Tipiracil

Structural formula
General
Surname	Tipiracil
other names	5-chloro-6 - [(2-imino-1-pyrrolidinyl) methyl] -2,4 (1 H , 3 H ) -pyrimidinedione; SML1552;
Molecular formula	C 9 H 11 ClN 4 O 2
Brief description	white solid (hydrochloride)
External identifiers / databases
PubChem	6323266
ChemSpider	13243748
DrugBank	DB02631
Wikidata	Q21098889
properties
Molar mass	242,67 g · mol -1
solubility	soluble in water (hydrochloride)
safety instructions
GHS hazard labeling ; no classification available
GHS hazard labeling ; no classification available
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Tipiracil is a synthetically produced chemical compound from the group of uracil derivatives (“pyrimidinediones”) and an analogue of the nucleobase thymine . The compound is used in combination with trifluridine in chemotherapy for the treatment of colorectal cancer . As an inhibitor of the enzyme thymidine phosphorylase , tipiracil prevents the otherwise too rapid breakdown of trifluridine. On April 25, 2016, the European Commission approved trifluridine / tipiracil for the treatment of adult patients with metastatic colorectal cancer for whom previously available therapy options have been exhausted or for patients for whom these treatments are not suitable.

properties

The hydrochloride salt of tipiracil is used medicinally. Tipiracil hydrochloride is a crystalline, non-hygroscopic powder that dissolves easily in water and in buffer solutions in the range of pH 1–12.

Trade name

Fixed combination of Tipiracil with trifluridine: Lonsurf (pharmaceutical company: Servier ).

Web links

Public Assessment Report (EPAR) of the European Medicines Agency (EMA) for: Lonsurf

Individual evidence

↑ ^a ^b Data sheet Tipiracil hydrochloride ≥98% (HPLC) from Sigma-Aldrich , accessed on June 27, 2016 ( PDF ).
↑ This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.
↑ ^a ^b Taiho's Lonsurf (R) (trifluridine and tipiracil hydrochloride) Tablets Approved In Japan for Treatment of Advanced Metastatic Colorectal Cancer . March 24, 2014.
↑ Tanaka, K. Sakamoto, H. Okabe, A. Fujioka, K. Yamamura, F. Nakagawa, H. Nagase, T. Yokogawa, K. Oguchi, K. Ishida, A. Osada, H. Kazuno, Y. Yamada , K. Matsuo: Repeated oral dosing of TAS-102 confers high trifluridine incorporation into DNA and sustained antitumor activity in mouse models . In: Oncology Reports . 32, No. 6, 2014, pp. 2319–26. doi : 10.3892 / or.2014.3487 . PMID 25230742 . PMC 4240496 (free full text).
↑ oncotrends.de: Trifluridine / Tipiracil approved for previously treated patients with metastatic colorectal cancer in Europe - Oncotrends , accessed on June 27, 2016.

[Sigma-1] Data sheet Tipiracil hydrochloride ≥98% (HPLC) from Sigma-Aldrich , accessed on June 27, 2016 ( PDF ).

[NV-2] This substance has either not yet been classified with regard to its hazardousness or a reliable and citable source has not yet been found.

[prnewswire-3] Taiho's Lonsurf (R) (trifluridine and tipiracil hydrochloride) Tablets Approved In Japan for Treatment of Advanced Metastatic Colorectal Cancer . March 24, 2014.

[4] Tanaka, K. Sakamoto, H. Okabe, A. Fujioka, K. Yamamura, F. Nakagawa, H. Nagase, T. Yokogawa, K. Oguchi, K. Ishida, A. Osada, H. Kazuno, Y. Yamada , K. Matsuo: Repeated oral dosing of TAS-102 confers high trifluridine incorporation into DNA and sustained antitumor activity in mouse models . In: Oncology Reports . 32, No. 6, 2014, pp. 2319–26. doi : 10.3892 / or.2014.3487 . PMID 25230742 . PMC 4240496 (free full text).

[oncotrends.de-5] trends.de: Trifluridine / Tipiracil approved for previously treated patients with metastatic colorectal cancer in Europe - Oncotrends , accessed on June 27, 2016.