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Dyclonine

PubChem CID
3180
Structure
Dyclonine_small.png
Dyclonine_3D_Structure.png
Molecular Formula
Synonyms
  • dyclonine
  • Dyclocaine
  • 586-60-7
  • Dyclonin
  • Diclonina
Molecular Weight
289.4 g/mol
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Dates
  • Create:
    2005-03-25
  • Modify:
    2025-01-11
Description
Dyclonine is n-Ethylpiperidine in which one of the hydrogens attached to the methyl group is substituted by a 4-butoxybenzoyl group. It has a role as a topical anaesthetic. It is a member of piperidines and an aromatic ketone.
Dyclonine is an oral anaesthetic found in Sucrets, an over the counter throat lozenge. It may also be found in some Cepacol sore throat spray products.
Dyclonine is an unclassified compound with local anesthetic effect. Dyclonine reversibly binds to activated sodium channels on the neuronal membrane, thereby decreasing the neuronal membrane's permeability to sodium ions, leading to an increased threshold for excitation. This reversibly stabilizes the membrane and inhibits depolarization, leading to the failure of a propagated action potential and subsequent conduction blockade. This results in a transient and reversible loss of sensation in a localized area of the body.

1 Structures

1.1 2D Structure

Chemical Structure Depiction
Dyclonine.png

1.2 3D Conformer

2 Names and Identifiers

2.1 Computed Descriptors

2.1.1 IUPAC Name

1-(4-butoxyphenyl)-3-piperidin-1-ylpropan-1-one
Computed by Lexichem TK 2.7.0 (PubChem release 2021.10.14)

2.1.2 InChI

InChI=1S/C18H27NO2/c1-2-3-15-21-17-9-7-16(8-10-17)18(20)11-14-19-12-5-4-6-13-19/h7-10H,2-6,11-15H2,1H3
Computed by InChI 1.0.6 (PubChem release 2021.10.14)

2.1.3 InChIKey

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

2.1.4 SMILES

CCCCOC1=CC=C(C=C1)C(=O)CCN2CCCCC2
Computed by OEChem 2.3.0 (PubChem release 2024.12.12)

2.2 Molecular Formula

C18H27NO2
Computed by PubChem 2.2 (PubChem release 2021.10.14)

2.3 Other Identifiers

2.3.1 CAS

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 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

  • Dyclone
  • dyclonine
  • dyclonine HCl
  • dyclonine hydrochloride
  • Sucrets
  • Tanac

2.4.2 Depositor-Supplied Synonyms

3 Chemical and Physical Properties

3.1 Computed Properties

Property Name
Molecular Weight
Property Value
289.4 g/mol
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
XLogP3-AA
Property Value
3.6
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
3
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
289.204179104 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Monoisotopic Mass
Property Value
289.204179104 Da
Reference
Computed by PubChem 2.2 (PubChem release 2021.10.14)
Property Name
Topological Polar Surface Area
Property Value
29.5 Ų
Reference
Computed by Cactvs 3.4.8.18 (PubChem release 2021.10.14)
Property Name
Heavy Atom Count
Property Value
21
Reference
Computed by PubChem
Property Name
Formal Charge
Property Value
0
Reference
Computed by PubChem
Property Name
Complexity
Property Value
292
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 Physical Description

Solid

3.2.2 Melting Point

174-175
Bockstahler, E.R.; U.S.Patent 2,771,391; November 20,1956; assigned to Allied Laboratories, Inc. Florestano, H.J., Jeffries, S.F., Osborne, C.E. and Bahler, M.E.; U.S. Patent 2,868,689; January 13, 1959; assigned to Allied Laboratories, Inc.

3.2.3 Solubility

Soluble (HCl salt)
4.60e-02 g/L

3.2.4 LogP

3.7
3.7

3.2.5 Dissociation Constants

Basic pKa
9
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

3.2.6 Collision Cross Section

178.11 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

Pharmaceuticals -> Listed in ZINC15
S55 | ZINC15PHARMA | Pharmaceuticals from ZINC15 | DOI:10.5281/zenodo.3247749
3.3.1.1 Human Drugs
Breast Feeding; Lactation; Anesthetics, Local
Pharmaceuticals
S72 | NTUPHTW | Pharmaceutically Active Substances from National Taiwan University | DOI:10.5281/zenodo.3955664

3.3.2 Endocrine Disruptors

Potential endocrine disrupting compound
S109 | PARCEDC | List of 7074 potential endocrine disrupting compounds (EDCs) by PARC T4.2 | DOI:10.5281/zenodo.10944198

4 Spectral Information

4.1 Mass Spectrometry

4.1.1 GC-MS

1 of 6
View All
NIST Number
65070
Library
Main library
Total Peaks
57
m/z Top Peak
121
m/z 2nd Highest
204
m/z 3rd Highest
148
Thumbnail
Thumbnail
2 of 6
View All
NIST Number
335340
Library
Replicate library
Total Peaks
55
m/z Top Peak
121
m/z 2nd Highest
148
m/z 3rd Highest
204
Thumbnail
Thumbnail

4.2 UV Spectra

4.2.1 UV-VIS Spectra

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

4.3 IR Spectra

4.3.1 FTIR Spectra

Technique
KBr WAFER
Source of Sample
The Dow Chemical Company
Copyright
Copyright © 1980, 1981-2024 John Wiley & Sons, Inc. All Rights Reserved.
Thumbnail
Thumbnail

6 Chemical Vendors

7 Drug and Medication Information

7.1 Drug Indication

Used to provide topical anesthesia of accessible mucous membranes prior to examination, endoscopy or instrumentation, or other procedures involving the esophagus, larynx, mouth, pharynx or throat, respiratory tract or trachea, urinary tract, or vagina. Also used to suppress the gag reflex and/or other laryngeal and esophageal reflexes to facilitate dental examination or procedures (including oral surgery), endoscopy, or intubation. Also used for relief of canker sores, cold sores or fever blister.

7.2 Drug Classes

Breast Feeding; Lactation; Anesthetics, Local

8 Pharmacology and Biochemistry

8.1 Pharmacodynamics

Dyclonine is an oral anasthetic. If substantial quantities of local anesthetics are absorbed through the mucosa, actions on the central nervous system (CNS) may cause CNS stimulation and/or CNS depression. Actions on the cardiovascular system may cause depression of cardiac conduction and excitability and, with some of these agents, peripheral vasodilation.

8.2 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.)

8.3 ATC Code

N - Nervous system

N01 - Anesthetics

N01B - Anesthetics, local

N01BX - Other local anesthetics

N01BX02 - Dyclonine

R - Respiratory system

R02 - Throat preparations

R02A - Throat preparations

R02AD - Anesthetics, local

R02AD04 - Dyclonine

8.4 Absorption, Distribution and Excretion

Absorption
Readily absorbed through mucous membranes into the systemic circulation. The rate of absorption is influenced by the vascularity or rate of blood flow at the site of application, the total dosage (concentration and volume) administered, and the duration of exposure. Absorption from mucous membranes of the throat or respiratory tract may be especially rapid.

8.5 Biological Half-Life

Approximately 30 to 60 minutes.

8.6 Mechanism of Action

Local anesthetics block both the initiation and conduction of nerve impulses by decreasing the neuronal membrane's permeability to sodium ions. This reversibly stabilizes the membrane and inhibits depolarization, resulting in the failure of a propagated action potential and subsequent conduction blockade.

8.7 Human Metabolite Information

8.7.1 Cellular Locations

  • Extracellular
  • Membrane

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 Toxicity

10.1 Toxicological Information

10.1.1 Effects During Pregnancy and Lactation

◉ Summary of Use during Lactation

No information is available on the use of dyclonine during breastfeeding. Topical dyclonine products should be wiped off thoroughly prior to nursing if they are applied to the breast or nipple area. Topical dyclonine is relatively safe, but allergic contact dermatitis has been reported following dyclonine use, so it is best kept away from the infant’s skin.

◉ 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.

10.1.2 Acute Effects

11 Associated Disorders and Diseases

12 Literature

12.1 Consolidated References

12.2 NLM Curated PubMed Citations

12.3 Springer Nature References

12.4 Thieme References

12.5 Chemical Co-Occurrences in Literature

12.6 Chemical-Gene Co-Occurrences in Literature

12.7 Chemical-Disease Co-Occurrences in Literature

13 Patents

13.1 Depositor-Supplied Patent Identifiers

13.2 WIPO PATENTSCOPE

13.3 Chemical Co-Occurrences in Patents

13.4 Chemical-Disease Co-Occurrences in Patents

13.5 Chemical-Gene Co-Occurrences in Patents

14 Interactions and Pathways

14.1 Protein Bound 3D Structures

14.1.1 Ligands from Protein Bound 3D Structures

PDBe Ligand Code
PDBe Structure Code
PDBe Conformer

14.2 Chemical-Target Interactions

14.3 Drug-Drug Interactions

14.4 Drug-Food Interactions

Take separate from meals. Using Dyclonine in the mouth or for relief of ulcers in the stomach may cause numbness of the mouth, which increases the risk of biting injury. Avoid ingesting food for 60 minutes after use, or until the numbness has subsided.

15 Biological Test Results

15.1 BioAssay Results

16 Classification

16.1 MeSH Tree

16.2 NCI Thesaurus Tree

16.3 ChEBI Ontology

16.4 KEGG: ATC

16.5 KEGG: Drug Groups

16.6 WHO ATC Classification System

16.7 ChemIDplus

16.8 ChEMBL Target Tree

16.9 NORMAN Suspect List Exchange Classification

16.10 CCSBase Classification

16.11 EPA DSSTox Classification

16.12 MolGenie Organic Chemistry Ontology

17 Information Sources

  1. CAS Common Chemistry
    LICENSE
    The data from CAS Common Chemistry is provided under a CC-BY-NC 4.0 license, unless otherwise stated.
    https://creativecommons.org/licenses/by-nc/4.0/
  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. 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
  6. Human Metabolome Database (HMDB)
    LICENSE
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    http://www.hmdb.ca/citing
  7. CCSbase
    CCSbase Classification
    https://ccsbase.net/
  8. ChEBI
  9. 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
  10. Open Targets
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    Datasets generated by the Open Targets Platform are freely available for download.
    https://platform-docs.opentargets.org/licence
  11. 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
  12. 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
  13. 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
  14. Therapeutic Target Database (TTD)
  15. Drugs and Lactation Database (LactMed)
  16. 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/
    Dyclonine
    NORMAN Suspect List Exchange Classification
    https://www.norman-network.com/nds/SLE/
  17. Japan Chemical Substance Dictionary (Nikkaji)
  18. 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
  19. Metabolomics Workbench
  20. 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
  21. SpectraBase
    4'-butoxy-3-piperidinopropiophenone, hydrochloride
    https://spectrabase.com/spectrum/YgAhIR9jYA
  22. 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
  23. 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
  24. 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
  25. Protein Data Bank in Europe (PDBe)
  26. 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
  27. Springer Nature
  28. 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/
  29. WHO Anatomical Therapeutic Chemical (ATC) Classification
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    https://www.whocc.no/copyright_disclaimer/
  30. Wikidata
  31. Wikipedia
  32. PubChem
  33. Medical Subject Headings (MeSH)
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    https://www.nlm.nih.gov/copyright.html
  34. MolGenie
    MolGenie Organic Chemistry Ontology
    https://github.com/MolGenie/ontology/
  35. PATENTSCOPE (WIPO)
  36. NCBI
CONTENTS