DoxifluridineA fluorinated pyrimidine with cytostatic activity

Doxifluridine (CAS 3094-09-5)

Doxifluridine | CAS 3094-09-5 is rated 5.0 out of 5 by 1.
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Synonym: Furtulon, Flutron, doxyfluridine, Doxifluridina, Doxifluridinum 5'-Doxifluridine, 5'dFUrd, 5-fluoro-5'-deoxyuridine
Application: A fluorinated pyrimidine with cytostatic activity
CAS Number: 3094-09-5
Purity: ≥99%
Molecular Weight: 246.19
Molecular Formula: C9H11FN2O5
* Refer to Certificate of Analysis for lot specific data (including water content).
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Doxifluridine is a fluorinated pyrimidine nucleoside, which displays cytostatic activity. It is known that this compound is the inactive form of 5-Fluorouridine (sc-221027), which is converted by enzymes in vivo . Studies indicate that 5-Fluorouridine causes apoptosis in HCT-116 colorectal carcinoma cells and along with cDNA microarray is a useful tool in studying the expression of 1,200 genes during apoptosis. It is believed that 5-Fluorouridine induces cytotoxicity in cells not only by inhibition of RNA synthesis and processing, but through other unknown mechanisms as well. Doxifluridine is an activator of NF κ B in macrophages.


References

1. Schmittgen, T.D., et al. 2005. Int. J. Oncol. 27: 297-306. PMID: 16010409

Physical State :
Solid
Solubility :
Soluble in water (50 mg/ml), DMSO (49 mg/ml at 25° C), ethanol (<1 mg/ml at 25° C), and methanol.
Storage :
Store at -20° C
Melting Point :
187-188° C
Density :
~1.6 g/cm3 (Predicted)
Refractive Index :
n20D 1.61 (Predicted)
Optical Activity :
α20D 20°±2°, c = 1 in water
IC50 :
L1210: IC50 = 3 µM (mouse); CCRF-CEM: IC50 = 22 µM (human)
Ki Data :
Thymidylate kinase: Ki= 0.56 mM (Mycobacterium tuberculosis)
pK Values :
pKa: 7.4, pKb: 5.34
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
WGK Germany :
2
RTECS :
YU7526000
PubChem CID :
18343
Merck Index :
14: 3437
MDL Number :
MFCD00866530
EC Number :
221-440-1
Beilstein Registry :
890191
SMILES :
C[C@H]1O[C@H](C(O)[C@H]1O)N1C=C(F)C(=O)NC1=O

Download SDS (MSDS)

Certificate of Analysis

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Rated 5 out of 5 by from Wang et al Wang et al. (PubMed ID 22255032) found that the prodrug, Doxifluridine, was converted into 5-fluorouracil by endogenous thymidine phosphorylase and led to cell death in colorectal cancer cells. -SCBT Publication Review
Date published: 2015-03-11
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