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3-Deazauridine

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3-Deazauridine Basic information

Product Name:
3-Deazauridine
Synonyms:
  • 4-HYDROXY-1-BETA-D-RIBOFURANOSYL-2[1H]PYRIDONE
  • 3-DEAZAURIDINE
  • 3-deazuridine
  • 4-hydroxy-1-beta-d-ribofuranosyl-2(1h)-pyridinon
  • 4-hydroxy-1-beta-d-ribofuranosyl-2(1h)-pyridinone
  • 4-hydroxy-1-beta-d-ribofuranosyl-2(1h)-pyridon
  • 3-DEAZAURIDINE CRYSTALLINE
  • 1-β-D-Ribofuranosyl-4-hydroxy-2-pyridone
CAS:
23205-42-7
MF:
C10H13NO6
MW:
243.21
EINECS:
245-488-8
Product Categories:
  • Bases & Related Reagents
  • Heterocycles
  • Intermediates & Fine Chemicals
  • Nucleotides
  • Pharmaceuticals
Mol File:
23205-42-7.mol
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3-Deazauridine Chemical Properties

Melting point:
233-235°C
Boiling point:
569.2±50.0 °C(Predicted)
Density 
1.718±0.06 g/cm3(Predicted)
storage temp. 
-20°C
solubility 
DMSO (Slightly), Methanol (Slightly), Water (Slightly)
form 
Solid
pka
4.50±1.00(Predicted)
color 
White to Pale Beige
InChI
InChI=1/C10H13NO6/c12-4-6-8(15)9(16)10(17-6)11-2-1-5(13)3-7(11)14/h1-3,6,8-10,12-13,15-16H,4H2/t6-,8-,9-,10-/s3
InChIKey
CBOKZNLSFMZJJA-FNMQVXAUNA-N
SMILES
[C@@H]1([C@H](O)[C@H](O)[C@@H](CO)O1)N1C=CC(O)=CC1=O |&1:0,1,3,5,r|
LogP
-1.693 (est)
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Safety Information

RTECS 
UV1148000
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3-Deazauridine Usage And Synthesis

Description

3-Deazauridine is a structural analog of uridine that inhibits the biosynthesis of Cytidine-5'-Triphosphate by competitive inhibition of Cytidine Triphosphate synthetase, which is considered to be the primary mode of action of this nucleoside analog. This compound has been shown to possess in vitro activity against leukemia L1210 tumor cells, Ehrlich ascites tumor cells, Escherichia coli, and Streptococcus faecium. Despite a paucity of clinical attention given to this drug as a single agent, it has generated much enthusiasm as a biological response modulator because of its synergistic effect with several antitumor agents, including Cytosine Arabinoside, 5-aza-2'-deoxycytidine, 5-azacytidine, thymidine and D-galactosamine. However, only the cytosine arabinoside/3-Deazauridine combination has been explored clinically[1-2].

Uses

Antimetabolite antiviral dosing regimen for hepatitis C virus or flaviviridae therapy.

Definition

ChEBI: 3-Deazauridine is a N-glycosyl compound.

References

[1] W J Moriconi, S Taylor, M Slavik. “3-Deazauridine (NSC 126849): an interesting modulator of biochemical response.” Investigational New Drugs 4 1 (1986): 67–84.
[2] W M Shannon, F M Schabel, G Arnett. “3-Deazauridine: inhibition of ribonucleic acid virus-induced cytopathogenic effects in vitro.” Antimicrobial Agents and Chemotherapy 2 3 (1972): 159–63.

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