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Details

Stereochemistry ABSOLUTE
Molecular Formula C23H24N4O6
Molecular Weight 452.4599
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of MERIMEPODIB

SMILES

COC1=C(C=CC(NC(=O)NC2=CC=CC(CNC(=O)O[C@H]3CCOC3)=C2)=C1)C4=CN=CO4

InChI

InChIKey=JBPUGFODGPKTDW-SFHVURJKSA-N
InChI=1S/C23H24N4O6/c1-30-20-10-17(5-6-19(20)21-12-24-14-32-21)27-22(28)26-16-4-2-3-15(9-16)11-25-23(29)33-18-7-8-31-13-18/h2-6,9-10,12,14,18H,7-8,11,13H2,1H3,(H,25,29)(H2,26,27,28)/t18-/m0/s1

HIDE SMILES / InChI

Molecular Formula C23H24N4O6
Molecular Weight 452.4599
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Merimepodib has immunosuppressive activity. It targets hepatitis C indirectly through the inhibition of inositol monophosphate dehydrogenase, which exerts an acute antiproliferative effect on lymphocyte proliferation due to their almost exclusive dependence on the de novo pathway for synthesis of guanosine. Phase II clinical trial study of merimepodib for the treatment of HCV infection and psoriasis were completed. The poor pharmacokinetic-pharmacodynamic results have resulted in discontinuation of clinical trials.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Primary
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
1748 ng/mL
100 mg 3 times / day steady-state, oral
MERIMEPODIB plasma
Homo sapiens
3195 ng/mL
200 mg 3 times / day steady-state, oral
MERIMEPODIB plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
3543 ng × h/mL
100 mg 3 times / day steady-state, oral
MERIMEPODIB plasma
Homo sapiens
8210 ng × h/mL
200 mg 3 times / day steady-state, oral
MERIMEPODIB plasma
Homo sapiens

PubMed

Sample Use Guides

In Vivo Use Guide
25 or 50 mg every 12h (24 weeks of treatment)
Route of Administration: Oral
In Vitro Use Guide
The IC50 values for VX-497 in Sprague-Dawley or Lewis rat lymphocytes were similar to the 100 nM human PBMC IC50 values.
Substance Class Chemical
Record UNII
2ZL2BA06FU
Record Status Validated (UNII)
Record Version