Teriflunomide

Teriflunomide

File:Teriflunomide structure.svg
Systematic (IUPAC) name
(2Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide
Clinical data
Pregnancy category	X (contraindicated)
Routes of administration	oral
Legal status
Legal status	investigational
Pharmacokinetic data
Protein binding	>99.3%
Biological half-life	2 weeks
Excretion	biliar, renal
Identifiers
CAS Number	163451-81-8
ATC code	none
PubChem	CID 5479847
Chemical data
Formula	C12H9F3N2O2
Molar mass	270.207 g/mol[[]]

Teriflunomide (previously A77 1726) is the active metabolite of leflunomide. Like leflunomide, it is used for rheumatoid arthritis. As of March 2010, teriflunomide is investigated in the Phase III clinical trial TEMSO as a medication for multiple sclerosis (MS). The study is expected to run until October 2010.

Mechanisms of action

Teriflunomide is an immunomodulatory drug inhibiting pyrimidine de novo synthesis by blocking the enzyme dihydroorotate dehydrogenase. It is uncertain whether this explains its effect on MS lesions.

Teriflunomide inhibits rapidly dividing cells, including activated T cells, which are thought to drive the disease process in MS. Teriflunomide may decrease the risk of infections compared to chemotherapy-like drugs because of its more-limited effects on the immune system.

It has been found that teriflunomid blocks the transcription factor NF-κB. It also inhibits tyrosine kinase enzymes, but only in high doses not clinically used.

Activation of leflunomide to teriflunomide

200px→200px↔200px

The structure which results from ring opening can interconvert between the E and Z enolic forms (and the corresponding keto-amide), with the Z enol being the most stable and therefore most predominant form.

See also

See Leflunomide for information on pharmacokinetics, side-effects, contraindications and other data.

References

pt:Teriflunomide sr:Teriflunomid