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

Molecular Formula	C12H14N2O6
Molecular Weight	282.2494
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

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
Synthesis and evaluation of some masked phosphate esters of the anti-herpesvirus drug 882C (netivudine) as potential antiviral agents.	1998-05	9875402
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.	1997-08	9298756
Multiple dose netivudine, a potent anti-varicella zoster virus agent, in healthy elderly volunteers and patients with shingles.	1996-03	9182115
Comparative activity of selected antiviral compounds against clinical isolates of varicella-zoster virus.	1995-04	7649195
Nucleic acid related compounds. 40. Synthesis and biological activities of 5-alkynyluracil nucleosides.	1983-05	6302254

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.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:27:17 GMT 2025` Edited by `admin` on `Mon Mar 31 18:27:17 GMT 2025`
Record UNII	F7K51T0Q1W
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

NETIVUDINE

Official Name

English

882C-87

Preferred 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

Classification Tree Code System Code

NCI_THESAURUS

C97452