Teriflunomide

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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[[Script error: No such module "String".]]
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Teriflunomide (previously A77 1726) is the active metabolite of leflunomide.[1] Like leflunomide, it is used for rheumatoid arthritis.[2] 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.[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

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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

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  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. ClinicalTrials.gov
  4. H. Spreitzer (March 13, 2006). "Neue Wirkstoffe - Teriflunomid". Österreichische Apothekerzeitung (in German) (6/2006). 
  5. Dr. Timothy Vollmer (May 28, 2009). "MS Therapies in the Pipeline: Teriflunomide". EMS News (May 28, 2009). 
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