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.

Structure

Similar Structures

Synonyms

1-(4-Butoxyphenyl)-3-(1-piperidinyl)-1-propanone
2-(1-piperidyl)ethyl p-butoxyphenyl ketone
3-piperidino-4'-butoxypropiophenone
4-butoxy-β-piperidinopropiophenone
4-n-butoxy-β-(1-piperidyl)propiophenone
4'-butoxy-3-piperidinopropiophenone
Diclonina
Dyclocaine
Dyclonin
Dyclonine
Dycloninum

Product Ingredients

Ingredient	UNII	CAS	InChI Key
Dyclonine hydrochloride	ZEC193879Q	536-43-6	KNZADIMHVBBPOA-UHFFFAOYSA-N

Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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DycloPro	Solution	5 mg/1mL	Topical	Septodont Inc	2019-09-01	Not applicable
DycloPro	Solution	10 mg/1mL	Topical	Septodont Inc	2019-09-01	Not applicable

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Over the Counter Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Cepacol Sore Throat Spray	Spray		Oral	Reckitt Benckiser	1999-07-01	2012-03-23
PerioRinse	Rinse	0.1 g/100mL	Dental; Oral; Topical; Transmucosal	Centura Pharmaceuticals, Inc	2016-06-16	Not applicable
Sore Throat Relief	Lozenge	3 mg	Oral	Stanley Pharmaceuticals, A Division Of Vita Health Products Inc.	Not applicable	Not applicable
Sucrets Black Cherry	Lozenge	3 mg/1	Oral	Insight Pharmaceuticals	2009-06-18	2017-08-31
Sucrets Childrens Cherry	Lozenge	1.2 mg/1	Oral	Insight Pharmaceuticals	2009-07-28	2017-08-31
Sucrets Extra Strength Mint Flav.loz 3mg	Lozenge		Oral	Smithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.	1994-12-31	1998-08-25
Sucrets for Kids	Lozenge		Oral	Insight Pharmaceuticals LLC	1997-08-15	Not applicable
Sucrets for Kids	Lozenge		Oral	Smithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.	1992-12-31	1998-08-25
Sucrets MS Wintergreen	Lozenge	3 mg/1	Oral	Insight Pharmaceuticals	2009-07-28	2017-08-31
Sucrets Regular Strength Lemon Flav.loz 2mg	Lozenge		Oral	Smithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.	1994-12-31	1998-08-25

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Mixture Products

Name	Ingredients	Dosage	Route	Labeller	Marketing Start	Marketing End
Ambix First Aid	Dyclonine hydrochloride (0.005 g/1g) + Phenol (0.005 g/1g)	Cream	Topical	Organics Corporation Of America Dba Ambix Laboratories	2013-08-22	Not applicable
Ambix First Aid	Dyclonine hydrochloride (0.005 g/1g) + Phenol (0.005 g/1g)	Cream	Topical	Suite K Value Added Services LLC	2013-08-19	2013-08-20
Benzethonium chloride and Dyclonine hydrochloride	Dyclonine hydrochloride (0.23 mg/29.6mL) + Benzethonium chloride (0.06 mg/29.6mL)	Liquid	Topical	Walgreen Company	2012-01-12	Not applicable
Benzethonium Chloride and Dyclonine Hydrochloride	Dyclonine hydrochloride (0.75 mg/10mL) + Benzethonium chloride (0.2 mg/10mL)	Liquid	Topical	CVS PHARMACY	2019-06-01	Not applicable
Benzethonium chloride Plus Dyclonine hydrochloride	Dyclonine hydrochloride (0.75 mg/10mL) + Benzethonium chloride (0.2 mg/10mL)	Liquid	Topical	CVS PHARMACY	2014-07-10	Not applicable
Benzethonium chloride Plus Dyclonine hydrochloride	Dyclonine hydrochloride (0.75 mg/9mL) + Benzethonium chloride (0.2 mg/9mL)	Liquid	Topical	Kroger Co.	2017-12-06	Not applicable
Benzethonium chloride Plus Dyclonine hydrochloride	Dyclonine hydrochloride (0.75 mg/9mL) + Benzethonium chloride (0.2 mg/9mL)	Liquid	Topical	HEB	2017-12-22	Not applicable
Benzethonium chloride Plus Dyclonine hydrochloride	Dyclonine hydrochloride (0.75 mg/9mL) + Benzethonium chloride (0.2 mg/9mL)	Liquid	Topical	Foodhold Usa	2017-12-19	Not applicable
Benzethonium chloride Plus Dyclonine hydrochloride	Dyclonine hydrochloride (0.75 mg/10mL) + Benzethonium chloride (0.2 mg/10mL)	Liquid	Topical	Harmon Store Inc.	2012-02-14	Not applicable
Benzethonium chloride Plus Dyclonine hydrochloride	Dyclonine hydrochloride (0.75 mg/10mL) + Benzethonium chloride (0.2 mg/10mL)	Liquid	Topical	Meijer Distribution Inc	2012-01-05	Not applicable

International/Other Brands

Dyclone (AstraZeneca)

Categories

UNII

078A24Q30O

CAS number

586-60-7

Weight

Average: 289.4125
Monoisotopic: 289.204179113

Chemical Formula

C₁₈H₂₇NO₂

InChI Key

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

IUPAC Name

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

SMILES

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

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.

Associated Conditions

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.

Target	Actions	Organism
ASodium channel protein type 10 subunit alpha	inhibitor	Humans

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Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available

Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Additional Data Available

Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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

Pharmacogenomic Effects/ADRs

Not Available

Interactions

Drug Interactions

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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2,5-Dimethoxy-4-ethylthioamphetamine	The risk or severity of adverse effects can be increased when Dyclonine is combined with 2,5-Dimethoxy-4-ethylthioamphetamine.
4-Bromo-2,5-dimethoxyamphetamine	The risk or severity of adverse effects can be increased when Dyclonine is combined with 4-Bromo-2,5-dimethoxyamphetamine.
4-Methoxyamphetamine	The risk or severity of adverse effects can be increased when Dyclonine is combined with 4-Methoxyamphetamine.
5-methoxy-N,N-dimethyltryptamine	The risk or severity of adverse effects can be increased when Dyclonine is combined with 5-methoxy-N,N-dimethyltryptamine.
7-Nitroindazole	The risk or severity of adverse effects can be increased when Dyclonine is combined with 7-Nitroindazole.
7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline	The risk or severity of adverse effects can be increased when Dyclonine is combined with 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline.
Acepromazine	The risk or severity of adverse effects can be increased when Dyclonine is combined with Acepromazine.
Aceprometazine	The risk or severity of adverse effects can be increased when Dyclonine is combined with Aceprometazine.
Acetazolamide	The risk or severity of adverse effects can be increased when Dyclonine is combined with Acetazolamide.
Acetophenazine	The risk or severity of adverse effects can be increased when Dyclonine is combined with Acetophenazine.

Additional Data Available

Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

An effect category for each drug interaction. Know how this interaction affects the subject drug.

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Food Interactions

Not Available

References

Synthesis Reference

Tianjiang Sun, Xiaohong Gu, Hongguo Lu, Min Chen, "Oral Preparation of Dyclonine Hydrochloride." U.S. Patent US20080200506, issued August 21, 2008.

US20080200506

General References

Not Available

External Links

Human Metabolome Database: HMDB0014783
KEGG Compound: C07881
PubChem Compound: 3180
PubChem Substance: 46506697
ChemSpider: 3068
BindingDB: 50240047
ChEBI: 4724
ChEMBL: CHEMBL1201217
ZINC: ZINC000001530940
Therapeutic Targets Database: DAP000509
PharmGKB: PA164748037
Drugs.com: Drugs.com Drug Page
Wikipedia: Dyclonine

ATC Codes

N01BX02 — Dyclonine

R02AD04 — Dyclonine

AHFS Codes

52:16.00 — Local Anesthetics

MSDS

Download (73.4 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
1, 2	Completed	Treatment	Gingivitis	1

Pharmacoeconomics

Manufacturers

Astrazeneca lp

Packagers

Gallipot
Long Wing International Inc.

Dosage forms

Form	Route	Strength
Cream	Topical
Liquid	Oral
Spray	Oral
Solution	Topical	10 mg/1mL
Solution	Topical	5 mg/1mL
Rinse	Dental; Oral; Topical; Transmucosal	0.1 g/100mL
Patch	Topical
Liquid	Topical
Lozenge	Oral	3 mg
Lozenge	Oral	3 mg/1
Lozenge	Oral	1.2 mg/1
Lozenge	Oral
Lozenge	Oral
Aerosol	Oral
Lozenge	Oral	2 mg/1
Gel	Topical

Prices

Unit description	Cost	Unit
Dyclonine hcl powder	4.9USD	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
melting point (°C)	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.
water solubility	Soluble (HCl salt)	Not Available
logP	3.7	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.046 mg/mL	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 Å²	ChemAxon
Rotatable Bond Count	8	ChemAxon
Refractivity	87.07 m³·mol^-1	ChemAxon
Polarizability	35.14 Å³	ChemAxon
Number of Rings	2	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted ADMET features

Property	Value	Probability
Human Intestinal Absorption	+	1.0
Blood Brain Barrier	+	0.9856
Caco-2 permeable	+	0.7155
P-glycoprotein substrate	Substrate	0.7596
P-glycoprotein inhibitor I	Inhibitor	0.8077
P-glycoprotein inhibitor II	Non-inhibitor	0.6392
Renal organic cation transporter	Inhibitor	0.7801
CYP450 2C9 substrate	Non-substrate	0.8107
CYP450 2D6 substrate	Non-substrate	0.5142
CYP450 3A4 substrate	Substrate	0.5313
CYP450 1A2 substrate	Inhibitor	0.8914
CYP450 2C9 inhibitor	Inhibitor	0.793
CYP450 2D6 inhibitor	Inhibitor	0.8932
CYP450 2C19 inhibitor	Non-inhibitor	0.9026
CYP450 3A4 inhibitor	Non-inhibitor	0.8574
CYP450 inhibitory promiscuity	Low CYP Inhibitory Promiscuity	0.5388
Ames test	Non AMES toxic	0.7961
Carcinogenicity	Non-carcinogens	0.8823
Biodegradation	Not ready biodegradable	0.7106
Rat acute toxicity	2.3661 LD50, mol/kg	Not applicable
hERG inhibition (predictor I)	Strong inhibitor	0.8071
hERG inhibition (predictor II)	Inhibitor	0.6351

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available

Taxonomy

Description: This compound belongs to the class of organic compounds known as alkyl-phenylketones. These are aromatic compounds containing a ketone substituted by one alkyl group, and a phenyl group.
Kingdom: Organic compounds
Super Class: Organic oxygen compounds
Class: Organooxygen compounds
Sub Class: Carbonyl compounds
Direct Parent: Alkyl-phenylketones
Alternative Parents: Phenoxy compounds / Phenol ethers / Benzoyl derivatives / Aryl alkyl ketones / Alkyl aryl ethers / Piperidines / Beta-amino ketones / Trialkylamines / Azacyclic compounds / Organopnictogen compounds
show 2 more
Substituents: Alkyl-phenylketone / Phenoxy compound / Benzoyl / Phenol ether / Aryl alkyl ketone / Alkyl aryl ether / Monocyclic benzene moiety / Beta-aminoketone / Piperidine / Benzenoid
show 12 more
Molecular Framework: Aromatic heteromonocyclic compounds
External Descriptors: piperidines, aromatic ketone (CHEBI:4724)

Targets

Details1. Sodium channel protein type 10 subunit alpha

Kind: Protein
Organism: Humans
Pharmacological action: Yes
Actions: Inhibitor

General Function: Voltage-gated sodium channel activity
Specific Function: Tetrodotoxin-resistant channel that mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference acro...
Gene Name: SCN10A
Uniprot ID: Q9Y5Y9
Uniprot Name: Sodium channel protein type 10 subunit alpha
Molecular Weight: 220623.605 Da

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:17139284]
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:17016423]
Roghani S, Duperon DF, Barcohana N: Evaluating the efficacy of commonly used topical anesthetics. Pediatr Dent. 1999 May-Jun;21(3):197-200. [PubMed:10355012]
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:9476974]

Drug created on June 13, 2005 07:24 / Updated on February 20, 2020 17:09

Dyclonine

Identification

Structure for Dyclonine (DB00645)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References