Merimepodib

HCID 153241

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Grundinformationen

CAS: 198821-22-6
Standard-SMILES: COc1cc(NC(=O)Nc2cccc(CNC(=O)O[C@H]3CCOC3)c2)ccc1-c1cnco1
InChIKey: JBPUGFODGPKTDW-SFHVURJKSA-N
Summenformel: C23H24N4O6
Durchschnittliche Molmasse: 452,5 g/mol
Monoisotopische Masse: 452,16958449

Überblick

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.

Namen und Bezeichner

Bevorzugter Name: Merimepodib
IUPAC: [(3S)-oxolan-3-yl] N-[[3-[[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoylamino]phenyl]methyl]carbamate
Englischer Name: MeriMepodib, VI-21497, VX-497
Summenformel: C23H24N4O6
Molmasse: 452.46

Namen und Synonyme

Merimepodib198821-22-6VX-497MMPD2ZL2BA06FUVI-21497VI-21,497DTXSID70173639Carbamic acid, ((3-((((3-methoxy-4-(5-oxazolyl)phenyl)amino)carbonyl)amino)phenyl)methyl)-, (3S)-tetrahydro-3-furanyl ester(3S)-oxolan-3-yl N-{[3-({[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoyl}amino)phenyl]methyl}carbamate(3S)-oxolan-3-yl N-((3-(((3-methoxy-4-(1,3-oxazol-5-yl)phenyl)carbamoyl)amino)phenyl)methyl)carbamatecarbamic acid, [[3-[[[[3-methoxy-4-(5-oxazolyl)phenyl]amino]carbonyl]amino]phenyl]methyl]-, (3S)-tetrahydro-3-furanyl ester

Weitere Namen anzeigen

VI 21497Merimepodib (VX-497)Merimepodib (VI-21497Merimepodib, 10 mM in DMSOMeriMepodib, VI-21497, VX-497VX497VX 497MMPVI21497VI 21497HCV,Inhibitor,Merimepodib,HBV,Hepatitis C virus,Hepatitis B virus,VX497,VX 497,inhibit,MMPD[[3-[[[[3-Methoxy-4-(5-oxazolyl)phenyl]amino]carbonyl]amino]phenyl]methyl]carbamic acid (3S)-tetrahydro-3-furanyl ester

MERIMEPODIBUMRefChem:811132DTXCID6096130(S)-tetrahydrofuran-3-yl 3-(3-(3-methoxy-4-(oxazol-5-yl)phenyl)ureido)benzylcarbamate[(3S)-oxolan-3-yl] N-[[3-[[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoylamino]phenyl]methyl]carbamateMFCD09837807Carbamic acid, N-[[3-[[[[3-methoxy-4-(5-oxazolyl)phenyl]amino]carbonyl]amino]phenyl]methyl]-, (3S)-tetrahydro-3-furanyl esterCHEMBL304087

Datenbank-Bezeichner

CAS: 198821-22-6
PubChem CID: 153241
DTXSID: DTXSID70173639
ChEMBL: CHEMBL304087
UNII: 2ZL2BA06FU
Nikkaji: J1.291.375C

Eigenschaften

Berechnete Struktureigenschaften

XLogP: 2,1
Polarare Oberfläche (TPSA): 124 Å²
H-Brücken-Donoren: 3
H-Brücken-Akzeptoren: 7
Frei drehbare Bindungen: 8
Schwere Atome: 33
Formalladung: 0
Komplexität: 652

Experimentelle und physikochemische Eigenschaften

DrugsPharmaceuticals -> Listed in ZINC15

LogP3.6

Physikochemische Eigenschaften

Siedepunkt: 571.4 · 571.4±50.0 °C(Predicted)
Dichte: 1.36 · 1.36±0.1 g/cm3(Predicted)
storage temp.: Sealed in dry,Room Temperature
Löslichkeit: 45.2 mg/mL · ≥45.2 mg/mL in DMSO; insoluble in EtOH; insoluble in H2O
Aggregatzustand: solid
pka: 11.66 · 11.66±0.46(Predicted)
Farbe: Off-white to light yellow

Sicherheit und Regulatorisches

Sicherheitsdaten

Alarmwort: Warnung
Gefahrenhinweise: Code Gefahrenhinweise Gefahrenklasse Abteilung Alarmwort Symbol P-Code H302

Chemie und Industrie

Pharmakologische Informationen

Pharmacodynamics · 1 Eintrag

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.

Mechanism of ActionMerimepodib 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.

Anwendungen · 2 Einträge

BeschreibungMerimepodib is an inhibitor of inosine-5''-monophosphate dehydrogenase (IMPDH; Kis = 7 and 10 nM for IMPDH type I and type II, respectively) with antiviral and immunosuppressant activities. It reduces Ebola, Lassa, chikungunya, Junin, and Zika virus titers in vitro and inhibits Zika virus replication in Huh7 cells (EC50 = 0.6 μM). Merimepodib inhibits the proliferation of PHA-stimulated T cells and SPAS-stimulated B cells (IC50s = 104 and 132 nM, respectively), effects that can be reversed by guanosine but not adenosine . In vivo, merimepodib (50 and 100 mg/kg) increases allograft survival in a murine skin transplantation model and prevents development of graft versus host disease (GVHD) in splenocyte allografted mice.

VerwendenInhibition of inosine monophosphate dehydrogenase (IMPDH), which has potential antiviral, antiproliferative, antiparasitic, and immunosuppressive activity.