baloxavir marboxil   Click here for help

GtoPdb Ligand ID: 11748

Synonyms: S-033188 | S033188 | Xofluza®
Approved drug
baloxavir marboxil is an approved drug (Japan & FDA (2018), EMA (2021))
Compound class: Synthetic organic
Comment: Baloxavir marboxil is an orally delivered anti-influenza virus drug. It is a prodrug that is converted to baloxavir [1]. Mechanistically baloxavir is a first-in-class inhibitor of the cap-endonuclease (CEN) activity of an acidic protein within the viral polymerase complex [3] that is essential for viral gene transcription and replication. Alternative influenza antivirals (e.g. oseltamivir, peramivir and zanamivir) target the neuraminidase enzyme that is required for fusion and entry of virus into the host cells, and the budding process that releases newly synthesised virions.

baloxavir marboxil 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 7
Hydrogen bond donors 0
Rotatable bonds 6
Topological polar surface area 124.84
Molecular weight 571.12
XLogP 4.13
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 COC(=O)OCOc1c(=O)ccn2c1C(=O)N1CCOC[C@H]1N2[C@@H]1c2ccccc2SCc2c1ccc(c2F)F
Isomeric SMILES COC(=O)OCOc1c2C(=O)N3CCOC[C@H]3N(n2ccc1=O)[C@H]1c2c(CSc3ccccc13)c(c(cc2)F)F
InChI InChI=1S/C27H23F2N3O7S/c1-36-27(35)39-14-38-25-19(33)8-9-31-24(25)26(34)30-10-11-37-12-21(30)32(31)23-15-6-7-18(28)22(29)17(15)13-40-20-5-3-2-4-16(20)23/h2-9,21,23H,10-14H2,1H3/t21-,23+/m1/s1
InChI Key RZVPBGBYGMDSBG-GGAORHGYSA-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/)
No information available.
Summary of Clinical Use Click here for help
Baloxavir marboxil is used to treat influenza A and influenza B infections, as a single, one-time dose. It is effective when administered within 48 hours of symptom onset, and can be given to patients ≥12 years of age.
Pharmacokinetics Click here for help
Biotransformation/Metabolism
Baloxavir marboxil is converted via UDP glucuronosyltransferase family 1 member A3 (UGT1A3) and CYP3A4 to the active metabolite baloxavir. UGT1A3 is the major route to conversion.
External links Click here for help
For extended ADME data see the following:

Electronic Medicines Compendium (eMC)
Drugs.com
European Medicines Agency (EMA)