkowski).

Derivative

Piperazine salt.

Nomenclature

CAS number: 70981-66-7
Piproxen; Numidan (Coop. Farm.).
(C14H14O3)2.C4H10N2; mol wt 546.65.
C 70.31%, H 7.01%, O 17.56%, N 5.12%.

Derivative

Sodium salt.

Nomenclature

CAS number: 26159-34-2
RS-3650; Aleve (Procter & Gamble); Anaprox (Syntex); Antalgin (Syntex); Apranax (Syntex); Axer Alfa (Alfa); Flanax (Syntex); Gynestrel (Recordati); Miranax (Syntex); Naprelan (Wyeth-Ayerst); Primeral (Master); Synflex (Recordati).
C14H13NaO3; mol wt 252.24.
C 66.66%, H 5.19%, Na 9.11%, O 19.03%.

Properties

Crystals from acetone, mp 244-246°. [α]D -11° (in methanol).

Therapeutic Category

Anti-inflammatory; analgesic; antipyretic.

Therapeutic Category (Veterinary)

Anti-inflammatory.

Keywords

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