TAS-102 (Trifluridine/Tipiracil HCl)

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MedKoo CAT#: 205641

CAS#: 733030-01-8

Description: TAS-102 is an investigational drug candidate for metastatic colorectal cancer. It contains trifluridine (TFT) and Tipiracil hydrochloride (TTP) in a molar ratio of 1;0.5. Trifluridine is a nucleoside analog, and tipiracil hydrochloride is a thymidine phosphorylase inhibitor, which prevents rapid metabolism of trifluiridine, increasing the bioavailability of trifluiridine. After oral administration of TAS-102, TFT is phosphorylated to the active monophosphate form TF-TMP, which binds covalently to the active site of thymidylate synthase, thereby reducing the nucleotide pool levels required for DNA replication. Furthermore, the triphosphate form TF-TTP can be incorporated into DNA, which induces DNA fragmentation and leads to the inhibition of tumor growth. TPI exhibits a dual effect: 1) an anti-angiogenic effect mediated through the inhibition of thymidine phosphorylase, which plays an important role in nucleotide metabolism and a variety of development processes, including angiogenesis, 2) increased bioavailability of the normally short-lived antimetabolite TFT by preventing its degradation into the inactive form trifluorothymine (TF-Thy). The synergistic effect of the components in TAS-102 may demonstrate antitumor activity in 5-FU-resistant cancer cells.

Chemical Structure

TAS-102 (Trifluridine/Tipiracil HCl)
CAS# 733030-01-8

Theoretical Analysis

MedKoo Cat#: 205641
Name: TAS-102 (Trifluridine/Tipiracil HCl)
CAS#: 733030-01-8
Chemical Formula: C19H23Cl2F3N6O7
Exact Mass:
Molecular Weight: 575.3232
Elemental Analysis: C, 39.67; H, 4.03; Cl, 12.32; F, 9.91; N, 14.61; O, 19.47

Size Price Shipping out time Quantity
25mg USD 150 Same day
50mg USD 250 Same day
100mg USD 450 Same day
200mg USD 650 Same day
500mg USD 850 Same day
1g USD 1250 Same day
2g USD 2050 2 Weeks
5g USD 3650 2 Weeks
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Pricing updated 2021-03-01. Prices are subject to change without notice.

TAS-102 (Trifluridine / tipiracil HCl), purity > 98%, is in stock. The same day shipping after order is received.

Related CAS #: 733030-01-8   (183204-72-0 (Tipiracil HCl)   70-00-8 (Trifluridine)    

Synonym: TAS102, TAS-102, TAS 102, Trifluridine/tipiracil hydrochloride

IUPAC/Chemical Name: 4-hydroxy-1-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-5-(trifluoromethyl)pyrimidin-2(1H)-one compound with 5-chloro-6-((2-iminopyrrolidin-1-yl)methyl)pyrimidine-2,4-diol (1:1) hydrochloride


InChi Code: InChI=1S/C10H11F3N2O5.C9H11ClN4O2.ClH/c11-10(12,13)4-2-15(9(19)14-8(4)18)7-1-5(17)6(3-16)20-7;10-7-5(12-9(16)13-8(7)15)4-14-3-1-2-6(14)11;/h2,5-7,16-17H,1,3H2,(H,14,18,19);11H,1-4H2,(H2,12,13,15,16);1H/t5-,6+,7+;;/m0../s1

SMILES Code: O=C1NC(C(C(F)(F)F)=CN1[C@@H]2O[C@H](CO)[C@@H](O)C2)=O.O=C3NC(C(Cl)=C(CN4C(CCC4)=N)N3)=O.[H]Cl

Solid powder

>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Soluble in DMSO, not in water

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:

Preparing Stock Solutions

The following data is based on the product molecular weight 575.3232 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Select a batch to recalculate based on the batch molecular weight:
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL

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  1: Nukatsuka M, Nakagawa F, Takechi T. Efficacy of Combination Chemotherapy Using a Novel Oral Chemotherapeutic Agent, TAS-102, with Oxaliplatin on Human Colorectal and Gastric Cancer Xenografts. Anticancer Res. 2015 Sep;35(9):4605-15. PubMed PMID: 26254349.

2: Doi T, Yoshino T, Fuse N, Boku N, Yamazaki K, Koizumi W, Shimada K, Takinishi Y, Ohtsu A. Phase I study of TAS-102 and irinotecan combination therapy in Japanese patients with advanced colorectal cancer. Invest New Drugs. 2015 Jul 12. [Epub ahead of print] PubMed PMID: 26163340.

3: Yamashita F, Komoto I, Oka H, Kuwata K, Takeuchi M, Nakagawa F, Yoshisue K, Chiba M. Exposure-dependent incorporation of trifluridine into DNA of tumors and white blood cells in tumor-bearing mouse. Cancer Chemother Pharmacol. 2015 Aug;76(2):325-33. doi: 10.1007/s00280-015-2805-9. Epub 2015 Jun 18. PubMed PMID: 26084259.

4: Drug Improves Survival in Refractory Colorectal Cancer. Cancer Discov. 2015 Jul;5(7):OF3. doi: 10.1158/2159-8290.CD-NB2015-077. Epub 2015 Jun 4. PubMed PMID: 26045012.

5: Cleghorn S. TAS-102 for metastatic refractory colorectal cancer. Lancet Oncol. 2015 Jul;16(7):e314. doi: 10.1016/S1470-2045(15)70246-9. Epub 2015 May 21. PubMed PMID: 26004375.

6: Mayor S. TAS-102 prolongs overall survival in refractory colorectal cancer, study shows. BMJ. 2015 May 14;350:h2620. doi: 10.1136/bmj.h2620. PubMed PMID: 25979138.

7: Mayer RJ, Van Cutsem E, Falcone A, Yoshino T, Garcia-Carbonero R, Mizunuma N, Yamazaki K, Shimada Y, Tabernero J, Komatsu Y, Sobrero A, Boucher E, Peeters M, Tran B, Lenz HJ, Zaniboni A, Hochster H, Cleary JM, Prenen H, Benedetti F, Mizuguchi H, Makris L, Ito M, Ohtsu A; RECOURSE Study Group. Randomized trial of TAS-102 for refractory metastatic colorectal cancer. N Engl J Med. 2015 May 14;372(20):1909-19. doi: 10.1056/NEJMoa1414325. PubMed PMID: 25970050.

8: Aiba K, Natori K. [Advance of salvage chemotherapy for colorectal cancer]. Gan To Kagaku Ryoho. 2015 Apr;42(4):394-7. Japanese. PubMed PMID: 25963685.

9: Sakamoto K, Yokogawa T, Ueno H, Oguchi K, Kazuno H, Ishida K, Tanaka N, Osada A, Yamada Y, Okabe H, Matsuo K. Crucial roles of thymidine kinase 1 and deoxyUTPase in incorporating the antineoplastic nucleosides trifluridine and 2'-deoxy-5-fluorouridine into DNA. Int J Oncol. 2015 Jun;46(6):2327-34. doi: 10.3892/ijo.2015.2974. Epub 2015 Apr 20. PubMed PMID: 25901475; PubMed Central PMCID: PMC4441292.

10: Takahashi K, Yoshisue K, Chiba M, Nakanishi T, Tamai I. Involvement of Concentrative Nucleoside Transporter 1 in Intestinal Absorption of Trifluridine Using Human Small Intestinal Epithelial Cells. J Pharm Sci. 2015 Sep;104(9):3146-53. doi: 10.1002/jps.24455. Epub 2015 Apr 21. PubMed PMID: 25900515.

11: Tsukihara H, Nakagawa F, Sakamoto K, Ishida K, Tanaka N, Okabe H, Uchida J, Matsuo K, Takechi T. 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. doi: 10.3892/or.2015.3876. Epub 2015 Mar 23. PubMed PMID: 25812794; PubMed Central PMCID: PMC4391594.

12: Lee HJ, Oh SJ, Lee EJ, Chung JH, Kim Y, Ryu JS, Kim SY, Lee SJ, Moon DH, Kim TW. Positron emission tomography imaging of human colon cancer xenografts in mice with [18F]fluorothymidine after TAS-102 treatment. Cancer Chemother Pharmacol. 2015 May;75(5):1005-13. doi: 10.1007/s00280-015-2718-7. Epub 2015 Mar 17. PubMed PMID: 25776904.

13: Nukatsuka M, Nakagawa F, Saito H, Sakata M, Uchida J, Takechi T. Efficacy of combination chemotherapy using a novel oral chemotherapeutic agent, TAS-102, with irinotecan hydrochloride on human colorectal and gastric cancer xenografts. Anticancer Res. 2015 Mar;35(3):1437-45. PubMed PMID: 25750295.

14: Matsuoka K, Iimori M, Niimi S, Tsukihara H, Watanabe S, Kiyonari S, Kiniwa M, Ando K, Tokunaga E, Saeki H, Oki E, Maehara Y, Kitao H. Trifluridine Induces p53-Dependent Sustained G2 Phase Arrest with Its Massive Misincorporation into DNA and Few DNA Strand Breaks. Mol Cancer Ther. 2015 Apr;14(4):1004-13. doi: 10.1158/1535-7163.MCT-14-0236. Epub 2015 Feb 19. PubMed PMID: 25700705.

15: Kotani D, Fukuoka S, Yoshino T. [Efficacy of TAS-102]. Gan To Kagaku Ryoho. 2015 Jan;42(1):1-5. Review. Japanese. PubMed PMID: 25596673.

16: Yasui H, Tsurita G, Imai K. DNA synthesis inhibitors for the treatment of gastrointestinal cancer. Expert Opin Pharmacother. 2014 Nov;15(16):2361-72. doi: 10.1517/14656566.2014.958074. Epub 2014 Sep 26. Review. PubMed PMID: 25256052.

17: Tanaka N, Sakamoto K, Okabe H, Fujioka A, Yamamura K, Nakagawa F, Nagase H, Yokogawa T, Oguchi K, Ishida K, Osada A, Kazuno H, Yamada Y, Matsuo K. Repeated oral dosing of TAS-102 confers high trifluridine incorporation into DNA and sustained antitumor activity in mouse models. Oncol Rep. 2014 Dec;32(6):2319-26. doi: 10.3892/or.2014.3487. Epub 2014 Sep 17. PubMed PMID: 25230742; PubMed Central PMCID: PMC4240496.

18: El-Naggar M, Ebbing E, Bijnsdorp I, van den Berg J, Peters GJ. Radiosensitization by thymidine phosphorylase inhibitor in thymidine phosphorylase negative and overexpressing bladder cancer cell lines. Nucleosides Nucleotides Nucleic Acids. 2014;33(4-6):413-21. doi: 10.1080/15257770.2014.892127. PubMed PMID: 24940699.

19: Peters GJ. Novel developments in the use of antimetabolites. Nucleosides Nucleotides Nucleic Acids. 2014;33(4-6):358-74. doi: 10.1080/15257770.2014.894197. Review. PubMed PMID: 24940694.

20: Utsugi T. New challenges and inspired answers for anticancer drug discovery and development. Jpn J Clin Oncol. 2013 Oct;43(10):945-53. doi: 10.1093/jjco/hyt131. Epub 2013 Sep 5. PubMed PMID: 24014883; PubMed Central PMCID: PMC3787805.

Additional Information

Since the synthesis of 5-Fluorouracil (5-FU) in 1957, fluoropyrimidines have been a very useful tool in the treatment of many types of cancer. Due to the drawbacks of 5-FU therapy, such as having to be administered over long periods of time via intravenous infusion and the development of resistance in tumors, the need for more convenient and efficacious fluoropyrimidine therapy has been desired. The fluoropyrimidine component of TAS-102, trifluridine, was first synthesized in 1964 by Heidelberger et al. By the late 1960s, Phase I and Phase II clinical trials of intravenous trifluridine alone initially proved to be disappointing. Its pharmacokinetic profile during these clinical trials showed that the drug exhibited a very short half-life while in serum (12 minutes post-injection). In response to its pharmacokinetic properties, adjustments in the dosing regimen demonstrated significant therapeutic benefits in patients with breast cancer and colon cancer; with this new regimen, doses would be given every three hours to total a daily amount of 2.5 mg/kg/day for 8 to 13 days, and as a result, eight out of 23 breast cancer patients were reported to have a therapeutic response while one in six patients with colon cancer showed a near complete response to therapy. Success of trifluridine as an effective anti-cancer agent was short lived, however, due to rapid tumor recurrence upon regression of therapy. Trifluridine therapy in oncology was thus halted. Researchers later found out that trifluridine, when taken orally, was broken down into the inactive metabolites 5-trifluoromethyluracil and 5-trifluoromethyl-2,4(1H,3,H)-pyrimidinedione (FTY) during its extensive first pass metabolism in the liver via the enzyme thymidine phosphorylase (TP). It was then hypothesized that orally administered FTD concentrations could be increased and maintained if the drug was given with a thymidine phosphorylase inhibitor (TPI). (from https://en.wikipedia.org/wiki/TAS-102)