NAVURIDINE

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 Search

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

Description
Sources: https://adisinsight.springer.com/drugs/800001006 | https://ncit.nci.nih.gov/ncitbrowser/ConceptReport.jsp?dictionary=NCI_Thesaurus&ns=NCI_Thesaurus&code=C83920 | https://www.ncbi.nlm.nih.gov/pubmed/14694989

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

Originator

Approval Year

PubMed

Title	Date	PubMed
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	2538549

Patents

Sample Use Guides

In Vivo Use Guide

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 UTC 2023` Edited by `admin` on `Fri Dec 15 15:32:52 UTC 2023`
Record UNII	PS28W65479
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

NAVURIDINE

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