tipiracil (CHEBI:90879)

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ChEBI Name	tipiracil

ChEBI ID	CHEBI:90879

Definition	A member of the class of pyrimidones that is uracil substituted by chloro and (2-iminopyrrolidin-1-yl)methyl groups at positions 5 and 6 respectively. Used (as the hydrochloride salt) in combination with trifluridine, a nucleoside metabolic inhibitor, for treatment of advanced/relapsed unresectable colorectal cancer.

Stars	This entity has been manually annotated by the ChEBI Team.

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Formula

C9H11ClN4O2

Net Charge

Average Mass

242.663

Monoisotopic Mass

242.05705

InChI

InChI=1S/C9H11ClN4O2/c10-7-5(12-9(16)13-8(7)15)4-14-3-1-2-6(14)11/h11H,1-4H2,(H2,12,13,15,16)

InChIKey

QQHMKNYGKVVGCZ-UHFFFAOYSA-N

SMILES

C1(=C(C(NC(N1)=O)=O)Cl)CN2C(CCC2)=N

Roles Classification
Biological Role(s):	EC 2.4.2.4 (thymidine phosphorylase) inhibitor An EC 2.4.2.* (pentosyltransferase) inhibitor that interferes with the action of thymidine phosphorylase (EC 2.4.2.4).

Application(s):	antineoplastic agent A substance that inhibits or prevents the proliferation of neoplasms.

ChEBI Ontology
Outgoing	tipiracil (CHEBI:90879) has functional parent uracil (CHEBI:17568) tipiracil (CHEBI:90879) has role antineoplastic agent (CHEBI:35610) tipiracil (CHEBI:90879) has role EC 2.4.2.4 (thymidine phosphorylase) inhibitor (CHEBI:90878) tipiracil (CHEBI:90879) is a carboxamidine (CHEBI:35359) tipiracil (CHEBI:90879) is a organochlorine compound (CHEBI:36683) tipiracil (CHEBI:90879) is a pyrimidone (CHEBI:38337) tipiracil (CHEBI:90879) is a pyrrolidines (CHEBI:38260) tipiracil (CHEBI:90879) is conjugate base of tipiracil(1+) (CHEBI:90880)

Incoming	tipiracil(1+) (CHEBI:90880) is conjugate acid of tipiracil (CHEBI:90879)

IUPAC Name

5-chloro-6-[(2-iminopyrrolidin-1-yl)methyl]pyrimidine-2,4(1H,3H)-dione

INN	Source
tipiracil	ChemIDplus

Last Modified

22 February 2017