ELVUCITABINE

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-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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/9873711 | https://www.ncbi.nlm.nih.gov/pubmed/12476956 | https://aidsinfo.nih.gov/drugs/385/elvucitabine/0/professional

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

PubMed

Title	Date	PubMed
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	8627596
Bis-S-acyl-2-thioethyl (SATE)-bearing monophosphate prodrug of beta-L-FD4C as potent anti-HBV agent.	1998 Jan 6	9871628
Anti-hepatitis B virus activity and metabolism of 2',3'-dideoxy-2',3'-didehydro-beta-L(-)-5-fluorocytidine.	1998 Jul	9661025
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	9661024
Synthesis and biological evaluation of a series of 2'-fluorinated-2',3'-dideoxy-2',3'-didehydro-(L)-nucleosides.	1998 Jul 7	9873396
Synthesis and comparative evaluation of two antiviral agents: beta-L-Fd4C and beta-D-Fd4C.	1998 Nov 17	9873711
Sensitivity of L-(-)2,3-dideoxythiacytidine resistant hepatitis B virus to other antiviral nucleoside analogues.	1999 Jun 15	10353255
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	10072683
Antiviral beta-L-nucleosides specific for hepatitis B virus infection.	2001	11594678
Antiviral activity of beta-L-2',3'-dideoxy-2',3'-didehydro-5-fluorocytidine in woodchucks chronically infected with woodchuck hepatitis virus.	2001 Apr	11257017
Anti-HBV specific beta-L-2'-deoxynucleosides.	2001 Apr-Jul	11563077
Antiviral L-nucleosides specific for hepatitis B virus infection.	2001 Jan	11120971
Mechanism of antiviral activities of 3'-substituted L-nucleosides against 3TC-resistant HBV polymerase: a molecular modelling approach.	2003 Nov	14968937
Novel 4'-substituted stavudine analog with improved anti-human immunodeficiency virus activity and decreased cytotoxicity.	2004 May	15105115
New nucleoside reverse transcriptase inhibitors for the treatment of HIV infections.	2004 Oct	15351346
In vitro activity of structurally diverse nucleoside analogs against human immunodeficiency virus type 1 with the K65R mutation in reverse transcriptase.	2005 Mar	15728915
Emerging anti-HIV drugs.	2005 May	15934866
Novel compounds for the treatment of HIV type-1 infection.	2009	19483267
Comparative study of the persistence of anti-HIV activity of deoxynucleoside HIV reverse transcriptase inhibitors after removal from culture.	2009 Apr 22	19386130
Elvucitabine data released at CROI.	2010 Mar	20235383

Patents

Substance Class	Chemical Created by `admin` on `Sat Dec 16 16:18:08 UTC 2023` Edited by `admin` on `Sat Dec 16 16:18:08 UTC 2023`
Record UNII	M09BUF90C0
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ELVUCITABINE

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