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
Elvucitabine data released at CROI.	2010-03	20235383
dD4FC development discontinued.	2006-05	16718907
Meeting notes from the 3rd IAS Conference. New drugs.	2005-10	16276591
HIV Pathogenesis and Treatment - Third International AIDS Society Conference.	2005-10	16254799
New drugs.	2005-07	16011526
In vitro activity of structurally diverse nucleoside analogs against human immunodeficiency virus type 1 with the K65R mutation in reverse transcriptase.	2005-03	15728915
Meeting notes from ICAAC. D-D4FC (Reverset): further data on treatment-experienced patients.	2005-01	15717377
New nucleoside reverse transcriptase inhibitors for the treatment of HIV infections.	2004-10	15351346
Potent antiviral effect of reverset in HIV-1-infected adults following a single oral dose.	2004-08	15456084
[New approaches in the treatment of hepatitis B].	2004-05-21	15160325
Investigating the effects of stereochemistry on incorporation and removal of 5-fluorocytidine analogs by mitochondrial DNA polymerase gamma: comparison of D- and L-D4FC-TP.	2004-04	15026203
Antiretroviral pipeline: new-drug reports from retroviruses conference.	2004-02-27	15119288
Biochemical and mechanistic basis for the activity of nucleoside analogue inhibitors of HIV reverse transcriptase.	2004	15193137
N4-acyl-modified D-2',3'-dideoxy-5-fluorocytidine nucleoside analogues with improved antiviral activity.	2003-03	12856919
HIV-1 resistance profile of the novel nucleoside reverse transcriptase inhibitor beta-D-2',3'-dideoxy-2',3'-didehydro-5-fluorocytidine (Reverset).	2003-01	12790516
Cellular pharmacology of D-d4FC, a nucleoside analogue active against drug-resistant HIV.	2003-01	12790515
Animal models for the study of HBV infection and the evaluation of new anti-HBV strategies.	2002-12	12534778
Antiviral activities and cellular toxicities of modified 2',3'-dideoxy-2',3'-didehydrocytidine analogues.	2002-12	12435688
Interactions of enantiomers of 2',3'-didehydro-2',3'-dideoxy-fluorocytidine with wild type and M184V mutant HIV-1 reverse transcriptase.	2002-12	12406504
ACH-126443 Achillion/Yale University.	2002-11	12476956
ViroLogic announces agreement with Achillion.	2002-03	11981960
Novel direct detection method for quantitative determination of intracellular nucleoside triphosphates using weak anion exchange liquid chromatography/tandem mass spectrometry.	2002	11992513
Potential use of antiviral L(-)nucleoside analogues for the prevention or treatment of viral associated cancers.	2001-01	11164188
Perspectives for the treatment of hepatitis B virus infections.	1999-07	10418752
Synthesis and biological evaluation of 2',3'-didehydro-2',3'- dideoxy-5-fluorocytidine (D4FC) analogues: discovery of carbocyclic nucleoside triphosphates with potent inhibitory activity against HIV-1 reverse transcriptase.	1999-03-11	10072683
Synthesis and comparative evaluation of two antiviral agents: beta-L-Fd4C and beta-D-Fd4C.	1998-11-17	9873711

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:33:01 GMT 2025` Edited by `admin` on `Mon Mar 31 18:33:01 GMT 2025`
Record UNII	KU8SPJ271W
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

DEXELVUCITABINE

Official Name

English

REVERSET

Preferred 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

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