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Compound

Teriflunomide

Also called Aubagio

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Part of the metabolic pathway of Leflunomide. See the timeline on the metabolic highway.

Overview

Teriflunomide, sold under the brand name Aubagio, is the active metabolite of leflunomide. Teriflunomide was investigated in the Phase III clinical trial TEMSO as a medication for multiple sclerosis (MS). The study was completed in July 2010. 2-year results were positive. 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." The drug was approved for use in the United States in September 2012 and for use in the European Union in August 2013.[1–7] WP

Risks and side effects

Adverse effects

The US Food and Drug Administration's prescribing information warns of potential hepatotoxicity (liver injury including liver failure) and teratogenicity (birth defects). Elavated ALT enzyme levels is the most common side effect (≥10% and ≥2% over placebo).[8] WP

Chemistry

Formula
C12H9F3N2O2 PC
CAS number
163451-81-8 PC
Molar mass (g/mol)
270.21 PC
IUPAC name (computed by PubChem)
(Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide PC
SMILES
C/C(=C(\C#N)/C(=O)NC1=CC=C(C=C1)C(F)(F)F)/O PC
InChIKey
UTNUDOFZCWSZMS-YFHOEESVSA-N PC
PubChem CID
54684141

Harm reduction information

No harm reduction data is on file for this compound yet. That means no dose, timing or combination data from PsychonautWiki or TripSit. Please don't guess a dose from similar compounds. If you have taken it and feel unwell, contact emergency services or a poison control center.

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User reports

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Pop culture

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Sources

  1. Journal / agency Magne D, Mézin F, Palmer G, Guerne PA. The active metabolite of leflunomide, A77 1726, increases proliferation of human synovial fibroblasts in presence of IL-1beta and TNF-alpha. Inflammation Research. November 2006. doi:10.1007/s00011-006-5196-x · PMID 17122964
  2. Other ClinicalTrialsGov NCT00134563 Phase III Study of Teriflunomide in Reducing the Frequency of Relapses and Accumulation of Disability in Patients With Multiple Sclerosis (TEMSO)
  3. Other Sanofi-Aventis' Teriflunomide Comes Up Trumps in Two-Year Phase III MS Trial. 15 October 2010
  4. Other Gever J. Teriflunomide Modest Help but Safe for MS. 4 June 2012
  5. Journal / agency Drug Approval Package: Aubagio (teriflunomide) Tablets NDA #202992. 5 November 2012
  6. Journal / agency FDA approves new multiple sclerosis treatment Aubagio
  7. Journal / agency Aubagio EPAR. 26 August 2013
  8. Journal / agency Aubagio- teriflunomide tablet, film coated. 21 November 2023

Text and values on this page are quoted from Wikipedia (CC BY-SA 4.0), PubChem (public domain). Each value links to the exact revision it came from.