Dyclonine

Identification

Summary

Dyclonine is an topical anesthetic used prior to examination to suppress the gag reflex or for pain relief from canker sores and fever blisters.

Brand Names
Dyclopro, Sucrets
Generic Name
Dyclonine
DrugBank Accession Number
DB00645
Background

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.

Type
Small Molecule
Groups
Approved
Structure
Weight
Average: 289.4125
Monoisotopic: 289.204179113
Chemical Formula
C18H27NO2
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

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.

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Associated Conditions
Indication TypeIndicationCombined Product DetailsApproval LevelAge GroupPatient CharacteristicsDose Form
Symptomatic treatment ofCough••• •••
Symptomatic treatment ofMouth irritation••• •••
Symptomatic treatment ofSore throat••• •••
Contraindications & Blackbox Warnings
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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
Humans
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

Adverse Effects
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Toxicity

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

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.
DrugInteraction
1,2-BenzodiazepineThe risk or severity of CNS depression can be increased when Dyclonine is combined with 1,2-Benzodiazepine.
AbemaciclibThe risk or severity of methemoglobinemia can be increased when Abemaciclib is combined with Dyclonine.
AbirateroneThe risk or severity of methemoglobinemia can be increased when Abiraterone is combined with Dyclonine.
AcetaminophenThe risk or severity of methemoglobinemia can be increased when Acetaminophen is combined with Dyclonine.
AcetazolamideThe risk or severity of methemoglobinemia can be increased when Acetazolamide is combined with Dyclonine.
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.

Products

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Product Ingredients
IngredientUNIICASInChI Key
Dyclonine hydrochlorideZEC193879Q536-43-6KNZADIMHVBBPOA-UHFFFAOYSA-N
International/Other Brands
Dyclone (AstraZeneca)
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
DycloProSolution10 mg/1mLTopicalSeptodont Inc2019-09-01Not applicableUS flag
DycloProSolution5 mg/1mLTopicalSeptodont Inc2019-09-01Not applicableUS flag
Over the Counter Products
NameDosageStrengthRouteLabellerMarketing StartMarketing EndRegionImage
Cepacol Sore Throat SpraySpray0.1 % w/wOralReckitt Benckiser1999-07-012012-03-23Canada flag
PerioRinseRinse0.1 g/100mLDental; Oral; Topical; TransmucosalCENTURA PHARMACEUTICALS INC2016-06-162018-07-31US flag
Sore Throat ReliefLozenge3 mg / lozOralStanley Pharmaceuticals, A Division Of Vita Health Products Inc.Not applicableNot applicableCanada flag
Sucrets Black CherryLozenge3 mg/1OralInsight Pharmaceuticals2009-06-182017-08-31US flag
Sucrets Childrens CherryLozenge1.2 mg/1OralInsight Pharmaceuticals2009-07-282017-08-31US flag
Mixture Products
NameIngredientsDosageRouteLabellerMarketing StartMarketing EndRegionImage
Ambix First AidDyclonine hydrochloride (0.005 g/1g) + Phenol (0.005 g/1g)CreamTopicalOrganics Corporation Of America Dba Ambix Laboratories2013-08-22Not applicableUS flag
Ambix First AidDyclonine hydrochloride (0.005 g/1g) + Phenol (0.005 g/1g)CreamTopicalSuite K Value Added Services LLC2013-08-192013-08-20US flag
Benzethonium chloride and Dyclonine hydrochlorideDyclonine hydrochloride (0.23 mg/29.6mL) + Benzethonium chloride (0.06 mg/29.6mL)LiquidTopicalWalgreen Company2012-01-12Not applicableUS flag
Benzethonium Chloride and Dyclonine HydrochlorideDyclonine hydrochloride (0.75 mg/30mL) + Benzethonium chloride (0.2 mg/30mL)LiquidTopicalRite Aid Corporation2020-02-01Not applicableUS flag
Benzethonium Chloride and Dyclonine HydrochlorideDyclonine hydrochloride (0.75 mg/10mL) + Benzethonium chloride (0.2 mg/10mL)LiquidTopicalCVS PHARMACY2019-06-01Not applicableUS flag

Categories

ATC Codes
N01BX02 — DyclonineR02AD04 — Dyclonine
Drug Categories
Chemical TaxonomyProvided by Classyfire
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 aryl ether / Alkyl-phenylketone / Amine / Aromatic heteromonocyclic compound / Aryl alkyl ketone / Azacycle / Benzenoid / Benzoyl / Beta-aminoketone / Ether
show 12 more
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
piperidines, aromatic ketone (CHEBI:4724)
Affected organisms
  • Humans and other mammals

Chemical Identifiers

UNII
078A24Q30O
CAS number
586-60-7
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

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
Human Metabolome Database
HMDB0014783
KEGG Compound
C07881
PubChem Compound
3180
PubChem Substance
46506697
ChemSpider
3068
BindingDB
50240047
RxNav
23744
ChEBI
4724
ChEMBL
CHEMBL1201217
ZINC
ZINC000001530940
Therapeutic Targets Database
DAP000509
PharmGKB
PA164748037
PDBe Ligand
N8R
Drugs.com
Drugs.com Drug Page
Wikipedia
Dyclonine
PDB Entries
7ugg
MSDS
Download (73.4 KB)

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount
1, 2CompletedTreatmentGingivitis1

Pharmacoeconomics

Manufacturers
  • Astrazeneca lp
Packagers
  • Gallipot
  • Long Wing International Inc.
Dosage Forms
FormRouteStrength
CreamTopical
LiquidOral
SprayOral0.1 % w/w
SolutionTopical10 mg/1mL
SolutionTopical5 mg/1mL
RinseDental; Oral; Topical; Transmucosal0.1 g/100mL
PatchTopical
LiquidTopical
LozengeOral3 mg/1
LozengeOral1.2 mg/1
LozengeOral
LozengeOral3 mg / loz
LozengeOral1.2 mg / loz
LozengeOral1.2 mg
LozengeOral2 mg / loz
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)16.29Chemaxon
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-MSsplash10-006t-9440000000-a86aac6d96e16aac8d02
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-0006-2090000000-736a6e320c5178232c9a
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-1190000000-9d0d38849d27b461c917
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-007n-7690000000-5f7b3495ec762d130d3c
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-000i-1690000000-53fc1a7a14e5790dba95
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-000g-9720000000-1f0efb8a121bef1c7a48
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-000j-0930000000-a35eca8c90b23894f97d
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
AdductCCS Value (Å2)Source typeSource
[M-H]-190.1628446
predicted
DarkChem Lite v0.1.0
[M-H]-172.77568
predicted
DeepCCS 1.0 (2019)
[M+H]+190.1959446
predicted
DarkChem Lite v0.1.0
[M+H]+175.13368
predicted
DeepCCS 1.0 (2019)
[M+Na]+190.2006446
predicted
DarkChem Lite v0.1.0
[M+Na]+181.22682
predicted
DeepCCS 1.0 (2019)

Targets

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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
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
  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. [Article]
  3. Roghani S, Duperon DF, Barcohana N: Evaluating the efficacy of commonly used topical anesthetics. Pediatr Dent. 1999 May-Jun;21(3):197-200. [Article]
  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. [Article]

Drug created at June 13, 2005 13:24 / Updated at March 18, 2024 16:48