DEXELVUCITABINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C9H10FN3O3
Molecular Weight	227.1924
Optical Activity	UNSPECIFIED
Defined Stereocenters	2 / 2
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

NC1=NC(=O)N(C=C1F)[C@@H]2O[C@H](CO)C=C2

InChI

InChIKey=HSBKFSPNDWWPSL-CAHLUQPWSA-N

InChI=1S/C9H10FN3O3/c10-6-3-13(9(15)12-8(6)11)7-2-1-5(4-14)16-7/h1-3,5,7,14H,4H2,(H2,11,12,15)/t5-,7+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C9H10FN3O3
Molecular Weight	227.1924
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	2 / 2
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://aidsinfo.nih.gov/drugs/521/dexelvucitabine/0/patient | http://i-base.info/htb/3297 | https://adisinsight.springer.com/drugs/800010500 | https://www.ncbi.nlm.nih.gov/pubmed/16011526

Dexelvucitabine is a cytidine analogue, which has been shown to be active in both naive and HIV-experienced individuals and has in vitro activity against a variety of NRTI-resistant strains. Dexelvucitabine belongs to a class of HIV drugs called nucleoside reverse transcriptaseinhibitors (NRTIs). In the Phase IIb study most side effects were generally mild and included headache, fatigue, and gastrointestinal disorders. However, some participants developed severe hyperlipasemia and pancreatitis. Drug development is discontinued due to 40% incidence of grade 4 hyperlipasemia including one case of pancreatitis.

Approval Year

PubMed

Title	Date	PubMed
Synthesis and comparative evaluation of two antiviral agents: beta-L-Fd4C and beta-D-Fd4C.	1998 Nov 17	9873711
Potential use of antiviral L(-)nucleoside analogues for the prevention or treatment of viral associated cancers.	2001 Jan	11164188
Animal models for the study of HBV infection and the evaluation of new anti-HBV strategies.	2002 Dec	12534778
Antiviral activities and cellular toxicities of modified 2',3'-dideoxy-2',3'-didehydrocytidine analogues.	2002 Dec	12435688
ACH-126443 Achillion/Yale University.	2002 Nov	12476956
HIV-1 resistance profile of the novel nucleoside reverse transcriptase inhibitor beta-D-2',3'-dideoxy-2',3'-didehydro-5-fluorocytidine (Reverset).	2003 Jan	12790516
N4-acyl-modified D-2',3'-dideoxy-5-fluorocytidine nucleoside analogues with improved antiviral activity.	2003 Mar	12856919
Biochemical and mechanistic basis for the activity of nucleoside analogue inhibitors of HIV reverse transcriptase.	2004	15193137
Potent antiviral effect of reverset in HIV-1-infected adults following a single oral dose.	2004 Aug	15456084
[New approaches in the treatment of hepatitis B].	2004 May 21	15160325
Meeting notes from the 3rd IAS Conference. New drugs.	2005 Oct	16276591
dD4FC development discontinued.	2006 May	16718907
Elvucitabine data released at CROI.	2010 Mar	20235383

Substance Class	Chemical Created by `admin` on `Fri Dec 15 16:37:55 GMT 2023` Edited by `admin` on `Fri Dec 15 16:37:55 GMT 2023`
Record UNII	KU8SPJ271W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEXELVUCITABINE

Official Name

English

dexelvucitabine [INN]

Common Name

English

(+)-4-AMINO-5-FLUORO-1-((2R,5S)-5-(HYDROXYMETHYL)-2,5-DIHYDROFURAN-2-YL)PYRIMIDIN-2(1H)-ONE

Systematic Name

English

YZ-817

Code

English

Dexelvucitabine [WHO-DD]

Common Name

English

REVERSET

Brand Name

English

CYTIDINE, 2',3'-DIDEHYDRO-2',3'-DIDEOXY-5-FLUORO

Common Name

English

DPC-817

Code

English

DEXELVUCITABINE [USAN]

Common Name

English

INCB-8721

Code

English

Classification Tree Code System Code

NCI_THESAURUS

C97452