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    Merimepodib

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    DIGITAL CONTENT

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    2D Structure
    Also known as: 198821-22-6, Vx-497, Mmpd, Vi-21497, 2zl2ba06fu, (s)-tetrahydrofuran-3-yl 3-(3-(3-methoxy-4-(oxazol-5-yl)phenyl)ureido)benzylcarbamate
    Molecular Formula
    C23H24N4O6
    Molecular Weight
    452.5  g/mol
    InChI Key
    JBPUGFODGPKTDW-SFHVURJKSA-N
    FDA UNII
    2ZL2BA06FU
    Merimepodib is an inosine monophosphate dehydrogenase (IMPDH) inhibitor with activity against hepatitis C virus (HCV). IMPDH catalyzes the rate-limiting step in the de novo synthesis of guanine nucleotides, and treatment with merimepodib reduces the intracellular guanine nucleotide levels that are required for RNA and DNA synthesis, resulting in antiproliferative and antiviral effect.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(3S)-oxolan-3-yl] N-[[3-[[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoylamino]phenyl]methyl]carbamate
    2.1.2 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
    2.1.3 InChI Key
    JBPUGFODGPKTDW-SFHVURJKSA-N
    2.1.4 Canonical SMILES
    COC1=C(C=CC(=C1)NC(=O)NC2=CC=CC(=C2)CNC(=O)OC3CCOC3)C4=CN=CO4
    2.1.5 Isomeric SMILES
    COC1=C(C=CC(=C1)NC(=O)NC2=CC=CC(=C2)CNC(=O)O[C@H]3CCOC3)C4=CN=CO4
    2.2 Other Identifiers
    2.2.1 UNII
    2ZL2BA06FU
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. N-3-(3-(3-methoxy-4-oxazol-5-ylphenyl)ureido)benzylcarbamic Acid Tetrahydrofuran-3-yl Ester

    2. Vx 497

    3. Vx-497

    2.3.2 Depositor-Supplied Synonyms

    1. 198821-22-6

    2. Vx-497

    3. Mmpd

    4. Vi-21497

    5. 2zl2ba06fu

    6. (s)-tetrahydrofuran-3-yl 3-(3-(3-methoxy-4-(oxazol-5-yl)phenyl)ureido)benzylcarbamate

    7. Vi-21,497

    8. Chembl304087

    9. [(3s)-oxolan-3-yl] N-[[3-[[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoylamino]phenyl]methyl]carbamate

    10. Vx497

    11. Merimepodib, Vi-21497, Vx-497

    12. (s)-tetrahydro-3-furyl (m-(3-(3-methoxy-4-(5-oxazolyl)phenyl)ureido)benzyl)carbamate

    13. Carbamic Acid, ((3-((((3-methoxy-4-(5-oxazolyl)phenyl)amino)carbonyl)amino)phenyl)methyl)-, (3s)-tetrahydro-3-furanyl Ester

    14. Vx 497

    15. Merimepodib [usan:inn]

    16. Unii-2zl2ba06fu

    17. Merimebodib

    18. Carbamic Acid, [[3-[[[[3-methoxy-4-(5-oxazolyl)phenyl]amino]carbonyl]amino]phenyl]methyl]-, (3s)-tetrahydro-3-furanyl Ester

    19. Merimepodib [usan]

    20. Merimepodib [mi]

    21. Merimepodib [inn]

    22. Merimepodib (usan/inn)

    23. Merimepodib [who-dd]

    24. Schembl329922

    25. Gtpl10741

    26. Dtxsid70173639

    27. [[3-[[[[3-methoxy-4-(5-oxazolyl)phenyl]amino]carbonyl]amino]phenyl]methyl]carbamic Acid (3s)-tetrahydro-3-furanyl Ester

    28. Bcp28336

    29. Ex-a1201

    30. Yha82122

    31. Zinc3975663

    32. Bdbm50102249

    33. Fd5020

    34. Mfcd09837807

    35. S6689

    36. Db04862

    37. N-3-(3-(3-methoxy-4-oxazol-5-ylphenyl)ureido)benzylcarbamic Acid Tetrahydrofuran-3-yl Ester

    38. Ncgc00378589-01

    39. Ac-35396

    40. As-75124

    41. Hy-13986

    42. D04936

    43. A919457

    44. Q1727082

    45. (3s)-oxolan-3-yl N-{[3-({[3-methoxy-4-(1,3-oxazol-5-yl)phenyl]carbamoyl}amino)phenyl]methyl}carbamate

    46. [(3s)-tetrahydrofuran-3-yl] N-[[3-[(3-methoxy-4-oxazol-5-yl-phenyl)carbamoylamino]phenyl]methyl]carbamate

    47. {3-[3-(3-methoxy-4-oxazol-5-yl-phenyl)-ureido]-benzyl}-carbamic Acid (s)-(tetrahydro-furan-3-yl) Ester

    48. {3-[3-(3-methoxy-4-oxazol-5-yl-phenyl)-ureido]-benzyl}-carbamic Acid Tetrahydro-furan-3-yl Ester

    49. Carbamic Acid, N-[[3-[[[[3-methoxy-4-(5-oxazolyl)phenyl]amino]carbonyl]amino]phenyl]methyl]-, (3s)-tetrahydro-3-furanyl Ester

    50. N-[3-3-[3-methoxy-4-(5-oxazolyl)phenyl]ureido]benzyl]carbamic Acid Tetrahydrofuran-3-(s)-yl Ester

    2.4 Create Date
    2005-08-01
    3 Chemical and Physical Properties
    Molecular Weight 452.5 g/mol
    Molecular Formula C23H24N4O6
    XLogP32.1
    Hydrogen Bond Donor Count3
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count8
    Exact Mass452.16958450 g/mol
    Monoisotopic Mass452.16958450 g/mol
    Topological Polar Surface Area124 Ų
    Heavy Atom Count33
    Formal Charge0
    Complexity652
    Isotope Atom Count0
    Defined Atom Stereocenter Count1
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Indication

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

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    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.

    5.2 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.