3-Deazauridine Property

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

RTECS 

UV1148000

Hazard and Precautionary Statements (GHS)

3-Deazauridine Chemical Properties,Usage,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.

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.