Benoxaprofen

Gefahreninformationscode (GHS)

• Bildanzeige (GHS)

  

• Alarmwort

  Warnung

Uniprofen Chemische Eigenschaften,Einsatz,Produktion Methoden

• Originator

  Opren,Dista Lilly,UK,1980

• Verwenden

  A non-steroidal anti-inflammatory ophthalmic agent.

• Definition

  ChEBI: A monocarboxylic acid that is propionic acid substituted at position 2 by a 2-(4-chlorophenyl)-1,3-benzoxazol-5-yl group. It was used as a non-steroidal anti-inflammatory drug until 1982 when it was withdrawn from the market due to adverse side-effects inc uding liver necrosis, photosensitivity, and carcinogenicity in animals.

• Manufacturing Process

  The 6-benzoxazolyl analog of the 5-benzoxazolyl product is prepared as follows:
  (a) Ethyl 2-(2-p-chlorophenyl-6-benzoxazolyl)propionate: A solution of ethyl 2-(3-hydroxy-4-aminophenyl)propionate (2.5 g) in pyridine (15 ml) was treated with p-chlorobenzoyl chloride (1.65 ml) at 5°C. After stirring for 2 hours at room temperature the solution was evaporated to dryness.
  The residue was heated at 220°C until no more water was evolved, then was allowed to cool. This yielded ethyl 2-(2-p-Chlorophenyl-6- benzoxazolyl)propionate.
  (b) 2-(2-p-Chlorophenyl-6-benzoxazolyl)propionic acid: A solution of ethyl 2- (2-chlorophenyl-6-benzoxazolyl)propionate (4 g) in aqueous sodium hydroxide (30 ml) was heated on a steam bath for one-half hour. On cooling the black solution was washed with chloroform. On acidification of the black solution with hydrochloric acid the mixture was extracted with chloroform. This solution on evaporation yielded 2-(2-p-chlorophenyl-6-benzoxazolyl)propionic acid, MP 196°C.

• Trademarks

  Oraflex (Lilly);90459 compound;Benoxapran;Bexopron;Compound 90459;Lilly 3794;Lilly 90459;Lrcl 3794;Oprenal.

• Therapeutic Function

  Antiinflammatory, Analgesic

• Weltgesundheitsorganisation (WHO)

  Benoxaprofen, a nonsteroidal antiinflammatory agent, was introduced in 1980 for the treatment of rheumatic disorders. Following reports of serious adverse effects, some of which were fatal, it was withdrawn in several countries prior to worldwide withdrawal by the manufacturer in 1982.

• Sicherheitsprofil

  Poison by ingestion, subcutaneous, and intraperitoneal routes. Moderately toxic to humans by ingestion.Human systemic effects by ingestion: jaundice and gynecomastia (excessive development of the male mammary glands), changes in kidney tubules, decreased

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