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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 of CLEVUDINE

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
MOL RATIO 1 MOL RATIO (average)
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

University of Georgia|Yale University School of Medicine|University of Alabama
2

Approval Year

Unknown
149,124

Targets

Primary TargetPharmacologyConditionPotency
DNA polymerase/reverse transcriptase
10
Inhibitor
8,504

Conditions

ConditionModalityTargetsHighest PhaseProduct
Chronic hepatitis B
16
 Primary
Approved
8,583
LEVOVIR

Cmax

ValueDoseCo-administeredAnalytePopulation
0.017 μg/mL
10 mg 1 times / day steady-state, oral
 CLEVUDINE plasma
Homo sapiens
0.056 μg/mL
30 mg 1 times / day steady-state, oral
 CLEVUDINE plasma
Homo sapiens
0.068 μg/mL
50 mg 1 times / day steady-state, oral
 CLEVUDINE plasma
Homo sapiens
0.4 μg/mL
50 mg 1 times / day steady-state, oral
 CLEVUDINE plasma
Homo sapiens
0.8 μg/mL
100 mg 1 times / day steady-state, oral
 CLEVUDINE plasma
Homo sapiens
1.6 μg/mL
200 mg 1 times / day steady-state, oral
 CLEVUDINE plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
0.54 μg × h/mL
10 mg 1 times / day steady-state, oral
 CLEVUDINE plasma
Homo sapiens
2.01 μg × h/mL
30 mg 1 times / day steady-state, oral
 CLEVUDINE plasma
Homo sapiens
2.95 μg × h/mL
50 mg 1 times / day steady-state, oral
 CLEVUDINE plasma
Homo sapiens
3 μg × h/mL
50 mg 1 times / day steady-state, oral
 CLEVUDINE plasma
Homo sapiens
5.7 μg × h/mL
100 mg 1 times / day steady-state, oral
 CLEVUDINE plasma
Homo sapiens
12.3 μg × h/mL
200 mg 1 times / day steady-state, oral
 CLEVUDINE plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
71.2 h
30 mg 1 times / day steady-state, oral
 CLEVUDINE plasma
Homo sapiens
72.9 h
50 mg 1 times / day steady-state, oral
 CLEVUDINE plasma
Homo sapiens
61 h
50 mg 1 times / day steady-state, oral
 CLEVUDINE plasma
Homo sapiens
43.6 h
100 mg 1 times / day steady-state, oral
 CLEVUDINE plasma
Homo sapiens
50.8 h
200 mg 1 times / day steady-state, oral
 CLEVUDINE plasma
Homo sapiens

Doses

PubMed

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
Record UNII
IN51MVP5F1
Record Status Validated (UNII)
Record Version
NIH
NCATS
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