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Teriflunomide: Wikis


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Systematic (IUPAC) name
CAS number 163451-81-8
ATC code none
PubChem 5479847
Chemical data
Formula C 12H9F3N2O2  
Mol. mass 270.207 g/mol
SMILES eMolecules & PubChem
Pharmacokinetic data
Bioavailability  ?
Protein binding >99.3%
Metabolism  ?
Half life 2 weeks
Excretion Biliar, renal
Therapeutic considerations
Pregnancy cat. X (contraindicated)
Legal status
Routes Oral

Teriflunomide (previously A77 1726) is the active metabolite of leflunomide.[1] Like leflunomide, it is used for rheumatoid arthritis.[2] As of September 2008, teriflunomide is investigated in the Phase III clinical trial TEMSO as a medication for multiple sclerosis (MS).[3]


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.[4]

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.[5]

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.[6]

Activation of leflunomide to teriflunomide

Leflunomide.svgE-Teriflunomide structure.svgTeriflunomide structure.svg

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.


  1. ^ Magne D, Mézin F, Palmer G, Guerne PA (2006). "The active metabolite of leflunomide, A77 1726, increases proliferation of human synovial fibroblasts in presence of IL-1beta and TNF-alpha". Inflamm. Res. 55 (11): 469–75. doi:10.1007/s00011-006-5196-x. PMID 17122964.  
  2. ^ Boyd, B, Castaner, J (2005). "Teriflunomide". Drugs of the Future 30 (11): 1102. doi:10.1358/dof.2005.030.11.948823.  
  3. ^
  4. ^ H. Spreitzer (March 13, 2006). "Neue Wirkstoffe - Teriflunomid" (in German). Österreichische Apothekerzeitung (6/2006).  
  5. ^ Dr. Timothy Vollmer (May 28, 2009). "MS Therapies in the Pipeline: Teriflunomide" (in English). eMS News (May 28, 2009).  
  6. ^ Breedveld, FC; Dayer, J-M (November 2000). "Leflunomide: mode of action in the treatment of rheumatoid arthritis". Ann Rheum Dis 59: 841–849. doi:10.1136/ard.59.11.841. PMID 11053058.  


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