VALTORCITABINE

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 Search

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

Molecular Formula	C14H22N4O5
Molecular Weight	326.3483
Charge	0
Count

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

Description
Sources: Turner, A. (1987) Logan Turner's Diseases of the Nose, Throat and Ear, 10Ed, page 2916, retrieved from: https://books.google.ru/books?id=2-nwinRKtBQC | https://www.ncbi.nlm.nih.gov/pubmed/15043399 | https://adisinsight.springer.com/drugs/800013710

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
hepatitis B virus DNA polymerase 3 Target ID: hepatitis B virus DNA polymerase Sources: https://www.drugdevelopment-technology.com/projects/valtorcitabine/	Inhibitor 8297

PubMed

Title	Date	PubMed
Antiviral beta-L-nucleosides specific for hepatitis B virus infection.	2001	11594678
Anti-HBV specific beta-L-2'-deoxynucleosides.	2001 Apr-Jul	11563077
Cross-resistance testing of next-generation nucleoside and nucleotide analogues against lamivudine-resistant HBV.	2005	16152756

Substance Class	Chemical Created by `admin` on `Fri Dec 15 18:45:02 GMT 2023` Edited by `admin` on `Fri Dec 15 18:45:02 GMT 2023`
Record UNII	D5YQG6AQXP
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

VALTORCITABINE

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