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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 ELVUCITABINE

SMILES

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

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

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
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 Apr 26
Bis-S-acyl-2-thioethyl (SATE)-bearing monophosphate prodrug of beta-L-FD4C as potent anti-HBV agent.
1998 Jan 6
Anti-hepatitis B virus activity and metabolism of 2',3'-dideoxy-2',3'-didehydro-beta-L(-)-5-fluorocytidine.
1998 Jul
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 Jul
Synthesis and biological evaluation of a series of 2'-fluorinated-2',3'-dideoxy-2',3'-didehydro-(L)-nucleosides.
1998 Jul 7
Synthesis and comparative evaluation of two antiviral agents: beta-L-Fd4C and beta-D-Fd4C.
1998 Nov 17
Sensitivity of L-(-)2,3-dideoxythiacytidine resistant hepatitis B virus to other antiviral nucleoside analogues.
1999 Jun 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 Mar 11
Antiviral beta-L-nucleosides specific for hepatitis B virus infection.
2001
Antiviral activity of beta-L-2',3'-dideoxy-2',3'-didehydro-5-fluorocytidine in woodchucks chronically infected with woodchuck hepatitis virus.
2001 Apr
Anti-HBV specific beta-L-2'-deoxynucleosides.
2001 Apr-Jul
Antiviral L-nucleosides specific for hepatitis B virus infection.
2001 Jan
Mechanism of antiviral activities of 3'-substituted L-nucleosides against 3TC-resistant HBV polymerase: a molecular modelling approach.
2003 Nov
Novel 4'-substituted stavudine analog with improved anti-human immunodeficiency virus activity and decreased cytotoxicity.
2004 May
New nucleoside reverse transcriptase inhibitors for the treatment of HIV infections.
2004 Oct
Emerging anti-HIV drugs.
2005 May
Novel compounds for the treatment of HIV type-1 infection.
2009
Comparative study of the persistence of anti-HIV activity of deoxynucleoside HIV reverse transcriptase inhibitors after removal from culture.
2009 Apr 22
Elvucitabine data released at CROI.
2010 Mar
Patents

Patents

Substance Class Chemical
Created
by admin
on Sat Jun 26 11:39:54 UTC 2021
Edited
by admin
on Sat Jun 26 11:39:54 UTC 2021
Record UNII
M09BUF90C0
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ELVUCITABINE
INN   USAN  
INN   USAN  
Official 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
ACH-126,443
Code 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 Sat Jun 26 11:39:54 UTC 2021 , Edited by admin on Sat Jun 26 11:39:54 UTC 2021
NCI_THESAURUS C97452
Created by admin on Sat Jun 26 11:39:54 UTC 2021 , Edited by admin on Sat Jun 26 11:39:54 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C73201
Created by admin on Sat Jun 26 11:39:54 UTC 2021 , Edited by admin on Sat Jun 26 11:39:54 UTC 2021
PRIMARY
EPA CompTox
181785-84-2
Created by admin on Sat Jun 26 11:39:54 UTC 2021 , Edited by admin on Sat Jun 26 11:39:54 UTC 2021
PRIMARY
DRUG BANK
DB06236
Created by admin on Sat Jun 26 11:39:54 UTC 2021 , Edited by admin on Sat Jun 26 11:39:54 UTC 2021
PRIMARY
WIKIPEDIA
ELVUCITABINE
Created by admin on Sat Jun 26 11:39:54 UTC 2021 , Edited by admin on Sat Jun 26 11:39:54 UTC 2021
PRIMARY
MESH
C099405
Created by admin on Sat Jun 26 11:39:54 UTC 2021 , Edited by admin on Sat Jun 26 11:39:54 UTC 2021
PRIMARY
PUBCHEM
469717
Created by admin on Sat Jun 26 11:39:54 UTC 2021 , Edited by admin on Sat Jun 26 11:39:54 UTC 2021
PRIMARY
FDA UNII
M09BUF90C0
Created by admin on Sat Jun 26 11:39:54 UTC 2021 , Edited by admin on Sat Jun 26 11:39:54 UTC 2021
PRIMARY
EVMPD
SUB177918
Created by admin on Sat Jun 26 11:39:54 UTC 2021 , Edited by admin on Sat Jun 26 11:39:54 UTC 2021
PRIMARY
CAS
181785-84-2
Created by admin on Sat Jun 26 11:39:54 UTC 2021 , Edited by admin on Sat Jun 26 11:39:54 UTC 2021
PRIMARY
ChEMBL
CHEMBL38700
Created by admin on Sat Jun 26 11:39:54 UTC 2021 , Edited by admin on Sat Jun 26 11:39:54 UTC 2021
PRIMARY
INN
8364
Created by admin on Sat Jun 26 11:39:54 UTC 2021 , Edited by admin on Sat Jun 26 11:39:54 UTC 2021
PRIMARY
Related Record Type Details
TARGET ORGANISM->INHIBITOR
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ACTIVE MOIETY