Teriflunomide 163451-81-8
Teriflunomide (previously A77 1726) is the active metabolite of leflunomide. Teriflunomide is investigated in the Phase III clinical trial TEMSO as a medication for multiple sclerosis (MS). The study is expected to run until October 2010. 2-year results were positive.
Mechanisms of action
Teriflunomide is an immunomodulatory drug inhibiting pyrimidine de novo synthesis by blocking the enzyme dihydroorotate dehydrogenase. 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 teriflunomid blocks the transcription factor NF-κB. It also inhibits tyrosine kinase enzymes, but only in high doses not clinically used.
Activation of leflunomide to teriflunomide
The structure which results from ring opening can interconvert between the E and Z enolic forms (and the corresponding keto-amide), with the Z enol being the most stable and therefore most predominant form.
| Systematic (IUPAC) name: | (2Z)-2-cyano-3-hydroxy-N-[4-(trifluoromethyl)phenyl]but-2-enamide |
|---|---|
| Teriflunomide CAS number: | 163451-81-8 |
| ATC code: | |
| PubChem: | 5479847 |
| DrugBank: | |
| Formula: | C12H9N2O2 |
| Molecular mass: | 270.207 g/mol |
| Teriflunomide Assay/Purity: | Typically NLT 98% |
