Tegafur
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MedKoo CAT#: 100805

CAS#: 17902-23-7

Description: Tegafur (INN) is a chemotherapeutic 5-FU prodrug used in the treatment of cancers. It is a component of tegafur-uracil. When metabolized, it becomes 5-FU. T egafur-uracil is a formulated therapeutic oral agent consisting of a combination of the 5-fluorouracil (5-FU) congener prodrug tegafur (tetrahydrofuranyl-5-fluorouracil) and uracil (1:4). The high concentration of uracil reversibly inhibits the uracil-reducing enzyme dihydropyrimidine dehydrogenase (DPD), thereby inhibiting first-pass DPD-mediated hepatic metabolism of the uracil analogue 5-FU and permitting administration of 5-FU as the orally bioavailable prodrug tegafur. Tegafur is bioactivated to 5-FU by liver microsomal cytochrome P450 enzymes.


Price and Availability

Size
Price

1g
USD 95
10g
USD 450
Size
Price

2g
USD 150
20g
USD 650
Size
Price

5g
USD 250
50g
USD 950

Tegafur, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week 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#: 100805
Name: Tegafur
CAS#: 17902-23-7
Chemical Formula: C8H9FN2O3
Exact Mass: 200.05972
Molecular Weight: 200.17
Elemental Analysis: C, 48.00; H, 4.53; F, 9.49; N, 14.00; O, 23.98


Synonym: oral fluorouraciluracil; Uracil and Ftorafur; Uracil and Tegafur; Uracil Foreign brand name: Uftoral; Abbreviation: UFT.

IUPAC/Chemical Name: 5-fluoro-1-(tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione

InChi Key: WFWLQNSHRPWKFK-UHFFFAOYSA-N

InChi Code: InChI=1S/C8H9FN2O3/c9-5-4-11(6-2-1-3-14-6)8(13)10-7(5)12/h4,6H,1-3H2,(H,10,12,13)

SMILES Code: O=C1NC(C(F)=CN1C2OCCC2)=O


Technical Data

Appearance:
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).

Harmonized System Code:
293490


Additional Information

 
The UFT combination was developed in the 1980s using tegafur, a pro-5FU drug. Tested and approved in various countries as a therapy for advanced colorectal cancer to replace 5FU, "patients appeared strongly to prefer treatment with UFT/LV over 5-FU/LV."  and has a low cost.  UFT is a first generation DIF, or DPD (DihydroPyrimidine Dehydrogenase) Inhibitory Flouropyrimidine drug. UFT is an oral agent with combines uracil, a competitive inhibitor of DPD, with the 5-FU prodrug tegafur in a 4:1 molar ratio. Excess uracil competes with 5-FU for DPD, thus inhibiting 5-FU catabolism. The tegafur is taken up by the cancer cells and breaks down into 5-FU, a substance that kills tumor cells. The uracil causes higher amounts of 5-FU to stay inside the cells and kill them. Ftorafur is a type of antimetabolite. The uracil has also been stated to help protect the gastrointestinal tract from 5-FU toxicity and the related metabolites, with less side effects than 5-FU and other 5-FU related (pro)drugs. Trials using UFT for cancer treatment include pancreatic cancer, colorectal cancer, liver cancer, adenocarcinoma of the lung and breast cancer with significant gains over existing treatments, with reduced side effects, improved quality of life, improved disease free survival and/or overall survival. In Japan, China and Korea, papers cite improved success utilizing UFT with cimetidine and/or PSK, both in trials with advanced colorectal cancer, and refractory individual cases of solid tumors with dismal prognoses. UFT has been administered on a continuous daily basis for 6 to 36 months at 300-400 mg per day in divided doses, in cycles of 5 days dosed at 300 mg/m2 per day, followed by the weekend off, or in cycles of 28 days dosed at 300-600 mg/m2 per day, followed by a week off. The low side effect profile of UFT allows continuous, extended treatments of several years. It is marketed by companies including Merck Serono, Korea United and Taiho, mostly in Asia, Europe, South America, Central America and South Africa. It is sold under a variety of names including: Tegafur-uracil, UFT, Ftorafur, Tefudex, Ufur and Uftoral. (source: http://en.wikipedia.org/wiki/Tegafur-uracil).
 
 


References

1: Kim J, Kim SH, Lee MG, Chung KY, Kim DS. Eccrine Squamous Syringometaplasia of Underlying Syringoma Associated with Tegafur/Gimeracil/Oteracil (TS-1). Acta Derm Venereol. 2015 Mar 13. doi: 10.2340/00015555-2092. [Epub ahead of print] PubMed PMID: 25766447.

2: Maolake A, Izumi K, Takahashi R, Itai S, Machioka K, Yaegashi H, Nohara T, Kitagawa Y, Kadono Y, Konaka H, Mizokami A, Namiki M. Efficacy of Tegafur-Uracil in Advanced Urothelial Cancer Patients after the Treatment Failure of Platinum-based Chemotherapy. Anticancer Res. 2015 Mar;35(3):1603-6. PubMed PMID: 25750316.

3: Suda H, Kochi M, Fujii M, Kanamori N, Mihara Y, Tamegai H, Funada T, Watanabe M, Takayama T. Complete response to uracil-tegafur alone in advanced rectal cancer. Hepatogastroenterology. 2014 Nov-Dec;61(136):2212-4. PubMed PMID: 25699353.

4: Sakaguchi I, Motohara T, Saito F, Takaishi K, Fukumatsu Y, Tohya T, Shibata S, Mimori H, Tashiro H, Katabuchi H. High-dose oral tegafur-uracil maintenance therapy in patients with uterine cervical cancer. J Gynecol Oncol. 2015 Feb 17. [Epub ahead of print] PubMed PMID: 25686399.

5: Wang HF, Lv JQ. The Clinical Evaluation of Tegafur Gimeracil Oteracil Combined with THP and DDP for Second-Line Treatment of Advanced Cardiac Carcinoma. Cell Biochem Biophys. 2015 Jan 25. [Epub ahead of print] PubMed PMID: 25618173.

6: Ishizuna K, Ninomiya J, Ogawa T, Kojima M, Tsuji E, Kawashima M, Nozaki M, Yamagishi H, Ueda Y. Effectiveness and safety of tegafur-gimeracil-oteracil potassium (TS-1) for metastatic breast cancer: a single-center retrospective study. Gan To Kagaku Ryoho. 2014 Dec;41(13):2577-82. PubMed PMID: 25596051.

7: Eguchi K, Oyama T, Tajima A, Abiko T, Sawafuji M, Horio H, Hashizume T, Matsutani N, Kato R, Nakayama M, Kawamura M, Kobayashi K. Intratumoral gene expression of 5-fluorouracil pharmacokinetics-related enzymes in stage I and II non-small cell lung cancer patients treated with uracil-tegafur after surgery: a prospective multi-institutional study in Japan. Lung Cancer. 2015 Jan;87(1):53-8. doi: 10.1016/j.lungcan.2014.10.013. Epub 2014 Nov 3. PubMed PMID: 25468199.

8: Inoue K, Sugiura F, Kogita A, Yoshioka Y, Sukegawa Y, Hida J, Okuno K. [Clinical trial of a seven-peptide vaccine and tegafur-uracil/leucovorin as combination therapy for advanced colorectal cancer]. Gan To Kagaku Ryoho. 2014 Oct;41(10):1276-9. Japanese. PubMed PMID: 25335716.

9: Shiono S, Harada M, Abiko M, Sato T, Takanashi I. [A case of recurrent lung cancer with bone metastases treated with tegafur-uracil and zoledronic acid for long-term survival]. Gan To Kagaku Ryoho. 2014 Jun;41(6):757-9. Japanese. PubMed PMID: 25129089.

10: Yamamiya I, Yoshisue K, Ishii Y, Yamada H, Yoshida K. Species variation in the enantioselective metabolism of tegafur to 5-fluorouracil among rats, dogs and monkeys. J Pharm Pharmacol. 2014 Dec;66(12):1686-97. doi: 10.1111/jphp.12304. Epub 2014 Aug 13. PubMed PMID: 25117829.