U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of VALNIVUDINE

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

Description

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

Unknown
139594
PubMed

PubMed

TitleDatePubMed
Alkyloxyphenyl furano pyrimidines as potent and selective anti-VZV agents with enhanced water solubility.
2002 Mar
Highly potent and selective inhibition of varicella-zoster virus replication by bicyclic furo[2,3-d]pyrimidine nucleoside analogues.
2003 May
Patents

Patents

20130331561
3
Name Type Language
VALNIVUDINE
INN   WHO-DD  
INN  
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
Created by admin on Sat Dec 16 05:41:35 GMT 2023 , Edited by admin on Sat Dec 16 05:41:35 GMT 2023
NCI_THESAURUS C281
Created by admin on Sat Dec 16 05:41:35 GMT 2023 , Edited by admin on Sat Dec 16 05:41:35 GMT 2023
Code System Code Type Description
EPA CompTox
DTXSID30241909
Created by admin on Sat Dec 16 05:41:35 GMT 2023 , Edited by admin on Sat Dec 16 05:41:35 GMT 2023
PRIMARY
NCI_THESAURUS
C152817
Created by admin on Sat Dec 16 05:41:35 GMT 2023 , Edited by admin on Sat Dec 16 05:41:35 GMT 2023
PRIMARY
WIKIPEDIA
FV-100
Created by admin on Sat Dec 16 05:41:35 GMT 2023 , Edited by admin on Sat Dec 16 05:41:35 GMT 2023
PRIMARY
INN
10397
Created by admin on Sat Dec 16 05:41:35 GMT 2023 , Edited by admin on Sat Dec 16 05:41:35 GMT 2023
PRIMARY
SMS_ID
100000174659
Created by admin on Sat Dec 16 05:41:35 GMT 2023 , Edited by admin on Sat Dec 16 05:41:35 GMT 2023
PRIMARY
PUBCHEM
16063377
Created by admin on Sat Dec 16 05:41:35 GMT 2023 , Edited by admin on Sat Dec 16 05:41:35 GMT 2023
PRIMARY
CAS
956483-02-6
Created by admin on Sat Dec 16 05:41:35 GMT 2023 , Edited by admin on Sat Dec 16 05:41:35 GMT 2023
PRIMARY
FDA UNII
0NJ5F6D4U7
Created by admin on Sat Dec 16 05:41:35 GMT 2023 , Edited by admin on Sat Dec 16 05:41:35 GMT 2023
PRIMARY
ACTIVE MOIETY
Structure of CF-1743
SALT/SOLVATE (PARENT)
Structure of VALNIVUDINE HYDROCHLORIDE
SUBSTANCE RECORD
Structure of VALNIVUDINE
NIH
NCATS
PRIVACY ACT
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966