91714-93-1 Usage
Description
Bromfenac sodium is a potent, orally-active, long-lasting peripheral analgesic with anti-inflammatory 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. Its 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 anti-inflammatory potency. Bromfenac is also an inhibitor of cyclooxygenase 2 (COX-2) that is selective over COX-1. It is used in the treatment of postoperative inflammation following cataract surgery.
Uses
Used in Pharmaceutical Industry:
Bromfenac sodium is used as an analgesic and anti-inflammatory agent for reducing prostaglandin production through inhibition of cyclooxygenase.
Used in Ophthalmology:
Bromfenac sodium is used as a postoperative anti-inflammatory agent for the treatment of inflammation following cataract surgery when administered as a 0.9% topical solution on a tapering schedule for 24 weeks.
Used in Research:
Bromfenac sodium is used to study its ability to bind to melanin, in the synthesis of bromfenac indolinone standard, and to analyze its permeability in porcine conjunctiva.
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.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 91714-93-1 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 9,1,7,1 and 4 respectively; the second part has 2 digits, 9 and 3 respectively.
Calculate Digit Verification of CAS Registry Number 91714-93:
(7*9)+(6*1)+(5*7)+(4*1)+(3*4)+(2*9)+(1*3)=141
141 % 10 = 1
So 91714-93-1 is a valid CAS Registry Number.
InChI:InChI=1/C15H12BrNO3.Na.H2O/c16-11-6-4-9(5-7-11)15(20)12-3-1-2-10(14(12)17)8-13(18)19;;/h1-7H,8,17H2,(H,18,19);;1H2/q;+1;/p-1
91714-93-1Relevant articles and documents
Refining method and preparation method of bromfenac sodium sesquihydrate
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Paragraph 0098-0100, (2021/01/29)
The invention relates to a refining method and preparation method of bromfenac sodium sesquihydrate. Specifically, the invention provides the refining method comprising the steps: (a) regulating pH ofan aqueous solution of a compound represented by the formula 2 to pH of 2-3 with an acidity regulator, and thus obtaining a regulated aqueous solution; (b) extracting the regulated aqueous solution obtained in the step (a) with a first solvent and separating the solution to obtain an organic phase; and (c) regulating the pH value of the organic phase obtained in the step (b) by using an alkalinity regulator so as to separate out a solid, namely the bromfenac sodium sesquihydrate, from the organic phase. The method has the advantages that the alkalinity of the bromfenac sodium sesquihydrate can be accurately controlled, the purity and content of the bromfenac sodium sesquihydrate are higher than those of a recrystallization method, the recrystallization heating and cooling process is avoided, operation is simplified, energy consumption is reduced, long-time stirring crystallization is not needed, the preparation period is shortened, and the yield is increased.
Simple preparation method of bromfenac sodium
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Paragraph 0077-0085, (2020/06/09)
The invention relates to a simple preparation method of bromfenac sodium, comprising the following steps: carrying out a condensation reaction between bromophenylacetonitrile and 2-nitrophenylacetic acid under the action of alkali to prepare 7-(4-bromophenyl)-3-carboxymethylbenzo [c] isoxazole (IV), carrying out a reduction reaction on the compound as shown in the formula IV, and alkalizing with sodium hydroxide for salifying to prepare bromfenac sodium. The method has the advantages of cheap and easily available raw materials, simple route, easy operation, low product cost, good product purity and high yield, and is suitable for industrial production.
Preparation method of bromfenac sodium intermediate
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Paragraph 0042; 0043, (2019/09/05)
The invention belongs to the field of medicinal chemistry, and particularly relates to a preparation method of bromfenac sodium and an intermediate thereof. The method comprises the steps that a new solvent system is adopted for preparing the intermediate, generation of brick-red by-products is avoided, the impurity content in the intermediate is greatly reduced, and the purity and yield of the intermediate are improved.
