1390. Bromfenac

Nomenclature

CAS number: 91714-94-2
2-Amino-3-(4-bromobenzoyl)benzeneacetic acid; AHR-10282.
C15H12BrNO3; mol wt 334.16.
C 53.91%, H 3.62%, Br 23.91%, N 4.19%, O 14.36%.

Description and references

Prostaglandin synthetase inhibitor; analog of amfenac, q.v. Prepn: D. A. Walsh et al., J. Med. Chem. 27, 1379 (1984). See also: R. G. Poser, US 4683242 (1987 to A. H. Robins). HPLC determn in plasma: M. A. Osman et al., J. Chromatogr. 489, 452 (1989). Pharmacology: L. F. Sancilio et al., Arzneim.-Forsch. 37, 513 (1987). Clinical pharmacokinetics: P. Hgger, P. Rohdewald, ibid. 43, 1114 (1993). Review: J. S. Wajdula et al. in Nonsteroidal Anti-inflammatory Drugs, A. J. Lewis, D. E. Furst, Eds. (Marcel Dekker, Inc., New York, 1994) 267-284. Evaluation of hepatotoxicity: R. J. Fontana et al., Liver Transpl. Surg. 5, 480 (1999). Clinical trial in allergic conjunctivitis: M. Miyake-Kashima et al., Jpn. J. Ophthalmol. 48, 587 (2004).

Chemical structure

Derivative

Monosodium salt sesquihydrate.

Nomenclature

CAS number: 120638-55-3; 91714-93-1 (monosodium salt)
AHR-10282B; Duract; Xibrom (ISTA).
C15H11BrNNaO3.1H2O; mol wt 365.15.
C 49.34%, H 3.31%, Br 21.88%, N 3.84%, Na 6.30%, O 15.34%.

Properties

Bright orange-yellow crystalline powder, mp 284-286° (dec). pKa 4.29. Sol in water, methanol, dilute base. Insol in chloroform, dilute acid.

Therapeutic Category

Anti-inflammatory (ophthalmic).

Keywords

Anti-inflammatory (Nonsteroidal); Arylacetic Acid Derivatives