tofacitinib   Click here for help

GtoPdb Ligand ID: 5677

Synonyms: CP-690,550 | CP-690550 | tasocitinib | Xeljanz®
Approved drug PDB Ligand Immunopharmacology Ligand
tofacitinib is an approved drug (FDA (2012), EMA (2017))
Compound class: Synthetic organic
Comment: Tofacitinib is an orally active, Type-1 Janus kinase (JAK) inhibitor and it was first approved by the US FDA in 2012. Tofacitinib was originally described as a selective JAK3 inhibitor [2], but subsequent analysis has revealed it to be a pan-JAK inhibitor, with predominant JAK1 inhibition [3,5].
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2D Structure
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Physico-chemical Properties
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Hydrogen bond acceptors 6
Hydrogen bond donors 1
Rotatable bonds 4
Topological polar surface area 88.91
Molecular weight 312.17
XLogP 1.34
No. Lipinski's rules broken 0
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Canonical SMILES N#CCC(=O)N1CCC(C(C1)N(c1ncnc2c1cc[nH]2)C)C
Isomeric SMILES N#CCC(=O)N1CC[C@H]([C@H](C1)N(c1ncnc2c1cc[nH]2)C)C
InChI InChI=1S/C16H20N6O/c1-11-5-8-22(14(23)3-6-17)9-13(11)21(2)16-12-4-7-18-15(12)19-10-20-16/h4,7,10-11,13H,3,5,8-9H2,1-2H3,(H,18,19,20)/t11-,13+/m1/s1