FLURBIPROFEN RACEMIC

3-Fluoro-4-phenyl-α-methylphenylacetic acid 1

M.p. 110-113°C (lit.3d 111-113.5°C).

1 H NMR (CDCl3, δ ppm) 7.51-7.55 (m, 2H), 7.49-7.37 (m, 4H), 7.21-7.16 (m, 2H), 3.85-3.78 (q, 1H, J = 7.1 Hz, CH), 1.60-1.57 (d, 3H, J = 7.1 Hz, CH3);

13C NMR (CDCl3 δ ppm) 180.4 (COOH), 161.3 & 158.0 (3-Ar-C), 140.9 & 140.8, 135.4, 130.9 & 130.8 (5-Ar-C), 128.9, 128.4, 128.2 & 128.0 (4-Ar-C), 127.7 (4′-Ar-C), 123.7 & 123.7 (6-Ar-C), 115.5 & 115.2 (2-Ar-C), 44.8 (CH), 18.0 (CH3).

(d) Sagami Chemical Research Center. Jpn. Kokai Tokkyo Koho JP 8216840, 1982 (Chem. Abstr. 1982, 97: 5996s).

RACEMIC

Flurbiprofen

CAS : 5104-49-4

: 2-Fluoro-a-methyl[1,1¢-biphenyl]-4-acetic acid

Additional Names: 2-(2-fluoro-4-biphenylyl)propionic acid; 3-fluoro-4-phenylhydratropic acid

Manufacturers’ Codes: BTS-18322; U-27182

Trademarks: Adfeed (Lead Chem.); Ansaid (Pfizer); Antadys (Thžamex); Cebutid (Boots); Froben (Boots); Flurofen (Boots); Ocufen (Allergan); Stayban (Boots); Zepolas (Mikasa)

Molecular Formula: C15H13FO2

Molecular Weight: 244.26

Percent Composition: C 73.76%, H 5.36%, F 7.78%, O 13.10%

Literature References: Prepn: FR M5737; Adams et al., US 3755427 (1968, 1973 both to Boots Co., Ltd.). Pharmacology: Chalmers et al., Ann. Rheum. Dis. 31, 319 (1972); ibid. 32,58 (1973); Glenn et al., Agents Actions 3, 210 (1973); Nishizawa et al.,Thromb. Res. 3, 577 (1973). HPLC determn in urine and plasma: J. M. Hutzler et al., J. Chromatogr. B 749, 119 (2000). Symposium on pharmacokinetics and clinical efficacy in pain management: Am. J. Med. 80, Suppl. 3A, 1-157 (1986).

Properties: Crystals from petr ether, mp 110-111°. Slightly sol in water (pH 7.0); readily sol in most polar solvents.

Melting point: mp 110-111°

Therap-Cat: Anti-inflammatory; analgesic.

Flurbiprofen NMR spectra analysis, Chemical CAS NO. 5104-49-4 NMR spectral analysis, Flurbiprofen C-NMR spectrum