Tipiracil

Tipiracil
Clinical data
License data	EU EMA: by INN;
Pharmacokinetic data
Bioavailability	≥27%
Protein binding	<8%
Metabolism	10
Elimination half-life	2.1–2.4 hrs
Excretion	Faeces (50%), urine (27%)
Identifiers
	IUPAC name 5-Chloro-6-[(2-imino-1-pyrrolidinyl)methyl]-2,4(1H,3H)-pyrimidinedione;
CAS Number	183204-74-2 ; 183204-72-0 (HCl);
PubChem CID	6323266;
DrugBank	DB09343;
ChemSpider	13243748;
UNII	NGO10K751P;
KEGG	D10467;
ChEBI	CHEBI:90879 ;
ChEMBL	ChEMBL235668;
CompTox Dashboard (EPA)	DTXSID601025833 ;
Chemical and physical data
Formula	C9H11ClN4O2
Molar mass	242.66 g·mol−1
3D model (JSmol)	Interactive image;
Solubility in water	5 mg/mL (20 °C)
	SMILES C1CC(=N)N(C1)Cc2c(c(=O)[nH]c(=O)[nH]2)Cl;
	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); Key:QQHMKNYGKVVGCZ-UHFFFAOYSA-N;

Tipiracil is a drug used in the treatment of cancer. It is approved for use in form of the combination drug trifluridine/tipiracil for the treatment of unresectable advanced or recurrent colorectal cancer.

Tipiracil helps maintain the blood concentration of trifluridine by inhibiting the enzyme thymidine phosphorylase which metabolizes trifluridine.

Clinical data

License data	EU EMA: by INN
Pharmacokinetic data
Bioavailability	≥27%
Protein binding	<8%
Metabolism	10
Elimination half-life	2.1–2.4 hrs
Excretion	Faeces (50%), urine (27%)
Identifiers
IUPAC name 5-Chloro-6-[(2-imino-1-pyrrolidinyl)methyl]-2,4(1H,3H)-pyrimidinedione
CAS Number	183204-74-2 183204-72-0 (HCl)
PubChem CID	6323266
DrugBank	DB09343
ChemSpider	13243748
UNII	NGO10K751P
KEGG	D10467
ChEBI	CHEBI:90879^Y
ChEMBL	ChEMBL235668
CompTox Dashboard (EPA)	DTXSID601025833
Chemical and physical data
Formula	C₉H₁₁ClN₄O₂
Molar mass	242.66 g·mol⁻¹
3D model (JSmol)	Interactive image
Solubility in water	5 mg/mL (20 °C)
SMILES C1CC(=N)N(C1)Cc2c(c(=O)[nH]c(=O)[nH]2)Cl
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) Key:QQHMKNYGKVVGCZ-UHFFFAOYSA-N