F8791

5-Fluoro-5′-deoxyuridine

Name: 5-Fluoro-5′-deoxyuridine
Brand: SIGMA

Synonym(s):

Doxifluridine, 5′dFUrd

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About This Item

Empirical Formula (Hill Notation):

C₉H₁₁FN₂O₅

CAS Number:

3094-09-5

Molecular Weight:

246.19

NACRES:

NA.77

PubChem Substance ID:

24278444

UNSPSC Code:

12352200

EC Number:

221-440-1

MDL number:

MFCD00866530

Key Documents

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InChI

1S/C9H11FN2O5/c1-3-5(13)6(14)8(17-3)12-2-4(10)7(15)11-9(12)16/h2-3,5-6,8,13-14H,1H3,(H,11,15,16)/t3-,5-,6-,8-/m1/s1

InChI key

ZWAOHEXOSAUJHY-ZIYNGMLESA-N

SMILES string

C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=C(F)C(=O)NC2=O

Quality Level

200

Related Categories

Bioactive Small Molecule Inhibitors

Biochem/physiol Actions

Doxifluridine is an antitumor agent efficient in tumors, cell lines or in fibroblasts transformed by H-ras or trk oncogenes. Possesses anticachectic activity which is independent of its antiproliferative activity.

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number

0000463711

0000404421

0000202370

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Synthesis and discovery of N-carbonylpyrrolidine- or N-sulfonylpyrrolidine-containing uracil derivatives as potent human deoxyuridine triphosphatase inhibitors.

Hitoshi Miyakoshi et al.

Journal of medicinal chemistry, 55(7), 2960-2969 (2012-03-13)

Recently, deoxyuridine triphosphatase (dUTPase) has emerged as a potential target for drug development as part of a new strategy of 5-fluorouracil-based combination chemotherapy. We have initiated a program to develop potent drug-like dUTPase inhibitors based on structure-activity relationship (SAR) studies

Reliability of tumor primary cultures as a model for drug response prediction: expression profiles comparison of tissues versus primary cultures from colorectal cancer patients.

Gregory Lucien Bellot et al.

Journal of cancer research and clinical oncology, 138(3), 463-482 (2011-12-22)

Since primary tumor cells from patients have been used as a model for assessment of drug response for individual patients, this study aims to evaluate the reliability of such a model in colorectal cancer (CRC) in predicting the response of

Metronomic doxifluridine chemotherapy combined with the anti-angiogenic agent TNP-470 inhibits the growth of human uterine carcinosarcoma xenografts.

Yasuko Naganuma et al.

Cancer science, 102(8), 1545-1552 (2011-06-03)

Uterine carcinosarcoma is a highly aggressive gynecological neoplasm that responds poorly to conventional chemotherapy and radiotherapy. Metronomic chemotherapy is accepted as a new approach for cancer treatment, and its underlying mechanism seems to involve the suppression of angiogenesis. However, the

Inhibition of EGFR phosphorylation in a panel of human breast cancer cells correlates with synergistic interactions between gefitinib and 5'-DFUR, the bioactive metabolite of Xeloda.

Maria Ait-Tihyaty et al.

Breast cancer research and treatment, 133(1), 217-226 (2011-09-15)

Capecitabine (Xeloda) is a prodrug of 5-FU used in the clinical management of advanced breast cancer. It is metabolized first in the liver by carboxylesterases to generate 5'-deoxy-5-flurocytidine ribose (5'-DFCR), which is subsequently converted to 5'-deoxy-5-fluorouridine ribose (5'-DFUR) by cytidine

Anticachectic activity of 5'-deoxy-5-fluorouridine in a murine tumor cachexia model, colon 26 adenocarcinoma.

Y Tanaka et al.

Cancer research, 50(15), 4528-4532 (1990-08-01)

Murine colon 26 adenocarcinoma causes a progressive weight loss and physiological changes associated with cachexia when it grows to a certain size. By the use of this tumor model several types of cytostatics were examined for their ability to alleviate

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5-Fluoro-5′-deoxyuridine

Select a Size

About This Item

Key Documents

Properties

InChI

InChI key

SMILES string

Quality Level

Related Categories

Description

Biochem/physiol Actions

Safety Information

Storage Class

wgk

flash_point_f

flash_point_c

ppe

Documentation

Certificates of Analysis (COA)

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Peer Reviewed Papers

Protocols and Articles

Articles

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