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Tetracaine

PubChem CID
5411
Structure
Tetracaine_small.png
Tetracaine_3D_Structure.png
Molecular Formula
Synonyms
  • tetracaine
  • 94-24-6
  • Amethocaine
  • 2-(Dimethylamino)ethyl 4-(butylamino)benzoate
  • Pontocaine
Molecular Weight
264.36 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-25
  • Modify:
    2025-01-18
Description
Tetracaine is a benzoate ester in which 4-N-butylbenzoic acid and 2-(dimethylamino)ethanol have combined to form the ester bond; a local ester anaesthetic (ester caine) used for surface and spinal anaesthesia. It has a role as a local anaesthetic. It is a benzoate ester and a tertiary amino compound.
Tetracaine is an ester local anaesthetic currently available in combination with lidocaine as a cream and patch.
Tetracaine is an Ester Local Anesthetic. The physiologic effect of tetracaine is by means of Local Anesthesia.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Tetracaine.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

2-(dimethylamino)ethyl 4-(butylamino)benzoate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C15H24N2O2/c1-4-5-10-16-14-8-6-13(7-9-14)15(18)19-12-11-17(2)3/h6-9,16H,4-5,10-12H2,1-3H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

GKCBAIGFKIBETG-UHFFFAOYSA-N
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.4 SMILES

CCCCNC1=CC=C(C=C1)C(=O)OCCN(C)C
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C15H24N2O2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

94-24-6

2.3.3 European Community (EC) Number

2.3.4 UNII

2.3.5 ChEBI ID

2.3.6 ChEMBL ID

2.3.7 DrugBank ID

2.3.8 DSSTox Substance ID

2.3.9 HMDB ID

2.3.10 KEGG ID

2.3.11 Metabolomics Workbench ID

2.3.12 NCI Thesaurus Code

2.3.13 Nikkaji Number

2.3.14 PharmGKB ID

2.3.15 Pharos Ligand ID

2.3.16 RXCUI

2.3.17 Wikidata

2.3.18 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Amethocaine
  • Ametop
  • Dicaine
  • Hydrochloride, Tetrracaine
  • Pantocaine
  • Pontocaine
  • Tetracaine
  • Tetracaine Monohydrochloride
  • Tetrakain
  • Tetrracaine Hydrochloride

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
264.36 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
3.7
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
4
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
9
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
264.183778013 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
264.183778013 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
41.6 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
19
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
249
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
0
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 Dissociation Constants

Basic pKa
8.49
Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds. Pharm Res. 2014; 31(4):1082-95. DOI:10.1007/s11095-013-1232-z. PMID:24249037
Basic pKa
8.5
Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds. Pharm Res. 2014; 31(4):1082-95. DOI:10.1007/s11095-013-1232-z. PMID:24249037
Basic pKa
8.6
Comparison of the accuracy of experimental and predicted pKa values of basic and acidic compounds. Pharm Res. 2014; 31(4):1082-95. DOI:10.1007/s11095-013-1232-z. PMID:24249037

3.2.2 Collision Cross Section

158.41 Ų [M+H-H2O]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

164.78 Ų [M+K]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

170.85 Ų [M+H]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

Ross et al. JASMS 2022; 33; 1061-1072. DOI:10.1021/jasms.2c00111
173.1 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]
173.5 Ų [M+H]+ [CCS Type: DT; Method: single field calibrated]

3.2.3 Kovats Retention Index

Standard non-polar
2221 , 2212 , 2212 , 2215 , 2218 , 2224 , 2229 , 2219 , 2215.3 , 2197 , 2230 , 2235 , 2219

3.3 SpringerMaterials Properties

3.4 Chemical Classes

Other Uses -> Pharmaceuticals

3.4.1 Drugs

Pharmaceuticals
S10 | SWISSPHARMA | Pharmaceutical List with Consumption Data | DOI:10.5281/zenodo.2623484
Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
3.4.1.1 Human Drugs
Breast Feeding; Lactation; Milk, Human; Anesthetics, Local
Human drug -> Active ingredient (TETRACAINE)
Pharmaceuticals
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664
Ophthalmological preparations > Local anaesthetics

4 Spectral Information

4.1 1D NMR Spectra

1D NMR Spectra

4.1.1 13C NMR Spectra

Instrument Name
Bruker WH-90
Copyright
Copyright © 2002-2024 Wiley-VCH Verlag GmbH & Co. KGaA. All Rights Reserved.
Thumbnail
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 8
View All
NIST Number
408051
Library
Main library
Total Peaks
99
m/z Top Peak
58
m/z 2nd Highest
71
m/z 3rd Highest
176
Thumbnail
Thumbnail
2 of 8
View All
NIST Number
125807
Library
Replicate library
Total Peaks
67
m/z Top Peak
58
m/z 2nd Highest
71
m/z 3rd Highest
176
Thumbnail
Thumbnail

4.2.2 MS-MS

1 of 10
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

176.106 100

120.0436 25.89

177.1091 10.40

118.0643 6.15

148.1108 3.39

Thumbnail
Thumbnail
2 of 10
View All
Spectra ID
Ionization Mode
Positive
Top 5 Peaks

176.1062 100

177.1092 12.11

120.0437 8.78

148.1109 2.16

220.1321 1.90

Thumbnail
Thumbnail

4.2.3 LC-MS

1 of 27
View All
Authors
Nikiforos Alygizakis, Katerina Galani, Nikolaos Thomaidis, University of Athens
Instrument
Bruker maXis Impact
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
10 eV
Fragmentation Mode
CID
Column Name
Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo
Retention Time
6.286 min
Precursor m/z
265.1911
Precursor Adduct
[M+H]+
Top 5 Peaks

265.1914 999

176.1064 952

266.1941 183

177.1094 118

220.1327 54

Thumbnail
Thumbnail
License
CC BY
2 of 27
View All
Authors
Nikiforos Alygizakis, Katerina Galani, Nikolaos Thomaidis, University of Athens
Instrument
Bruker maXis Impact
Instrument Type
LC-ESI-QTOF
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
20 eV
Fragmentation Mode
CID
Column Name
Acclaim RSLC C18 2.2um, 2.1x100mm, Thermo
Retention Time
6.270 min
Precursor m/z
265.1911
Precursor Adduct
[M+H]+
Top 5 Peaks

176.107 999

220.1327 155

221.1356 21

178.1118 11

265.1903 9

Thumbnail
Thumbnail
License
CC BY

4.3 IR Spectra

4.3.1 FTIR Spectra

Technique
KBr WAFER
Source of Sample
American Hoechst Corporation
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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4.3.2 ATR-IR Spectra

Instrument Name
Bio-Rad FTS
Technique
ATR-Film (MeCl2) (DuraSamplIR II)
Source of Spectrum
Forensic Spectral Research
Source of Sample
Alltech Associates, Inc., Grace Davison Discovery Sciences
Catalog Number
Free base of 01791
Lot Number
Free base of N-272
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

Ophthalmic tetracaine is indicated for the for procedures requiring a rapid and short- acting topical ophthalmic anesthetic. The combination lidocaine and tetracaine patch is indicated for local dermal analgesia for superficial dermatological procedures and superficial venous access. The combination lidocaine and tetracaine cream is intended to provide topical local analgesia for superficial dermatological procedures.

7.2 Drug Classes

Breast Feeding; Lactation; Milk, Human; Anesthetics, Local

7.3 WHO Essential Medicines

Drug
Drug Classes
Ophthalmological preparations > Local anaesthetics
Formulation
Local - Ophthalmological - Solution (eye drops): 0.5% (hydrochloride)
Indication
Local anaesthetics

7.4 FDA Approved Drugs

7.5 FDA Orange Book

7.6 FDA National Drug Code Directory

7.7 Drug Labels

Drug and label
Active ingredient and drug

7.8 Clinical Trials

7.8.1 ClinicalTrials.gov

7.8.2 EU Clinical Trials Register

7.8.3 NIPH Clinical Trials Search of Japan

8 Pharmacology and Biochemistry

8.1 MeSH Pharmacological Classification

Anesthetics, Local
Drugs that block nerve conduction when applied locally to nerve tissue in appropriate concentrations. They act on any part of the nervous system and on every type of nerve fiber. In contact with a nerve trunk, these anesthetics can cause both sensory and motor paralysis in the innervated area. Their action is completely reversible. (From Gilman AG, et. al., Goodman and Gilman's The Pharmacological Basis of Therapeutics, 8th ed) Nearly all local anesthetics act by reducing the tendency of voltage-dependent sodium channels to activate. (See all compounds classified as Anesthetics, Local.)

8.2 FDA Pharmacological Classification

1 of 2
FDA UNII
0619F35CGV
Active Moiety
TETRACAINE
Pharmacological Classes
Established Pharmacologic Class [EPC] - Ester Local Anesthetic
Pharmacological Classes
Chemical Structure [CS] - Esters
Pharmacological Classes
Physiologic Effects [PE] - Local Anesthesia
FDA Pharmacology Summary
Tetracaine is an Ester Local Anesthetic. The physiologic effect of tetracaine is by means of Local Anesthesia.
2 of 2
Non-Proprietary Name
TETRACAINE
Pharmacological Classes
Local Anesthesia [PE]; Esters [CS]; Ester Local Anesthetic [EPC]

8.3 ATC Code

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

N01 - Anesthetics

N01B - Anesthetics, local

N01BA - Esters of aminobenzoic acid

N01BA03 - Tetracaine

S - Sensory organs

S01 - Ophthalmologicals

S01H - Local anesthetics

S01HA - Local anesthetics

S01HA03 - Tetracaine

D - Dermatologicals

D04 - Antipruritics, incl. antihistamines, anesthetics, etc.

D04A - Antipruritics, incl. antihistamines, anesthetics, etc.

D04AB - Anesthetics for topical use

D04AB06 - Tetracaine

C - Cardiovascular system

C05 - Vasoprotectives

C05A - Agents for treatment of hemorrhoids and anal fissures for topical use

C05AD - Local anesthetics

C05AD02 - Tetracaine

8.4 Absorption, Distribution and Excretion

Absorption
Systemic absorption of anaesthetic from the combination cream is directly related to the duration and surface area of application. Although peak plasma concentrations for lidocaine were measured, plasma levels for tetracaine could not be determined due to low levels (<0.9 ng/mL)
Volume of Distribution
Tetracaine is rapidly hydrolyzed in the plasma; therefore, volume of distribution could not be determined.
Clearance
Tetracaine is hydrolyzed rapidly in the plasma; therefore, clearance has not been determined.

8.5 Metabolism / Metabolites

Tetracaine is rapidly hydrolyzed by plasma esterases to the following primary metabolites: para-aminobenzoic acid and diethylaminoethanol. The activity of both metabolites is unspecified.

8.6 Biological Half-Life

Tetracaine is hydrolyzed rapidly in the plasma; therefore, half-life has not been determined.

8.7 Mechanism of Action

Tetracaine is an ester-type anesthetic and produces local anesthesia by blocking the sodium ion channels involved in the initiation and conduction of neuronal impulses.

9 Use and Manufacturing

9.1 Uses

Sources/Uses
Used as a local anesthetic by dentists and other surgeons; [Kanerva, p. 1748]
Kanerva - Rustemeyer L, Elsner P, John SM, Maibach HI (eds). Kanerva's Occupational Dermatology, 2nd Ed. Berlin: Springer-Verlag, 2012., p. 1748

Use (kg; approx.) in Germany (2009): >50

Consumption (g per capita; approx.) in Germany (2009): 0.000611

Calculated removal (%): 44.3

9.1.1 Use Classification

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients
Pharmaceuticals
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664

10 Safety and Hazards

10.1 Hazards Identification

10.1.1 GHS Classification

Pictogram(s)
Acute Toxic
Irritant
Health Hazard
Signal
Danger
GHS Hazard Statements

H301 (97.6%): Toxic if swallowed [Danger Acute toxicity, oral]

H317 (92.9%): May cause an allergic skin reaction [Warning Sensitization, Skin]

H351 (92.9%): Suspected of causing cancer [Warning Carcinogenicity]

Precautionary Statement Codes

P203, P261, P264, P270, P272, P280, P301+P316, P302+P352, P318, P321, P330, P333+P317, P362+P364, 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 42 reports by companies from 4 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. 3 (97.6%)

Skin Sens. 1 (92.9%)

Carc. 2 (92.9%)

10.1.3 Hazards Summary

Procaine allergy used to be a common skin sensitizer for dentists. There exists cross-reactivity between procaine, benzocaine, and tetracaine but not with lidocaine and other amide-type local anesthetics currently used. [Kanerva, p. 434]
Kanerva - Rustemeyer L, Elsner P, John SM, Maibach HI (eds). Kanerva's Occupational Dermatology, 2nd Ed. Berlin: Springer-Verlag, 2012., p. 434

10.2 Other Safety Information

Chemical Assessment

IMAP assessments - Benzoic acid, 4-(butylamino)-, 2-(dimethylamino)ethyl ester: Environment tier I assessment

IMAP assessments - Benzoic acid, 4-(butylamino)-, 2-(dimethylamino)ethyl ester: Human health tier I assessment

11 Toxicity

11.1 Toxicological Information

11.1.1 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

No information is available on the use of tetracaine during breastfeeding. Based on the low excretion of other local anesthetics into breastmilk, a single dose of injected tetracaine during breastfeeding, such as for a dental procedure, is unlikely to adversely affect the breastfed infant. However, an alternate drug may be preferred, especially while nursing a newborn or preterm infant. Topical application of tetracaine to the mother is unlikely to affect her breastfed infant if it is applied away from the breast. Only water-miscible cream or gel products should be applied to the breast because ointments may expose the infant to high levels of mineral paraffins via licking.

◉ 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 Adverse Effects

Skin Sensitizer - An agent that can induce an allergic reaction in the skin.

11.1.3 Acute Effects

11.1.4 Protein Binding

Tetracaine is rapidly hydrolyzed in the plasma; therefore, protein binding could not be determined.

12 Associated Disorders and Diseases

Associated Occupational Diseases with Exposure to the Compound
Contact dermatitis, allergic [Category: Skin Disease]

13 Literature

13.1 Consolidated References

13.2 NLM Curated PubMed Citations

13.3 Springer Nature References

13.4 Thieme References

13.5 Chemical Co-Occurrences in Literature

13.6 Chemical-Gene Co-Occurrences in Literature

13.7 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

15.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

15.2 Chemical-Target Interactions

15.3 Drug-Drug 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: ATC

17.5 KEGG: Target-based Classification of Drugs

17.6 KEGG: Drug Groups

17.7 WHO ATC Classification System

17.8 FDA Pharm Classes

17.9 ChemIDplus

17.10 ChEMBL Target Tree

17.11 UN GHS Classification

17.12 NORMAN Suspect List Exchange Classification

17.13 CCSBase Classification

17.14 EPA DSSTox Classification

17.15 MolGenie Organic Chemistry Ontology

18 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    Benzoic acid, 4-(butylamino)-, 2-(dimethylamino)ethyl ester
    https://services.industrialchemicals.gov.au/search-assessments/
  2. 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/
  3. ChemIDplus
    ChemIDplus Chemical Information Classification
    https://pubchem.ncbi.nlm.nih.gov/source/ChemIDplus
  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. EPA DSSTox
    CompTox Chemicals Dashboard Chemical Lists
    https://comptox.epa.gov/dashboard/chemical-lists/
  6. 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
  7. 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
  8. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  9. ChEBI
  10. FDA Pharm Classes
    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
  11. 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
  12. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  13. 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
  14. IUPAC Digitized pKa Dataset
    aniline, N-butyl-4-(2-dimethylaminoethoxycarbonyl)-
    https://github.com/IUPAC/Dissociation-Constants
  15. 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
  16. 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
  17. 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
  18. Therapeutic Target Database (TTD)
  19. Haz-Map, Information on Hazardous Chemicals and Occupational Diseases
    LICENSE
    Copyright (c) 2022 Haz-Map(R). All rights reserved. Unless otherwise indicated, all materials from Haz-Map are copyrighted by Haz-Map(R). No part of these materials, either text or image may be used for any purpose other than for personal use. Therefore, reproduction, modification, storage in a retrieval system or retransmission, in any form or by any means, electronic, mechanical or otherwise, for reasons other than personal use, is strictly prohibited without prior written permission.
    https://haz-map.com/About
  20. DailyMed
  21. Drugs and Lactation Database (LactMed)
  22. 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
  23. 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/
    TETRACAINE
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  24. WHO Model Lists of Essential Medicines
    LICENSE
    Permission from WHO is not required for the use of WHO materials issued under the Creative Commons Attribution-NonCommercial-ShareAlike 3.0 Intergovernmental Organization (CC BY-NC-SA 3.0 IGO) license.
    https://www.who.int/about/policies/publishing/copyright
  25. EU Clinical Trials Register
  26. 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
  27. 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
  28. 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
  29. NIST Mass Spectrometry Data Center
    LICENSE
    Data covered by the Standard Reference Data Act of 1968 as amended.
    https://www.nist.gov/srd/public-law
  30. Japan Chemical Substance Dictionary (Nikkaji)
  31. 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
    Target-based classification of drugs
    http://www.genome.jp/kegg-bin/get_htext?br08310.keg
  32. MassBank Europe
  33. MassBank of North America (MoNA)
    LICENSE
    The content of the MoNA database is licensed under CC BY 4.0.
    https://mona.fiehnlab.ucdavis.edu/documentation/license
  34. Metabolomics Workbench
  35. NIPH Clinical Trials Search of Japan
  36. SpectraBase
    4-Butylamino-benzoic acid, 2-dimethylamino-ethyl ester
    https://spectrabase.com/spectrum/8ChMOwW8iPZ
    TETRACAINE HYDROCHLORIDE U.S.P.
    https://spectrabase.com/spectrum/32CN4mbDBpO
  37. 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
  38. NMRShiftDB
  39. 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/
  40. PharmGKB
    LICENSE
    PharmGKB data are subject to the Creative Commons Attribution-ShareALike 4.0 license (https://creativecommons.org/licenses/by-sa/4.0/).
    https://www.pharmgkb.org/page/policies
  41. Pharos
    LICENSE
    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
  42. Protein Data Bank in Europe (PDBe)
  43. RCSB Protein Data Bank (RCSB PDB)
    LICENSE
    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
  44. Springer Nature
  45. SpringerMaterials
    Benzoic acid, 4-(butylamino)-, 2-(dimethylamino)ethyl ester
    https://materials.springer.com/substanceprofile/docs/smsid_ikqgjwlotdzebqxe
  46. 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/
  47. Wikidata
  48. Wikipedia
  49. Medical Subject Headings (MeSH)
    LICENSE
    Works produced by the U.S. government are not subject to copyright protection in the United States. Any such works found on National Library of Medicine (NLM) Web sites may be freely used or reproduced without permission in the U.S.
    https://www.nlm.nih.gov/copyright.html
  50. PubChem
  51. GHS Classification (UNECE)
  52. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  53. PATENTSCOPE (WIPO)
  54. NCBI
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