Navuridine

HCID 55262CAS 84472-85-5

Basic information

Standard SMILES
[N-]=[N+]=N[C@H]1C[C@H](n2ccc(=O)[nH]c2=O)O[C@@H]1CO
InChIKey
ZSNNBSPEFVIUDS-SHYZEUOFSA-N
Molecular formula
C9H11N5O4
Average molar mass
253.22 g/mol
Monoisotopic mass
253.08110383

Overview

Navuridine is a dideoxyuridine inhibitor of HIV reverse transcriptase that is related to zidovudine. Navuridine exhibits a relatively short half-life and incomplete oral bioavailability and has not been developed into a clinical drug.

Names & identifiers

Preferred name
Navuridine
IUPAC
1-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione

Names & synonyms

Navuridine84472-85-5AZdU3'-AZIDO-2',3'-DIDEOXYURIDINEAZddUCS-87NavuridinaUridine, 3'-azido-2',3'-dideoxy-NSC-380882PS28W654793'-azido-2',3'dideoxyuridinenavuridinum
Show more names
NSC380882RefChem:9275253'-azido-2'-3'-dideoxyuridineNavuridine [INN]1-((2R,4S,5S)-4-azido-5-(hydroxymethyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dioneMFCD008703241-[(2R,4S,5S)-4-azido-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dioneAzUrd

Database identifiers

CAS
84472-85-5
PubChem CID
55262
DTXSID
DTXSID901004737
ChEMBL
CHEMBL591804
UNII
PS28W65479
Nikkaji
J329.218E

Properties

Computed structural properties

XLogP
-0.3
Topological polar surface area
93.2 Ų
Hydrogen bond donors
2
Hydrogen bond acceptors
6
Rotatable bonds
3
Heavy atoms
18

Experimental & physicochemical properties

SpringerMaterials Properties15N nuclear magnetic resonance spectrum
LogP-0.37

Related reactions

7 records

Linked notes

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