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

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
Structure--activity relationships of 1-(2-Deoxy-2-fluoro-beta-L-arabinofuranosyl)pyrimidine nucleosides as anti-hepatitis B virus agents.	1996 Jul 5	8709113
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
Current and future antiviral agents for chronic hepatitis B.	2003 Mar	12615847
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.

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