Valdecoxib

Structural formula
General
Non-proprietary name	Valdecoxib
other names	4- (5-methyl-3-phenyl-isoxazol-4-yl) benzenesulfonamide
Molecular formula	C 16 H 14 N 2 O 3 S
Brief description	colorless to yellowish powder
External identifiers / databases
EC number	803-082-3
ECHA InfoCard	100.229.918
PubChem	119607
DrugBank	DB00580
Wikidata	Q347613
Drug information
ATC code	M01 AH03
Drug class	Cyclooxygenase-2 inhibitors
properties
Molar mass	314.36 g · mol -1
solubility	soluble in methanol and ethanol ; ≥ 25 mg ml −1 in DMSO ;
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
H and P phrases	H: 361d-373-410
	P: 273-281-501
Toxicological data	800 mg kg −1 ( LD 50 , rat, female , oral ) ; 1600 mg kg −1 ( LD 50 , rat, male , oral ) ;
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Valdecoxib (trade name Bextra ^® ) is a drug from the group of cyclooxygenase-2 inhibitors (syn. COX-2 inhibitors or coxibs) from Pfizer .

In February 2005, the US FDA ordered Pfizer to withdraw valdecoxib from the market. The reasons were:

Lack of long-term data on cardiovascular safety
Severe allergic skin reactions have been reported after the use of valdecoxib
Lack of evidence of an advantage of valdecoxib over other NSAIDs

After being suspended in 2005, European approval has now expired.

Pfizer was tried again in September 2009 for illegally marketing the analgesic . The company had agreed to pay a total of $ 2.3 billion in damages for the civil and criminal charges; this is the largest sum ever paid as a fine by a pharmaceutical company .

Individual evidence

↑ ^a ^b ^c ^d ^e ^f data sheet valdecoxib from Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).
^ Sarfaraz K. Niazi: Handbook of Pharmaceutical Manufacturing Formulations. Taylor & Francis, 2004, ISBN 978-0-849-31746-0 , p. 260 ( limited preview in Google book search).
↑ FDA: Public Health Advisory - FDA Announces Important Changes and Additional Warnings for COX-2 Selective and Non-Selective Non-Steroidal Anti-Inflammatory Drugs (NSAIDs) , April 7, 2005.
↑ EMEA document 358234/2005 (PDF; 142 kB).
↑ Gardiner Harris: Pfizer Pays $ 2.3 Billion to Settle Marketing Case . In: The New York Times . September 2, 2009, ISSN 0362-4331 ( nytimes.com [accessed July 4, 2020]).

[Sigma-1] ↑ ^a ^b ^c ^d ^e ^f data sheet valdecoxib from Sigma-Aldrich , accessed on May 20, 2017 ( PDF ).

[Handbook-2] Sarfaraz K. Niazi: Handbook of Pharmaceutical Manufacturing Formulations. Taylor & Francis, 2004, ISBN 978-0-849-31746-0 , p. 260 ( limited preview in Google book search).

[3] FDA: Public Health Advisory - FDA Announces Important Changes and Additional Warnings for COX-2 Selective and Non-Selective Non-Steroidal Anti-Inflammatory Drugs (NSAIDs) , April 7, 2005.

[4] EMEA document 358234/2005 (PDF; 142 kB).

[5] Gardiner Harris: Pfizer Pays $ 2.3 Billion to Settle Marketing Case . In: The New York Times . September 2, 2009, ISSN 0362-4331 ( nytimes.com [accessed July 4, 2020]).