leflunomide   Click here for help

GtoPdb Ligand ID: 6825

Synonyms: Arabloc® | Arava® | HWA 486 | HWA-486 | lefunamide | SU-101
Approved drug Immunopharmacology Ligand
leflunomide is an approved drug (FDA (1998), EMA (1999))
Compound class: Synthetic organic
Comment: Inhibits dihydroorotate dehydrogenase.
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2D Structure
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Physico-chemical Properties
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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
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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)
1. Munier-Lehmann H, Vidalain PO, Tangy F, Janin YL. (2013)
On dihydroorotate dehydrogenases and their inhibitors and uses.
J Med Chem, 56 (8): 3148-67. [PMID:23452331]
2. Papageorgiou C, Albert R, Floersheim P, Lemaire M, Bitch F, Weber HP, Andersen E, Hungerford V, Schreier MH. (1998)
Pyrazole bioisosteres of leflunomide as B-cell immunosuppressants for xenotransplantation and chronic rejection: scope and limitations.
J Med Chem, 41 (18): 3530-8. [PMID:9719606]