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Identification
NameDyclonine
Accession NumberDB00645  (APRD00940)
TypeSmall Molecule
GroupsApproved
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
SynonymLanguageCode
1-(4-Butoxyphenyl)-3-(1-piperidinyl)-1-propanoneNot AvailableNot Available
2-(1-Piperidyl)ethyl P-butoxyphenyl ketoneNot AvailableNot Available
3-Piperidino-4'-butoxypropiophenoneNot AvailableNot Available
4-Butoxy-beta-piperidinopropiophenoneNot AvailableNot Available
4-N-Butoxy-beta-(1-piperidyl)propiophenoneNot AvailableNot Available
4'-Butoxy-3-piperidinopropiophenoneNot AvailableNot Available
DicloninaSpanishINN
DyclocaineNot AvailableIS
DycloninGermanINN
DyclonineFrenchINN
DycloninumLatinINN
Prescription ProductsNot Available
Generic Prescription ProductsNot Available
Over the Counter ProductsNot Available
International Brands
NameCompany
DycloneAstraZeneca
SucretsInsight Pharmaceuticals
Brand mixtures
Brand NameIngredients
Skin Shield Liquid BandageAlcohol Anhydrous + Benzethonium Chloride + Dyclonine Hydrochloride
Tanac Medicated GelAllantoin + Dyclonine Hydrochloride
Salts
Name/CASStructureProperties
Dyclonine hydrochloride
Thumb
  • InChI Key: KNZADIMHVBBPOA-UHFFFAOYSA-N
  • Monoisotopic Mass: 325.180856852
  • Average Mass: 325.873
DBSALT000651
Categories
CAS number586-60-7
WeightAverage: 289.4125
Monoisotopic: 289.204179113
Chemical FormulaC18H27NO2
InChI KeyBZEWSEKUUPWQDQ-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
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as phenylpropylamines. These are compounds containing a phenylpropylamine moiety, which consists of a phenyl group substituted at the third carbon by an propan-1-amine.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassPhenylpropylamines
Direct ParentPhenylpropylamines
Alternative Parents
Substituents
  • Phenylpropylamine
  • Acetophenone
  • Aryl alkyl ketone
  • Aryl ketone
  • Phenol ether
  • Benzoyl
  • Alkyl aryl ether
  • Piperidine
  • Beta-aminoketone
  • Tertiary aliphatic amine
  • Tertiary amine
  • Ketone
  • Azacycle
  • Organoheterocyclic compound
  • Ether
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External Descriptors
Pharmacology
IndicationUsed 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.
PharmacodynamicsDyclonine 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 actionLocal 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.
AbsorptionReadily 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 distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeApproximately 30 to 60 minutes.
ClearanceNot Available
ToxicitySymptoms of overdose include cardiovascular system depression, CNS toxicity, and methemoglobinemia.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 substrateInhibitor0.793
CYP450 2D6 substrateInhibitor0.8932
CYP450 2C19 substrateNon-inhibitor0.9026
CYP450 3A4 substrateNon-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
Pharmacoeconomics
Manufacturers
  • Astrazeneca lp
Packagers
Dosage formsNot Available
Prices
Unit descriptionCostUnit
Dyclonine hcl powder4.9USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateSolid
Experimental Properties
PropertyValueSource
melting point174-175Bockstahler, 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 RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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 ReferenceNot Available
External Links
ATC CodesN01BX02R02AD04
AHFS Codes
  • 52:16.00
PDB EntriesNot Available
FDA labelNot Available
MSDSDownload (73.4 KB)
Interactions
Drug InteractionsNo interactions found.
Food InteractionsNot Available

Targets

1. Sodium channel protein type 10 subunit alpha

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium channel protein type 10 subunit alpha Q9Y5Y9 Details

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
  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
  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
  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

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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:11