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Brivaracetam

PubChem CID
9837243
Structure
Brivaracetam_small.png
Brivaracetam_3D_Structure.png
Molecular Formula
Synonyms
  • Brivaracetam
  • 357336-20-0
  • Briviact
  • UCB 34714
  • UCB-34714
Molecular Weight
212.29 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2006-10-25
  • Modify:
    2025-02-01
Description
Brivaracetam is a non-proteinogenic amino acid derivative that is butanamide in which the pro-S hydrogen at position 2 is replaced by a (4R)-2-oxo-4-propylpyrrolidin-1-yl. Used for treatment of partial onset seizures related to epilepsy. It has a role as an anticonvulsant. It is a gamma-lactam and a non-proteinogenic amino acid derivative. It is functionally related to a L-alpha-aminobutyric acid.
Brivaracetam is a DEA Schedule V controlled substance. Substances in the DEA Schedule V have a low potential for abuse relative to substances listed in Schedule IV and consist primarily of preparations containing limited quantities of certain narcotics. It is a Depressants substance.
Brivaracetam is a racetam derivative of levetiracetam used in the treatment of partial-onset seizures. Brivaracetam binds SV2A with 20 times higher affinity than levetiracetam. It is available under the brand name Briviact made by UCB. Briviact received FDA approval on February 19, 2016.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Brivaracetam.png

1.2 3D Conformer

1.3 Crystal Structures

COD records with this CID as component

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

(2S)-2-[(4R)-2-oxo-4-propylpyrrolidin-1-yl]butanamide
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C11H20N2O2/c1-3-5-8-6-10(14)13(7-8)9(4-2)11(12)15/h8-9H,3-7H2,1-2H3,(H2,12,15)/t8-,9+/m1/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

MSYKRHVOOPPJKU-BDAKNGLRSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCC[C@@H]1CC(=O)N(C1)[C@@H](CC)C(=O)N
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C11H20N2O2
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 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DEA Code Number

2710 (DEA schedule V controlled substance)

2.3.7 DrugBank ID

2.3.8 DSSTox Substance ID

2.3.9 KEGG ID

2.3.10 Metabolomics Workbench ID

2.3.11 NCI Thesaurus Code

2.3.12 Nikkaji Number

2.3.13 PharmGKB ID

2.3.14 Pharos Ligand ID

2.3.15 RXCUI

2.3.16 Wikidata

2.3.17 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • (2S)-2-((4R)-2-oxo-4-propylpyrrolidin-1-yl)butanamide
  • 1-pyrrolidineacetamide, alpha-ethyl-2-oxo-4-propyl-, (alphaS,4R)-
  • 2-(2-oxo-4-propylpyrrolidin-1-yl)butanamide
  • brivaracetam
  • Briviact
  • UCB 34714
  • UCB-34714
  • UCB34714

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
212.29 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
1
Reference
Computed by XLogP3 3.0 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Donor Count
Property Value
1
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Hydrogen Bond Acceptor Count
Property Value
2
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
5
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
212.152477885 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
212.152477885 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
63.4 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
15
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
253
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 Chemical Classes

3.2.1 Drugs

Pharmaceuticals -> Antiepileptics
S57 | GREEKPHARMA | Suspect Pharmaceuticals from the National Organization of Medicine, Greece | DOI:10.5281/zenodo.3248883
Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
3.2.1.1 Human Drugs
Breast Feeding; Lactation; Anticonvulsants
Human drug -> Prescription
Human drug -> None (Tentative Approval); Discontinued; Active ingredient (BRIVARACETAM)
Human drugs -> Antiepileptics -> Human pharmacotherapeutic group -> EMA Drug Category
Paediatric drug

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

Source of Spectrum
CAY-2023-690-0
Catalog Number
23873
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.2 IR Spectra

4.2.1 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Neat
Source of Spectrum
Forensic Spectral Research
Source of Sample
Cayman Chemical Company
Catalog Number
<a href=https://www.caymanchem.com/product/34685>34685</a>
Lot Number
0626253-8
Copyright
Copyright © 2019-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.3 Raman Spectra

Technique
FT-Raman
Source of Spectrum
Forensic Spectral Research
Source of Sample
Cayman Chemical Company
Catalog Number
<a href=https://www.caymanchem.com/product/34685>34685</a>
Lot Number
0626253-8
Copyright
Copyright © 2015-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

Used as adjunctive therapy for partial-onset seizures in patients 16 years of age or older.
Briviact is indicated as adjunctive therapy in the treatment of partial-onset seizures with or without secondary generalisation in adult and adolescent patients from 16 years of age with epilepsy.

7.2 LiverTox Summary

Brivaracetam is a relatively unique anticonvulsant that is typically used in combination with other antiepileptic medications for partial onset seizures. Brivaracetam has been linked to rare instances of serum aminotransferase and alkaline phosphatase elevations during treatment and is suspected of causing rare cases of clinically apparent drug induced liver disease.

7.3 Drug Classes

Breast Feeding; Lactation; Anticonvulsants
Anticonvulsants

7.4 FDA Medication Guides

Drug
Active Ingredient
BRIVARACETAM
Form;Route
SOLUTION;INTRAVENOUS
Company
UCB INC
Date
5/17/23
Drug
Active Ingredient
BRIVARACETAM
Form;Route
SOLUTION;ORAL
Company
UCB INC
Date
5/17/23
Drug
Active Ingredient
BRIVARACETAM
Form;Route
TABLET;ORAL
Company
UCB INC
Date
5/17/23

7.5 FDA Approved Drugs

7.6 FDA Orange Book

7.7 FDA National Drug Code Directory

7.8 Drug Labels

Drug and label
Active ingredient and drug

7.9 Clinical Trials

7.9.1 ClinicalTrials.gov

7.9.2 EU Clinical Trials Register

7.9.3 NIPH Clinical Trials Search of Japan

7.10 DEA Drug and Chemical Information

7.10.1 DEA Controlled Substances

1 of 2
Substance
Brivaracetam
Synonym(s)
(2S)-2-[(4R)-2-oxo-4-propylpyrrolidin-1-yl] butanamide|BRV|UCB-34714|Briviact
DEA Controlled Substances Code Number
2710
Controlled Substances Act Schedule
Schedule V - Substances in the DEA Schedule V have a low potential for abuse relative to substances listed in Schedule IV and consist primarily of preparations containing limited quantities of certain narcotics.
Class
Depressants
2 of 2
Non-Proprietary Name
BRIVARACETAM
DEA Substances Act Schedule
Schedule V

7.11 EMA Drug Information

1 of 4
View All
Category
Human drugs
Therapeutic area
Epilepsy
Active Substance
Brivaracetam
INN/Common name
brivaracetam
Pharmacotherapeutic Classes
Antiepileptics
Status
This medicine is authorized for use in the European Union
Company
UCB Pharma SA
Market Date
2016-01-13
2 of 4
View All
Type
Paediatric investigation
Active Substance
Therapeutic Area
Neurology
Drug Form
Film-coated tablet, Oral solution, Solution for injection
Administration Route
Oral use, Intravenous use
Decision Type
PM: decision on the application for modification of an agreed PIP
Decision Date
2021-04-09

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

Brivaracetam binds SV2A with high affinity. SV2A is known to play a role in epileptogenesis through modulation of synaptic GABA release. It is thought that brivaracetam exerts its anti-epileptogenic effects through its binding to SV2A. Brivaracetam is also known to inhibit Na+ channels which may also contribute to its anti-epileptogenic action.

8.2 MeSH Pharmacological Classification

Anticonvulsants
Drugs used to prevent SEIZURES or reduce their severity. (See all compounds classified as Anticonvulsants.)

8.3 FDA Pharmacological Classification

1 of 2
FDA UNII
U863JGG2IA
Active Moiety
BRIVARACETAM
Pharmacological Classes
Mechanisms of Action [MoA] - Epoxide Hydrolase Inhibitors
FDA Pharmacology Summary
The mechanism of action of brivaracetam is as an Epoxide Hydrolase Inhibitor.
2 of 2
Non-Proprietary Name
BRIVARACETAM
Pharmacological Classes
Epoxide Hydrolase Inhibitors [MoA]

8.4 ATC Code

N03AX23
S76 | LUXPHARMA | Pharmaceuticals Marketed in Luxembourg | Pharmaceuticals marketed in Luxembourg, as published by d'Gesondheetskeess (CNS, la caisse nationale de sante, www.cns.lu), mapped by name to structures using CompTox by R. Singh et al. (in prep.). List downloaded from https://cns.public.lu/en/legislations/textes-coordonnes/liste-med-comm.html. Dataset DOI:10.5281/zenodo.4587355

N - Nervous system

N03 - Antiepileptics

N03A - Antiepileptics

N03AX - Other antiepileptics

N03AX23 - Brivaracetam

8.5 Absorption, Distribution and Excretion

Absorption
Nearly 100% oral bioavailability.
Route of Elimination
\>95% excreted in urine with <10% of the parent compound unchanged. <1% excreted in feces.
Volume of Distribution
0.5L/kg.
Clearance
CL/F of 0.7-1.07 mL/min kg. Clearance is primarily metabolic with less than 10% of the parent drug excreted unchanged.

8.6 Metabolism / Metabolites

Primarily metabolized by hydrolysis of the acetamide moeity to form a carboxylic acid metabolite. Another metabolite is created via oxidation of the propyl side chain by CYP2C8 as well as CYP3A4, CYP2C19, and CYP2B6. Some conjugation with glucuronic acid and taurine account for a small amount of metabolism.

8.7 Biological Half-Life

7-8h.

8.8 Mechanism of Action

The precise mechanism of brivaracetam's anti-epileptogenic activity is unknown.

9 Use and Manufacturing

9.1 Uses

9.1.1 Use Classification

Human drugs -> Antiepileptics -> 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

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Pictogram(s)
Irritant
Signal
Warning
GHS Hazard Statements
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
Precautionary Statement Codes

P264, P270, P301+P317, P330, and P501

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

ECHA C&L Notifications Summary

Aggregated GHS information provided per 2 reports by companies from 1 notifications to the ECHA C&L Inventory.

Information may vary between notifications depending on impurities, additives, and other factors. The percentage value in parenthesis indicates the notified classification ratio from companies that provide hazard codes. Only hazard codes with percentage values above 10% are shown.

10.1.2 Hazard Classes and Categories

Acute Tox. 4 (100%)

10.2 Regulatory Information

DEA Controlled Substances
DEA schedule V controlled substance

11 Toxicity

11.1 Toxicological Information

11.1.1 Hepatotoxicity

Prospective studies reported that chronic brivaracetam therapy was not accompanied by significant elevations in serum aminotransferase levels and clinically apparent liver injury was not observed. Brivaracetam has had limited general use, but has not been linked to instances of clinically apparent liver injury. Levetiracetam, an anticonvulsant with similar structure and mechanism of action, has been linked to rare instances of acute liver injury, generally arising within 1 to 20 weeks and presenting with a hepatocellular pattern of injury without immunoallergic or autoimmune features. Whether similar cases will be linked to brivaracetam is not known.

Likelihood score: E (unlikely cause of clinically apparent liver injury).

11.1.2 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

Limited information on use of brivaracetam during breastfeeding indicates that infants might have serum levels in the therapeutic range with exclusive breastfeeding, but undetectable levels with partial breastfeeding. If brivaracetam is required by the mother, it is not necessarily a reason to discontinue breastfeeding, but monitor the infant for drowsiness, agitation, adequate weight gain, and developmental milestones, especially in younger, exclusively breastfed infants and when using combinations of drugs. Measurement of infant serum levels may help rule out toxicity if there is a concern.

◉ Effects in Breastfed Infants

Three infants, including one pair of twins, were breastfed while their mothers were taking brivaracetam. The twins were partially breastfed twice daily by a mother taking only brivaracetam and the other infant was exclusively breastfed by a mother taking brivaracetam, lacosamide and perampanel for 6 weeks, then partially breastfed. None of the infants exhibited reduced wakefulness or feeding problems. At one year of age, the mothers reported normal development.

◉ Effects on Lactation and Breastmilk

Relevant published information was not found as of the revision date.

11.1.3 Protein Binding

<20% bound to plasma proteins.

12 Associated Disorders and Diseases

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Wiley References

13.6 Chemical Co-Occurrences in Literature

13.7 Chemical-Gene Co-Occurrences in Literature

13.8 Chemical-Disease Co-Occurrences in Literature

14 Patents

14.1 Depositor-Supplied Patent Identifiers

14.2 WIPO PATENTSCOPE

14.3 FDA Orange Book Patents

14.4 Chemical Co-Occurrences in Patents

14.5 Chemical-Disease Co-Occurrences in Patents

14.6 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Protein Bound 3D Structures

15.2 Chemical-Target Interactions

15.3 Drug-Drug Interactions

15.4 Drug-Food Interactions

  • Avoid alcohol. Taking Brivaracetam with alcohol may increase alcohol's effects on attention, memory, and psychomotor functioning.
  • Take with or without food.

16 Biological Test Results

16.1 BioAssay Results

17 Classification

17.1 MeSH Tree

17.2 NCI Thesaurus Tree

17.3 ChEBI Ontology

17.4 KEGG: Drug

17.5 KEGG: USP

17.6 KEGG: ATC

17.7 KEGG: Target-based Classification of Drugs

17.8 KEGG: Drug Groups

17.9 KEGG: Drug Classes

17.10 WHO ATC Classification System

17.11 FDA Pharm Classes

17.12 ChemIDplus

17.13 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

17.14 ChEMBL Target Tree

17.15 UN GHS Classification

17.16 Drug Enforcement Administration (DEA) Classification

17.17 NORMAN Suspect List Exchange Classification

17.18 EPA DSSTox Classification

17.19 FDA Drug Type and Pharmacologic Classification

17.20 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. CAS Common Chemistry
    LICENSE
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    https://creativecommons.org/licenses/by-nc/4.0/
  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
    (S)-2-((R)-2-oxo-4-propylpyrrolidin-1-yl)butanamide
    https://echa.europa.eu/substance-information/-/substanceinfo/100.118.642
    (S)-2-((R)-2-oxo-4-propylpyrrolidin-1-yl)butanamide (EC: 801-184-2)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/61700
  6. FDA Global Substance Registration System (GSRS)
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  7. ChEBI
  8. Drug Enforcement Administration (DEA)
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    https://www.justice.gov/legalpolicies
    DEA drug and chemical classification
    https://www.dea.gov/drug-information/drug-scheduling
  9. FDA Pharm Classes
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  10. LiverTox
  11. NCI Thesaurus (NCIt)
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  12. Open Targets
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    http://www.ebi.ac.uk/Information/termsofuse.html
  14. Comparative Toxicogenomics Database (CTD)
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    http://ctdbase.org/about/legal.jsp
  15. Drug Gene Interaction database (DGIdb)
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    http://www.dgidb.org/downloads
  16. IUPHAR/BPS Guide to PHARMACOLOGY
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    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  17. Therapeutic Target Database (TTD)
  18. ClinicalTrials.gov
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  19. Crystallography Open Database (COD)
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    https://creativecommons.org/publicdomain/zero/1.0/
  20. DailyMed
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  23. Drugs and Lactation Database (LactMed)
  24. Drugs@FDA
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  25. EU Clinical Trials Register
  26. FDA Orange Book
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  27. NORMAN Suspect List Exchange
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    https://creativecommons.org/licenses/by/4.0/
    Brivaracetam
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  28. WHO Anatomical Therapeutic Chemical (ATC) Classification
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  30. Japan Chemical Substance Dictionary (Nikkaji)
  31. KEGG
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    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
    Target-based classification of drugs
    http://www.genome.jp/kegg-bin/get_htext?br08310.keg
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  33. NIPH Clinical Trials Search of Japan
  34. NLM RxNorm Terminology
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    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  35. PharmGKB
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    https://www.pharmgkb.org/page/policies
  36. Pharos
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    https://pharos.nih.gov/about
  37. RCSB Protein Data Bank (RCSB PDB)
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    Data files contained in the PDB archive (ftp://ftp.wwpdb.org) are free of all copyright restrictions and made fully and freely available for both non-commercial and commercial use. Users of the data should attribute the original authors of that structural data.
    https://www.rcsb.org/pages/policies
  38. SpectraBase
  39. Springer Nature
  40. Thieme Chemistry
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    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/
  41. Wikidata
  42. Wikipedia
  43. Wiley
  44. PubChem
  45. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  46. GHS Classification (UNECE)
  47. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  48. PATENTSCOPE (WIPO)
  49. NCBI
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