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

Details

Stereochemistry ABSOLUTE
Molecular Formula C14H22N4O5
Molecular Weight 326.3483
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of VALTORCITABINE

SMILES

CC(C)[C@H](N)C(=O)O[C@@H]1C[C@H](O[C@H]1CO)N2C=CC(N)=NC2=O

InChI

InChIKey=VFCYZPOEGWLYRM-QCZKYFFMSA-N
InChI=1S/C14H22N4O5/c1-7(2)12(16)13(20)23-8-5-11(22-9(8)6-19)18-4-3-10(15)17-14(18)21/h3-4,7-9,11-12,19H,5-6,16H2,1-2H3,(H2,15,17,21)/t8-,9+,11+,12+/m1/s1

HIDE SMILES / InChI
Torcitabine is the beta-L-enantiomer of the natural nucleoside D-cytidine. The drug was under development as an antiviral agent for the treatment of chronic hepatitis B virus infection. Torcitabine has poor oral bioavailability, but its 3’,5’-derivative ester (val-L-dC) and the 3’-monovaline ester, valtorcitabine dihydrochloride, have excellent oral bioavailability and consequently the torcitabine prodrug, valtorcitabine, has replaced torcitabine in clinical development. Torcitabine is active against hepadnaviruses, specifically human hepatitis B virus (HBV), duck hepatitis virus (DHBV) and woodchuck hepatitis virus (WHV). Torcitabine triphosphate is a selective inhibitor of the polymerase enzyme of HBV.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
PubMed

PubMed

TitleDatePubMed
Antiviral beta-L-nucleosides specific for hepatitis B virus infection.
2001
Anti-HBV specific beta-L-2'-deoxynucleosides.
2001 Apr-Jul
Cross-resistance testing of next-generation nucleoside and nucleotide analogues against lamivudine-resistant HBV.
2005
Name Type Language
VALTORCITABINE
INN  
INN  
Official Name English
3'-VAL-L-DC
Common Name English
valtorcitabine [INN]
Common Name English
L-VALINE, 3'-ESTER WITH 2'-DEOXYCYTIDINE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C29575
Created by admin on Fri Dec 15 18:45:03 GMT 2023 , Edited by admin on Fri Dec 15 18:45:03 GMT 2023
NCI_THESAURUS C281
Created by admin on Fri Dec 15 18:45:03 GMT 2023 , Edited by admin on Fri Dec 15 18:45:03 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C95912
Created by admin on Fri Dec 15 18:45:03 GMT 2023 , Edited by admin on Fri Dec 15 18:45:03 GMT 2023
PRIMARY
ChEMBL
CHEMBL2106499
Created by admin on Fri Dec 15 18:45:03 GMT 2023 , Edited by admin on Fri Dec 15 18:45:03 GMT 2023
PRIMARY
INN
8345
Created by admin on Fri Dec 15 18:45:03 GMT 2023 , Edited by admin on Fri Dec 15 18:45:03 GMT 2023
PRIMARY
SMS_ID
300000037066
Created by admin on Fri Dec 15 18:45:03 GMT 2023 , Edited by admin on Fri Dec 15 18:45:03 GMT 2023
PRIMARY
PUBCHEM
9927346
Created by admin on Fri Dec 15 18:45:03 GMT 2023 , Edited by admin on Fri Dec 15 18:45:03 GMT 2023
PRIMARY
CAS
380886-95-3
Created by admin on Fri Dec 15 18:45:03 GMT 2023 , Edited by admin on Fri Dec 15 18:45:03 GMT 2023
PRIMARY
FDA UNII
D5YQG6AQXP
Created by admin on Fri Dec 15 18:45:03 GMT 2023 , Edited by admin on Fri Dec 15 18:45:03 GMT 2023
PRIMARY
DRUG BANK
DB06187
Created by admin on Fri Dec 15 18:45:03 GMT 2023 , Edited by admin on Fri Dec 15 18:45:03 GMT 2023
PRIMARY
EPA CompTox
DTXSID60870342
Created by admin on Fri Dec 15 18:45:03 GMT 2023 , Edited by admin on Fri Dec 15 18:45:03 GMT 2023
PRIMARY