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    Beta-D-N4-hydroxycytidine

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    2D Structure
    Also known as: N4-hydroxycytidine, Eidd-1931, Beta-d-n4-hydroxycytidine, N-hydroxycytidine, 3258-02-4, 4-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. Eidd-1931

    3. Beta-d-n4-hydroxycytidine

    4. N-hydroxycytidine

    5. 3258-02-4

    6. 4-n-hydroxycytidine

    7. C3d11pv2o4

    8. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(hydroxyamino)pyrimidin-2-one

    9. 1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-(hydroxyimino)-3,4-dihydropyrimidin-2(1h)-one

    10. 4-oxime Uridine

    11. N-4-hydroxycytidine

    12. Cytidine, N-hydroxy-

    13. Ccris 1074

    14. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-(hydroxyimino)-3,4-dihydropyrimidin-2(1h)-one

    15. Unii-c3d11pv2o4

    16. Eidd1931

    17. Beta-d-n(4)-hydroxycytidine

    18. N-hydroxy-3,4-dihydrocytidine

    19. Schembl5190819

    20. Chembl2178720

    21. Eidd 1931

    22. Gtpl10735

    23. Dtxsid20186274

    24. Chebi:180654

    25. Ex-a3655

    26. Mfcd01675695

    27. At13085

    28. Bs-47105

    29. Hy-125033

    30. Cs-0088698

    31. 1-((2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-4-(hydroxyamino)pyrimidin-2(1h)-one

    32. 1-((2r,3r,4s,5r)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-4-hydroxyamino-1h-pyrimidin-2-one

    33. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-4-(hydroxyamino)-1,2-dihydropyrimidin-2-one

    34. 1-[(2r,3r,4s,5r)-3,4-dihydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl]-4-(hydroxyamino)pyrimidin-2-one

    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 Mass259.08043514 g/mol
    Monoisotopic Mass259.08043514 g/mol
    Topological Polar Surface Area135 Ų
    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.