Sitaxentan

Sitaxentan
Clinical data
Other names	TBC-11251
AHFS/Drugs.com	International Drug Names
License data	EU EMA: by sitaxentan sodium;
Routes of; administration	Oral
ATC code	C02KX03 (WHO) ;
Legal status
Legal status	Withdrawn;
Pharmacokinetic data
Bioavailability	70 to 100%
Protein binding	>99%
Metabolism	Hepatic (CYP2C9- and CYP3A4-mediated)
Elimination half-life	10 hours
Excretion	Renal (50 to 60%); Fecal (40 to 50%)
Identifiers
	IUPAC name N-(4-chloro-3-methyl-5-isoxazolyl)-2-[[4,5-(methylenedioxy)-o-tolyl]acetyl]-3-thiophenesulfonamide;
CAS Number	184036-34-8 ; 210421-64-0 (sodium salt);
PubChem CID	216235;
IUPHAR/BPS	3950;
DrugBank	DB06268;
ChemSpider	21106381;
UNII	J9QH779MEM;
KEGG	D07171;
ChEMBL	ChEMBL282724;
CompTox Dashboard (EPA)	DTXSID0057673 ;
Chemical and physical data
Formula	C18H15ClN2O6S2
Molar mass	454.90 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES Cc1cc2OCOc2cc1CC(=O)c3sccc3S(=O)(=O)Nc4onc(C)c4Cl;

Sitaxentan sodium (TBC-11251) is a medication for the treatment of pulmonary arterial hypertension (PAH).^[1] It was marketed as Thelin by Encysive Pharmaceuticals until Pfizer purchased Encysive in February 2008. In 2010, Pfizer voluntarily removed sitaxentan from the market due to concerns about liver toxicity.^[2]

^ Barst RJ, Langleben D, Frost A, Horn EM, Oudiz R, Shapiro S, et al. (February 2004). "Sitaxsentan therapy for pulmonary arterial hypertension". American Journal of Respiratory and Critical Care Medicine. 169 (4): 441–447. doi:10.1164/rccm.200307-957OC. PMID 14630619.
^ Citing liver damage, Pfizer withdraws Thelin, Associated Press, December 12, 2010

[1] Barst RJ, Langleben D, Frost A, Horn EM, Oudiz R, Shapiro S, et al. (February 2004). "Sitaxsentan therapy for pulmonary arterial hypertension". American Journal of Respiratory and Critical Care Medicine. 169 (4): 441–447. doi:10.1164/rccm.200307-957OC. PMID 14630619.

[Pfizer-2] Citing liver damage, Pfizer withdraws Thelin, Associated Press, December 12, 2010

[1]

[2]