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
Click here for help

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.

✖
Click here for structure editor
Physico-chemical Properties
Click here for help

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.

✖
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
Click here for help

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/)

✖
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/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (2018)  |  Japan (2018)  |  EMA (2021)
International Nonproprietary Names Click here for help
INN number INN
10491 baloxavir marboxil
Synonyms Click here for help
S-033188 | S033188 | Xofluza®
Database Links Click here for help
CAS Registry No. 1985606-14-1 (source: WHO INN record)
ChEMBL Ligand CHEMBL4297503
DrugBank Ligand DB13997
GtoPdb PubChem SID 458923783
PubChem CID 124081896
Search Google for chemical match using the InChIKey RZVPBGBYGMDSBG-GGAORHGYSA-N
Search Google for chemicals with the same backbone RZVPBGBYGMDSBG
Search PubMed clinical trials baloxavir marboxil
Search PubMed titles baloxavir marboxil
Search PubMed titles/abstracts baloxavir marboxil
UniChem Compound Search for chemical match using the InChIKey RZVPBGBYGMDSBG-GGAORHGYSA-N
UniChem Connectivity Search for chemical match using the InChIKey RZVPBGBYGMDSBG-GGAORHGYSA-N

Product suppliers

View disclaimer

Sponsored products disclaimer

Product supplier links are provided as a service to assist in identifying commercial suppliers of reagents that are mentioned on the IUPHAR/BPS Guide to PHARMACOLOGY database website, and do not imply their endorsement by NC-IUPHAR.

Links are provided in return for sponsorship, used to fund improvements to this database. The sponsorship account is managed and audited by the University of Edinburgh, a charitable body registered in Scotland, SC005336. If you are interested in sponsoring the database, please contact us.

✖

MedChemExpress
Baloxavir marboxil (links to external site)
Cat. No. HY-109025