DrugBank: Dyclonine (DB00645)

targets (1)

Identification

Name

Dyclonine

Accession Number

DB00645 (APRD00940)

Type

small molecule

Groups

approved

Description

Dyclonine is an oral anaesthetic found in Sucrets, an over the counter throat lozenge. It is also found in some varieties of the Cepacol sore throat spray.

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Not Available

Salts

Not Available

Brand names

Name	Company
Diclonia
Diclonina
Diclonina [INN-Spanish]
Dyclocaine
Dyclocainum
Dyclone
Dyclonin
Dyclonine HCL
Dyclonine hydrochloride
Dycloninum [INN-Latin]
Dyclothane
Tanaclone

Brand mixtures

Brand Name	Ingredients
Skin Shield Liquid Bandage	Alcohol Anhydrous + Benzethonium Chloride + Dyclonine Hydrochloride
Tanac Medicated Gel	Allantoin + Dyclonine Hydrochloride

Categories

Anesthetics, Local
Anesthetics, Mucosal-Local

CAS number

586-60-7

Weight

Average: 289.4125
Monoisotopic: 289.204179113

Chemical Formula

C₁₈H₂₇NO₂

InChI Key

InChIKey=BZEWSEKUUPWQDQ-UHFFFAOYSA-N

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

Plain Text

IUPAC Name

1-(4-butoxyphenyl)-3-(piperidin-1-yl)propan-1-one

SMILES

CCCCOC1=CC=C(C=C1)C(=O)CCN1CCCCC1

Plain Text

Mass Spec

Not Available

Taxonomy

Kingdom

Organic

Classes

Phenylpropylamines
Acetophenones and Derivatives

Substructures

Phenols and Derivatives
Ethers
Benzene and Derivatives
Aliphatic and Aryl Amines
Heterocyclic compounds
Aromatic compounds
Anisoles
Phenylpropylamines
Benzoyl Derivatives
Acetophenones and Derivatives
Phenyl Esters
Piperidines
Ketones

Pharmacology

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.

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.

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.

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.

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half life

Approximately 30 to 60 minutes.

Clearance

Not Available

Toxicity

Symptoms of overdose include cardiovascular system depression, CNS toxicity, and methemoglobinemia.

Affected organisms

Humans and other mammals

Pathways

Not Available

Pharmacoeconomics

Manufacturers

Astrazeneca lp

Packagers

Dosage forms

Form	Route	Strength
Lozenge	Oral
Spray	Oral

Prices

Unit description	Cost	Unit
Dyclonine hcl powder	4.9 USD	g

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

solid

Experimental Properties

Property	Value	Source
water solubility	Soluble (HCl salt)	Not Available
logP	3.7	Not Available

Predicted Properties

Property	Value	Source
water solubility	4.60e-02 g/l	ALOGPS
logP	4.11	ALOGPS
logP	3.68	ChemAxon
logS	-3.8	ALOGPS
pKa (strongest acidic)	15.88	ChemAxon
pKa (strongest basic)	8.36	ChemAxon
physiological charge	1	ChemAxon
hydrogen acceptor count	3	ChemAxon
hydrogen donor count	0	ChemAxon
polar surface area	29.54	ChemAxon
rotatable bond count	8	ChemAxon
refractivity	87.07	ChemAxon
polarizability	35.14	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Compound	C07881
PubChem Compound	3180
PubChem Substance	46506697
ChemSpider	3068
ChEBI	4724
ChEMBL	4724
Therapeutic Targets Database	DAP000509
PharmGKB	PA164748037
Drug Product Database	2238651
Drugs.com	http://www.drugs.com/cdi/dyclonine-lozenges.html
Wikipedia	http://en.wikipedia.org/wiki/Dyclonine

ATC Codes

N01BX02
R02AD04

AHFS Codes

52:16.00

PDB Entries

Not Available

FDA label

Not Available

MSDS

show (73.4 KB)

Interactions

Drug Interactions

Searched, but no interactions found.

Food Interactions

Not Available

Targets
1. Sodium channel protein type 10 subunit alpha Pharmacological action: yes Actions: inhibitor This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms Organism class: human UniProt ID: Q9Y5Y9 Gene: SCN10A Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed Roghani S, Duperon DF, Barcohana N: Evaluating the efficacy of commonly used topical anesthetics. Pediatr Dent. 1999 May-Jun;21(3):197-200. Pubmed Tella SR, Goldberg SR: Monoamine transporter and sodium channel mechanisms in the rapid pressor response to cocaine. Pharmacol Biochem Behav. 1998 Feb;59(2):305-12. Pubmed

Targets

1. Sodium channel protein type 10 subunit alpha

Pharmacological action: yes
Actions: inhibitor

This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms

Organism class: human
UniProt ID: Q9Y5Y9 Link_out

Gene: SCN10A Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
Roghani S, Duperon DF, Barcohana N: Evaluating the efficacy of commonly used topical anesthetics. Pediatr Dent. 1999 May-Jun;21(3):197-200. Pubmed
Tella SR, Goldberg SR: Monoamine transporter and sodium channel mechanisms in the rapid pressor response to cocaine. Pharmacol Biochem Behav. 1998 Feb;59(2):305-12. Pubmed

Comments

Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19