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T7205

Sigma-Aldrich

Tegafur

≥98% (HPLC), powder

Synonym(s):

5-Fluoro-1-(tetrahydro-2-furyl)uracil, Ftorafur, Tegafur

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About This Item

Empirical Formula (Hill Notation):
C8H9FN2O3
CAS Number:
17902-23-7
Molecular Weight:
200.17
EC Number:
241-846-2
MDL number:
MFCD00012351
UNSPSC Code:
12352200
PubChem Substance ID:
329826861
NACRES:
NA.77

Assay

≥98% (HPLC)

form

powder

color

white to off-white

mp

171-173 °C (lit.)

solubility

DMSO: >50 mg/mL

storage temp.

room temp

SMILES string

FC1=CN(C2CCCO2)C(=O)NC1=O

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)

InChI key

WFWLQNSHRPWKFK-UHFFFAOYSA-N

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Application

Tegafur has been used as an internal standard for the analysis of 5′DFCR (5′deoxyfluorocytidine) and 5′DFUR (5′deoxyfluorouridine) using HPLC techniques. Tegafur has also been used as an internal standard for the chromatographic assay of azidothymidine (AZT).

Biochem/physiol Actions

Tegafur is a pro-drug of 5-fluorouracil, an antimetabolite used as an antineoplastic agent. It has been used as adjuvant chemotherapy for curatively resected colorectal cancer therapy.

Preparation Note

Tegafur is soluble in DMSO at a concentration that is greater than 50 mg/ml.

Pictograms

Skull and crossbones
GHS06

Signal Word

Danger

Hazard Statements

H301 + H311 + H331

Hazard Classifications

Acute Tox. 3 Dermal - Acute Tox. 3 Inhalation - Acute Tox. 3 Oral

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Terence C Tang et al.
Neoplasia (New York, N.Y.), 12(3), 264-274 (2010-03-18)
Hepatocellular carcinoma (HCC) is an intrinsically chemotherapy refractory malignancy. Development of effective therapeutic regimens would be facilitated by improved preclinical HCC models. Currently, most models consist of subcutaneous human tumor transplants in immunodeficient mice; however, these do not reproduce the
Li-Feng Liu et al.
Chinese medical journal, 125(11), 1931-1935 (2012-08-14)
The pharmacokinetics of zidovudine (AZT) are possibly influenced by weight, age, sex, liver and renal functions, severity of disease, and ethnicity. Currently, little information is available on the steady-state pharmacokinetics of AZT in Chinese HIV-infected patients. The current study aimed
Muhammad Wasif Saif et al.
Expert opinion on investigational drugs, 18(3), 335-348 (2009-02-27)
S-1 is an oral fluoropyrimidine that is designed to improve the antitumor activity of 5-fluorouracil (5-FU) concomitantly with an intent to reduce its toxicity. S-1 consists of tegafur, a prodrug of 5-FU combined with two 5-FU biochemical modulators:5-chloro-2,4-dihydroxypyridine (gimeracil or
P M Hoff
Investigational new drugs, 18(4), 331-342 (2000-11-18)
Protracted intravenous regimens of fluorouracil (5-FU) may be superior and better tolerated than intravenous bolus dosing. An effective oral regimen would allow a protracted course of 5-FU without the need for central venous lines and the associated increase in complications.
Thierry Besnard et al.
Journal of chromatography. B, Analytical technologies in the biomedical and life sciences, 870(1), 117-120 (2008-06-20)
The 5FU prodrug capecitabine undergoes a 3-step enzymatic conversion, including the conversion of 5'DFRC into 5'DFUR by cytidine deaminase (CDA). The presence of CDA activity in blood led us to analyze the possible ex vivo conversion of 5'DFCR into 5'DFUR
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