Bromfenac (Xibrom, ISTA Pharmaceuticals, Irvine, USA; Bronuck, Senju Pharmaceutical, Osaka, Japan) is indicated for the treatment of postoperative inflammation and the reduction of ocular pain in patients after undergoing cataract extraction. For this task, one drop of Xibrom may be applied to the affected eye twice daily beginning 24 hours after cataract surgery and continuing for the first 2 weeks of the postoperative period. The clinical safety and efficacy of bromfenac have been extensively studied in diverse comparative investigations, including the treatment of external or anterior ocular inflammatory diseases, allergic conjunctivitis, scleritis, and postoperative inflammation.The results of two phase III multicenter, randomized double-masked placebo-controlled clinical trials showed that bromfenac ophthalmic solution 0.09% was effective in the rapid resolution of ocular pain after cataract surgery, and there was a statistically significant difference between the bromfenac and placebo groups demonstrated in these phase III clinical trials.
ChEBI: Amfenac in which the the hydrogen at the 4 position of the benzoyl group is substituted by bromine. It is used for the management of ocular pain and treatment of postoperative inflammation in patients who have undergone cataract extraction. It was withdraw
from the US market in 1998, following concerns over off-label abuse and hepatic failure.
Reaction of (2-aminophenyl)-(4-bromophenyl)-methanone with
methylsulfanylacetic acid ethyl ester and tert-butyl hypochlorite gives a
corresponding sulfonium salt. This salt was transformed to initially to the
betaine. Electrocyclic rearrangement of that transient intermediate leads, after
rearomatization, to the homoanthranilic acid. Internal ester-amine interchange
leads then to 4-bromophenyl-(3-(methylthio)indolin-7-yl)methanone. The
thiomethyl group is then removed with Raney nickel to give 4-bromophenyl-
(indolin-7-yl)methanone. Saponification of this intermediate affords the (2-
amino-3-(4-bromobenzoyl)-phenyl)-acetic acid (Bromfenac).
In practice it is usually used as sodium salt.
Analgesicá Antiinflammatory
The drug is rapidly absorbed and excreted.
The drug’s long duration of anti-inflammatory
action despite its short half-life deserves further
investigation.
Bromfenac, used as the sodium
salt, is a non-steroidal anti-inflammatory drug
acting via inhibition of COX-1 and COX-2. It
was launched in Japan in 2000 by Senju for
topical treatment of ocular inflammation
and has been approved in the United States in
2006 for the treatment of pain following cataract
surgery. It was used for the short-term treatment
of acute pain, but it was withdrawn for this indication
in June 1998 because of several postmarketing
reports of severe hepatic failure
The cyclization of 2-amino-4’-
bromobenzophenone with ethyl 2-(methylthio)
acetate with tert-butyl hypochlorite as
catalyst in dichloromethane at 70 ?C gives 7-
(4-bromobenzoyl)-3-(methylthio)-2,3-dihydro-
1H-indol-2-one, which is desulfurized by treatment
with Raney nickel in THF yielding 7-(4-
bromobenzoyl)-2,3-dihydro-1H-indol-2-one.
Finally, this compound is hydrolyzed with refluxing
3 M aqueous NaOH and acidified with
concentrated HCl .
Veterinary Drugs and Treatments
Bromfenac is a nonsteroidal anti-inflammatory drug (NSAID) by
virtue of its ability to block prostaglandin synthesis by inhibiting
cyclooxygenase 1 and 2. Bromfenac is indicated for treatment of
postoperative inflammation in patients who have undergone cataract
extraction.
