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    Chemistry

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    Also known as: Eidd 2801, Eidd2801, Molnupiravir, 2349386-89-4, Mk-4482, Molnupiravir [inn]
    Molecular Formula
    C13H19N3O7
    Molecular Weight
    329.31  g/mol
    InChI Key
    HTNPEHXGEKVIHG-QCNRFFRDSA-N
    FDA UNII
    YA84KI1VEW
    Molnupiravir
    Molnupiravir is an orally bioavailable prodrug of EIDD-1931, the synthetic ribonucleoside derivative N4-hydroxycytidine and ribonucleoside analog, with potential antiviral activity against a variety of RNA viruses. Upon oral administration, molnupiravir, being a prodrug, is metabolized into its active form EIDD-1931 and converted into its triphosphate (TP) form. The TP form of EIDD-1931 is incorporated into RNA and inhibits the action of viral RNA-dependent RNA polymerase. This results in the termination of RNA transcription and decreases viral RNA production, and viral RNA replication.
    1 2D Structure

    Molnupiravir

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    [(2R,3S,4R,5R)-3,4-dihydroxy-5-[4-(hydroxyamino)-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl 2-methylpropanoate
    2.1.2 InChI
    InChI=1S/C13H19N3O7/c1-6(2)12(19)22-5-7-9(17)10(18)11(23-7)16-4-3-8(15-21)14-13(16)20/h3-4,6-7,9-11,17-18,21H,5H2,1-2H3,(H,14,15,20)/t7-,9-,10-,11-/m1/s1
    2.1.3 InChI Key
    HTNPEHXGEKVIHG-QCNRFFRDSA-N
    2.1.4 Canonical SMILES
    CC(C)C(=O)OCC1C(C(C(O1)N2C=CC(=NC2=O)NO)O)O
    2.1.5 Isomeric SMILES
    CC(C)C(=O)OC[C@@H]1[C@H]([C@H]([C@@H](O1)N2C=CC(=NC2=O)NO)O)O
    2.2 Other Identifiers
    2.2.1 UNII
    YA84KI1VEW
    2.3 Synonyms
    2.3.1 MeSH Synonyms

    1. ((2r,3s,4r,5r)-3,4-dihydroxy-5-((4z)-4-(hydroxyimino)-2-oxo-3,4- Dihydropyrimidin-1(2h)-yl)oxolan-2-yl)methyl 2-methylpropanoate

    2. Lagevrio

    3. Mk-4482

    4. Molnupiravir

    2.3.2 Depositor-Supplied Synonyms

    1. Eidd 2801

    2. Eidd2801

    3. Molnupiravir

    4. 2349386-89-4

    5. Mk-4482

    6. Molnupiravir [inn]

    7. 2492423-29-5

    8. Molnupiravir [usan]

    9. Molnupiravir [who-dd]

    10. Ya84ki1vew

    11. Eidd 1931-isopropyl Ester

    12. Uridine, 4-oxime, 5'-(2-methylpropanoate), (4z)-

    13. N4-hydroxycytidine, 5'-isopropyl Ester

    14. ((2r,3s,4r,5r)-3,4-dihydroxy-5-((4z)-4-(hydroxyimino)-2-oxo-3,4- Dihydropyrimidin-1(2h)-yl)oxolan-2-yl)methyl 2-methylpropanoate

    15. ((2r,3s,4r,5r)-3,4-dihydroxy-5-(4-(hydroxyamino)-2-oxopyrimidin-1(2h)-yl)tetrahydrofuran-2-yl)methyl Isobutyrate

    16. [(2r,3s,4r,5r)-3,4-dihydroxy-5-[4-(hydroxyamino)-2-oxopyrimidin-1-yl]oxolan-2-yl]methyl 2-methylpropanoate

    17. Lagevrio

    18. Who 11853

    19. ((2r,3s,4r,5r)-3,4-dihydroxy-5-(4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2h)-yl)tetrahydrofuran-2-yl)methyl Isobutyrate

    20. Molnupiravirum

    21. Unii-ya84ki1vew

    22. Pro-eidd-1931

    23. Molnupiravir [jan]

    24. Eidd-2801(molnupiravir)

    25. Chembl4650320

    26. Eidd 1931 5'-isopropylester

    27. Gtpl10737

    28. Med.21724, Compound 182

    29. Chebi:180653

    30. Bdbm429508

    31. Dtxsid501028058

    32. Bcp32744

    33. Eidd-1931 Isopropyl Ester

    34. Ex-a3432

    35. Mfcd32663515

    36. Mk4482

    37. S8969

    38. At13078

    39. N(4)-hydroxycytidine 5'-isopropylester

    40. Ac-35171

    41. As-84465

    42. Beta-d-n4 Hydroxycytidine-5'-isopropyl Ester

    43. Beta-d-n(4)-hydroxycytidine-5'-isopropyl Ester

    44. A936190

    45. .beta.-d-n4 Hydroxycytidine-5'-isopropyl Ester

    46. N-hydroxy-5'-o-(2-methylpropanoyl)-3,4-dihydrocytidine

    47. Eidd 2801; Eidd2801; Uridine, 4-oxime, 5'-(2-methylpropanoate

    48. ((2r,3s,4r,5r)-3,4-dihydroxy-5-((e)-4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2h)-yl)tetrahydrofuran-2-yl)methyl Isobutyrate

    49. ((2r,3s,4r,5r)-3,4-dihydroxy-5-((z)-4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2h)-yl)tetrahydrofuran-2-yl)methyl Isobutyrate

    50. [(2r,3s,4r,5r)-3,4-dihydroxy-5-[(4e)-4-(hydroxyimino)-2-oxo-1,2,3,4-tetrahydropyrimidin-1-yl]oxolan-2-yl]methyl 2-methylpropanoate

    51. {(2r,3s,4r,5r)-3,4-dihydroxy-5-[4-(hydroxyimino)-2-oxo-3,4-dihydropyrimidin-1(2h)-yl]tetrahydrofuran-2-yl}methyl 2-methylpropanoate

    2.4 Create Date
    2020-03-16
    3 Chemical and Physical Properties
    Molecular Weight 329.31 g/mol
    Molecular Formula C13H19N3O7
    XLogP3-0.8
    Hydrogen Bond Donor Count4
    Hydrogen Bond Acceptor Count7
    Rotatable Bond Count6
    Exact Mass329.12229995 g/mol
    Monoisotopic Mass329.12229995 g/mol
    Topological Polar Surface Area141 Ų
    Heavy Atom Count23
    Formal Charge0
    Complexity534
    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 molnupiravir are being studied for its activity against a number of viral infections including influenza, MERS-CoV, and SARS-CoV-2. Molnupiravir is approved in the UK for reducing the risk of hospitalization and death in mild to moderate COVID-19 cases for patients at increased risk of severe disease (eg. with obesity, diabetes mellitus, heart disease, or are over 60 years old).

    Treatment of Coronavirus disease 2019 (COVID-19)

    5 Pharmacology and Biochemistry
    5.1 MeSH Pharmacological Classification

    Antiviral Agents

    Agents used in the prophylaxis or therapy of VIRUS DISEASES. Some of the ways they may act include preventing viral replication by inhibiting viral DNA polymerase; binding to specific cell-surface receptors and inhibiting viral penetration or uncoating; inhibiting viral protein synthesis; or blocking late stages of virus assembly. (See all compounds classified as Antiviral Agents.)

    5.2 Absorption, Distribution and Excretion

    Absorption

    After an 800 mg oral dose of molnupiravir every 12 hours, the active compound (N4-hydroxycytidine) reaches a Cmax of 2970 ng/mL, with a Tmax of 1.5 hours, and an AUC0-12h of 8360 h\*ng/mL.

    Route of Elimination

    3% of an oral molnupiravir dose is eliminated in the urine as the active metabolite N4-hydroxycytidine.

    5.3 Metabolism/Metabolites

    Molnupiravir is hydrolyzed to [N4-hydroxycytidine], which distributes into tissues. Once inside cells, N4-hydroxycytidine is phosphorylated to the 5'-triphosphate form.

    5.4 Biological Half-Life

    The half life of the active metabolite, N4-hydroxycytidine, is 3.3 hours.

    5.5 Mechanism of Action

    Molnupiravir is hydrolyzed _in vivo_ to N4-hydroxycytidine, which is phosphorylated in tissue to the active 5-triphosphate form, and 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.

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    06-May-2021
    28-Sep-2024
    KGS
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    Average Price (USD/KGS)

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    Quantity (KGS) & Unit rate (USD/KGS) over time

    API Imports and Exports

    Importing Country Total Quantity
    (KGS)    		 Average Price
    (USD/KGS)    		 Number of Transactions

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