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
Thumb
Synonyms
  • 1-(4-Butoxyphenyl)-3-(1-piperidinyl)-1-propanone
  • 2-(1-Piperidyl)ethyl P-butoxyphenyl ketone
  • 3-Piperidino-4'-butoxypropiophenone
  • 4-Butoxy-beta-piperidinopropiophenone
  • 4-N-Butoxy-beta-(1-piperidyl)propiophenone
  • 4'-Butoxy-3-piperidinopropiophenone
  • Diclonina
  • Dyclocaine
  • Dyclonin
  • Dyclonine
  • Dycloninum
Product Ingredients
IngredientUNIICASInChI Key
Dyclonine hydrochlorideZEC193879Q536-43-6KNZADIMHVBBPOA-UHFFFAOYSA-N
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Cepacol Sore Throat SpraySpray0.1 %OralReckitt Benckiser1999-07-012012-03-23Canada
PerioRinseRinse0.1 g/100mLDental; Oral; Topical; TransmucosalCentura Pharmaceuticals, Inc2016-06-16Not applicableUs
Sore Throat ReliefLozenge3 mgOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.Not applicableNot applicableCanada
Sucrets Black CherryLozenge3 mg/1OralInsight Pharmaceuticals2009-06-182017-08-31Us
Sucrets Childrens CherryLozenge1.2 mg/1OralInsight Pharmaceuticals2009-07-282017-08-31Us
Sucrets Extra Strength Mint Flav.loz 3mgLozenge3 mgOralSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.1994-12-311998-08-25Canada
Sucrets for KidsLozenge1.2 mgOralInsight Pharmaceuticals1997-08-15Not applicableCanada
Sucrets for KidsLozenge1.2 mgOralSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.1992-12-311998-08-25Canada
Sucrets MS WintergreenLozenge3 mg/1OralInsight Pharmaceuticals2009-07-282017-08-31Us
Sucrets Regular Strength Lemon Flav.loz 2mgLozenge2 mgOralSmithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc.1994-12-311998-08-25Canada
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing End
Ambix First AidDyclonine hydrochloride (0.005 g/1g) + Phenol (0.005 g/1g)CreamTopicalSuite K Value Added Services LLC2013-08-192013-08-20Us
Ambix First AidDyclonine hydrochloride (0.005 g/1g) + Phenol (0.005 g/1g)CreamTopicalOrganics Corporation Of America Dba Ambix Laboratories2013-08-22Not applicableUs
Benzethonium chloride and Dyclonine hydrochlorideDyclonine hydrochloride (0.23 mg/29.6mL) + Benzethonium chloride (0.06 mg/29.6mL)LiquidTopicalWalgreen2012-01-12Not applicableUs
Benzethonium chloride Plus Dyclonine hydrochlorideDyclonine hydrochloride (0.75 mg/9mL) + Benzethonium chloride (0.20 mg/9mL)LiquidTopicalHarris Teeter2014-07-10Not applicableUs
Benzethonium chloride Plus Dyclonine hydrochlorideDyclonine hydrochloride (0.75 mg/10mL) + Benzethonium chloride (0.20 mg/10mL)LiquidTopicalCVS Health2014-07-10Not applicableUs
Benzethonium chloride Plus Dyclonine hydrochlorideDyclonine hydrochloride (0.75 mg/9mL) + Benzethonium chloride (0.20 mg/9mL)LiquidTopicalKroger2017-12-06Not applicableUs
Benzethonium chloride Plus Dyclonine hydrochlorideDyclonine hydrochloride (0.75 mg/9mL) + Benzethonium chloride (0.2 mg/9mL)LiquidTopicalChain Drug Consortium2005-12-07Not applicableUs
Benzethonium chloride Plus Dyclonine hydrochlorideDyclonine hydrochloride (0.75 mg/9mL) + Benzethonium chloride (0.20 mg/9mL)LiquidTopicalPremier Brands Of America Inc2018-01-03Not applicableUs
Benzethonium chloride Plus Dyclonine hydrochlorideDyclonine hydrochloride (0.75 mg/9mL) + Benzethonium chloride (0.20 mg/9mL)LiquidTopicalL. Perrigo Company2017-12-20Not applicableUs
Benzethonium chloride Plus Dyclonine hydrochlorideDyclonine hydrochloride (0.75 mg/9mL) + Benzethonium chloride (0.20 mg/9mL)LiquidTopicalRite Aid2017-12-22Not applicableUs
International/Other Brands
Dyclone (AstraZeneca) / Sucrets (Insight Pharmaceuticals)
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.

TargetActionsOrganism
ASodium channel protein type 10 subunit alpha
inhibitor
Human
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
DrugInteraction
7-NitroindazoleThe risk or severity of adverse effects can be increased when Dyclonine is combined with 7-Nitroindazole.
AcepromazineThe risk or severity of adverse effects can be increased when Dyclonine is combined with Acepromazine.
AceprometazineThe risk or severity of adverse effects can be increased when Dyclonine is combined with Aceprometazine.
AdipiplonThe risk or severity of adverse effects can be increased when Dyclonine is combined with Adipiplon.
AgomelatineThe risk or severity of adverse effects can be increased when Dyclonine is combined with Agomelatine.
AlaproclateThe risk or severity of adverse effects can be increased when Dyclonine is combined with Alaproclate.
AlfaxaloneThe risk or severity of adverse effects can be increased when Dyclonine is combined with Alfaxalone.
AlfentanilThe risk or severity of adverse effects can be increased when Alfentanil is combined with Dyclonine.
AlimemazineThe risk or severity of adverse effects can be increased when Dyclonine is combined with Alimemazine.
AllopregnanoloneThe risk or severity of adverse effects can be increased when Dyclonine is combined with Allopregnanolone.
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
ChEBI
4724
ChEMBL
CHEMBL1201217
Therapeutic Targets Database
DAP000509
PharmGKB
PA164748037
Drugs.com
Drugs.com Drug Page
Wikipedia
Dyclonine
ATC Codes
N01BX02 — DyclonineR02AD04 — Dyclonine
AHFS Codes
  • 52:16.00 — Local Anesthetics
MSDS
Download (73.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2CompletedTreatmentGingival Inflammation1

Pharmacoeconomics

Manufacturers
  • Astrazeneca lp
Packagers
  • Gallipot
  • Long Wing International Inc.
Dosage forms
FormRouteStrength
CreamTopical
LiquidOral
SprayOral0.1 %
RinseDental; Oral; Topical; Transmucosal0.1 g/100mL
PatchTopical
LiquidTopical
LozengeOral3 mg/1
LozengeOral1.2 mg/1
LozengeOral
LozengeOral1.2 mg
LozengeOral2 mg
LozengeOral3 mg
AerosolOral.1 %
LozengeOral2 mg/1
GelTopical
Prices
Unit descriptionCostUnit
Dyclonine hcl powder4.9USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
PropertyValueSource
melting point (°C)174-175Bockstahler, 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 solubilitySoluble (HCl salt)Not Available
logP3.7Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.046 mg/mLALOGPS
logP4.11ALOGPS
logP3.68ChemAxon
logS-3.8ALOGPS
pKa (Strongest Acidic)15.88ChemAxon
pKa (Strongest Basic)8.36ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count0ChemAxon
Polar Surface Area29.54 Å2ChemAxon
Rotatable Bond Count8ChemAxon
Refractivity87.07 m3·mol-1ChemAxon
Polarizability35.14 Å3ChemAxon
Number of Rings2ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.9856
Caco-2 permeable+0.7155
P-glycoprotein substrateSubstrate0.7596
P-glycoprotein inhibitor IInhibitor0.8077
P-glycoprotein inhibitor IINon-inhibitor0.6392
Renal organic cation transporterInhibitor0.7801
CYP450 2C9 substrateNon-substrate0.8107
CYP450 2D6 substrateNon-substrate0.5142
CYP450 3A4 substrateSubstrate0.5313
CYP450 1A2 substrateInhibitor0.8914
CYP450 2C9 inhibitorInhibitor0.793
CYP450 2D6 inhibitorInhibitor0.8932
CYP450 2C19 inhibitorNon-inhibitor0.9026
CYP450 3A4 inhibitorNon-inhibitor0.8574
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.5388
Ames testNon AMES toxic0.7961
CarcinogenicityNon-carcinogens0.8823
BiodegradationNot ready biodegradable0.7106
Rat acute toxicity2.3661 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Strong inhibitor0.8071
hERG inhibition (predictor II)Inhibitor0.6351
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot 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

Kind
Protein
Organism
Human
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
  1. 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]
  2. 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]
  3. 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]
  4. 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 September 22, 2018 22:25