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

Details

Stereochemistry ABSOLUTE
Molecular Formula C9H13N3O4
Molecular Weight 227.2172
Optical Activity UNSPECIFIED
Defined Stereocenters 3 / 3
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of TORCITABINE

SMILES

NC1=NC(=O)N(C=C1)[C@@H]2C[C@@H](O)[C@H](CO)O2

InChI

InChIKey=CKTSBUTUHBMZGZ-CHKWXVPMSA-N
InChI=1S/C9H13N3O4/c10-7-1-2-12(9(15)11-7)8-3-5(14)6(4-13)16-8/h1-2,5-6,8,13-14H,3-4H2,(H2,10,11,15)/t5-,6+,8+/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
TORCITABINE
INN   USAN  
USAN   INN  
Official Name English
torcitabine [INN]
Common Name English
NV-02C
Code English
TORCITABINE [USAN]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1557
Created by admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
NCI_THESAURUS C29575
Created by admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
NCI_THESAURUS C281
Created by admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
Code System Code Type Description
USAN
MM-29
Created by admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
PRIMARY
FDA UNII
6BZN07BMW3
Created by admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
PRIMARY
EPA CompTox
DTXSID30960542
Created by admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
PRIMARY
SMS_ID
300000017952
Created by admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
PRIMARY
NCI_THESAURUS
C73200
Created by admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
PRIMARY
ChEMBL
CHEMBL554563
Created by admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
PRIMARY
PUBCHEM
159354
Created by admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
PRIMARY
CAS
40093-94-5
Created by admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
PRIMARY
INN
8272
Created by admin on Fri Dec 15 15:48:52 GMT 2023 , Edited by admin on Fri Dec 15 15:48:52 GMT 2023
PRIMARY