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

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 of ELVUCITABINE

SMILES

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

InChI

InChIKey=HSBKFSPNDWWPSL-VDTYLAMSSA-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+/m1/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

Elvucitabine (ACH-126443 or beta-L-Fd4C) is a reverse transcriptase inhibitor exerting antiviral properties. Elvucitabine, an L-cytosine nucleoside analog, is intracellularly phosphorylated to its active 5′-triphosphate metabolite, which has an intracellular half-life of at least 20 hours. Elvucitabine triphosphate inhibits the activity of HIV reverse transcriptase by competing with natural substrates and by causing DNA chain termination after incorporation into viral DNA. Elvucitabine has also demonstrated in vitro and in vivo activity against HBV. Achillion, under license from Vion is developing elvucitabine for the potential treatment of HIV and hepatitis B virus (HBV) infection.

Originator

Approval Year

Unknown
149124
PubMed

PubMed

TitleDatePubMed
Elvucitabine data released at CROI.
2010-03
Comparative study of the persistence of anti-HIV activity of deoxynucleoside HIV reverse transcriptase inhibitors after removal from culture.
2009-04-22
Novel compounds for the treatment of HIV type-1 infection.
2009
Emerging anti-HIV drugs.
2005-05
In vitro activity of structurally diverse nucleoside analogs against human immunodeficiency virus type 1 with the K65R mutation in reverse transcriptase.
2005-03
New nucleoside reverse transcriptase inhibitors for the treatment of HIV infections.
2004-10
Novel 4'-substituted stavudine analog with improved anti-human immunodeficiency virus activity and decreased cytotoxicity.
2004-05
Mechanism of antiviral activities of 3'-substituted L-nucleosides against 3TC-resistant HBV polymerase: a molecular modelling approach.
2003-11
Anti-HBV specific beta-L-2'-deoxynucleosides.
2001-09-21
Antiviral activity of beta-L-2',3'-dideoxy-2',3'-didehydro-5-fluorocytidine in woodchucks chronically infected with woodchuck hepatitis virus.
2001-04
Antiviral L-nucleosides specific for hepatitis B virus infection.
2001-01
Antiviral beta-L-nucleosides specific for hepatitis B virus infection.
2001
Sensitivity of L-(-)2,3-dideoxythiacytidine resistant hepatitis B virus to other antiviral nucleoside analogues.
1999-06-15
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
Synthesis and comparative evaluation of two antiviral agents: beta-L-Fd4C and beta-D-Fd4C.
1998-11-17
Synthesis and biological evaluation of a series of 2'-fluorinated-2',3'-dideoxy-2',3'-didehydro-(L)-nucleosides.
1998-07-07
Anti-hepatitis B virus activity and metabolism of 2',3'-dideoxy-2',3'-didehydro-beta-L(-)-5-fluorocytidine.
1998-07
Metabolism of 2',3'-dideoxy-2',3'-didehydro-beta-L(-)-5-fluorocytidine and its activity in combination with clinically approved anti-human immunodeficiency virus beta-D(+) nucleoside analogs in vitro.
1998-07
Bis-S-acyl-2-thioethyl (SATE)-bearing monophosphate prodrug of beta-L-FD4C as potent anti-HBV agent.
1998-01-06
Design and synthesis of 2',3'-dideoxy-2',3'-didehydro-beta-L-cytidine (beta-L-d4C) and 2',3'-dideoxy 2',3'-didehydro-beta-L-5-fluorocytidine (beta-L-Fd4C), two exceptionally potent inhibitors of human hepatitis B virus (HBV) and potent inhibitors of human immunodeficiency virus (HIV) in vitro.
1996-04-26
Patents

Patents

20030229225
1
Substance Class Chemical
Created
by admin
on Wed Apr 02 07:37:10 GMT 2025
Edited
by admin
on Wed Apr 02 07:37:10 GMT 2025
Record UNII
M09BUF90C0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ELVUCITABINE
INN   USAN  
INN   USAN  
Official Name English
ACH-126,443
Preferred Name English
ELVUCITABINE [USAN]
Common Name English
4-Amino-5-fluoro-1-[(2S,5R)-5-(hydroxymethyl)-2,5-dihydrofuran-2-yl]pyrimidin-2(1H)-one
Systematic Name English
ACH-126443
Code English
BETA-L-FD4C
Common Name English
L-FD4C
Common Name English
2(1H)-PYRIMIDINONE, 4-AMINO-1-((2S,5R)-2,5-DIHYDRO-5-(HYDROXYMETHYL)-2-FURANYL)-5-FLUORO-
Systematic Name English
elvucitabine [INN]
Common Name English
.BETA.-L-FD4C
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C1557
Created by admin on Wed Apr 02 07:37:10 GMT 2025 , Edited by admin on Wed Apr 02 07:37:10 GMT 2025
NCI_THESAURUS C97452
Created by admin on Wed Apr 02 07:37:10 GMT 2025 , Edited by admin on Wed Apr 02 07:37:10 GMT 2025
Code System Code Type Description
NCI_THESAURUS
C73201
Created by admin on Wed Apr 02 07:37:10 GMT 2025 , Edited by admin on Wed Apr 02 07:37:10 GMT 2025
PRIMARY
EPA CompTox
DTXSID20171185
Created by admin on Wed Apr 02 07:37:10 GMT 2025 , Edited by admin on Wed Apr 02 07:37:10 GMT 2025
PRIMARY
DRUG BANK
DB06236
Created by admin on Wed Apr 02 07:37:10 GMT 2025 , Edited by admin on Wed Apr 02 07:37:10 GMT 2025
PRIMARY
SMS_ID
100000163593
Created by admin on Wed Apr 02 07:37:10 GMT 2025 , Edited by admin on Wed Apr 02 07:37:10 GMT 2025
PRIMARY
WIKIPEDIA
ELVUCITABINE
Created by admin on Wed Apr 02 07:37:10 GMT 2025 , Edited by admin on Wed Apr 02 07:37:10 GMT 2025
PRIMARY
MESH
C099405
Created by admin on Wed Apr 02 07:37:10 GMT 2025 , Edited by admin on Wed Apr 02 07:37:10 GMT 2025
PRIMARY
PUBCHEM
469717
Created by admin on Wed Apr 02 07:37:10 GMT 2025 , Edited by admin on Wed Apr 02 07:37:10 GMT 2025
PRIMARY
FDA UNII
M09BUF90C0
Created by admin on Wed Apr 02 07:37:10 GMT 2025 , Edited by admin on Wed Apr 02 07:37:10 GMT 2025
PRIMARY
EVMPD
SUB177918
Created by admin on Wed Apr 02 07:37:10 GMT 2025 , Edited by admin on Wed Apr 02 07:37:10 GMT 2025
PRIMARY
CAS
181785-84-2
Created by admin on Wed Apr 02 07:37:10 GMT 2025 , Edited by admin on Wed Apr 02 07:37:10 GMT 2025
PRIMARY
ChEMBL
CHEMBL38700
Created by admin on Wed Apr 02 07:37:10 GMT 2025 , Edited by admin on Wed Apr 02 07:37:10 GMT 2025
PRIMARY
USAN
OO-44
Created by admin on Wed Apr 02 07:37:10 GMT 2025 , Edited by admin on Wed Apr 02 07:37:10 GMT 2025
PRIMARY
INN
8364
Created by admin on Wed Apr 02 07:37:10 GMT 2025 , Edited by admin on Wed Apr 02 07:37:10 GMT 2025
PRIMARY
Related Record Type Details
HUMAN IMMUNODEFICIENCY VIRUS TYPE 1
TARGET ORGANISM->INHIBITOR
Related Record Type Details
Structure of ELVUCITABINE
ACTIVE MOIETY
NIH
NCATS
PRIVACY NOTICE
ACCESSIBILITY
DISCLAIMER
HHS VULNERABILITY DISCLOSURE
For language access assistance, contact the NCATS Public Information Officer
National Center for Advancing Translational Sciences (NCATS),
6701 Democracy Boulevard, Bethesda MD 20892-4874 • 301-594-8966