NETIVUDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C12H14N2O6
Molecular Weight	282.2494
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC#CC1=CN([C@@H]2O[C@H](CO)[C@@H](O)[C@@H]2O)C(=O)NC1=O

InChI

InChIKey=QLOCVMVCRJOTTM-SDNRWEOFSA-N

InChI=1S/C12H14N2O6/c1-2-3-6-4-14(12(19)13-10(6)18)11-9(17)8(16)7(5-15)20-11/h4,7-9,11,15-17H,5H2,1H3,(H,13,18,19)/t7-,8-,9+,11-/m1/s1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/7695306 | https://adisinsight.springer.com/drugs/800001256

Netivudine [882C, 882C87, BW 882, Py-araU, Zonavir®] is an orally active thymidine analogue which was being investigated as a treatment for herpes zoster virus infections. Netivudine is a nucleoside analog with potent, specific activity against varicella-zoster virus. It is approximately seven times as potent as acyclovir with an in vitro 50% inhibitory concentration of 1 to 2 uM.

Originator

Approval Year

PubMed

Title	Date	PubMed
Structure-activity relationship of the affinity of 5-substituted uracil nucleoside analogues for varicella-zoster virus thymidine kinase and their activity against varicella-zoster virus.	1997 Aug	9298756
Synthesis and evaluation of some masked phosphate esters of the anti-herpesvirus drug 882C (netivudine) as potential antiviral agents.	1998 May	9875402

Patents

Sample Use Guides

In Vivo Use Guide

Three groups of eight elderly volunteers received 400 or 800 mg netivudine or placebo once daily for 8 days.

Route of Administration: Oral

In Vitro Use Guide

The IC50 of Netivudine (882C87) against VZV ranges from 0.6 to 3.8 uM.

Name

Type

Language

NETIVUDINE

Official Name

English

1-.BETA.-D-ARABINOFURANOSYL-5-(1-PROPYNYL)URACIL

Common Name

English

NETIVUDINE [MART.]

Common Name

English

netivudine [INN]

Common Name

English

882C87

Code

English

Netivudine [WHO-DD]

Common Name

English

882C-87

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C97452