CLEVUDINE

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C10H13FN2O5
Molecular Weight	260.219
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=CN([C@H]2O[C@@H](CO)[C@H](O)[C@H]2F)C(=O)NC1=O

InChI

InChIKey=GBBJCSTXCAQSSJ-XQXXSGGOSA-N

InChI=1S/C10H13FN2O5/c1-4-2-13(10(17)12-8(4)16)9-6(11)7(15)5(3-14)18-9/h2,5-7,9,14-15H,3H2,1H3,(H,12,16,17)/t5-,6+,7-,9-/m0/s1

HIDE SMILES / InChI

Molecular Formula	C10H13FN2O5
Molecular Weight	260.219
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/23774432 | https://www.ncbi.nlm.nih.gov/pubmed/19584963 | https://www.ncbi.nlm.nih.gov/pubmed/18505177

Clevudine (also known as L-FMAU) is a nucleos(t)ide reverse transcriptase inhibitor, which inhibits the DNA synthesis activity of the hepatitis B virus polymerase. The drug was approved in Korea and Philippines and is being marketed under the names Levovir and Revovir. The drug is indicated in patients with chronic hepatitis B virus infection. Upon administration, clevudine is metabolized to the active metabolite, clevudine triphosphate, which is responsible for the inhibition of viral polymerase.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
DNA polymerase/reverse transcriptase 10 Target ID: CHEMBL2362994 Sources: https://www.ncbi.nlm.nih.gov/pubmed/23774432	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Chronic hepatitis B 16 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19584963	Primary		Approved 8429	LEVOVIR Approved Use Chronic hepatitis B.

PubMed

Title	Date	PubMed
Inhibition of Epstein-Barr virus replication by a novel L-nucleoside, 2'-fluoro-5-methyl-beta-L-arabinofuranosyluracil.	1996 Apr 12	8651944
Inhibition of hepatitis B virus by a novel L-nucleoside, 2'-fluoro-5-methyl-beta-L-arabinofuranosyl uracil.	1996 Feb	8834884
Structure--activity relationships of 1-(2-Deoxy-2-fluoro-beta-L-arabinofuranosyl)pyrimidine nucleosides as anti-hepatitis B virus agents.	1996 Jul 5	8709113
Sensitivity of L-(-)2,3-dideoxythiacytidine resistant hepatitis B virus to other antiviral nucleoside analogues.	1999 Jun 15	10353255
Structure-activity relationships of L-dioxolane uracil nucleosides as anti-Epstein Barr virus agents.	1999 Jun 17	10377226
Antiviral activity of clevudine [L-FMAU, (1-(2-fluoro-5-methyl-beta, L-arabinofuranosyl) uracil)] against woodchuck hepatitis virus replication and gene expression in chronically infected woodchucks (Marmota monax).	2001 Jan	11124844
In vitro susceptibilities of wild-type or drug-resistant hepatitis B virus to (-)-beta-D-2,6-diaminopurine dioxolane and 2'-fluoro-5-methyl-beta-L-arabinofuranosyluracil.	2001 Sep	11502520
Inhibitory activity of dioxolane purine analogs on wild-type and lamivudine-resistant mutants of hepadnaviruses.	2002 Sep	12198665
In vitro activity of potential anti-poxvirus agents.	2003 Jan	12615301
Comparison of anti-hepatitis B virus activities of lamivudine and clevudine by a quantitative assay.	2003 Jan	12499209
Assessment of the effect of phosphorylated metabolites of anti-human immunodeficiency virus and anti-hepatitis B virus pyrimidine analogs on the behavior of human deoxycytidylate deaminase.	2003 Jan	12488542
Current and future antiviral agents for chronic hepatitis B.	2003 Mar	12615847
Mechanism of antiviral activities of 3'-substituted L-nucleosides against 3TC-resistant HBV polymerase: a molecular modelling approach.	2003 Nov	14968937
Cellular and virological mechanisms of HBV drug resistance.	2006 Feb	16364492
Noncompetitive inhibition of hepatitis B virus reverse transcriptase protein priming and DNA synthesis by the nucleoside analog clevudine.	2013 Sep	23774432

Patents

Sample Use Guides

In Vivo Use Guide

The drug is taken orally at a dose of 30 mg/day.

Route of Administration: Oral

In Vitro Use Guide

Antiviral activity of clevudine was tested in 2.2.15 cells (a human hepatoma cell line transfected with the HBV genome). The cell line was treated with the drug for 72 h and EC50 value was found to be 0.1 uM. In H1 cells treated for 5 days the EC50 value was 5 uM.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 15:05:43 UTC 2023` Edited by `admin` on `Fri Dec 15 15:05:43 UTC 2023`
Record UNII	IN51MVP5F1
Record Status	`Validated (UNII)`
Record Version

Download

Name

Type

Language

CLEVUDINE

Official Name

English

L-FMAU

Code

English

1-(2-DEOXY-2-FLUORO-.BETA.-L-ARABINOFURANOSYL)THYMINE

Common Name

English

Clevudine [WHO-DD]

Common Name

English

clevudine [INN]

Common Name

English

CLEVUDINE [USAN]

Common Name

English

LEVOVIR

Brand Name

English

2,4(1H,3H)-PYRIMIDINEDIONE, 1-(2-DEOXY-2-FLUORO-.BETA.-L-ARABINOFURANOSYL)-5-METHYL-

Common Name

English

CLEVUDINE [MI]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C281