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3-Deazauridine

3-Deazauridine Structure
CAS No.
23205-42-7
Chemical Name:
3-Deazauridine
Synonyms
NSC-126849;3-deazuridine;3-DEAZAURIDINE;3-DEAZAURIDINE CRYSTALLINE;3Deazauridine,3 Deazauridine;3-Deazauridine,anticancer antiviral;1-β-D-Ribofuranosyl-4-hydroxy-2-pyridone;4-Hydroxy-1-(β-D-ribofuranosyl)-2-pyridone;4-Hydroxy-1-β-D-ribofuranosyl-2(1H)pyridone;4-Hydroxy-1-(beta-D-ribofuranosyl)-2-pyridone
CBNumber:
CB4125871
Molecular Formula:
C10H13NO6
Molecular Weight:
243.21
MOL File:
23205-42-7.mol
Modify Date:
2023/12/20 10:15:24

3-Deazauridine 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)

SAFETY

Risk and Safety Statements

RTECS  UV1148000

3-Deazauridine Chemical Properties,Uses,Production

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.

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.

3-Deazauridine Preparation Products And Raw materials

Raw materials

Preparation Products

3-Deazauridine Suppliers

Global( 74)Suppliers
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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 4-Hydroxy-1-(β-D-ribofuranosyl)-2-pyridone 4-Hydroxy-1-β-D-ribofuranosyl-2(1H)pyridone 4-Hydroxy-1-(β-D-ribofuranosyl)-1,2-dihydropyridin-2-one 4-Hydroxy-1-β-D-ribofuranosyl-2(1H)-pyridinone NSC-126849 4-Hydroxy-1-(beta-D-ribofuranosyl)-2-pyridone 1-[(2R,3R,4S,5R)-3,4-DIHYDROXY-5-(HYDROXYMETHYL)OXOLAN-2-YL]-2-HYDROXYPYRIDIN-4-ONE 2(1H)-Pyridinone, 4-hydroxy-1-β-D-ribofuranosyl- 3-Deazauridine, 4-Hydroxy-1-beta-D-ribofuranosyl-2(1H)-pyridinone, 3-DAU, NSC 126849 2(1H)-Pyridinone,4-hydroxy-1-b-D-ribofuranosyl- 1-((2R,3R,4S,5R)-3,4-Dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-hydroxypyridin-2(1H)-one 3-Deazauridine,4-Hydroxy-1-beta-D-ribofuranosyl-2(1H)-pyridinone, synthetase inhibitor, anticancer drug, NSC126849, 3D2U 4-Hydroxy-1-beta-D-ribofuranosyl-2(1H)-pyridinone, NSC126849 3Deazauridine,3 Deazauridine 3-Deazauridine,anticancer antiviral 23205-42-7 232005-42-7 20235-47-2 C10H13NO6 Bases & Related Reagents Heterocycles Intermediates & Fine Chemicals Nucleotides Pharmaceuticals