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Teriflunomide: Wikis

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Teriflunomide
Systematic (IUPAC) name
(2Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide
Identifiers
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]

Contents

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.

References

  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" (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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