| Identification | Back Directory | [Name]
3-DEAZAURIDINE | [CAS]
23205-42-7 | [Synonyms]
NSC-126849
3-deazuridine
3-DEAZAURIDINE
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-(beta-D-ribofuranosyl)-2-pyridone
4-hydroxy-1-beta-d-ribofuranosyl-2(1h)-pyridon
4-Hydroxy-1-β-D-ribofuranosyl-2(1H)-pyridinone
4-HYDROXY-1-BETA-D-RIBOFURANOSYL-2[1H]PYRIDONE
2(1H)-Pyridinone,4-hydroxy-1-b-D-ribofuranosyl-
2(1H)-Pyridinone, 4-hydroxy-1-β-D-ribofuranosyl-
4-hydroxy-1-beta-d-ribofuranosyl-2(1h)-pyridinon
4-hydroxy-1-beta-d-ribofuranosyl-2(1h)-pyridinone
4-Hydroxy-1-(β-D-ribofuranosyl)-1,2-dihydropyridin-2-one
1-[(2R,3R,4S,5R)-3,4-DIHYDROXY-5-(HYDROXYMETHYL)OXOLAN-2-YL]-2-HYDROXYPYRIDIN-4-ONE
3-Deazauridine, 4-Hydroxy-1-beta-D-ribofuranosyl-2(1H)-pyridinone, 3-DAU, NSC 126849 | [EINECS(EC#)]
245-488-8 | [Molecular Formula]
C10H13NO6 | [MDL Number]
MFCD00006522 | [MOL File]
23205-42-7.mol | [Molecular Weight]
243.21 |
| Chemical Properties | Back Directory | [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) |
| Hazard Information | Back Directory | [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. | [in vivo]
3-Deazauridine (DAUR) (250 mg/kg/day; i.p; 1-9 days) shows moderate activity against L1210 leukemia cells in mice[1].
3-Deazauridine (ip; 5 times doses) has the lethal dose of 250 mg/kg/day and 417 mg/kg/day, the toxic dose low of 62.5 mg/kg/day and 104 mg/kg/day, the highest non-toxic dose of 31.25 mg/kg/day and 52 mg/kg/day, in beagle dogs and rhesus monkeys, respectively[1].
| [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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