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F8791

Sigma-Aldrich

5-Fluoro-5′-deoxyuridine

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
EC Number:
221-440-1
MDL number:
MFCD00866530
UNSPSC Code:
12352200
PubChem Substance ID:
24278444
NACRES:
NA.77

Quality Level

200

SMILES string

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

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

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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_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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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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
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
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
G J Peters et al.
International journal of cancer, 54(3), 450-455 (1993-05-28)
Malignant activation of oncogenes ras or trk is implicated in a number of solid tumors and leukemias. We determined the chemosensitivity profile of wild-type mouse NIH-3T3 fibroblasts, and that of NIH-3T3 lines transformed by the H-ras (S2-721) and trk (106-632)
Linda Connelly et al.
Breast cancer research : BCR, 13(4), R83-R83 (2011-09-03)
Metastasis from primary tumor to the lungs is a major cause of the mortality associated with breast cancer. Both immune and inflammatory responses impact whether circulating mammary tumor cells successfully colonize the lungs leading to established metastases. Nuclear factor -kappaB
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