| Identification | Back Directory | [Name]
Bromfenac sodium | [CAS]
91714-93-1 | [Synonyms]
Bronuck
AHR 10282R
Ahr 10282b
Bromfenac sodium
Bromfenac Sodium b
bromfenac sodium salt
Bromfenac sodium USP/EP/BP
Sodium [2-amino-3-(4-bromobenzoyl)phenyl]acetate
sodium 2-(2-amino-3-(4-bromobenzoyl)phenyl)acetate
2-AMINO-3-(4-BROMOBENZOYL)PHENYLACETIC ACID SODIUM
2-Amino-3-(4-bromobenzoyl)phenylacetic acid sodium salt
2-{2-aMino-3-[(4-broMophenyl)carbonyl]phenyl}acetic acid
2-Amino-3-(4-bromobenzoyl)benzeneacetic acid sodium salt
Benzeneacetic acid, 2-amino-3-(4-bromobenzoyl)-, monosodium salt
Bromfenac sodium###7-(4-Bromobenzoyl)-1,3- dihydro-2H-indol-2-one
Benzeneacetic acid, 2-amino-3-(4-bromobenzoyl)-, sodium salt (1:1) | [EINECS(EC#)]
804-379-0 | [Molecular Formula]
C15H11BrNNaO3 | [MDL Number]
MFCD03701673 | [MOL File]
91714-93-1.mol | [Molecular Weight]
356.15 |
| Chemical Properties | Back Directory | [Description]
Bromfenac Sodium was launched in the US as a potent, orally-active, long lasting peripheral analgesic with antiinflammatory properties. It is structurally similar to ketoprofen and diclofenac and can be prepared in three steps from 2-amino-4’-bromophenone using Gassman’s oxindole synthesis. Duract’s biological effects are a result of its ability to reduce prostaglandin production through inhibition of cyclooxygenase. As a 4-bromo derivative of Amfenac, this modification increased the duration of analgesic activity and antiinflammatory potency. It was also free of any CNS, cardiovascular or autonomic effects. In comparison, 5 mg of Duract was equipotent to 650 mg of ASA and 25 mg was slightly more potent than 400 mg of Ibuprofen. | [Melting point ]
285 ºC | [storage temp. ]
2-8°C | [solubility ]
H2O: ≥5mg/mL | [form ]
powder | [color ]
faint yellow to dark yellow | [InChIKey]
HZFGMQJYAFHESD-UHFFFAOYSA-M | [Uses]
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. | [CAS DataBase Reference]
91714-93-1 |
| Hazard Information | Back Directory | [Definition]
ChEBI: The sodium salt of bromfenac. Note that 'bromfenac sodium' commonly refers to the sesquihydrate (120638-55-3); this is the anhydrous form. | [Originator]
American Home Products (US) | [Manufacturing Process]
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. | [Brand name]
Duract | [Therapeutic Function]
Analgesicá Antiinflammatory | [Biochem/physiol Actions]
Bromfenac exhibits antipyretic and prostaglandin synthetase inhibiting properties. It has therapeutic properties against the reduction of ocular pain and inflammation in postoperative cataract patients. Bromfenac acts as an effective agent against allergic conjunctivitis. It has the potential to treat acute muscle pain, osteoarthritis, and rheumatoid arthritis. | [storage]
Store at -20°C |
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