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Baloxavir Marboxil

PubChem CID
124081896
Structure
Baloxavir Marboxil_small.png
Baloxavir Marboxil_3D_Structure.png
Molecular Formula
Synonyms
  • Baloxavir marboxil
  • 1985606-14-1
  • Xofluza
  • S-033188
  • baloxavir-marboxil
Molecular Weight
571.6 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2017-02-17
  • Modify:
    2025-01-18
Description
Baloxavir marboxil is an antiviral drug used to treat influenza. More specifically, it is a first-in-class cap-dependent endonuclease inhibitor that works to block influenza virus proliferation. It is a prodrug of [baloxavir] with an improved absorption profile than its active metabolite due to the addition of a phenolic hydroxyl group to its structure. Baloxavir marboxil was first globally approved in Japan in February 2018, followed by the US approval in October, 2018. It was also approved by the European Commission on January 7, 2021.
Baloxavir Marboxil is an orally bioavailable prodrug and influenza cap-dependent endonuclease (CEN) inhibitor, with antiviral activity. Upon administration of baloxavir marboxil, the agent is converted by hydrolysis to its active metabolite baloxavir. Baloxavir targets, binds to and inhibits the CEN activity of the influenza polymerase acidic (PA) protein, an influenza virus-specific enzyme in the viral RNA polymerase complex required for the initiation of influenza gene transcription. By inhibiting PA endonuclease, influenza virus mRNA replication is halted. This reduces viral load and prevents further influenza infection.
BALOXAVIR MARBOXIL is a small molecule drug with a maximum clinical trial phase of IV (across all indications) that was first approved in 2018 and is indicated for viral disease and influenza and has 2 investigational indications.
See also: Baloxavir (has active moiety).

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Baloxavir Marboxil.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

[(3R)-2-[(11S)-7,8-difluoro-6,11-dihydrobenzo[c][1]benzothiepin-11-yl]-9,12-dioxo-5-oxa-1,2,8-triazatricyclo[8.4.0.03,8]tetradeca-10,13-dien-11-yl]oxymethyl methyl carbonate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 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
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

RZVPBGBYGMDSBG-GGAORHGYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

COC(=O)OCOC1=C2C(=O)N3CCOC[C@H]3N(N2C=CC1=O)[C@H]4C5=C(CSC6=CC=CC=C46)C(=C(C=C5)F)F
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C27H23F2N3O7S
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEMBL ID

2.3.5 DrugBank ID

2.3.6 DSSTox Substance ID

2.3.7 KEGG ID

2.3.8 Metabolomics Workbench ID

2.3.9 NCI Thesaurus Code

2.3.10 RXCUI

2.3.11 Wikidata

2.3.12 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • (((12aR)-12-((11S)-7,8-difluoro-6,11-dihydrodibenzo(b,E)thiepin-11-yl)-6,8-dioxo-3,4,6,8,12,12ahexahydro-1H-(1,4)oxazino(3,4-C)pyrido(2,1-F)(1,2,4)triazin-7-yl)oxy)methyl methyl carbonate
  • (12aR)-12-((11S)-7,8-difluoro-6,11-dihydrodibenzo(b,e)thiepin-11-yl)-7-hydroxy-3,4,12,12a-tetrahydro-1h-(1,4)oxazino(3,4-c)pyrido(2,1-f)(1,2,4)triazine-6,8-dione
  • baloxavir
  • baloxavir marboxil
  • Xofluza

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
571.6 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
3.8
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
0
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
12
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
6
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
571.12247758 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
571.12247758 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
123 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
40
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
1090
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Isotope Atom Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Atom Stereocenter Count
Property Value
2
Reference
Computed by PubChem
Property Name
Undefined Atom Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Defined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Undefined Bond Stereocenter Count
Property Value
0
Reference
Computed by PubChem
Property Name
Covalently-Bonded Unit Count
Property Value
1
Reference
Computed by PubChem
Property Name
Compound Is Canonicalized
Property Value
Yes
Reference
Computed by PubChem (release 2021.10.14)

3.2 Experimental Properties

3.2.1 Solubility

3.2.2 LogP

3.3 Chemical Classes

3.3.1 Drugs

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
Pharmaceuticals -> Anti infectives for systemic use -> Antivirals for systemic use
S92 | FLUOROPHARMA | List of ~340 ATC classified fluoro-pharmaceuticals | DOI:10.5281/zenodo.5979646
3.3.1.1 Human Drugs
Human drug -> Prescription; Discontinued
Human drug -> Active ingredient (BALOXAVIR MARBOXIL)
Human drugs -> Antivirals for systemic use -> Human pharmacotherapeutic group -> EMA Drug Category
Paediatric drug

5 Chemical Vendors

6 Drug and Medication Information

6.1 Drug Indication

Baloxavir marboxil is an influenza virus polymerase acidic (PA) endonuclease inhibitor indicated for the treatment of acute uncomplicated influenza in patients who have been symptomatic for no more than 48 hours and who are otherwise healthy adults and pediatric patients five years of age and older, or patients 12 years of age and older who are at high risk of developing influenza-related complications. The drug is also indicated for post-exposure prophylaxis of influenza in patients five years of age and older following contact with an individual who has influenza. In Europe, it is approved for use in patients aged one year and above for these indications. Baloxavir marboxil is associated with a risk for loss of efficacy due to changes in influenza virus such as changes in virus subtypes, emergence of virus resistance, and changes in viral virulence; therefore, the drug should be used after considering available information on drug susceptibility patterns for circulating influenza virus strains.
Treatment of influenzaXofluza is indicated for the treatment of uncomplicated influenza in patients aged 1 year and above. Post exposure prophylaxis of influenzaXofluza is indicated for post-exposure prophylaxis of influenza in individuals aged 1 year and above. Xofluza should be used in accordance with official recommendations.
Prevention of influenza infection, Treatment of influenza

6.2 FDA Approved Drugs

6.3 FDA Orange Book

6.4 FDA National Drug Code Directory

6.5 Drug Labels

Drug and label
Active ingredient and drug

6.6 Clinical Trials

6.6.1 ClinicalTrials.gov

6.6.2 EU Clinical Trials Register

6.6.3 NIPH Clinical Trials Search of Japan

6.7 EMA Drug Information

1 of 2
Medicine
Category
Human drugs
Therapeutic area
Influenza, Human
Active Substance
Baloxavir marboxil
INN/Common name
baloxavir marboxil
Pharmacotherapeutic Classes
Antivirals for systemic use
Status
This medicine is authorized for use in the European Union
Company
Roche Registration GmbH
Market Date
2021-01-07
2 of 2
Type
Paediatric investigation
Active Substance
Therapeutic Area
Infectious diseases
Drug Form
Film-coated tablet, Granules for oral suspension
Administration Route
Oral use
Decision Type
PM: decision on the application for modification of an agreed PIP
Decision Date
2022-09-09

6.8 Japan PMDA Drugs

1 of 2
Brand Name
Xofluza
Non-proprietary Name
Baloxavir marboxil
Approval Note
Initial Approval
Approval Date
February 2018
Review Document
2 of 2
Brand Name
Xofluza
Non-proprietary Name
Baloxavir marboxil
Approval Note
Partial Change Approval
Approval Date
November 2020
Review Document

7 Pharmacology and Biochemistry

7.1 Pharmacodynamics

Baloxavir marboxil is an antiviral drug that works against influenza virus to block viral replication. It has an 50% inhibitory concentration (IC50) of 1.4 to 3.1 nM for influenza A viruses and 4.5 to 8.9 nM for influenza B viruses in a polymerase acidic (PA) endonuclease assay. In murine models of influenza and avian influenza A, baloxavir reduced pulmonary viral loads and increased survival rates of mice. The reduction of viral titer was observed within 24 hours of administration, in a dose-dependent manner.

7.2 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.)
Enzyme Inhibitors
Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)

7.3 FDA Pharmacological Classification

Non-Proprietary Name
BALOXAVIR MARBOXIL
Pharmacological Classes
Polymerase Acidic Endonuclease Inhibitors [MoA]; Polymerase Acidic Endonuclease Inhibitor [EPC]; Chelating Activity [MoA]

7.4 ATC Code

J - Antiinfectives for systemic use

J05 - Antivirals for systemic use

J05A - Direct acting antivirals

J05AX - Other antivirals

J05AX25 - Baloxavir marboxil

7.5 Absorption, Distribution and Excretion

Absorption
Following oral administration of 40 mg baloxavir marboxil in adolescents and adults aged 12 years and older, the AUC was 5520 ng x hr/mL and the Cmax was 68.9 ng/mL. Following a 80 mg dose, the the AUC was 6930 ng x hr/mL and the Cmax was 82.5 ng/mL. The Tmax is about four hours. Food decreased Cmax by 48% and AUC0-inf by 36%. In pediatric patients aged five to 12 years of age weighing less than 20 kg, the AUCinf was 5830 ng x hr/mL and the Cmax was 148 ng/mL following a 2 mg/kg dose. The AUCinf was 4360 ng x hr/mL and the Cmax was 81.1 ng/mL following a 40 mg dose in pediatric patients who weigh greater than or equal to 20 kg. The Tmax ranged from 3.5 to 4.5 hours.
Route of Elimination
Baloxavir is primarily eliminated by biliary excretion. About 80.1% of the total dose is excreted in feces. About 14.7% of the dose is excreted in urine, where 3.3% of the recovered dose is the unchanged parent drug.
Volume of Distribution
The volume of distribution is 1180 L.
Clearance
Clearance of baloxavir is 10.3 L/h.

7.6 Metabolism / Metabolites

Baloxavir predominantly undergoes UGT1A3-mediated metabolism to form glucuronic acid conjugate. It is subsequently metabolized by CYP3A4 to form sulfoxide.

7.7 Biological Half-Life

The apparent terminal elimination half-life of baloxavir is 79.1 hours.

7.8 Mechanism of Action

The influenza virus RNA polymerase complex is a heterotrimer made up of three protein subunits - polymerase basic protein 1 (PB1), polymerase basic protein 2 (PB2), and polymerase acidic protein (PA). This polymerase complex is an influenza virus-specific enzyme essential for viral gene transcription and replication, with its subunits playing different roles in viral mRNA synthesis. The PB2 subunit binds to the cap of host cellular pre-messenger RNA, allowing the PA protein - a cap-dependent endonuclease - to cleave the capped pre-messenger RNA. This initial step of mRNA synthesis by the PA protein, also known as the "cap-snatching process," provides an RNA primer for the PB1 subunit, which carries out its RNA-dependent RNA polymerase function to proceed with viral mRNA transcription. After administration, the prodrug baloxavir marboxil is almost completely hydrolyzed by esterases in the gastrointestinal lumen, intestinal epithelium, liver and blood to its active metabolite, baloxavir. Baloxavir selectively inhibits the PA protein, blocking the initiation of mRNA synthesis and ultimately influenza virus proliferation. Cap-dependent endonuclease is a highly conserved region across influenza strains; however, baloxavir is still vulnerable to resistance because amino acid substitutions in the PA protein can lead to reduced viral susceptibility to baloxavir.

8 Use and Manufacturing

8.1 Uses

8.1.1 Use Classification

Human drugs -> Antivirals for systemic use -> Human pharmacotherapeutic group -> EMA Drug Category
Human Drugs -> EU pediatric investigation plans
Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients

9 Safety and Hazards

9.1 Hazards Identification

9.1.1 GHS Classification

Pictogram(s)
Environmental Hazard
Signal
Warning
GHS Hazard Statements
H411 (100%): Toxic to aquatic life with long lasting effects [Hazardous to the aquatic environment, long-term hazard]
Precautionary Statement Codes

P273, P391, and P501

(The corresponding statement to each P-code can be found at the GHS Classification page.)

ECHA C&L Notifications Summary
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.

9.1.2 Hazard Classes and Categories

Aquatic Chronic 2 (100%)

10 Toxicity

10.1 Toxicological Information

10.1.1 Protein Binding

Baloxavir, the active metabolite, is 92.9–93.9% bound to human serum proteins. The ratio of blood cell to blood is 48.5–54.4%.

11 Associated Disorders and Diseases

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Thieme References

12.5 Chemical Co-Occurrences in Literature

12.6 Chemical-Gene Co-Occurrences in Literature

12.7 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 FDA Orange Book Patents

13.4 Chemical Co-Occurrences in Patents

13.5 Chemical-Disease Co-Occurrences in Patents

13.6 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Chemical-Target Interactions

14.2 Drug-Drug Interactions

14.3 Drug-Food Interactions

  • Avoid antacids. Baloxavir may form a chelate with polyvalent cations in antacids, which may decrease plasma concentrations of baloxavir.
  • Avoid milk and dairy products. Baloxavir may form a chelate with polyvalent cations such as calcium in dairy products, which may decrease plasma concentrations of baloxavir.
  • Avoid multivalent ions. Multivalent ions such as magnesium, calcium, and aluminum can form a chelate with baloxavir, which can reduce the absorption of baloxavir.
  • Take with or without food. Food reduces drug absorption, but not to a clinically significant extent.

15 Biological Test Results

15.1 BioAssay Results

16 Classification

16.1 MeSH Tree

16.2 NCI Thesaurus Tree

16.3 KEGG: Drug

16.4 KEGG: USP

16.5 KEGG: ATC

16.6 KEGG: Drug Groups

16.7 KEGG : Antimicrobials

16.8 KEGG: Drug Classes

16.9 WHO ATC Classification System

16.10 ChemIDplus

16.11 ChEMBL Target Tree

16.12 UN GHS Classification

16.13 NORMAN Suspect List Exchange Classification

16.14 EPA DSSTox Classification

16.15 FDA Drug Type and Pharmacologic Classification

16.16 PFAS and Fluorinated Organic Compounds in PubChem

16.17 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
    [[(12aR)-12-[(11S)-7,8-Difluoro-6,11-dihydrodibenzo[b,e]thiepin-11-yl]-3,4,6,8,12,12a-hexahydro-6,8-dioxo-1H-[1,4]oxazino[3,4-c]pyrido[2,1-f][1,2,4]triazin-7-yl]oxy]methyl methyl carbonate
    https://commonchemistry.cas.org/detail?cas_rn=1985606-14-1
  2. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  3. DrugBank
    LICENSE
    Creative Common's Attribution-NonCommercial 4.0 International License (http://creativecommons.org/licenses/by-nc/4.0/legalcode)
    https://www.drugbank.ca/legal/terms_of_use
  4. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  5. European Chemicals Agency (ECHA)
    LICENSE
    Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: "Source: European Chemicals Agency, http://echa.europa.eu/". Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
    https://echa.europa.eu/web/guest/legal-notice
    ({(12aR)-12-[(11S)-7,8-difluoro-6,11-dihydrodibenzo[b,e]thiepin-11-yl]-6,8-dioxo-3,4,6,8,12,12ahexahydro-1H-[1,4]oxazino[3,4-c]pyrido[2,1-f][1,2,4]triazin-7-yl}oxy)methyl methyl carbonate
    https://echa.europa.eu/substance-information/-/substanceinfo/100.314.975
    ({(12aR)-12-[(11S)-7,8-difluoro-6,11-dihydrodibenzo[b,e]thiepin-11-yl]-6,8-dioxo-3,4,6,8,12,12ahexahydro-1H-[1,4]oxazino[3,4-c]pyrido[2,1-f][1,2,4]triazin-7-yl}oxy)methyl methyl carbonate (EC: 862-996-0)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/309860
  6. FDA Global Substance Registration System (GSRS)
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  7. ChEMBL
    LICENSE
    Access to the web interface of ChEMBL is made under the EBI's Terms of Use (http://www.ebi.ac.uk/Information/termsofuse.html). The ChEMBL data is made available on a Creative Commons Attribution-Share Alike 3.0 Unported License (http://creativecommons.org/licenses/by-sa/3.0/).
    http://www.ebi.ac.uk/Information/termsofuse.html
  8. Drug Gene Interaction database (DGIdb)
    LICENSE
    The data used in DGIdb is all open access and where possible made available as raw data dumps in the downloads section.
    http://www.dgidb.org/downloads
  9. Therapeutic Target Database (TTD)
  10. ClinicalTrials.gov
    LICENSE
    The ClinicalTrials.gov data carry an international copyright outside the United States and its Territories or Possessions. Some ClinicalTrials.gov data may be subject to the copyright of third parties; you should consult these entities for any additional terms of use.
    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  11. DailyMed
  12. NCI Thesaurus (NCIt)
    LICENSE
    Unless otherwise indicated, all text within NCI products is free of copyright and may be reused without our permission. Credit the National Cancer Institute as the source.
    https://www.cancer.gov/policies/copyright-reuse
  13. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  14. European Medicines Agency (EMA)
    LICENSE
    Information on the European Medicines Agency's (EMA) website is subject to a disclaimer and copyright and limited reproduction notices.
    https://www.ema.europa.eu/en/about-us/legal-notice
  15. Drugs@FDA
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  16. EU Clinical Trials Register
  17. FDA Orange Book
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  18. Japan Pharmaceuticals and Medical Devices Agency (PMDA)
  19. KEGG
    LICENSE
    Academic users may freely use the KEGG website. Non-academic use of KEGG generally requires a commercial license
    https://www.kegg.jp/kegg/legal.html
    Therapeutic category of drugs in Japan
    http://www.genome.jp/kegg-bin/get_htext?br08301.keg
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
  20. Metabolomics Workbench
  21. National Drug Code (NDC) Directory
    LICENSE
    Unless otherwise noted, the contents of the FDA website (www.fda.gov), both text and graphics, are not copyrighted. They are in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from FDA. Credit to the U.S. Food and Drug Administration as the source is appreciated but not required.
    https://www.fda.gov/about-fda/about-website/website-policies#linking
  22. NIPH Clinical Trials Search of Japan
  23. NLM RxNorm Terminology
    LICENSE
    The RxNorm Terminology is created by the National Library of Medicine (NLM) and is in the public domain and may be republished, reprinted and otherwise used freely by anyone without the need to obtain permission from NLM. Credit to the U.S. National Library of Medicine as the source is appreciated but not required. The full RxNorm dataset requires a free license.
    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  24. NORMAN Suspect List Exchange
    LICENSE
    Data: CC-BY 4.0; Code (hosted by ECI, LCSB): Artistic-2.0
    https://creativecommons.org/licenses/by/4.0/
    [(2-{12,13-difluoro-9-thiatricyclo[9.4.0.0³,?]pentadeca-1(15),3(8),4,6,11,13-hexaen-2-yl}-9,12-dioxo-5-oxa-1,2,8-triazatricyclo[8.4.0.0³,?]tetradeca-10,13-dien-11-yl)oxy]methyl methyl carbonate
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  25. Springer Nature
  26. Thieme Chemistry
    LICENSE
    The Thieme Chemistry contribution within PubChem is provided under a CC-BY-NC-ND 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc-nd/4.0/
  27. WHO Anatomical Therapeutic Chemical (ATC) Classification
    LICENSE
    Use of all or parts of the material requires reference to the WHO Collaborating Centre for Drug Statistics Methodology. Copying and distribution for commercial purposes is not allowed. Changing or manipulating the material is not allowed.
    https://www.whocc.no/copyright_disclaimer/
  28. Wikidata
  29. Wikipedia
  30. PubChem
  31. Medical Subject Headings (MeSH)
    LICENSE
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    https://www.nlm.nih.gov/copyright.html
  32. GHS Classification (UNECE)
  33. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  34. PATENTSCOPE (WIPO)
CONTENTS