Description
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.
Chemical properties
| Chemical formula | Net charge | Average mass |
|---|---|---|
| C9H11ClN4O2 | 0 | 242.663 |
Nomenclature
| IUPAC | SMILES | InChI | InChIKey |
|---|---|---|---|
| 5-chloro-6-[(2-iminopyrrolidin-1-yl)methyl]pyrimidine-2,4(1H,3H)-dione | C1(=C(C(NC(N1)=O)=O)Cl)CN2C(CCC2)=N | 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) | QQHMKNYGKVVGCZ-UHFFFAOYSA-N |
Citations
- 2015. New Medical Devices. P & T : A Peer-reviewed Journal For Formulary Management. 40(10).
- Aimono, Y, et al. 2015. [Initial Evaluation of the Efficacy and Safety of Tablets Containing Trifluridine and Tipiracil Hydrochloride--Safety Measures Devised by a Multidisciplinary Team Including a Pharmaceutical Outpatient Clinic]. Gan To Kagaku Ryoho. Cancer & Chemotherapy. 42(7).
- Bendell, JC, et al. 2015. Phase 1 study of oral TAS-102 in patients with refractory metastatic colorectal cancer. Cancer Chemotherapy and Pharmacology. 76(5).
- Chen, J, et al. 2016. TAS-102 an Emerging Oral Fluoropyrimidine. Anticancer Research. 36(1).
- Doi, T, et al. 2015. Phase I study of TAS-102 and irinotecan combination therapy in Japanese patients with advanced colorectal cancer. Investigational New Drugs. 33(5).
- Gohil, K, et al. 2015. Pharmaceutical Approval Update. P & T : A Peer-reviewed Journal For Formulary Management. 40(11).
- Kotani, D, et al. 2016. Safety and Efficacy of Trifluridine/Tipiracil Monotherapy in Clinical Practice for Patients With Metastatic Colorectal Cancer: Experience at a Single Institution. Clinical Colorectal Cancer. 15(3).
- Lee, SJ, et al. 2014. Thymidine phosphorylase influences [(18)F]fluorothymidine uptake in cancer cells and patients with non-small cell lung cancer. European Journal of Nuclear Medicine and Molecular Imaging. 41(7).
- Lenz, HJ, et al. 2015. TAS-102, a novel antitumor agent: a review of the mechanism of action. Cancer Treatment Reviews. 41(9).
- Mayer, RJ, et al. 2015. Randomized trial of TAS-102 for refractory metastatic colorectal cancer. The New England Journal of Medicine. 372(20).
- Miyamoto, Y, et al. 2015. A novel antimetabolite: TAS-102 for metastatic colorectal cancer. Expert Review of Clinical Pharmacology. 9(3).
- Nukatsuka, M, et al. 2015. Efficacy of combination chemotherapy using a novel oral chemotherapeutic agent, TAS-102, with irinotecan hydrochloride on human colorectal and gastric cancer xenografts. Anticancer Research. 35(3).
- Nukatsuka, M, et al. 2015. Efficacy of Combination Chemotherapy Using a Novel Oral Chemotherapeutic Agent, TAS-102, with Oxaliplatin on Human Colorectal and Gastric Cancer Xenografts. Anticancer Research. 35(9).
- Sakamoto, K, et al. 2015. Crucial roles of thymidine kinase 1 and deoxyUTPase in incorporating the antineoplastic nucleosides trifluridine and 2'-deoxy-5-fluorouridine into DNA. International Journal of Oncology. 46(6).
- Salvatore, L, et al. 2015. TAS-102 for the treatment of metastatic colorectal cancer. Expert Review of Anticancer Therapy. 15(11).
- Takahashi, K, et al. 2015. Involvement of Concentrative Nucleoside Transporter 1 in Intestinal Absorption of Trifluridine Using Human Small Intestinal Epithelial Cells. Journal of Pharmaceutical Sciences. 104(9).
- Tanaka, N, et al. 2014. Repeated oral dosing of TAS-102 confers high trifluridine incorporation into DNA and sustained antitumor activity in mouse models. Oncology Reports. 32(6).
- Tsukihara, H, et al. 2015. Efficacy of combination chemotherapy using a novel oral chemotherapeutic agent, TAS-102, together with bevacizumab, cetuximab, or panitumumab on human colorectal cancer xenografts. Oncology Reports. 33(5).
- Uboha, N, et al. 2015. TAS-102: a novel antimetabolite for the 21st century. Future Oncology (London, England). 12(2).
- Yamashita, F, et al. 2015. Exposure-dependent incorporation of trifluridine into DNA of tumors and white blood cells in tumor-bearing mouse. Cancer Chemotherapy and Pharmacology. 76(2).
- Zaniboni, A, et al. 2016. New active drugs for the treatment of advanced colorectal cancer. World Journal of Gastrointestinal Surgery. 7(12).