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    BDBM430624

    BUILDING BLOCK

    PharmaCompass
    Xls

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    2D Structure
    Also known as: N4-hydroxycytidine, 3258-02-4, Beta-d-n4-hydroxycytidine, Eidd-1931, Uridine, 4-oxime, N-hydroxycytidine
    Molecular Formula
    C9H13N3O6
    Molecular Weight
    259.22  g/mol
    InChI Key
    XCUAIINAJCDIPM-XVFCMESISA-N
    FDA UNII
    C3D11PV2O4
    N4-Hydroxyctidine, or EIDD-1931, is a ribonucleoside analog which induces mutations in RNA virions. N4-hydroxycytidine was first described in the literature in 1980 as a potent mutagen of bacteria and phage. It has shown antiviral activity against Venezuelan equine encephalitis virus, and the human coronavirus HCoV-NL63 in vitro. N4-hydroxycytodine has been shown to inhibit SARS-CoV-2 as well as other human and bat coronaviruses in mice and human airway epithelial cells. It is orally bioavailable in mice and distributes into tissue before becoming the active 5-triphosphate form, which is incorporated into the genome of new virions, resulting in the accumulation of inactivating mutations. In non-human primates, N4-hydroxycytidine was poorly orally bioavailable. A [remdesivir] resistant mutant mouse hepatitis virus has also been shown to have increased sensitivity to N4-hydroxycytidine. The prodrug of N4-hydroxycytidine, [EIDD-2801], is also being investigated for its broad spectrum activity against the coronavirus family of viruses.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(hydroxyamino)pyrimidin-2-one
    2.1.2 InChI
    InChI=1S/C9H13N3O6/c13-3-4-6(14)7(15)8(18-4)12-2-1-5(11-17)10-9(12)16/h1-2,4,6-8,13-15,17H,3H2,(H,10,11,16)/t4-,6-,7-,8-/m1/s1
    2.1.3 InChI Key
    XCUAIINAJCDIPM-XVFCMESISA-N
    2.1.4 Canonical SMILES
    C1=CN(C(=O)N=C1NO)C2C(C(C(O2)CO)O)O
    2.1.5 Isomeric SMILES
    C1=CN(C(=O)N=C1NO)[C@H]2[C@@H]([C@@H]([C@H](O2)CO)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    C3D11PV2O4
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. 4-oxime Uridine

    2. Beta-d-n4-hydroxycytidine

    3. Eidd-1931

    4. N4-hydroxycytidine

    2.3.2 Depositor-Supplied Synonyms

    1. N4-hydroxycytidine

    2. 3258-02-4

    3. Beta-d-n4-hydroxycytidine

    4. Eidd-1931

    5. Uridine, 4-oxime

    6. N-hydroxycytidine

    7. 4-n-hydroxycytidine

    8. Eidd1931

    9. C3d11pv2o4

    10. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(hydroxyamino)pyrimidin-2-one

    11. 1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-(hydroxyimino)-3,4-dihydropyrimidin-2(1h)-one

    12. 4-oxime Uridine

    13. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(hydroxyamino)-1,2-dihydropyrimidin-2-one

    14. N-4-hydroxycytidine

    15. Cytidine, N-hydroxy-

    16. Ccris 1074

    17. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-(hydroxyimino)-3,4-dihydropyrimidin-2(1h)-one

    18. Unii-c3d11pv2o4

    19. Beta-d-n(4)-hydroxycytidine

    20. N-hydroxy-3,4-dihydrocytidine

    21. Schembl5190819

    22. Chembl2178720

    23. Schembl24780346

    24. Eidd 1931

    25. Gtpl10735

    26. Dtxsid20186274

    27. Chebi:180654

    28. Bdbm430624

    29. Ex-a3655

    30. Mfcd01675695

    31. At13085

    32. Bs-47105

    33. Hy-125033

    34. Cs-0088698

    35. En300-7534996

    36. Z4171362498

    37. 1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-(hydroxyamino)pyrimidin-2(1h)-one

    38. 1-((2r,3r,4s,5r)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-hydroxyamino-1h-pyrimidin-2-one

    39. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(hydroxyimino)-1,2,3,4-tetrahydropyrimidin-2-one

    40. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-(hydroxyamino)pyrimidin-2-one

    2.3.3 Other Synonyms

    1. Uridine, 4-oxime

    2.4 Create Date
    2005-08-01
    3 Chemical and Physical Properties
    Molecular Weight 259.22 g/mol
    Molecular Formula C9H13N3O6
    XLogP3-2.2
    Hydrogen Bond Donor Count5
    Hydrogen Bond Acceptor Count6
    Rotatable Bond Count3
    Exact Mass g/mol
    Monoisotopic Mass g/mol
    Topological Polar Surface Area135
    Heavy Atom Count18
    Formal Charge0
    Complexity398
    Isotope Atom Count0
    Defined Atom Stereocenter Count4
    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

    N4-hydroxycytidine and its prodrug [EIDD-2801] is being studied for its activity against a number of viral infections including influenza, MERS-CoV, and SARS-CoV-2.

    5 Pharmacology and Biochemistry
    5.1 Absorption, Distribution and Excretion

    Absorption

    N4-hydroxycytidine is orally bioavailable in mice but poorly bioavailable in non-human primates.

    5.2 Metabolism/Metabolites

    N4-hydroxycytidine distributes into tissues where it is is phosphorylated to the 5'-triphosphate form.

    5.3 Mechanism of Action

    N4-hydroxycytidine is phosphorylated in tissue to the active 5-triphosphate form, which is incorporated into the genome of new virions, resulting in the accumulation of inactivating mutations, known as viral error catastrophe. A [remdesivir] resistant mutant mouse hepatitis virus has also been shown to have increased sensitivity to N4-hydroxycytidine.