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.


Chemical Structure

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Tipiracil HCl
CAS# 183204-72-0 (HCl)

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

Size Price Shipping out time Quantity
100mg USD 150 Same day
500mg USD 450 Same day
1g USD 650 Same day
5g USD 1450 Same day
10g USD 2250 Same day
100g USD 6950 Same day
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Pricing updated 2021-02-26. Prices are subject to change without notice.

Tipiracil HCl, purity > 98%, is in stock. Same day shipping after order is received.

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

Synonym: 5-CIMU; TAS-1-462, MA-1; Tipiracil HCl, TPI; TAS-102; Lonsurf.

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

Appearance:
White to off-white solid powder

Purity:
>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).

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).

HS Tariff Code:
2934.99.9001

Preparing Stock Solutions

The following data is based on the product molecular weight 279.12318 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: Kang C, Dhillon S, Deeks ED. Trifluridine/Tipiracil: A Review in Metastatic Gastric Cancer. Drugs. 2019 Sep;79(14):1583-1590. doi: 10.1007/s40265-019-01195-w. Review. Erratum in: Drugs. 2019 Sep 18;:. PubMed PMID: 31489588; PubMed Central PMCID: PMC6751145.

2: Trifluridine/tipiracil for colorectal cancer. Aust Prescr. 2018 Oct;41(5):171. doi: 10.18773/austprescr.2018.053. Epub 2018 Sep 11. Review. PubMed PMID: 30410217; PubMed Central PMCID: PMC6202293.

3: Vaflard P, Ederhy S, Torregrosa C, André T, Cohen R, Lopez-Trabada D. [Fluoropyrimidines cardiac toxicity: 5-fluorouracil, capecitabine, compound S-1 and trifluridine/tipiracil]. Bull Cancer. 2018 Jul - Aug;105(7-8):707-719. doi: 10.1016/j.bulcan.2018.05.005. Epub 2018 Jun 28. Review. French. PubMed PMID: 29960638.

4: Martinez-Perez J, Riesco-Martinez MC, Garcia-Carbonero R. The safety of trifluridine and tipiracil for the treatment of metastatic colorectal cancer. Expert Opin Drug Saf. 2018 Jun;17(6):643-650. doi: 10.1080/14740338.2018.1475557. Epub 2018 May 23. Review. PubMed PMID: 29745737.

5: Peeters M, Cervantes A, Moreno Vera S, Taieb J. Trifluridine/tipiracil: an emerging strategy for the management of gastrointestinal cancers. Future Oncol. 2018 Jul;14(16):1629-1645. doi: 10.2217/fon-2018-0147. Epub 2018 Apr 27. Review. PubMed PMID: 29701076.

6: Ramaekers BLT, Wolff R, van Giessen A, Pouwels X, Fayter D, Lang S, Armstrong N, Worthy G, Duffy S, Kleijnen J, Joore MA. Trifluridine-Tipiracil for Previously Treated Metastatic Colorectal Cancer: An Evidence Review Group Perspective of a NICE Single Technology Appraisal. Pharmacoeconomics. 2018 Mar;36(3):285-288. doi: 10.1007/s40273-017-0591-4. Review. PubMed PMID: 29177842; PubMed Central PMCID: PMC5834593.

7: Puthiamadathil JM, Weinberg BA. Emerging combination therapies for metastatic colorectal cancer - impact of trifluridine/tipiracil. Cancer Manag Res. 2017 Oct 3;9:461-469. doi: 10.2147/CMAR.S113320. eCollection 2017. Review. PubMed PMID: 29056855; PubMed Central PMCID: PMC5635852.

8: Sunakawa Y, Izawa N, Mizukami T, Horie Y, Hirakawa M, Arai H, Ogura T, Tsuda T, Nakajima TE. Profile of trifluridine/tipiracil hydrochloride in the treatment of metastatic colorectal cancer: efficacy, safety, and place in therapy. Onco Targets Ther. 2017 Sep 15;10:4599-4605. doi: 10.2147/OTT.S106101. eCollection 2017. Review. PubMed PMID: 28979148; PubMed Central PMCID: PMC5608085.

9: White T, Larson H, Minnella A, Hochster HS. Metastatic Colorectal Cancer: Management With Trifluridine/Tipiracil
. Clin J Oncol Nurs. 2017 Apr 1;21(2):E30-E37. doi: 10.1188/17.CJON.E30-E37. Review. PubMed PMID: 28315543.

10: Lee JJ, Chu E. Adherence, Dosing, and Managing Toxicities With Trifluridine/Tipiracil (TAS-102). Clin Colorectal Cancer. 2017 Jun;16(2):85-92. doi: 10.1016/j.clcc.2017.01.003. Epub 2017 Jan 25. Review. PubMed PMID: 28242161; PubMed Central PMCID: PMC5743195.

11: Burness CB, Duggan ST. Trifluridine/Tipiracil: A Review in Metastatic Colorectal Cancer. Drugs. 2016 Sep;76(14):1393-402. doi: 10.1007/s40265-016-0633-9. Review. PubMed PMID: 27568360.

12: Weinberg BA, Marshall JL, Salem ME. Trifluridine/tipiracil and regorafenib: new weapons in the war against metastatic colorectal cancer. Clin Adv Hematol Oncol. 2016 Aug;14(8):630-8. Review. PubMed PMID: 27487107.

13: Jeffers KD. Trifluridine/Tipiracil: Old Drug, New Tricks. J Adv Pract Oncol. 2016 May-Jun;7(4):449-453. Epub 2016 May 1. Review. PubMed PMID: 29226002; PubMed Central PMCID: PMC5679033.

14: Kitao H, Matsuoka K, Iimori M, Tokunaga E, Saeki H, Oki E, Miyamoto Y, Baba H, Maehara Y. [Antitumor Molecular Mechanism of Trifluridine and Tipiracil Hydrochloride (TAS-102: TFTD)]. Gan To Kagaku Ryoho. 2016 Jan;43(1):8-14. Review. Japanese. PubMed PMID: 26809521.



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