Teriflunomide

Teriflunomide
Ball-and-stick model of the teriflunomide molecule
Clinical data
Trade namesAubagio
Other namesA77 1726
AHFS/Drugs.comMonograph
MedlinePlusa613010
License data
Pregnancy
category
  • AU: X (High risk)[1]
  • Contraindicated[1]
Routes of
administration		By mouth
ATC code
Legal status
Legal status
Pharmacokinetic data
Protein binding>99.3%
Elimination half-life2 weeks
ExcretionBile duct/fecal, kidney
Identifiers
  • (2Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.170.077 Edit this at Wikidata
Chemical and physical data
FormulaC12H9F3N2O2
Molar mass270.211 g·mol−1
3D model (JSmol)
  • O=C(Nc1ccc(cc1)C(F)(F)F)C(/C#N)=C(/C)O
  • 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- checkY
  • Key:UTNUDOFZCWSZMS-YFHOEESVSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Teriflunomide, sold under the brand name Aubagio, is the active metabolite of leflunomide.[6] Teriflunomide was investigated in the Phase III clinical trial TEMSO as a medication for multiple sclerosis (MS). The study was completed in July 2010.[7] 2-year results were positive.[8] 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."[9] The drug was approved for use in the United States in September 2012[10][11] and for use in the European Union in August 2013.[5]

  1. ^ a b "Teriflunomide (Aubagio) Use During Pregnancy". Drugs.com. 11 September 2019. Retrieved 2 March 2020.
  2. ^ "FDA-sourced list of all drugs with black box warnings (Use Download Full Results and View Query links.)". nctr-crs.fda.gov. FDA. Retrieved 22 October 2023.
  3. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 16 August 2023.
  4. ^ "Aubagio- teriflunomide tablet, film coated". DailyMed. 21 November 2023. Retrieved 13 June 2024.
  5. ^ a b "Aubagio EPAR". European Medicines Agency (EMA). 26 August 2013. Retrieved 13 June 2024.
  6. ^ Magne D, Mézin F, Palmer G, Guerne PA (November 2006). "The active metabolite of leflunomide, A77 1726, increases proliferation of human synovial fibroblasts in presence of IL-1beta and TNF-alpha". Inflammation Research. 55 (11): 469–75. doi:10.1007/s00011-006-5196-x. PMID 17122964. S2CID 47034503.
  7. ^ Clinical trial number NCT00134563 for "Phase III Study of Teriflunomide in Reducing the Frequency of Relapses and Accumulation of Disability in Patients With Multiple Sclerosis (TEMSO)" at ClinicalTrials.gov
  8. ^ "Sanofi-Aventis' Teriflunomide Comes Up Trumps in Two-Year Phase III MS Trial". Genetic Engineering & Biotechnology News. 15 October 2010.
  9. ^ Gever J (4 June 2012). "Teriflunomide Modest Help but Safe for MS". medpage. Joint meeting of the Consortium of Multiple Sclerosis Centers and the Americas Committee for Treatment and Research in Multiple Sclerosis. Retrieved 4 June 2012.
  10. ^ "Drug Approval Package: Aubagio (teriflunomide) Tablets NDA #202992". U.S. Food and Drug Administration (FDA). 5 November 2012. Retrieved 1 March 2020.
  11. ^ "FDA approves new multiple sclerosis treatment Aubagio" (Press release). U.S. Food and Drug Administration (FDA). Archived from the original on 13 September 2012. Retrieved 14 September 2012.