Merimepodib

Synonyms :
MMPD

Status : investigational

Description

Merimepodib (VX-497) is a novel noncompetitive inhibitor of IMPDH. Merimepodib is orally bioavailable and inhibits the proliferation of primary human, mouse, rat, and dog lymphocytes at concentrations of approximately 100 nM.

Used

For the treatment of hepatitis C virus (HCV) infection.

Mechanism Of Action

Merimepodib is a orally active inhibitor of inosine monophospate dehydrogenase (IMPDH). IMPDH inhibition leads to a reduction in intracellular guanosine triphosphate (GTP), a molecule required for DNA and RNA synthesis.

Pharmacodynamics

Merimepodib, an oral drug, contains a novel inhibitor of inosine monophosphate dehydrogenase (IMPDH), an enzyme responsible for stimulating the production of lymphocytes. Merimepodib has the potential to exert direct antiviral activity, as well as affect the immune response by acting on lymphocyte migration and proliferation. Consequently, merimepodib may be an effective treatment for hepatitis C virus (HCV) infection, as the disease involves both viral proliferation and liver inflammation.

Chemical Classification

This compound belongs to the class of organic compounds known as n-phenylureas. These are compounds containing a N-phenylurea moiety, which is structurally characterized by a phenyl group linked to one nitrogen atom of a urea group.

N-phenylureas

Organic compounds

Benzenoids

Benzene and substituted derivatives

N-phenylureas

Chemical Name

MMPD

Calculated Property

kind Value Source
logP 1.74 ALOGPS
logS -3.6 ALOGPS
Water Solubility 1.10e-01 g/l ALOGPS
logP 1.94 ChemAxon
IUPAC Name (3S)-oxolan-3-yl N-{[3-({[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoyl}amino)phenyl]methyl}carbamate ChemAxon
Traditional IUPAC Name (3S)-oxolan-3-yl N-{[3-({[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoyl}amino)phenyl]methyl}carbamate ChemAxon
Molecular Weight 452.4599 ChemAxon
Monoisotopic Weight 452.16958452 ChemAxon
SMILES COC1=C(C=CC(NC(=O)NC2=CC=CC(CNC(=O)O[C@H]3CCOC3)=C2)=C1)C1=CN=CO1 ChemAxon
Molecular Formula C23H24N4O6 ChemAxon
InChI 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 ChemAxon
InChIKey InChIKey=JBPUGFODGPKTDW-SFHVURJKSA-N ChemAxon
Polar Surface Area (PSA) 123.95 ChemAxon
Refractivity 121.39 ChemAxon
Polarizability 45.46 ChemAxon
Rotatable Bond Count 8 ChemAxon
H Bond Acceptor Count 5 ChemAxon
H Bond Donor Count 3 ChemAxon
pKa (strongest acidic) 11.22 ChemAxon
pKa (strongest basic) 0.57 ChemAxon
Physiological Charge 0 ChemAxon
Number of Rings 4 ChemAxon
Bioavailability 1 ChemAxon
Rule of Five 1 ChemAxon
Ghose Filter 1 ChemAxon
MDDR-Like Rule 1 ChemAxon

Affected organism

Hepatitis C virus, RSV and other RNA/DNA viruses

Target within organism

  • Inosine-5′-monophosphate dehydrogenase : in Streptococcus pyogenes