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Terconazole

PubChem CID
441383
Structure
Terconazole_small.png
Terconazole_3D_Structure.png
Molecular Formula
Synonyms
  • terconazole
  • 67915-31-5
  • Fungistat
  • Triaconazole
  • Terazol 7
Molecular Weight
532.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-06-24
  • Modify:
    2024-12-07
Description
(2R,4S)-terconazole is a 1-(4-{[2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-isopropylpiperazine in which positions 2 and 4 of the 1,3-dioxolane moiety have R and S configuration, respectively. It is an enantiomer of a (2S,4R)-terconazole.

Terconazole is an antifungal prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of vulvovaginal candidiasis.

Vulvovaginal candidiasis can be an opportunistic infection (OI) of HIV.

Terconazole is an anti-fungal drug that is mainly used to treat vaginal yeast infections (or vaginal candidiasis). It is classified as a triazole ketal derivative. Terconazole was initially approved by the FDA in 1987. This drug is available in cream and suppository forms and both have demonstrated high levels of safety, efficacy, and tolerability in clinical trials.Due to the existence of 2 stereocentres, there are 4 possible stereoisomers for terconazole.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Terconazole.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-[4-[[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-4-propan-2-ylpiperazine
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C26H31Cl2N5O3/c1-19(2)31-9-11-32(12-10-31)21-4-6-22(7-5-21)34-14-23-15-35-26(36-23,16-33-18-29-17-30-33)24-8-3-20(27)13-25(24)28/h3-8,13,17-19,23H,9-12,14-16H2,1-2H3/t23-,26-/m0/s1
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

BLSQLHNBWJLIBQ-OZXSUGGESA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CC(C)N1CCN(CC1)C2=CC=C(C=C2)OC[C@H]3CO[C@](O3)(CN4C=NC=N4)C5=C(C=C(C=C5)Cl)Cl
Computed by OEChem 2.3.0 (PubChem release 2021.10.14)

2.2 Molecular Formula

C26H31Cl2N5O3
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 ChEBI ID

2.3.4 ChEMBL ID

2.3.5 DrugBank ID

2.3.6 DSSTox Substance ID

2.3.7 HMDB ID

2.3.8 KEGG ID

2.3.9 Metabolomics Workbench ID

2.3.10 NCI Thesaurus Code

2.3.11 Nikkaji Number

2.3.12 NSC 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

  • 1-(4-((2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-4-(1-methylethyl)piperazine
  • Fungistat
  • Gyno-Terazol
  • R 42470
  • Terazol
  • terconazole

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
532.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
4.8
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
7
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
531.1803953 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
531.1803953 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
64.9Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
36
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
693
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 Physical Description

Solid

3.2.2 Melting Point

126.3°C
126.3 °C

3.2.3 Solubility

1.16e-02 g/L

3.2.4 LogP

4.5
4.5

3.3 Chemical Classes

3.3.1 Drugs

3.3.1.1 Human Drugs
Breast Feeding; Lactation; Anti-Infective Agents; Antifungal Agents;
Human drug -> Prescription; Discontinued; Active ingredient (TERCONAZOLE)
Human drug -> Discontinued

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 1H NMR Spectra

Instrument Name
Varian CFT-20
Copyright
Copyright © 2009-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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4.2 Mass Spectrometry

4.2.1 GC-MS

Source of Spectrum
CJ-0-53-0
Copyright
Copyright © 2020-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.2.2 MS-MS

Spectra ID
Ionization Mode
positive
Top 5 Peaks

219.150055 100

532.187805 65.90

192.102264 54.18

534.184631 41.68

277.191498 33.66

Thumbnail
Thumbnail
Notes
instrument=qTof

4.3 UV Spectra

4.3.1 UV-VIS Spectra

Copyright
Copyright © 2008-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.4 IR Spectra

4.4.1 FTIR Spectra

Technique
KBr WAFER
Source of Sample
J. Heeres, Janssen Pharmaceutica, Beerse, Belgium
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.4.2 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/23959>23959</a>
Lot Number
0519016-1
Copyright
Copyright © 2019-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

4.5 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/23959>23959</a>
Lot Number
0519016-1
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

For the treatment of candidiasis (a yeast-like fungal infection) of the vulva and vagina.

7.2 Drug Classes

Breast Feeding; Lactation; Anti-Infective Agents; Antifungal Agents;

7.3 FDA Approved Drugs

7.4 FDA Orange Book

7.5 FDA National Drug Code Directory

7.6 Drug Labels

Drug and label
Active ingredient and drug

7.7 HIV / AIDS and Opportunistic Infection Drugs

What is Terconazole

Terconazole is an antifungal prescription medicine approved by the U.S. Food and Drug Administration (FDA) for the treatment of vulvovaginal candidiasis.

Vulvovaginal candidiasis can be&nbsp;an opportunistic infection (OI) of HIV.

Drug Class
Antifungal (Azole)

7.8 Clinical Trials

7.8.1 ClinicalTrials.gov

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

Terconazole is a triazole antifungal agent available for intravaginal use. It is structurally related to imidazole-derivative antifungal agents, although terconazole and other triazoles have 3 nitrogens in the azole ring. By inhibiting the 14-alpha-demethylase (lanosterol 14-alpha-demethylase), Terconazole inhibits ergosterol synthesis. Depletion of ergosterol in fungal membrane disrupts the structure and many functions of fungal membrane leading to inhibition of fungal growth.

8.2 MeSH Pharmacological Classification

Antifungal Agents
Substances that destroy fungi by suppressing their ability to grow or reproduce. They differ from FUNGICIDES, INDUSTRIAL because they defend against fungi present in human or animal tissues. (See all compounds classified as Antifungal Agents.)

8.3 FDA Pharmacological Classification

Non-Proprietary Name
TERCONAZOLE
Pharmacological Classes
Azole Antifungal [EPC]; Azoles [CS]

8.4 ATC Code

G - Genito urinary system and sex hormones

G01 - Gynecological antiinfectives and antiseptics

G01A - Antiinfectives and antiseptics, excl. combinations with corticosteroids

G01AG - Triazole derivatives

G01AG02 - Terconazole

8.5 Absorption, Distribution and Excretion

Absorption
Following intravaginal administration of terconazole in humans, absorption ranged from 5-8% in three hysterectomized subjects and 12-16% in two non-hysterectomized subjects with tubal ligations
Route of Elimination
Following oral (30 mg) administration of 14C-labelled terconazole, excretion of radioactivity was both by renal (32-56%) and fecal (47-52%) routes.

8.6 Metabolism / Metabolites

Systemically absorbed drug appears to be rapidly and extensively metabolized. Terconazole primarily undergoes oxidatative N- and O-dealkylation, dioxolane ring cleavage, and conjugation.

8.7 Biological Half-Life

6.9 hours (range 4.0-11.3)

8.8 Mechanism of Action

Terconazole may exert its antifungal activity by disrupting normal fungal cell membrane permeability. Terconazole and other triazole antifungal agents inhibit cytochrome P450 14-alpha-demethylase in susceptible fungi, which leads to the accumulation of lanosterol and other methylated sterols and a decrease in ergosterol concentration. Depletion of ergosterol in the membrane disrupts the structure and function of the fungal cell leading to a decrease or inhibition of fungal growth.

8.9 Human Metabolite Information

8.9.1 Cellular Locations

Membrane

9 Use and Manufacturing

9.1 Uses

9.1.1 Use Classification

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 (59.6%): Harmful if swallowed [Warning Acute toxicity, oral]

H315 (42.6%): Causes skin irritation [Warning Skin corrosion/irritation]

H319 (42.6%): Causes serious eye irritation [Warning Serious eye damage/eye irritation]

H335 (42.6%): May cause respiratory irritation [Warning Specific target organ toxicity, single exposure; Respiratory tract irritation]

H413 (40.4%): May cause long lasting harmful effects to aquatic life [Hazardous to the aquatic environment, long-term hazard]

Precautionary Statement Codes

P261, P264, P264+P265, P270, P271, P273, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, 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 94 reports by companies from 3 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.

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 (59.6%)

Skin Irrit. 2 (42.6%)

Eye Irrit. 2 (42.6%)

STOT SE 3 (42.6%)

Aquatic Chronic 4 (40.4%)

11 Toxicity

11.1 Toxicological Information

11.1.1 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

Vaginal terconazole has not been studied during breastfeeding. Other antifungal agents may be preferred, especially while nursing a newborn or preterm infant

◉ Effects in Breastfed Infants

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

◉ Effects on Lactation and Breastmilk

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

11.1.2 Protein Binding

94.9%

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 Chemical Co-Occurrences in Patents

14.4 Chemical-Disease Co-Occurrences in Patents

14.5 Chemical-Gene Co-Occurrences in Patents

15 Interactions and Pathways

15.1 Chemical-Target Interactions

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: USP

17.5 KEGG: ATC

17.6 KEGG: Drug Groups

17.7 KEGG : Antimicrobials

17.8 KEGG: Drug Classes

17.9 WHO ATC Classification System

17.10 ChEMBL Target Tree

17.11 UN GHS Classification

17.12 NORMAN Suspect List Exchange Classification

17.13 EPA DSSTox Classification

17.14 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. BindingDB
    LICENSE
    All data curated by BindingDB staff are provided under the Creative Commons Attribution 3.0 License (https://creativecommons.org/licenses/by/3.0/us/).
    https://www.bindingdb.org/rwd/bind/info.jsp
  2. 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
  3. Comparative Toxicogenomics Database (CTD)
    LICENSE
    It is to be used only for research and educational purposes. Any reproduction or use for commercial purpose is prohibited without the prior express written permission of NC State University.
    http://ctdbase.org/about/legal.jsp
  4. 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
  5. Therapeutic Target Database (TTD)
  6. CAS Common Chemistry
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    https://creativecommons.org/licenses/by-nc/4.0/
  7. DTP/NCI
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    https://www.cancer.gov/policies/copyright-reuse
  8. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  9. 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
  10. Human Metabolome Database (HMDB)
    LICENSE
    HMDB is offered to the public as a freely available resource. Use and re-distribution of the data, in whole or in part, for commercial purposes requires explicit permission of the authors and explicit acknowledgment of the source material (HMDB) and the original publication (see the HMDB citing page). We ask that users who download significant portions of the database cite the HMDB paper in any resulting publications.
    http://www.hmdb.ca/citing
  11. ChEBI
  12. Drug Database, Clinicalinfo.hiv.gov
    LICENSE
    Unless otherwise noted, material presented on the HIV.gov website is considered Federal government information and is in the public domain. That means this information may be freely copied and distributed. We request that you use appropriate attribution to HIV.gov.
    https://www.hiv.gov/about-us/mission-and-team
  13. NCI Thesaurus (NCIt)
    LICENSE
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    https://www.cancer.gov/policies/copyright-reuse
  14. Open Targets
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    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  15. ClinicalTrials.gov
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    https://clinicaltrials.gov/ct2/about-site/terms-conditions#Use
  16. DailyMed
  17. Drugs and Lactation Database (LactMed)
  18. Drugs@FDA
    LICENSE
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  19. FDA Orange Book
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  20. Japan Chemical Substance Dictionary (Nikkaji)
  21. 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
    Anatomical Therapeutic Chemical (ATC) classification
    http://www.genome.jp/kegg-bin/get_htext?br08303.keg
  22. Metabolomics Workbench
  23. National Drug Code (NDC) Directory
    LICENSE
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    https://www.fda.gov/about-fda/about-website/website-policies#linking
  24. NLM RxNorm Terminology
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    https://www.nlm.nih.gov/research/umls/rxnorm/docs/termsofservice.html
  25. PharmGKB
    LICENSE
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    https://www.pharmgkb.org/page/policies
  26. Pharos
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    Data accessed from Pharos and TCRD is publicly available from the primary sources listed above. Please respect their individual licenses regarding proper use and redistribution.
    https://pharos.nih.gov/about
  27. SpectraBase
    cis-1-{p-{{2-(2,4-dichlorophenyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]1,3-dioxolan-4-yl}methoxy}phenyl}-4-isopropylpiperazine
    https://spectrabase.com/spectrum/2dIRzcrB0FD
    cis-1-{p-{{2-(2,4-DICHLOROPHENYL)-2-[(1H-1,2,4-TRIAZOL-1-YL)METHYL]-1,3-DIOXOLAN-4-YL}METHOXY}PHENYL}-4-ISOPROPYLPIPERAZINE
    https://spectrabase.com/spectrum/Euv4PNDBUFA
    cis-1-{p-{{2-(2,4-dichlorophenyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]-1,3-dioxolan-4-yl]methoxy]phenyl}-4-isopropylpiperazine
    https://spectrabase.com/spectrum/Dlcdk9vLBlI
    1-(4-{[(2R,4S)-2-(2,4-dichlorophenyl)-2-(1H-1,2,4-triazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-isopropylpiperazine
    https://spectrabase.com/spectrum/A8Oo63GJaCD
  28. Springer Nature
  29. Thieme Chemistry
    LICENSE
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    https://creativecommons.org/licenses/by-nc-nd/4.0/
  30. WHO Anatomical Therapeutic Chemical (ATC) Classification
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    https://www.whocc.no/copyright_disclaimer/
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    https://www.nlm.nih.gov/copyright.html
  36. GHS Classification (UNECE)
  37. 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/
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  38. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  39. PATENTSCOPE (WIPO)
  40. NCBI
CONTENTS