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Details

Stereochemistry ABSOLUTE
Molecular Formula C10H16FN2O14P3
Molecular Weight 500.1587
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of CLEVUDINE TRIPHOSPHATE

SMILES

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

InChI

InChIKey=RUKRVHYQIIURNV-XQXXSGGOSA-N
InChI=1S/C10H16FN2O14P3/c1-4-2-13(10(16)12-8(4)15)9-6(11)7(14)5(25-9)3-24-29(20,21)27-30(22,23)26-28(17,18)19/h2,5-7,9,14H,3H2,1H3,(H,20,21)(H,22,23)(H,12,15,16)(H2,17,18,19)/t5-,6+,7-,9-/m0/s1

HIDE SMILES / InChI
Molecular Formula C10H16FN2O14P3
Molecular Weight 500.1587
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

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

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Inhibitor
8504
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
LEVOVIR

Approved Use

Chronic hepatitis B.
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.017 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/18363895/
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CLEVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.056 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/18363895/
30 mg 1 times / day steady-state, oral
dose: 30 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CLEVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.068 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/18363895/
50 mg 1 times / day steady-state, oral
dose: 50 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CLEVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.4 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15239097/
50 mg 1 times / day steady-state, oral
dose: 50 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CLEVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.8 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15239097/
100 mg 1 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CLEVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
1.6 μg/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15239097/
200 mg 1 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CLEVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.54 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/18363895/
10 mg 1 times / day steady-state, oral
dose: 10 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CLEVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.01 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/18363895/
30 mg 1 times / day steady-state, oral
dose: 30 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CLEVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
2.95 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/18363895/
50 mg 1 times / day steady-state, oral
dose: 50 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CLEVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
3 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15239097/
50 mg 1 times / day steady-state, oral
dose: 50 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CLEVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
5.7 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15239097/
100 mg 1 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CLEVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
12.3 μg × h/mL
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15239097/
200 mg 1 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CLEVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
71.2 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/18363895/
30 mg 1 times / day steady-state, oral
dose: 30 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CLEVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
72.9 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/18363895/
50 mg 1 times / day steady-state, oral
dose: 50 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CLEVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
61 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15239097/
50 mg 1 times / day steady-state, oral
dose: 50 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CLEVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
43.6 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15239097/
100 mg 1 times / day steady-state, oral
dose: 100 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CLEVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
50.8 h
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/15239097/
200 mg 1 times / day steady-state, oral
dose: 200 mg
route of administration: Oral
experiment type: STEADY-STATE
co-administered:
CLEVUDINE plasma
Homo sapiens
population: UNHEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
200 mg 1 times / day multiple, oral
Highest studied dose
Dose: 200 mg, 1 times / day
Route: oral
Route: multiple
Dose: 200 mg, 1 times / day
Sources:
https://pubmed.ncbi.nlm.nih.gov/15239097/
unhealthy, ADULT
Health Status: unhealthy
Age Group: ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
https://pubmed.ncbi.nlm.nih.gov/15239097/
Sources:
https://pubmed.ncbi.nlm.nih.gov/15239097/
PubMed

PubMed

TitleDatePubMed
Noncompetitive inhibition of hepatitis B virus reverse transcriptase protein priming and DNA synthesis by the nucleoside analog clevudine.
2013-09
Cellular and virological mechanisms of HBV drug resistance.
2006-02
Mechanism of antiviral activities of 3'-substituted L-nucleosides against 3TC-resistant HBV polymerase: a molecular modelling approach.
2003-11
Current and future antiviral agents for chronic hepatitis B.
2003-03
In vitro activity of potential anti-poxvirus agents.
2003-01
Comparison of anti-hepatitis B virus activities of lamivudine and clevudine by a quantitative assay.
2003-01
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.
2003-01
Inhibitory activity of dioxolane purine analogs on wild-type and lamivudine-resistant mutants of hepadnaviruses.
2002-09
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.
2001-09
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).
2001-01
Structure-activity relationships of L-dioxolane uracil nucleosides as anti-Epstein Barr virus agents.
1999-06-17
Sensitivity of L-(-)2,3-dideoxythiacytidine resistant hepatitis B virus to other antiviral nucleoside analogues.
1999-06-15
Structure--activity relationships of 1-(2-Deoxy-2-fluoro-beta-L-arabinofuranosyl)pyrimidine nucleosides as anti-hepatitis B virus agents.
1996-07-05
Inhibition of Epstein-Barr virus replication by a novel L-nucleoside, 2'-fluoro-5-methyl-beta-L-arabinofuranosyluracil.
1996-04-12
Inhibition of hepatitis B virus by a novel L-nucleoside, 2'-fluoro-5-methyl-beta-L-arabinofuranosyl uracil.
1996-02
Patents

Patents

EP1284720 B1
2
US5753789 A
2
WO1995020595 A1
2

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 Mon Mar 31 21:56:09 GMT 2025
Edited
by admin
on Mon Mar 31 21:56:09 GMT 2025
Record UNII
GYY7PAS72J
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
2,4(1H,3H)-PYRIMIDINEDIONE, 1-(2-DEOXY-2-FLUORO-5-O-(HYDROXY((HYDROXY(PHOSPHONOOXY)PHOSPHINYL)OXY)PHOSPHINYL)-.BETA.-L-ARABINOFURANOSYL)-5-METHYL-
Preferred Name English
CLEVUDINE TRIPHOSPHATE
MI  
Common Name English
L-FMAU-TP
Common Name English
CLEVUDINE TRIPHOSPHATE [MI]
Common Name English
Code System Code Type Description
CAS
174625-00-4
Created by admin on Mon Mar 31 21:56:09 GMT 2025 , Edited by admin on Mon Mar 31 21:56:09 GMT 2025
PRIMARY
MERCK INDEX
m3621
Created by admin on Mon Mar 31 21:56:09 GMT 2025 , Edited by admin on Mon Mar 31 21:56:09 GMT 2025
PRIMARY Merck Index
PUBCHEM
503024
Created by admin on Mon Mar 31 21:56:09 GMT 2025 , Edited by admin on Mon Mar 31 21:56:09 GMT 2025
PRIMARY
FDA UNII
GYY7PAS72J
Created by admin on Mon Mar 31 21:56:09 GMT 2025 , Edited by admin on Mon Mar 31 21:56:09 GMT 2025
PRIMARY
Related Record Type Details
HEPATITIS B VIRUS
TARGET ORGANISM->INHIBITOR
Related Record Type Details
Structure of CLEVUDINE
PRODRUG -> METABOLITE ACTIVE
Structure of Fosclevudine Alafenamide
PRODRUG -> METABOLITE ACTIVE
Related Record Type Details
Structure of CLEVUDINE TRIPHOSPHATE
ACTIVE MOIETY
NIH
NCATS
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