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molnupiravir   Click here for help

GtoPdb Ligand ID: 10737

Synonyms: EIDD-2801 | EIDD2801 | Lagevrio® | MK-4482 | MK4482
Approved drug PDB Ligand
molnupiravir is an approved drug (UK (2021))
Compound class: Synthetic organic
Comment: Molnupiravir (EIDD-2801, MK-4482) is an oral, broad-spectrum antiviral drug [1,8]. The proposed INN molnupiravir was released by the WHO in a special release to cover COVID-related therapeutics in October 2020 (Proposed INN: List 124-COVID-19). Chemically molnupiravir is the isopropylester prodrug of the ribonucleoside analogue β-D-N4-hydroxycytidine (EIDD-1931, or N-hydroxycytidine) [10-11]. Functionally, the active form of molnupiravir is incorporated into the virus' RNA by the viral RNA-dependent RNA polymerase (RdRp) during replication, which results in lethal mutagenesis [4]. Molnupiravir was originally designed by Emory University scientists to inhibit replication of influenza virus. It has subsequently been tested for activity against other RNA viruses, including pandemic SARS-CoV-2, SARS-CoV and MERS-CoV [14]. Molnupiravir was being progressed for COVID-19 in a collaboration between Ridgeback Biotherapeutics and Merck. In vivo therapeutic and prophylactic potential was reported in a peer reviewed manuscript in February 2021 [12].
There is concern that molnupiravir may induce mutations in the host, based on evidence from mammalian cell culture experiments [13] and using the Ames test (bacteria).

molnupiravir is commercially available from our sponsors

2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 6
Hydrogen bond donors 4
Rotatable bonds 6
Topological polar surface area 143.14
Molecular weight 329.12
XLogP 0
No. Lipinski's rules broken 0

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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Canonical SMILES ONc1ccn(c(=O)n1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)COC(=O)C(C)C
Isomeric SMILES ONc1ccn(c(=O)n1)[C@@H]1O[C@@H]([C@H]([C@H]1O)O)COC(=O)C(C)C
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
InChI Key HTNPEHXGEKVIHG-QCNRFFRDSA-N

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. UK MHRA (2021)
Is prodrug? Yes
Active form β-D-N4-hydroxycytidine
Synonyms Click here for help
EIDD-2801 | EIDD2801 | Lagevrio® | MK-4482 | MK4482
Database Links Click here for help
CAS Registry No. 2349386-89-4 (source: WHO INN record)
DrugCentral Ligand 5377
GtoPdb PubChem SID 405067330
PubChem CID 145996610
RCSB PDB Ligand XMO
Search Google for chemical match using the InChIKey HTNPEHXGEKVIHG-QCNRFFRDSA-N
Search Google for chemicals with the same backbone HTNPEHXGEKVIHG
UniChem Compound Search for chemical match using the InChIKey HTNPEHXGEKVIHG-QCNRFFRDSA-N
UniChem Connectivity Search for chemical match using the InChIKey HTNPEHXGEKVIHG-QCNRFFRDSA-N

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MedChemExpress
Molnupiravir (links to external site)
Cat. No. HY-135853
(Same InChi Key)