51234-28-7 Usage
Originator
Opren,Dista Lilly,UK,1980
Uses
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 It was used as a non-steroidal anti-inflammatory drug until 1982 when it was withdrawn from the market due to adverse side-effects inc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.
Brand name
Oraflex (Lilly);90459 compound;Benoxapran;Bexopron;Compound 90459;Lilly 3794;Lilly 90459;Lrcl 3794;Oprenal.
Therapeutic Function
Antiinflammatory, Analgesic
World Health Organization (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serious adverse effects, some of which were fatal, it was withdrawn in several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.
Safety Profile
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
Check Digit Verification of cas no
The CAS Registry Mumber 51234-28-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 5,1,2,3 and 4 respectively; the second part has 2 digits, 2 and 8 respectively.
Calculate Digit Verification of CAS Registry Number 51234-28:
(7*5)+(6*1)+(5*2)+(4*3)+(3*4)+(2*2)+(1*8)=87
87 % 10 = 7
So 51234-28-7 is a valid CAS Registry Number.
InChI:InChI=1/C16H12ClNO3/c1-9(16(19)20)11-4-7-14-13(8-11)18-15(21-14)10-2-5-12(17)6-3-10/h2-9H,1H3,(H,19,20)
51234-28-7Relevant articles and documents
GLC and NMR analysis of isomeric impurities in the new anti inflammatory agent benoxaprofen
Browner,Cockerill,Maidment,Rackham,Snook
, p. 1305 - 1309 (1976)
-
Thallium in Organic Synthesis. 65. A Novel Synthesis of Benzoxazoles from Anilides
Taylor, Edward C.,Katz, Alan H.,Alvarado, Sergio I.,McKillop, Alexander
, p. 1607 - 1609 (2007/10/02)
-
Esters and amides containing the 1-(4-chlorobenzoyl)-5-methoxy-2-methyl-1H-indole-3-acetyl moiety
-
, (2008/06/13)
Compounds of the formula STR1 wherein each X, which may be identical or different from the other X, is oxygen or imino; R1 is hydrogen, fluorine, chlorine or bromine; R2 and R3, which may be identical or different from each other, are each hydrogen; unsubstituted or mono-substituted alkyl of 1 to 6 carbon atoms, where the substituent is phenyl or dialkylamino with 1 to 3 carbon atoms in each alkyl moiety; pyridyl; or cycloalkyl of 5 to 7 carbon atoms; R2 and R3, together with each other and the nitrogen atoms to which they are attached, are pyrrolidino, piperidino, hexamethyleneimino, morpholino, N-aryl-piperazino or N-(alkyl of 1 to 3 carbon atoms)-piperazino; A is cycloalkylene of 5 to 7 carbon atoms; unsubstituted or substituted alkylene of 2 to 10 carbon atoms, where the substituents are one to two alkyls of 1 to 3 carbon atoms each, one to two carbalkoxys of 2 to 4 carbon atoms each, one to two phenyls, one to four hydroxyls, one halomethyl, one hydroxymethyl, one alkanoyloxy of 1 to 18 carbon atoms, one alkanoyloxymethyl of 1 to 18 carbon atoms in the alkanoyl moiety or one STR2 where R1, R2 and R3 have the meanings previously defined; or alkylene of 2 to 10 carbon atoms interrupted by oxygen, sulfur, sulfoxide, sulfonyl, phenyl, cyclohexyl, pyridyl, piperazino or unsubstituted or substituted imino, where the substituent on the imino group is alkyl of 1 to 6 carbon atoms, phenyl or phenylalkyl of 1 to 3 carbon atoms in the alkyl moiety; B is the acyl residue of an antiphlogistic carboxylic acid; and their non-toxic, pharmacologically acceptable acid addition salts. The compounds as well as their salts are useful as anti-inflammatories.
