CHEBI:71200 - tofacitinib

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ChEBI Name tofacitinib
ChEBI ID CHEBI:71200
Definition A pyrrolopyrimidine that is pyrrolo[2,3-d]pyrimidine substituted at position 4 by an N-methyl,N-(1-cyanoacetyl-4-methylpiperidin-3-yl)amino moiety. Used as its citrate salt to treat moderately to severely active rheumatoid arthritis.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C16H20N6O
Net Charge 0
Average Mass 312.36960
Monoisotopic Mass 312.170
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
InChIKey UJLAWZDWDVHWOW-YPMHNXCESA-N
SMILES C[C@@H]1CCN(C[C@@H]1N(C)c1ncnc2[nH]ccc12)C(=O)CC#N
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Biological Role(s): EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor
An EC 2.7.10.* (protein-tyrosine kinase) inhibitor that specifically blocks the action of non-specific protein-tyrosine kinase (EC 2.7.10.2).
Application(s): antirheumatic drug
A drug used to treat rheumatoid arthritis.
View more via ChEBI Ontology
ChEBI Ontology
Outgoing tofacitinib (CHEBI:71200) has role antirheumatic drug (CHEBI:35842)
tofacitinib (CHEBI:71200) has role EC 2.7.10.2 (non-specific protein-tyrosine kinase) inhibitor (CHEBI:76617)
tofacitinib (CHEBI:71200) is a N-acylpiperidine (CHEBI:48591)
tofacitinib (CHEBI:71200) is a nitrile (CHEBI:18379)
tofacitinib (CHEBI:71200) is a pyrrolopyrimidine (CHEBI:38670)
tofacitinib (CHEBI:71200) is a tertiary amino compound (CHEBI:50996)
Incoming tofacitinib citrate (CHEBI:71197) has part tofacitinib (CHEBI:71200)
IUPAC Name
3-{(3R,4R)-4-methyl-3-[methyl(7H-pyrrolo[2,3-d]pyrimidin-4-yl)amino]piperidin-1-yl}-3-oxopropanenitrile
INNs Sources
tofacitinib WHO MedNet
tofacitinib WHO MedNet
tofacitinib WHO MedNet
tofacitinibum WHO MedNet
Synonym Source
Tasocitinib KEGG DRUG
Manual Xrefs Databases
4713 DrugCentral
D09970 KEGG DRUG
LSM-1227 LINCS
MI1 PDBeChem
Tofacitinib Wikipedia
WO2007012953 Patent
WO2007107318 Patent
WO2010123919 Patent
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Registry Numbers Types Sources
11647225 Reaxys Registry Number Reaxys
477600-75-2 CAS Registry Number ChemIDplus
477600-75-2 CAS Registry Number KEGG DRUG
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Last Modified
22 February 2017