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Details

Stereochemistry ABSOLUTE
Molecular Formula C9H10FN3O3
Molecular Weight 227.1928
Optical Activity UNSPECIFIED
Defined Stereocenters 2 / 2
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DEXELVUCITABINE

SMILES

C1=C[C@]([H])(n2cc(c(=N)nc2O)F)O[C@]1([H])CO

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 227.1928
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 0
Optical Activity UNSPECIFIED

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

PubMed

TitleDatePubMed
Synthesis and comparative evaluation of two antiviral agents: beta-L-Fd4C and beta-D-Fd4C.
1998 Nov 17
Perspectives for the treatment of hepatitis B virus infections.
1999 Jul
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 Mar 11
Potential use of antiviral L(-)nucleoside analogues for the prevention or treatment of viral associated cancers.
2001 Jan
Novel direct detection method for quantitative determination of intracellular nucleoside triphosphates using weak anion exchange liquid chromatography/tandem mass spectrometry.
2002
Animal models for the study of HBV infection and the evaluation of new anti-HBV strategies.
2002 Dec
Antiviral activities and cellular toxicities of modified 2',3'-dideoxy-2',3'-didehydrocytidine analogues.
2002 Dec
Interactions of enantiomers of 2',3'-didehydro-2',3'-dideoxy-fluorocytidine with wild type and M184V mutant HIV-1 reverse transcriptase.
2002 Dec
ViroLogic announces agreement with Achillion.
2002 Mar
ACH-126443 Achillion/Yale University.
2002 Nov
HIV-1 resistance profile of the novel nucleoside reverse transcriptase inhibitor beta-D-2',3'-dideoxy-2',3'-didehydro-5-fluorocytidine (Reverset).
2003 Jan
Cellular pharmacology of D-d4FC, a nucleoside analogue active against drug-resistant HIV.
2003 Jan
N4-acyl-modified D-2',3'-dideoxy-5-fluorocytidine nucleoside analogues with improved antiviral activity.
2003 Mar
Biochemical and mechanistic basis for the activity of nucleoside analogue inhibitors of HIV reverse transcriptase.
2004
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 Apr
Potent antiviral effect of reverset in HIV-1-infected adults following a single oral dose.
2004 Aug
Antiretroviral pipeline: new-drug reports from retroviruses conference.
2004 Feb 27
[New approaches in the treatment of hepatitis B].
2004 May 21
New nucleoside reverse transcriptase inhibitors for the treatment of HIV infections.
2004 Oct
Meeting notes from ICAAC. D-D4FC (Reverset): further data on treatment-experienced patients.
2005 Jan
New drugs.
2005 Jul
In vitro activity of structurally diverse nucleoside analogs against human immunodeficiency virus type 1 with the K65R mutation in reverse transcriptase.
2005 Mar
dD4FC development discontinued.
2006 May
Elvucitabine data released at CROI.
2010 Mar
Substance Class Chemical
Created
by admin
on Sat Jun 26 11:39:55 UTC 2021
Edited
by admin
on Sat Jun 26 11:39:55 UTC 2021
Record UNII
KU8SPJ271W
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DEXELVUCITABINE
INN   USAN   WHO-DD  
USAN   INN  
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
Created by admin on Sat Jun 26 11:39:56 UTC 2021 , Edited by admin on Sat Jun 26 11:39:56 UTC 2021
Code System Code Type Description
DRUG BANK
DB12470
Created by admin on Sat Jun 26 11:39:56 UTC 2021 , Edited by admin on Sat Jun 26 11:39:56 UTC 2021
PRIMARY
ChEMBL
CHEMBL109831
Created by admin on Sat Jun 26 11:39:56 UTC 2021 , Edited by admin on Sat Jun 26 11:39:56 UTC 2021
PRIMARY
NCI_THESAURUS
C76928
Created by admin on Sat Jun 26 11:39:56 UTC 2021 , Edited by admin on Sat Jun 26 11:39:56 UTC 2021
PRIMARY
PUBCHEM
64973
Created by admin on Sat Jun 26 11:39:56 UTC 2021 , Edited by admin on Sat Jun 26 11:39:56 UTC 2021
PRIMARY
EPA CompTox
134379-77-4
Created by admin on Sat Jun 26 11:39:56 UTC 2021 , Edited by admin on Sat Jun 26 11:39:56 UTC 2021
PRIMARY
INN
8730
Created by admin on Sat Jun 26 11:39:56 UTC 2021 , Edited by admin on Sat Jun 26 11:39:56 UTC 2021
PRIMARY
WIKIPEDIA
DEXELVUCITABINE
Created by admin on Sat Jun 26 11:39:56 UTC 2021 , Edited by admin on Sat Jun 26 11:39:56 UTC 2021
PRIMARY
FDA UNII
KU8SPJ271W
Created by admin on Sat Jun 26 11:39:56 UTC 2021 , Edited by admin on Sat Jun 26 11:39:56 UTC 2021
PRIMARY
CAS
134379-77-4
Created by admin on Sat Jun 26 11:39:56 UTC 2021 , Edited by admin on Sat Jun 26 11:39:56 UTC 2021
PRIMARY
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