VALNIVUDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C27H35N3O6
Molecular Weight	497.5833
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CCCCCC1=CC=C(C=C1)C2=CC3=CN([C@H]4C[C@H](O)[C@@H](COC(=O)[C@@H](N)C(C)C)O4)C(=O)N=C3O2

InChI

InChIKey=FJRRWJMFUNGZBJ-RBVMOCNTSA-N

InChI=1S/C27H35N3O6/c1-4-5-6-7-17-8-10-18(11-9-17)21-12-19-14-30(27(33)29-25(19)36-21)23-13-20(31)22(35-23)15-34-26(32)24(28)16(2)3/h8-12,14,16,20,22-24,31H,4-7,13,15,28H2,1-3H3/t20-,22+,23+,24-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C27H35N3O6
Molecular Weight	497.5833
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/27943311 | https://www.ncbi.nlm.nih.gov/pubmed/20054098 | https://www.ncbi.nlm.nih.gov/pubmed/26524331

Valnivudine, also known as FV-100, a prodrug that has been indicated as a potential antiviral for the treatment of shingles (herpes zoster) that could both reduce the pain burden of the acute episode and reduce the incidence of post‐herpetic neuralgia compared to available treatments. Phase I clinical trial with FV100 showed safety and tolerability in healthy volunteers. Valnivudine also participated in phase III, where its efficacy was compared with valacyclovir; however, the study was terminated.

Originator

Approval Year

PubMed

Title	Date	PubMed
Highly potent and selective inhibition of varicella-zoster virus by bicyclic furopyrimidine nucleosides bearing an aryl side chain.	2000 Dec 28	11150169
Novel aryl substituted bicyclic furo nucleosides as extremely potent and selective anti-VZV agents.	2001 Apr-Jul	11563040
Chemotherapy of varicella-zoster virus by a novel class of highly specific anti-VZV bicyclic pyrimidine nucleosides.	2002 Jul 18	12084470
Alkyloxyphenyl furano pyrimidines as potent and selective anti-VZV agents with enhanced water solubility.	2002 Mar	12238533
Lack of susceptibility of bicyclic nucleoside analogs, highly potent inhibitors of varicella-zoster virus, to the catabolic action of thymidine phosphorylase and dihydropyrimidine dehydrogenase.	2002 May	11961132
Bicyclic nucleoside inhibitors of varicella-zoster virus: effect of terminal aryl substitution in the side-chain.	2002 Sep	12630674
Highly potent and selective inhibition of varicella-zoster virus replication by bicyclic furo[2,3-d]pyrimidine nucleoside analogues.	2003 May	12647310
Synthesis and antiviral evaluation of some 3'-fluoro bicyclic nucleoside analogues.	2004	15043132
Inactivity of the bicyclic pyrimidine nucleoside analogues against simian varicella virus (SVV) does not correlate with their substrate activity for SVV-encoded thymidine kinase.	2004 Mar 19	14985094
FV-100: the most potent and selective anti-varicella zoster virus agent reported to date.	2010 Jan 5	20054098
Herpes simplex virus and varicella zoster virus: recent advances in therapy.	2015 Dec	26524331
FV-100 versus valacyclovir for the prevention of post-herpetic neuralgia and the treatment of acute herpes zoster-associated pain: A randomized-controlled trial.	2017 Jul	27943311

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 05:41:35 GMT 2023` Edited by `admin` on `Sat Dec 16 05:41:35 GMT 2023`
Record UNII	0NJ5F6D4U7
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VALNIVUDINE

Official Name

English

((2R,3S,5R)-3-HYDROXY-5-(2-OXO-6-(4-PENTYLPHENYL)FURO(2,3- D)PYRIMIDIN-3(2H)-YL)OXOLAN-2-YL)METHYL L-VALINATE ANTIVIRAL

Common Name

English

FV-100 FREE BASE

Code

English

Valnivudine [WHO-DD]

Common Name

English

valnivudine [INN]

Common Name

English

L-VALINE, 5'-ESTER WITH 3-(2-DEOXY-.BETA.-D-ERYTHRO-PENTOFURANOSYL)-6-(4-PENTYLPHENYL)FURO(2,3-D)PYRIMIDIN-2(3H)-ONE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1557