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Details

Stereochemistry ACHIRAL
Molecular Formula C12H9F3N2O2
Molecular Weight 270.2073
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of LEFLUNOMIDE

SMILES

CC1=C(C=NO1)C(=O)NC2=CC=C(C=C2)C(F)(F)F

InChI

InChIKey=VHOGYURTWQBHIL-UHFFFAOYSA-N
InChI=1S/C12H9F3N2O2/c1-7-10(6-16-19-7)11(18)17-9-4-2-8(3-5-9)12(13,14)15/h2-6H,1H3,(H,17,18)

HIDE SMILES / InChI

Description

Teriflunomide (trade name Aubagio, marketed by Sanofi) is the active metabolite of leflunomide and it acts as an immunomodulatory agent by inhibiting pyrimidine synthesis by blocking the enzyme dihydroorotate dehydrogenase. Teriflunomide was investigated in the Phase III clinical trial TEMSO as a medication for multiple sclerosis (MS). The drug was approved by the FDA on September 13, 2012 and in the European Union on August 26, 2013. It is uncertain whether this explains its effect on MS lesions. 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. It has been found that teriflunomide blocks the transcription factor NF-κB. It also inhibits tyrosine kinase enzymes, but only in high doses not clinically used.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
160.0 nM [Ki]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
AUBAGIO
Palliative
ARAVA

Cmax

ValueDoseCo-administeredAnalytePopulation
1.06 μg/mL
7 mg single, oral
TERIFLUNOMIDE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
100 μg × h/mL
7 mg single, oral
TERIFLUNOMIDE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
243 h
7 mg single, oral
TERIFLUNOMIDE plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
1%
TERIFLUNOMIDE plasma
Homo sapiens

Doses

AEs

PubMed

Sample Use Guides

In Vivo Use Guide
20 mg once daily
Route of Administration: Oral
In Vitro Use Guide
Cell cultures were inoculated with feline herpesvirus-1 (FHV-1) and treated simultaneously with concentrations of A77 (active metabolite of leflunomide, A77 1726) ranging from 0 to 200 uM. Concentrations of A77 > or = 20 uM were associated with substantial reduction in plaque number and viral load. Concentrations > or = 100 uM were associated with complete suppression of plaque formation. At low concentrations of A77, clusters of intracytoplasmic virus particles that appeared to lack tegument and an external membrane were detected.