tofacitinib (CHEBI:71200)

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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

Average Mass

312.36960

Monoisotopic Mass

312.16986

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.

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

Last Modified

29 August 2019