Structure via PubChem · Public domain (PubChem)
teriflunomide
Sign in to saveAlso known as A77 1726, Aubagio®, flucyamide, HMR-1726, A 77-1726, HMR 1726, A 771726, (Z)-2-cyano-alpha,alpha,alpha-trifluoro-3-hydroxy-p-crotonotoluidide
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 S
Key facts
- Drug.Verifiedfields
- changed
- Drug.Watchedfields
- changed
- Drug.verifiedrevid
- 470602409
- Drug.image
- Teriflunomide_structure.svg
- Drug.image_class
- skin-invert-image
- Drug.image2
- Teriflunomide 3D ball.png
- Drug.image_class2
- bg-transparent
- Drug.alt2
- Ball-and-stick model of the teriflunomide molecule
- Drug.tradename
- Aubagio
- Drug.MedlinePlus
- a613010
- Drug.DailyMedID
- Teriflunomide
- Drug.pregnancy_AU
- X
- Drug.pregnancy_category
- Contraindicated
- Drug.routes_of_administration
- By mouth
- Drug.ATC_prefix
- L04
- Drug.ATC_suffix
- AK02
- Drug.legal_AU
- S4
- Drug.legal_BR
- C1
via Wikipedia infobox
Chemical data
- Formula
- C12H9F3N2O2
- Molecular weight
- 270.21 g/mol
- IUPAC name
- (Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide
- SMILES
- C/C(=C(\C#N)/C(=O)NC1=CC=C(C=C1)C(F)(F)F)/O
- InChIKey
- UTNUDOFZCWSZMS-YFHOEESVSA-N
- XLogP
- 3.3
- Polar surface area
- 73.1 Ų
- H-bond donors
- 2
- H-bond acceptors
- 6
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Approved
- Molecule type
- Small molecule
- First approval
- 2012
- Admin. routes
- oral
- Indications
- kidney disease, celiac disease, tropical spastic paraparesis, multiple sclerosis
via ChEMBL · EBI
Wikidata facts
- Mass
- 270.062
- Has use
- medication
Show 9 more facts
- chemical formula
- C₁₂H₉F₃N₂O₂
- medical condition treated
- multiple sclerosis
- isomeric SMILES
- C/C(=C(\C#N)/C(=O)NC1=CC=C(C=C1)C(F)(F)F)/O
- canonical SMILES
- CC(=C(C#N)C(=O)NC1=CC=C(C=C1)C(F)(F)F)O
- World Health Organisation international non-proprietary name
- teriflunomide
- defined daily dose
- 14
- Commons category
- Teriflunomide
- legal status (medicine)
- boxed warning
- native label
- Aubagio
Sources (9)
via Wikidata · CC0
~3 min read
Encyclopedic overview
4 sectionsContents
- Adverse effects
- Mechanisms of action
- Activation of leflunomide to teriflunomide
- References
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.
==Adverse effects==
Excerpted from Wikipedia’s “teriflunomide” article, available under the CC BY-SA 4.0 licence.