tofacitinib   

GtoPdb Ligand ID: 5677

Synonyms: CP-690,550 | CP-690550 | tasocitinib | Xeljanz®
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
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
SMILES / InChI / InChIKey
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
InChI Key UJLAWZDWDVHWOW-YPMHNXCESA-N
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (2012), EMA (2017))
IUPAC Name
3-[(3R,4R)-4-methyl-3-[methyl({7H-pyrrolo[2,3-d]pyrimidin-4-yl})amino]piperidin-1-yl]-3-oxopropanenitrile
International Nonproprietary Names
INN number INN
9298 tofacitinib
Synonyms
CP-690,550 | CP-690550 | tasocitinib | Xeljanz®
Database Links
CAS Registry No. 477600-75-2
ChEMBL Ligand CHEMBL221959
DrugCentral Ligand 4713
GtoPdb PubChem SID 178102304
PubChem CID 9926791
RCSB PDB Ligand MI1
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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)
Wikipedia Tofacitinib