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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H11N5O4
Molecular Weight 253.2147
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 1
Charge 0

SHOW SMILES / InChI
Structure of NAVURIDINE

SMILES

OC[C@H]1O[C@H](C[C@@H]1N=[N+]=[N-])N2C=CC(=O)NC2=O

InChI

InChIKey=ZSNNBSPEFVIUDS-SHYZEUOFSA-N
InChI=1S/C9H11N5O4/c10-13-12-5-3-8(18-6(5)4-15)14-2-1-7(16)11-9(14)17/h1-2,5-6,8,15H,3-4H2,(H,11,16,17)/t5-,6+,8+/m0/s1

HIDE SMILES / InChI

Molecular Formula C9H11N5O4
Molecular Weight 253.2147
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 3 / 3
E/Z Centers 1
Optical Activity UNSPECIFIED

Navuridine (AzddU) is a nucleoside analogue which demonstrated significant anti-HIV activity and low toxicity in preclinical studies. The drug was originally developed by University of Georgia. 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.

CNS Activity

Curator's Comment: Navuridine (AzddU) and AZT penetrated the cerebrospinal fluid (CSF) with concentration ratios in CSF:serum ranging from 0.05 to 0.25 one hour after drug administration in rhesus monkeys.

Approval Year

PubMed

PubMed

TitleDatePubMed
Replication of human immunodeficiency virus in monocytes. Granulocyte/macrophage colony-stimulating factor (GM-CSF) potentiates viral production yet enhances the antiviral effect mediated by 3'-azido-2'3'-dideoxythymidine (AZT) and other dideoxynucleoside congeners of thymidine.
1989 Mar 1
Patents

Sample Use Guides

Rhesus monkeys: Oral absorption of Navuridine (AzddU) was virtually complete after 60 mg/kg. However, bioavailability of both nucleosides was markedly lower (less than 50%) after 200 mg/kg. Young adult male rhesus monkeys weighing 5-6 kg were used for all intravenous and oral studies. Each monkey received a single dose of AzddU or AZT. AzddU, 60 mg/kg, was administered intravenously (20 ml) as a bolus to three monkeys (563D, AP21, and RJN2) and 60 mg/kg AZT was similarly administered to one monkey (N785). For oral bioavailability studies, each of two monkeys received 60 mg/kg (AP19 and RKOl) or 200 mg/kg (634D and N854) AzddU in 50 ml water by gastric intubation. One monkey received 60 mg/kg (RFL1) AZT orally and two monkeys were given 200 mg/kg (231D and AP17) AZT orally.
Route of Administration: Other
In Vitro Use Guide
Navuridine (AzddU) inhibited HIV-1 replication in human peripheral blood mononuclear (PBM) cells in the 0.18 to 0.46 uM range.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:32:52 GMT 2023
Edited
by admin
on Fri Dec 15 15:32:52 GMT 2023
Record UNII
PS28W65479
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
NAVURIDINE
INN   MART.  
INN  
Official Name English
3'-AZIDO-2',3'DIDEOXYURIDINE
Systematic Name English
NSC-380882
Code English
AZDDU
Common Name English
CS-87
Code English
AZU
Common Name English
3'-AZIDO-2',3'-DIDEOXYURIDINE
Systematic Name English
URIDINE, 3'-AZIDO-2',3'-DIDEOXY-
Systematic Name English
navuridine [INN]
Common Name English
AZDU
Common Name English
NAVURIDINE [MART.]
Common Name English
Classification Tree Code System Code
FDA ORPHAN DRUG 39889
Created by admin on Fri Dec 15 15:32:52 GMT 2023 , Edited by admin on Fri Dec 15 15:32:52 GMT 2023
NCI_THESAURUS C1557
Created by admin on Fri Dec 15 15:32:52 GMT 2023 , Edited by admin on Fri Dec 15 15:32:52 GMT 2023
NCI_THESAURUS C97452
Created by admin on Fri Dec 15 15:32:52 GMT 2023 , Edited by admin on Fri Dec 15 15:32:52 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID901004737
Created by admin on Fri Dec 15 15:32:52 GMT 2023 , Edited by admin on Fri Dec 15 15:32:52 GMT 2023
PRIMARY
CAS
84472-85-5
Created by admin on Fri Dec 15 15:32:52 GMT 2023 , Edited by admin on Fri Dec 15 15:32:52 GMT 2023
PRIMARY
MESH
C058803
Created by admin on Fri Dec 15 15:32:52 GMT 2023 , Edited by admin on Fri Dec 15 15:32:52 GMT 2023
PRIMARY
NSC
380882
Created by admin on Fri Dec 15 15:32:52 GMT 2023 , Edited by admin on Fri Dec 15 15:32:52 GMT 2023
PRIMARY
PUBCHEM
55262
Created by admin on Fri Dec 15 15:32:52 GMT 2023 , Edited by admin on Fri Dec 15 15:32:52 GMT 2023
PRIMARY
FDA UNII
PS28W65479
Created by admin on Fri Dec 15 15:32:52 GMT 2023 , Edited by admin on Fri Dec 15 15:32:52 GMT 2023
PRIMARY
INN
8002
Created by admin on Fri Dec 15 15:32:52 GMT 2023 , Edited by admin on Fri Dec 15 15:32:52 GMT 2023
PRIMARY
ChEMBL
CHEMBL591804
Created by admin on Fri Dec 15 15:32:52 GMT 2023 , Edited by admin on Fri Dec 15 15:32:52 GMT 2023
PRIMARY
NCI_THESAURUS
C83920
Created by admin on Fri Dec 15 15:32:52 GMT 2023 , Edited by admin on Fri Dec 15 15:32:52 GMT 2023
PRIMARY
SMS_ID
300000034237
Created by admin on Fri Dec 15 15:32:52 GMT 2023 , Edited by admin on Fri Dec 15 15:32:52 GMT 2023
PRIMARY
Related Record Type Details
TARGET -> INHIBITOR
TARGET ORGANISM->INHIBITOR
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