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Details

Stereochemistry ABSOLUTE
Molecular Formula C18H26FN3O6
Molecular Weight 399.4139
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MERICITABINE

SMILES

CC(C)C(=O)OC[C@H]1O[C@@H](N2C=CC(N)=NC2=O)[C@](C)(F)[C@@H]1OC(=O)C(C)C

InChI

InChIKey=MLESJYFEMSJZLZ-MAAOGQSESA-N
InChI=1S/C18H26FN3O6/c1-9(2)14(23)26-8-11-13(28-15(24)10(3)4)18(5,19)16(27-11)22-7-6-12(20)21-17(22)25/h6-7,9-11,13,16H,8H2,1-5H3,(H2,20,21,25)/t11-,13-,16-,18-/m1/s1

HIDE SMILES / InChI

Molecular Formula C18H26FN3O6
Molecular Weight 399.4139
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

Mericitabine is a specific inhibitor of hepatitis C virus (HCV) replication that target NS5B polymerase. Mericitabine, a prodrug, is hydrolyzed in vivo to produce PSI-6130. It had been studied in phase II clinical trials for the treatment of chronic hepatitis C. However, while it showed a good safety profile in clinical trials, it was not sufficiently effective to be used as a standalone agent.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
0.61 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
0.557 μg/mL
1000 mg single, oral
RO5012433 plasma
Homo sapiens
0.854 μg/mL
2000 mg single, oral
RO5012433 plasma
Homo sapiens
0.361 μg/mL
500 mg single, oral
RO5012433 plasma
Homo sapiens
10.2 μg/mL
2000 mg single, oral
RO4995855 plasma
Homo sapiens
4.23 μg/mL
500 mg single, oral
RO4995855 plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
11.2 μg × h/mL
1000 mg single, oral
RO5012433 plasma
Homo sapiens
20.5 μg × h/mL
2000 mg single, oral
RO5012433 plasma
Homo sapiens
6.35 μg × h/mL
500 mg single, oral
RO5012433 plasma
Homo sapiens
113 μg × h/mL
2000 mg single, oral
RO4995855 plasma
Homo sapiens
28.8 μg × h/mL
500 mg single, oral
RO4995855 plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
22.7 h
1000 mg single, oral
RO5012433 plasma
Homo sapiens
21.8 h
2000 mg single, oral
RO5012433 plasma
Homo sapiens
19 h
500 mg single, oral
RO5012433 plasma
Homo sapiens
5.54 h
2000 mg single, oral
RO4995855 plasma
Homo sapiens
4.96 h
500 mg single, oral
RO4995855 plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
1500 mg doses twice daily for 2 weeks
Route of Administration: Oral
In Vitro Use Guide
A stable HCV 1b replicon cell (Gt 1b Con1) line was treated with the NS5B nucleoside inhibitor R7128 (prodrug PSI-6130). Inhibition of HCV replicon-encoded Renilla luciferase reporter activity after 3 days of incubation was calculated - EC50 = 0.61 uM.
Substance Class Chemical
Record UNII
TA63JX8X52
Record Status Validated (UNII)
Record Version