Teriflunomide

Names

[ Name ]:
Teriflunomide

[Synonym ]:
(2Z)-2-Cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide
Aubagio
(Z)-2-cyano-3-hydroxy-N-(4-(trifluoromethyl)phenyl)but-2-enamide
(Z)-2-Cyano-3-hydroxy-but-2-enoic acid (4-trifluoromethyl-phenyl)-amide
2-Butenamide, 2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-, (2Z)-
(2Z)-2-Cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]-2-butenamide
Teriflunomide
(Z)-2-Cyano-a',a',a'-trifluoro-3-hydroxy-p-crotonotoluidide
A771726
Leflunomide Impurity 2

Biological Activity

[Description]:

Teriflunomide is the active metabolite of leflunomide, an approved therapy for rheumatoid arthritis. It inhibits pyrimidine synthesis and therefore potently decreases T cell and B cell proliferation.

[Related Catalog]:

Signaling Pathways >> Others >> Others

Research Areas >> Inflammation/Immunology

[In Vitro]

Teriflunomide primarily acts as an inhibitor of dihydroorotate dehydrogenase (DHODH), a key mitochondrial enzyme involved in the de novo synthesis of pyrimidines in rapidly proliferating cells. By reducing the activity of high-avidity proliferating T lymphocytes and B lymphocytes, teriflunomide likely attenuates the inflammatory response to autoantigens in MS. Thus, teriflunomide can be considered a cytostatic rather than a cytotoxic drug to leukocytes[1].

[In Vivo]

Teriflunomide has demonstrated beneficial effects in two independent animal models of demyelinating disease. In the dark agouti rat model of experimental autoimmune encephalitis (EAE), teriflunomide administration results in clinical, histopathological, and electrophysiological evidence of efficacy both as a prophylactic and therapeutic agent. Similarly, in the female Lewis rat model of EAE, teriflunomide administration results in beneficial prophylactic and therapeutic clinical effects, with a delay in disease onset and symptom severity[1].

[References]

[1]. Oh J, et al. An update of teriflunomide for treatment of multiple sclerosis. Ther Clin Risk Manag. 2013;9:177-90.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.4±0.1 g/cm3

[ Boiling Point ]:
410.8±45.0 °C at 760 mmHg

[ Molecular Formula ]:
C₁₂H₉F₃N₂O₂

[ Molecular Weight ]:
270.207

[ Flash Point ]:
202.3±28.7 °C

[ Exact Mass ]:
270.061615

[ PSA ]:
73.12000

[ LogP ]:
2.51

[ Vapour Pressure ]:
0.0±1.0 mmHg at 25°C

[ Index of Refraction ]:
1.552

[ Storage condition ]:
-20°C

MSDS

Click to get detail MSDS

Safety Information

[ Symbol ]:

GHS07

[ Signal Word ]:
Warning

[ Hazard Statements ]:
H302

[ Hazard Codes ]:
Xn

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2942000000

Customs

[ HS Code ]: 2942000000