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
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes (FDA (2012), EMA (2017))
IUPAC Name Click here for help
International Nonproprietary Names Click here for help
INN number INN
9298 tofacitinib
Synonyms Click here for help
CP-690,550 | CP-690550 | tasocitinib | Xeljanz®
Database Links Click here for help
Specialist databases
Reactome Drug Reactome logo R-ALL-9678779
Reactome Reaction Reactome logo R-HSA-9679028, R-HSA-9678561, R-HSA-9678737, R-HSA-9678935
Other databases
CAS Registry No. 477600-75-2
ChEMBL Ligand CHEMBL221959
DrugCentral Ligand 4713
GtoPdb PubChem SID 178102304
PubChem CID 9926791
Search Google for chemical match using the InChIKey UJLAWZDWDVHWOW-YPMHNXCESA-N
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Search PubMed clinical trials tofacitinib
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SynPHARM 85282 (in complex with Janus kinase 2)
85283 (in complex with Janus kinase 3)
85284 (in complex with tyrosine kinase 2)
UniChem Compound Search for chemical match using the InChIKey UJLAWZDWDVHWOW-YPMHNXCESA-N
UniChem Connectivity Search for chemical match using the InChIKey UJLAWZDWDVHWOW-YPMHNXCESA-N
Wikipedia Tofacitinib