| Identification | Back Directory | [Name]
Tipiracil | [CAS]
183204-72-0 | [Synonyms]
CS-1684
Tipiracil
Tipiralacil
Tipiracil HCl
Tipiracil-001-HCl
Reaxys ID: 25670890
Tipiracil (hydrochloride)
Tipiracil hydrochloride(TPI)
Tipiracil-13C-15N2 HClTipiracil HCl
5-Chloro-6-(2-iminopyrrolidin-1-ylmethyl)uracil hydrochloride
5-chloro-6-[(2-iminopyrrolidin-1-yl)methyl]-1H-pyrimidine-2,4-dione,hydrochloride
2,4(1H,3H)-PyriMidinedione,5-chloro-6-[(2-iMino-1-pyrrolidinyl)Methyl] hydrochloride
5-Chloro-6-[(2-imino-1-pyrrolidinyl)methyl]-2,4(1H,3H)-pyrimidinedione monohydrochloride
2,4(1H,3H)-Pyrimidinedione,5-chloro-6-[(2-imino-1-pyrrolidinyl)methyl]-, hydrochloride (1:1)
5-Chloro-6-(2-iminopyrrolidin-1-ylmethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dione hydrochloride | [Molecular Formula]
C9H12Cl2N4O2 | [MDL Number]
MFCD01571384 | [MOL File]
183204-72-0.mol | [Molecular Weight]
279.123 |
| Chemical Properties | Back Directory | [Melting point ]
245℃ (decomposition) | [storage temp. ]
2-8°C | [solubility ]
DMSO (Slightly, Heated), Water (Slightly) | [form ]
powder | [color ]
white to beige | [Water Solubility ]
H2O: 5mg/mL, clear (warmed) | [Stability:]
Hygroscopic |
| Hazard Information | Back Directory | [Description]
Tipiracil (TPI) is a potent and competitive inhibitor of thymidine phosphorylase (TPase) with an IC50 value of 35 nM for human placental TPase.1 It is selective for TPase over other pyrimidine-metabolizing enzymes (IC50s = >1 mM for UPase, OPRTase, TK, and DPDase). TPI inhibits the phosphorolysis and degradation of trifluorothymidine (Item No. 21366), a cytotoxic nucleoside, in human breast and colon carcinoma tumor samples. Oral administration of TPI (12.5-50 mg/kg) enhances the anti-tumor activity of trifluorothymidine in a mouse AZ-521 stomach cancer xenograft model. Formulations containing TPI have been used for the treatment of metastatic colorectal cancer.2 | [Uses]
Tipiracil Hydrochloride serves as a treatment for metastatic colorectal cancer (mCRC). A thymidine phosphorylase inhibitor. | [Definition]
ChEBI: A hydrochloride obtained by combining tipiracil with one equivalent of hydrochloric acid. Used in combination with trifluridine, a nucleoside metabolic inhibitor, for treatment of advanced/relapsed unresectable colorectal cancer. | [Biochem/physiol Actions]
Tipiracil is an inhibitor of thymidine phosphorylase. Tipiracil is used in combination with trifluridine as TAS-102 for the treatment of refractory metastatic colorectal cancer. Tipiracil increases the bioavailability of trifluridine by blocking the enzyme that would otherwise protect the tumors by metabolizing trifluridine. | [target]
thymidine phosphorylase | [References]
1. tsukihara h1, nakagawa f2, sakamoto k et al. efficacy of combination chemotherapy using a novel oral chemotherapeutic agent, tas-102, together with bevacizumab, cetuximab, or panitumumab on human colorectal cancer xenografts. oncol rep. 2015 may;33(5):2135-42. 2. dexter dl, wolberg wh, ansfield fj, helson l and heidelberger c: the clinical pharmacology of 5-trifluoro-methyl-2'-deoxyuridine. cancer res 32: 247-253, 1972.3. fukushima m, suzuki n, emura t et al. structure and activity of specific inhibitors of thymidine phosphorylase to potentiate the function of antitumor 2'-deoxyribonucleosides. biochem pharmacol 59: 1227-1236, 2000. |
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