Bromfenac

Title: Bromfenac
CAS Registry Number: 91714-94-2
CAS Name: 2-Amino-3-(4-bromobenzoyl)benzeneacetic acid
Manufacturers' Codes: AHR-10282
Molecular Formula: C15H12BrNO3
Molecular Weight: 334.16
Percent Composition: C 53.91%, H 3.62%, Br 23.91%, N 4.19%, O 14.36%
Literature 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. Högger, 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).
Derivative Type: Monosodium salt sesquihydrate
CAS Registry Number: 120638-55-3; 91714-93-1 (monosodium salt)
Manufacturers' Codes: AHR-10282B
Trademarks: Duract; Xibrom (ISTA)
Molecular Formula: C15H11BrNNaO3.1½H2O
Molecular Weight: 365.15
Percent Composition: 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.
Melting point: mp 284-286° (dec)
pKa: pKa 4.29
Therap-Cat: Anti-inflammatory (ophthalmic).
Keywords: Anti-inflammatory (Nonsteroidal); Arylacetic Acid Derivatives.
Bromhexine Bromic Acid Bromindione Bromine Pentafluoride Bromine Trifluoride

Bromfenac
Bromfenac.svg
Systematic (IUPAC) name
2-[2-amino-3-(4-bromobenzoyl)phenyl]acetic acid
Clinical data
Trade names Bromday, Prolensa
AHFS/Drugs.com monograph
MedlinePlus a611018
Pregnancy cat. C
Legal status -only (US)
Routes Oral (discontinued)
ophthalmic
Identifiers
CAS number 91714-94-2 YesY
ATC code S01BC11
PubChem CID 60726
DrugBank DB00963
ChemSpider 54730 YesY
UNII 864P0921DW YesY
KEGG D07541 YesY
ChEBI CHEBI:240107 YesY
ChEMBL CHEMBL1077 YesY
Chemical data
Formula C15H12BrNO3 
Mol. mass 334.16g/mol
 YesY (what is this?)  (verify)

Bromfenac is a non-steroidal anti-inflammatory drug (NSAID) marketed in the US as an ophthalmic solution (current brand names Prolensa and Bromday, prior formulation brand name Xibrom, which has since been discontinued.) by ISTA Pharmaceuticals for short-term, local use. Prolensa and Bromday are the once-daily formulation of bromfenac, while Xibrom was approved for twice-daily administration. Bromfenac is indicated for the treatment of ocular inflammation and pain after cataract surgery, though it may be prescribed in an off-label manner by the physician.

For ophthalmic use, bromfenac has been prescribed more than 20,000,000 times across the world. As an eye drop, it has been available since 2000, starting in Japan where it was sold as Bronuck. It was first FDA approved for use in the United States in 2005, and it was marketed as Xibrom, twice-daily. In October 2010 Bromday received FDA approval as a new, once-daily formulation. More recently, in 2013, Prolensa has also been approved by the FDA. The bromfenac molecule will be marketed in Europe and other worldwide markets with agreements from Bausch & Lomb, Croma Pharma, and other companies.

Bromfenac was formerly marketed in the United States by Wyeth-Ayerst in an oral formulation called Duract for short-term relief of pain (less than 10 days at a time). It was brought to market in July, 1997, and was withdrawn June 22, 1998 following numerous reports of hepatotoxicity in patients who had taken the medication for longer than the recommended 10-day period. The dose was one 25 mg capsule every 6 to 8 hours, or two capsules if taken with a high-fat meal, up to a maximum of 150 mg per day.