leflunomide   

GtoPdb Ligand ID: 6825

Synonyms: Arabloc® | Arava® | HWA 486 | HWA-486 | lefunamide | SU-101
leflunomide is an approved drug (FDA (1998), EMA (1999))
Compound class: Synthetic organic
Comment: Inhibits dihydroorotate dehydrogenase.
2D Structure
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Physico-chemical Properties
Hydrogen bond acceptors 2
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 55.13
Molecular weight 270.06
XLogP 2.79
No. Lipinski's rules broken 0
SMILES / InChI / InChIKey
Canonical SMILES O=C(c1cnoc1C)Nc1ccc(cc1)C(F)(F)F
Isomeric SMILES O=C(c1cnoc1C)Nc1ccc(cc1)C(F)(F)F
InChI 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)
InChI Key VHOGYURTWQBHIL-UHFFFAOYSA-N
No information available.
Summary of Clinical Use
Used to treat active rheumatoid arthritis (improve physical function and slow progression), prevention of acute/chronic rejection following organ transplant (as an FDA designated orphan drug).
Mechanism Of Action and Pharmacodynamic Effects
Leflunomide acts as a pyrimidine synthesis inhibitor. It is rapidly and almost completely metabolized following oral administration to its pharmacologically active metabolite, A77 1726. Its mechanism of action has not been fully resolved but appears to be associated with a reduction in the pyrimidine level, which in turn has an inhibitory effect on autoimmune T cells [1].
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