Tipiracil HCl
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MedKoo CAT#: 206037

CAS#: 183204-72-0 (HCl)

Description: Tipiralacil, also known as TPI, is a thymidine phosphorylase inhibitor (TPI). Tipiracil is one of the active components in TAS-102, which is an anticancer drug candidate currently in clinical trials. TAS-102 consists of the cytotoxin Trifluridine and the thymidine phosphorylase inhibitor (TPI) tipiracil. Trifluridine is incorporated into DNA during DNA synthesis and inhibits tumor cell growth. Tipiracil protects trifluridine from being broken down when taken orally. TAS-102 was approved in Japan in 2015.


Price and Availability

Size
Price

100mg
USD 150
5g
USD 1450
Size
Price

500mg
USD 450
10g
USD 2250
Size
Price

1g
USD 650
100g
USD 6950

Tipiracil HCl, purity > 98%, is in stock. Same day shipping after order is received. Delivery time: overnight (USA/Canada); 3-5 days (worldwide). Shipping fee: from $30.00 (USA); from $45.00 (Canada); from $70.00 (international).


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206037
Name: Tipiracil HCl
CAS#: 183204-72-0 (HCl)
Chemical Formula: C9H12Cl2N4O2
Exact Mass: 278.03373
Molecular Weight: 279.12318
Elemental Analysis: C, 38.73; H, 4.33; Cl, 25.40; N, 20.07; O, 11.46


Related CAS #: 183204-72-0 (HCl)   183204-74-2 (free base)  

Synonym: TAS-1-462, MA-1; Tipiracil HCl, TPI; TAS-102.

IUPAC/Chemical Name: 5-chloro-6-((2-iminopyrrolidin-1-yl)methyl)pyrimidine-2,4(1H,3H)-dione hydrochloride

InChi Key: KGHYQYACJRXCAT-UHFFFAOYSA-N

InChi Code: InChI=1S/C9H11ClN4O2.ClH/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);1H

SMILES Code: O=C1NC(C(Cl)=C(CN2C(CCC2)=N)N1)=O.[H]Cl


Technical Data

Appearance:
White to off-white solid powder

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

Safety Data Sheet (MSDS):

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).

Solubility:
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).

Harmonized System Code:
293490


Additional Information

  
 
 
 


References

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: Aimono Y, Kamoshida T, Sakamoto R, Nemoto M, Saito Y, Aoyama Y, Maruyama T. [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. 2015 Jul;42(7):817-20. Japanese. PubMed PMID: 26197742.

3: 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.

4: 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.

5: 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.

6: 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.

7: 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.

8: 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.

9: 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.

10: 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.

11: Lee SJ, Yeo JS, Lee HJ, Lee EJ, Kim SY, Jang SJ, Lee JJ, Ryu JS, Moon DH. Thymidine phosphorylase influences [(18)F]fluorothymidine uptake in cancer cells and patients with non-small cell lung cancer. Eur J Nucl Med Mol Imaging. 2014 Jul;41(7):1327-35. doi: 10.1007/s00259-014-2712-z. Epub 2014 Feb 22. PubMed PMID: 24562648.