Ketcher 01081617042D 1   1.00000     0.00000     0

 16 17  0     0  0            999 V2000
   11.2913   -5.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   11.2913   -4.4280    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1494   -3.9234    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.0579   -4.4280    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.0579   -5.4376    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   12.1494   -5.9424    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
   13.9161   -5.9424    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   12.1494   -2.9138    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   10.4332   -3.9234    0.0000 Cl  0  0  0  0  0  0  0  0  0  0  0  0
   10.4332   -5.9424    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.5750   -5.4376    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
    8.6664   -5.8414    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.0102   -5.1347    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4645   -4.2765    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    9.4740   -4.4785    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    8.4665   -6.8168    0.0000 N   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  2  0     0  0
  2  3  1  0     0  0
  3  4  1  0     0  0
  4  5  1  0     0  0
  5  6  1  0     0  0
  1  6  1  0     0  0
  5  7  2  0     0  0
  3  8  2  0     0  0
  2  9  1  0     0  0
  1 10  1  0     0  0
 10 11  1  0     0  0
 11 12  1  0     0  0
 12 13  1  0     0  0
 13 14  1  0     0  0
 14 15  1  0     0  0
 11 15  1  0     0  0
 12 16  2  0     0  0
M  END
> <ID>
CHEBI:90879

> <NAME>
tipiracil

> <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.

> <STAR>
3

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

> <INN>
tipiracil

> <FORMULA>
C9H11ClN4O2

> <MASS>
242.663

> <MONOISOTOPIC_MASS>
242.05705

> <CHARGE>
0

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

> <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

> <CAS_REGISTRY_NUMBER>
183204-74-2

> <REAXYS_REGISTRY_NUMBER>
9272220

> <CHEMIDPLUS>
183204-74-2

> <WIKIPEDIA_ACCESSION>
Tipiracil

> <PUBMED_CITATION>
24562648; 25230742; 25750295; 25812794; 25900515; 25901475; 25970050; 26084259; 26163340; 26197742; 26254349; 26370544; 26428513; 26509228; 26535019; 26609205; 26616466; 26677869; 26722024; 26723516; 26730280

$$$$