Teriflunomide

Teriflunomide
Clinical data
Trade names	Aubagio
Other names	A77 1726
AHFS/Drugs.com	Monograph
MedlinePlus	a613010
License data	US DailyMed: Teriflunomide;
Pregnancy; category	AU: X (High risk); Contraindicated;
Routes of; administration	By mouth
ATC code	L04AK02 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only); BR: Class C1 (Other controlled substances); US: ℞-only; EU: Rx-only;
Pharmacokinetic data
Protein binding	>99.3%
Elimination half-life	2 weeks
Excretion	Bile duct/fecal, kidney
Identifiers
	IUPAC name (2Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide;
CAS Number	163451-81-8 ;
PubChem CID	54684141;
IUPHAR/BPS	6844;
DrugBank	DB08880 ;
ChemSpider	16737143 ;
UNII	1C058IKG3B;
KEGG	D10172 ;
ChEBI	CHEBI:68540 ;
ChEMBL	ChEMBL973 ;
CompTox Dashboard (EPA)	DTXSID80893457 ;
ECHA InfoCard	100.170.077
Chemical and physical data
Formula	C12H9F3N2O2
Molar mass	270.211 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES O=C(Nc1ccc(cc1)C(F)(F)F)C(/C#N)=C(/C)O;
	InChI InChI=1S/C12H9F3N2O2/c1-7(18)10(6-16)11(19)17-9-4-2-8(3-5-9)12(13,14)15/h2-5,18H,1H3,(H,17,19)/b10-7- ; Key:UTNUDOFZCWSZMS-YFHOEESVSA-N ;
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Teriflunomide, sold under the brand name Aubagio, is the active metabolite of leflunomide. Teriflunomide was investigated in the Phase III clinical trial TEMSO as a medication for multiple sclerosis (MS). The study was completed in July 2010. 2-year results were positive. However, the subsequent TENERE head-to-head comparison trial reported that "although permanent discontinuations [of therapy] were substantially less common among MS patients who received teriflunomide compared with interferon beta-1a, relapses were more common with teriflunomide." The drug was approved for use in the United States in September 2012 and for use in the European Union in August 2013.