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Nicardipine

PubChem CID
4474
Structure
Nicardipine_small.png
Nicardipine_3D_Structure.png
Molecular Formula
Synonyms
  • nicardipine
  • 55985-32-5
  • Nicardipino
  • Nicardipinum
  • Perpidine
Molecular Weight
479.5 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-25
  • Modify:
    2025-01-18
Description
Nicardipine is a racemate comprising equimolar amounts of (R)- and (S)-nicardipine. It is a calcium channel blocker which is used to treat hypertension. It has a role as an antihypertensive agent, a calcium channel blocker, a vasodilator agent and an autophagy inhibitor. It contains a (S)-nicardipine and a (R)-nicardipine.
Nicardipine is a Dihydropyridine Calcium Channel Blocker. The mechanism of action of nicardipine is as a Calcium Channel Antagonist, and Cytochrome P450 3A4 Inhibitor, and Cytochrome P450 2D6 Inhibitor, and Cytochrome P450 2C8 Inhibitor, and Cytochrome P450 2C19 Inhibitor.
Nicardipine is a second generation calcium channel blocker used in the treatment of hypertension and stable angina pectoris. Nicardipene therapy has been associated with a low rate of transient serum enzyme elevations, but has not been linked convincingly to instances of clinically apparent liver injury with jaundice.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Nicardipine.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

5-O-[2-[benzyl(methyl)amino]ethyl] 3-O-methyl 2,6-dimethyl-4-(3-nitrophenyl)-1,4-dihydropyridine-3,5-dicarboxylate
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C26H29N3O6/c1-17-22(25(30)34-4)24(20-11-8-12-21(15-20)29(32)33)23(18(2)27-17)26(31)35-14-13-28(3)16-19-9-6-5-7-10-19/h5-12,15,24,27H,13-14,16H2,1-4H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

CC1=C(C(C(=C(N1)C)C(=O)OCCN(C)CC2=CC=CC=C2)C3=CC(=CC=C3)[N+](=O)[O-])C(=O)OC
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C26H29N3O6
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

55985-32-5

2.3.2 European Community (EC) Number

2.3.3 UNII

2.3.4 ChEBI ID

2.3.5 ChEMBL ID

2.3.6 DrugBank ID

2.3.7 DSSTox Substance ID

2.3.8 HMDB ID

2.3.9 KEGG ID

2.3.10 Metabolomics Workbench ID

2.3.11 NCI Thesaurus Code

2.3.12 PharmGKB ID

2.3.13 Pharos Ligand ID

2.3.14 RXCUI

2.3.15 Wikidata

2.3.16 Wikipedia

2.4 Synonyms

2.4.1 MeSH Entry Terms

  • Antagonil
  • Cardene
  • Cardene I.V.
  • Cardene SR
  • Dagan
  • Flusemide
  • Hydrochloride, Nicardipine
  • LA, Nicardipine
  • Lecibral
  • Lincil
  • Loxen
  • Lucenfal
  • Nicardipine
  • Nicardipine Hydrochloride
  • Nicardipine LA
  • Nicardipino Ratiopharm
  • Nicardipino Seid
  • Perdipine
  • Ridene
  • Vasonase
  • Y 93
  • Y-93
  • Y93

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
479.5 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3
Property Value
3.8
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
8
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Rotatable Bond Count
Property Value
10
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Exact Mass
Property Value
479.20563565 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
479.20563565 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
114 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
35
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
856
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
1
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

136-138 °C
PhysProp
136 - 138 °C

3.2.3 Solubility

2.2 mg/L
2.47e-03 g/L

3.2.4 LogP

3.82
SANGSTER (1993)
3.6

3.2.5 Collision Cross Section

212.1 Ų [M+H]+ [CCS Type: TW; Method: Major Mix IMS/Tof Calibration Kit (Waters)]

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

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

210.83 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

3.3 Chemical Classes

3.3.1 Drugs

3.3.1.1 Human Drugs
Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Calcium Channel Blockers; Vasodilator Agents
Human drug -> Discontinued
Pharmaceuticals
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664

4 Spectral Information

4.1 1D NMR Spectra

4.1.1 13C NMR Spectra

1 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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2 of 2
Copyright
Copyright © 2016-2024 W. Robien, Inst. of Org. Chem., Univ. of Vienna. All Rights Reserved.
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4.2 Mass Spectrometry

4.2.1 GC-MS

1 of 5
View All
NIST Number
379749
Library
Main library
Total Peaks
167
m/z Top Peak
91
m/z 2nd Highest
134
m/z 3rd Highest
147
Thumbnail
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2 of 5
View All
NIST Number
247323
Library
Replicate library
Total Peaks
133
m/z Top Peak
91
m/z 2nd Highest
134
m/z 3rd Highest
147
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4.2.2 MS-MS

1 of 8
View All
Spectra ID
Ionization Mode
Negative
Top 5 Peaks

108.0218 100

162.0563 56.22

79.019 55.18

104.0507 49.70

224.0718 48.36

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2 of 8
View All
Spectra ID
Ionization Mode
Negative
Top 5 Peaks

122.0247 100

108.0217 45.60

224.0717 31.75

95.0139 23.09

164.0717 21.72

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4.2.3 LC-MS

1 of 22
View All
Authors
Elapavalore, A.; Kondić, T.; Singh, R.; Schymanski, E.
Instrument
Q Exactive Orbitrap (Thermo Scientific)
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
15
Fragmentation Mode
HCD
Column Name
Acquity BEH C18 1.7um, 2.1x150mm (Waters)
Retention Time
14.916 min
Precursor m/z
480.2129
Precursor Adduct
[M+H]+
Top 5 Peaks

480.213 999

166.1226 411

315.0974 272

148.112 155

359.1236 71

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License
CC BY
Reference
Elapavalore, A.; Kondić, T.; et al., Adding Open Spectral Data to MassBank and PubChem Using Open Source Tools to Support Non-Targeted Exposomics of Mixtures (submitted).
2 of 22
View All
Authors
Elapavalore, A.; Kondić, T.; Singh, R.; Schymanski, E.
Instrument
Q Exactive Orbitrap (Thermo Scientific)
Instrument Type
LC-ESI-QFT
MS Level
MS2
Ionization Mode
POSITIVE
Ionization
ESI
Collision Energy
30
Fragmentation Mode
HCD
Column Name
Acquity BEH C18 1.7um, 2.1x150mm (Waters)
Retention Time
14.916 min
Precursor m/z
480.2129
Precursor Adduct
[M+H]+
Top 5 Peaks

315.0973 999

148.112 549

166.1226 302

359.1237 245

91.0542 223

Thumbnail
Thumbnail
License
CC BY
Reference
Elapavalore, A.; Kondić, T.; et al., Adding Open Spectral Data to MassBank and PubChem Using Open Source Tools to Support Non-Targeted Exposomics of Mixtures (submitted).

4.3 IR Spectra

4.3.1 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 01438
Lot Number
Free base of 511000197
Copyright
Copyright © 2012-2024 John Wiley & Sons, Inc. All Rights Reserved.
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6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

Used for the management of patients with chronic stable angina and for the treatment of hypertension.

7.2 LiverTox Summary

Nicardipine is a second generation calcium channel blocker used in the treatment of hypertension and stable angina pectoris. Nicardipene therapy has been associated with a low rate of transient serum enzyme elevations, but has not been linked convincingly to instances of clinically apparent liver injury with jaundice.

7.3 Drug Classes

Breast Feeding; Lactation; Milk, Human; Antihypertensive Agents; Calcium Channel Blockers; Vasodilator Agents
Cardiovascular Agents

7.4 FDA National Drug Code Directory

7.5 Drug Labels

Drug and label
Active ingredient and drug

7.6 Clinical Trials

7.6.1 ClinicalTrials.gov

7.6.2 EU Clinical Trials Register

7.6.3 NIPH Clinical Trials Search of Japan

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

Nicardipine, a dihydropyridine calcium-channel blocker, is used alone or with an angiotensin-converting enzyme inhibitor, to treat hypertension, chronic stable angina pectoris, and Prinzmetal's variant angina. Nicardipine is similar to other peripheral vasodilators. Nicardipine inhibits the influx of extra cellular calcium across the myocardial and vascular smooth muscle cell membranes possibly by deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum. The decrease in intracellular calcium inhibits the contractile processes of the myocardial smooth muscle cells, causing dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload.

8.2 MeSH Pharmacological Classification

Calcium Channel Blockers
A class of drugs that act by selective inhibition of calcium influx through cellular membranes. (See all compounds classified as Calcium Channel Blockers.)
Antihypertensive Agents
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS. (See all compounds classified as Antihypertensive Agents.)
Vasodilator Agents
Drugs used to cause dilation of the blood vessels. (See all compounds classified as Vasodilator Agents.)

8.3 FDA Pharmacological Classification

1 of 2
FDA UNII
CZ5312222S
Active Moiety
NICARDIPINE
Pharmacological Classes
Mechanisms of Action [MoA] - Calcium Channel Antagonists
Pharmacological Classes
Established Pharmacologic Class [EPC] - Dihydropyridine Calcium Channel Blocker
Pharmacological Classes
Chemical Structure [CS] - Dihydropyridines
Pharmacological Classes
Mechanisms of Action [MoA] - Cytochrome P450 3A4 Inhibitors
Pharmacological Classes
Mechanisms of Action [MoA] - Cytochrome P450 2D6 Inhibitors
Pharmacological Classes
Mechanisms of Action [MoA] - Cytochrome P450 2C8 Inhibitors
Pharmacological Classes
Mechanisms of Action [MoA] - Cytochrome P450 2C19 Inhibitors
FDA Pharmacology Summary
Nicardipine is a Dihydropyridine Calcium Channel Blocker. The mechanism of action of nicardipine is as a Calcium Channel Antagonist, and Cytochrome P450 3A4 Inhibitor, and Cytochrome P450 2D6 Inhibitor, and Cytochrome P450 2C8 Inhibitor, and Cytochrome P450 2C19 Inhibitor.
2 of 2
Non-Proprietary Name
NICARDIPINE
Pharmacological Classes
Cytochrome P450 2C8 Inhibitors [MoA]; Cytochrome P450 2D6 Inhibitors [MoA]; Dihydropyridine Calcium Channel Blocker [EPC]; Cytochrome P450 2C19 Inhibitors [MoA]; Dihydropyridines [CS]; Calcium Channel Antagonists [MoA]; Cytochrome P450 3A4 Inhibitors [MoA]

8.4 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

C - Cardiovascular system

C08 - Calcium channel blockers

C08C - Selective calcium channel blockers with mainly vascular effects

C08CA - Dihydropyridine derivatives

C08CA04 - Nicardipine

8.5 Absorption, Distribution and Excretion

Absorption
While nicardipine is completely absorbed, it is subject to saturable first pass metabolism and the systemic bioavailability is about 35% following a 30 mg oral dose at steady state.
Route of Elimination
Nicardipine has been shown to be rapidly and extensively metabolized by the liver.
Volume of Distribution
8.3 L/kg
Clearance
0.4 L/hr∙kg [Following infusion]

8.6 Metabolism / Metabolites

Nicardipine HCl is metabolized extensively by the liver.
Nicardipine has known human metabolites that include Dehydronicardipine and De-benzylated nicardipine.
S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

8.7 Biological Half-Life

8.6 hours

8.8 Mechanism of Action

By deforming the channel, inhibiting ion-control gating mechanisms, and/or interfering with the release of calcium from the sarcoplasmic reticulum, nicardipine inhibits the influx of extracellular calcium across the myocardial and vascular smooth muscle cell membranes The decrease in intracellular calcium inhibits the contractile processes of the myocardial smooth muscle cells, causing dilation of the coronary and systemic arteries, increased oxygen delivery to the myocardial tissue, decreased total peripheral resistance, decreased systemic blood pressure, and decreased afterload.

8.9 Human Metabolite Information

8.9.1 Cellular Locations

  • Cytoplasm
  • Membrane

8.10 Transformations

9 Use and Manufacturing

9.1 Uses

9.1.1 Use Classification

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)
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 Other Safety Information

Chemical Assessment

IMAP assessments - 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl 2-[methyl(phenylmethyl)amino]ethyl ester: Environment tier I assessment

IMAP assessments - 3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl 2-[methyl(phenylmethyl)amino]ethyl ester: Human health tier I assessment

11 Toxicity

11.1 Toxicological Information

11.1.1 Hepatotoxicity

Nicardipine has not been associated with significant increases in rates of elevations in serum aminotransferase or alkaline phosphatase levels, even with chronic long term therapy. Cases of idiosyncratic liver injury have not been published, although a single instance of marked serum enzyme elevations without jaundice has been reported with the use of intravenous nicardipine. Large trials of nicardipine have not mentioned liver injury, serum aminotransferase elevations or discontinuation of drug because of hepatic adverse events. Thus, clinically apparent liver injury with jaundice due to nicardipine must be rare, if it occurs at all.

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

The reason why some calcium channel blockers are known to cause idiosyncratic liver injury while others such as nicardipine do not, is unknown.

Drug Class: Cardiovascular Agents, Calcium Channel Blockers

Other Drugs in the Subclass, Calcium Channel Blockers: Amlodipine, Diltiazem, Felodipine, Isradipine, Nifedipine, Nimodipine, Nisoldipine, Verapamil

11.1.2 Drug Induced Liver Injury

Compound
nicardipine
DILI Annotation
Ambiguous DILI-concern
Severity Grade
3
Label Section
Adverse reactions
References

M Chen, V Vijay, Q Shi, Z Liu, H Fang, W Tong. FDA-Approved Drug Labeling for the Study of Drug-Induced Liver Injury, Drug Discovery Today, 16(15-16):697-703, 2011. PMID:21624500 DOI:10.1016/j.drudis.2011.05.007

M Chen, A Suzuki, S Thakkar, K Yu, C Hu, W Tong. DILIrank: the largest reference drug list ranked by the risk for developing drug-induced liver injury in humans. Drug Discov Today 2016, 21(4): 648-653. PMID:26948801 DOI:10.1016/j.drudis.2016.02.015

11.1.3 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

Because of the low levels of nicardipine in breastmilk, amounts ingested by the infant are small and would not be expected to cause any adverse effects in breastfed infants. No special precautions are required.

◉ 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.

11.1.4 Acute Effects

11.1.5 Protein Binding

>95%

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

15.2 Drug-Drug Interactions

15.3 Drug-Food Interactions

  • Avoid grapefruit products.
  • Take with or without food. The absorption is unaffected by food.

16 Biological Test Results

16.1 BioAssay Results

17 Taxonomy

18 Classification

18.1 MeSH Tree

18.2 NCI Thesaurus Tree

18.3 ChEBI Ontology

18.4 KEGG: ATC

18.5 KEGG: Target-based Classification of Drugs

18.6 KEGG: Drug Groups

18.7 WHO ATC Classification System

18.8 FDA Pharm Classes

18.9 ChemIDplus

18.10 IUPHAR / BPS Guide to PHARMACOLOGY Target Classification

18.11 ChEMBL Target Tree

18.12 UN GHS Classification

18.13 NORMAN Suspect List Exchange Classification

18.14 CCSBase Classification

18.15 EPA DSSTox Classification

18.16 MolGenie Organic Chemistry Ontology

19 Information Sources

  1. Australian Industrial Chemicals Introduction Scheme (AICIS)
    3,5-Pyridinedicarboxylic acid, 1,4-dihydro-2,6-dimethyl-4-(3-nitrophenyl)-, methyl 2-[methyl(phenylmethyl)amino]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
    2-(benzylmethylamino)ethyl methyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)pyridine-3,5-dicarboxylate
    https://echa.europa.eu/substance-information/-/substanceinfo/100.054.466
    2-(benzylmethylamino)ethyl methyl 1,4-dihydro-2,6-dimethyl-4-(m-nitrophenyl)pyridine-3,5-dicarboxylate (EC: 259-932-3)
    https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/47790
  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. 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
  9. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  10. ChEBI
  11. 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
  12. LiverTox
  13. 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
  14. Open Targets
    LICENSE
    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  15. 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
  16. 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
  17. DailyMed
  18. 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
  19. IUPHAR/BPS Guide to PHARMACOLOGY
    LICENSE
    The Guide to PHARMACOLOGY database is licensed under the Open Data Commons Open Database License (ODbL) https://opendatacommons.org/licenses/odbl/. Its contents are licensed under a Creative Commons Attribution-ShareAlike 4.0 International License (http://creativecommons.org/licenses/by-sa/4.0/)
    https://www.guidetopharmacology.org/about.jsp#license
    Guide to Pharmacology Target Classification
    https://www.guidetopharmacology.org/targets.jsp
  20. Drug Induced Liver Injury Rank (DILIrank) Dataset
    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
  21. 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/
    Nicardipine
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  22. Drugs and Lactation Database (LactMed)
  23. 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
  24. EU Clinical Trials Register
  25. 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
  26. 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
  27. 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
  28. MassBank Europe
  29. 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
  30. Metabolomics Workbench
  31. Natural Product Activity and Species Source (NPASS)
  32. NIPH Clinical Trials Search of Japan
  33. SpectraBase
    NICARDIPINE;2,6-DIMETHYL-3-METHOXYCARBONYL-5-(N-METHYL-N-PHENYLMETHYL)-AMINOETHOXYCARBONYL-4-(3-NITROPHENYL)-1,4-DIHYDROPYRIDINE
    https://spectrabase.com/spectrum/LjoOrUsJkV7
    NICARDIPINE;2,6-DIMETHYL-3-METHOXYCARBONYL-5-(N-METHYL-N-PHENYLMETHYL)-AMINOETHOXYCARBONYL-4-(3-NITROPHENYL)-1,4-DIHYDROPYRIDINE
    https://spectrabase.com/spectrum/63O4I5pAwsh
  34. 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
  35. 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/
  36. Therapeutic Target Database (TTD)
  37. 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
  38. 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
  39. Springer Nature
  40. 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/
  41. Wikidata
  42. Wikipedia
  43. Wiley
  44. 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
  45. PubChem
  46. GHS Classification (UNECE)
  47. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  48. PATENTSCOPE (WIPO)
  49. NCBI
CONTENTS