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

Large-scale screening data

DiscoveRx KINOMEscan® screen Click here for help
A screen of 72 inhibitors against 456 human kinases. Quantitative data were derived using DiscoveRx KINOMEscan® platform.
Reference: 4,14

Key to terms and symbols Click column headers to sort
Target Name in screen Sp. Type Action Value Parameter
Janus kinase 3 JAK3(JH1domain-catalytic) Hs Inhibitor Inhibition 9.8 pKd
Janus kinase 2 JAK2(JH1domain-catalytic) Hs Inhibitor Inhibition 9.2 pKd
Janus kinase 1 JAK1(JH1domain-catalytic) Hs Inhibitor Inhibition 8.8 pKd
tyrosine kinase 2 TYK2(JH1domain-catalytic) Hs Inhibitor Inhibition 8.3 pKd
doublecortin like kinase 3 DCAMKL3 Hs Inhibitor Inhibition 7.9 pKd
tyrosine kinase non receptor 1 TNK1 Hs Inhibitor Inhibition 6.9 pKd
protein kinase N1 PKN1 Hs Inhibitor Inhibition 6.8 pKd
NUAK family, SNF1-like kinase, 2 SNARK Hs Inhibitor Inhibition 6.6 pKd
Rho associated coiled-coil containing protein kinase 2 ROCK2 Hs Inhibitor Inhibition 6.4 pKd
LCK proto-oncogene, Src family tyrosine kinase LCK Hs Inhibitor Inhibition 6.3 pKd
Displaying the top 10 targets  View all targets in screen »
EMD Millipore KinaseProfilerTM screen/Reaction Biology Kinase HotspotSM screen Click here for help
A screen profiling 158 kinase inhibitors (Calbiochem Protein Kinase Inhibitor Library I and II, catalogue numbers 539744 and 539745) for their inhibitory activity at 1µM and 10µM against 234 human recombinant kinases using the EMD Millipore KinaseProfilerTM service.

A screen profiling the inhibitory activity of 178 commercially available kinase inhibitors at 0.5µM against a panel of 300 recombinant protein kinases using the Reaction Biology Corporation Kinase HotspotSM platform.

Reference: 1,6

Key to terms and symbols Click column headers to sort
Target Name in screen Sp. Type Action % Activity remaining at 0.5µM % Activity remaining at 1µM % Activity remaining at 10µM
Janus kinase 3 JAK3/JAK3 Hs Inhibitor Inhibition 1.9
Janus kinase 1 nd/JAK1 Hs Inhibitor Inhibition 2.3
Janus kinase 2 JAK2/JAK2 Hs Inhibitor Inhibition 5.1
tyrosine kinase 2 nd/TYK2 Hs Inhibitor Inhibition 12.0
protein kinase N1 nd/PKN1(PRK1) Hs Inhibitor Inhibition 16.5
leucine rich repeat kinase 2 nd/LRRK2 Hs Inhibitor Inhibition 51.3
EPH receptor B3 EphB3/EPHB3 Hs Inhibitor Inhibition 54.9
megakaryocyte-associated tyrosine kinase nd/CTK(MATK) Hs Inhibitor Inhibition 66.9
Rho associated coiled-coil containing protein kinase 2 ROCK-II/ROCK2 Hs Inhibitor Inhibition 69.9
NUAK family kinase 1 ARK5/ARK5(NUAK1) Hs Inhibitor Inhibition 71.2
Displaying the top 10 targets  View all targets in screen »