Benoxaprofen

Structural formula
	Structural formula without stereochemistry: ; 1: 1 mixture ( racemate ) of ( R ) form ; and ( S ) form
General
Non-proprietary name	Benoxaprofen
other names	( RS ) -2- [2- (4-chlorophenyl) -5-benzoxazoyl] propionic acid ( IUPAC )
Molecular formula	C 16 H 12 ClNO 3
External identifiers / databases
EC number	257-069-7
ECHA InfoCard	100.051.864
PubChem	39941
ChemSpider	36518
DrugBank	DB04812
Wikidata	Q420082
Drug information
ATC code	M01 AE06
Drug class	Non-opioid analgesic
properties
Molar mass	301.72 g · mol -1
Physical state	firmly
Melting point	189-190 ° C
pK s value	3.5
solubility	Water: 52 mg l −1 at 25 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS hazard labeling ; no classification available
Toxicological data	118 mg kg −1 ( LD 50 , rat , oral ) ; 800 mg kg −1 ( LD 50 , mouse , oral ) ; 168 mg kg −1 ( TD Lo , woman , oral, 2 weeks ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Benoxaprofen is a chlorine- containing, heterocyclic compound, which is derived from oxazole and propionic acid. As a medicinal substance, benoxaprofen, like the similar ibuprofen, belongs to the group of non-steroidal anti-inflammatory drugs or anti-inflammatory drugs . The drug was developed by Eli Lilly in the 1980s and used as an analgesic , antipyretic and anti-inflammatory drug . After severe side effects such as strong allergic reactions ( photosensitivity ) to the drug and liver damage with hundreds of deaths occurred in Great Britain , the drug's approval was withdrawn again. The former preparation Oraflex ^® is no longer available.

Appearance and properties

The waxy white substance belongs to the group of propionic acid derivatives. It is produced from 4-aminophenyl-α-methylacetonitrile after nitration and hydrogenation by reaction with pyridine and subsequent reaction with hydrogen chloride . Benoxaprofen was used in medicines as the sodium salt.

Individual evidence

↑ ^a ^b ^c Bruchhausen, Ebel, Frahm, Hackenthal: Hagers Handbook of Pharmaceutical Practice. Folgewerk, Vol. 7, pp. 403-404, 1999, Springer-Verlag, ISBN 3-540-52632-3 .
↑ ^a ^b Entry on benoxaprofen in the ChemIDplus database of the United States National Library of Medicine (NLM) .
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ Yakuri to Chiryo. in: Pharmacology and Therapeutics. Vol. 9, p. 4445, 1981 .
^ Journal of Medicinal Chemistry. Vol. 18, p. 53, 1975 .
↑ Nephron. Vol. 35, p. 279, 1983 .
^ David Coburn, Carl D'Arcy, George Murray Torrance: Health and Canadian Society: Sociological Perspectives. 3rd edition, University of Toronto Press, 1998, ISBN 978-0-8020-8052-3 , p. 487 ( limited preview in Google book search).

[Hager-1] Bruchhausen, Ebel, Frahm, Hackenthal: Hagers Handbook of Pharmaceutical Practice. Folgewerk, Vol. 7, pp. 403-404, 1999, Springer-Verlag, ISBN 3-540-52632-3 .

[ChemIDplus-2] Entry on benoxaprofen in the ChemIDplus database of the United States National Library of Medicine (NLM) .

[NV-3] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[4] Yakuri to Chiryo. in: Pharmacology and Therapeutics. Vol. 9, p. 4445, 1981 .

[5] Journal of Medicinal Chemistry. Vol. 18, p. 53, 1975 .

[6] Nephron. Vol. 35, p. 279, 1983 .

[7] David Coburn, Carl D'Arcy, George Murray Torrance: Health and Canadian Society: Sociological Perspectives. 3rd edition, University of Toronto Press, 1998, ISBN 978-0-8020-8052-3 , p. 487 ( limited preview in Google book search).