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Dyclonine
Identification
- Name
- Dyclonine
- Accession Number
- DB00645
- Description
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
Structure for Dyclonine (DB00645)
- 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.
- Associated Conditions
- Contraindications & Blackbox Warnings
Learn about our commercial Contraindications & Blackbox Warnings data.
Learn More- 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 inhibitorHumans - 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
Learn about our commercial Adverse Effects data.
Learn More- 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 Unlock Additional DataAcetazolamide 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. Aclidinium Dyclonine may increase the central nervous system depressant (CNS depressant) activities of Aclidinium. Agomelatine The risk or severity of adverse effects can be increased when Dyclonine is combined with Agomelatine. Alfentanil The risk or severity of adverse effects can be increased when Dyclonine is combined with Alfentanil. Alimemazine The risk or severity of adverse effects can be increased when Dyclonine is combined with Alimemazine. Almotriptan The risk or severity of adverse effects can be increased when Dyclonine is combined with Almotriptan. Alosetron The risk or severity of adverse effects can be increased when Dyclonine is combined with Alosetron. Alprazolam The risk or severity of adverse effects can be increased when Alprazolam is combined with Dyclonine. Alverine The risk or severity of adverse effects can be increased when Dyclonine is combined with Alverine. Additional Data Available- Extended DescriptionExtended Description
Extended description of the mechanism of action and particular properties of each drug interaction.
Learn more - Severity
- Evidence Level
- ActionAction
An effect category for each drug interaction. Know how this interaction affects the subject drug.
Learn more
- 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
- Product Ingredients
Ingredient UNII CAS InChI Key Dyclonine hydrochloride ZEC193879Q 536-43-6 KNZADIMHVBBPOA-UHFFFAOYSA-N - International/Other Brands
- Dyclone (AstraZeneca)
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataDycloPro Solution 5 mg/1mL Topical Septodont Inc 2019-09-01 Not applicable US 
DycloPro Solution 10 mg/1mL Topical Septodont Inc 2019-09-01 Not applicable US Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Over the Counter Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Unlock Additional DataCepacol Sore Throat Spray Spray Oral Reckitt Benckiser 1999-07-01 2012-03-23 Canada 
PerioRinse Rinse 0.1 g/100mL Dental; Oral; Topical; Transmucosal CENTURA PHARMACEUTICALS INC 2016-06-16 2018-07-31 US Sore Throat Relief Lozenge 3 mg Oral Stanley Pharmaceuticals, A Division Of Vita Health Products Inc. Not applicable Not applicable Canada Sucrets Black Cherry Lozenge 3 mg/1 Oral Insight Pharmaceuticals 2009-06-18 2017-08-31 US Sucrets Childrens Cherry Lozenge 1.2 mg/1 Oral Insight Pharmaceuticals 2009-07-28 2017-08-31 US Sucrets Extra Strength Mint Flav.loz 3mg Lozenge Oral Smithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc. 1994-12-31 1998-08-25 Canada Sucrets for Kids Lozenge Oral Smithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc. 1992-12-31 1998-08-25 Canada Sucrets for Kids Lozenge Oral Insight Pharmaceuticals LLC 1997-08-15 Not applicable Canada Sucrets MS Wintergreen Lozenge 3 mg/1 Oral Insight Pharmaceuticals 2009-07-28 2017-08-31 US Sucrets Regular Strength Lemon Flav.loz 2mg Lozenge Oral Smithkline Beecham Consumer Healthcare, Division Of Smithkline Beecham Inc. 1994-12-31 1998-08-25 Canada Additional Data Available- Application NumberApplication Number
A unique ID assigned by the FDA when a product is submitted for approval by the labeller.
Learn more - Product CodeProduct Code
A governmentally-recognized ID which uniquely identifies the product within its regulatory market.
Learn more
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image 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 US 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 US 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 US 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 US Benzethonium chloride Plus Dyclonine hydrochloride Dyclonine hydrochloride (0.75 mg/9mL) + Benzethonium chloride (0.2 mg/9mL) Liquid Topical Topco Associates LLC 2014-07-10 Not applicable US Benzethonium chloride Plus Dyclonine hydrochloride Dyclonine hydrochloride (0.75 mg/9mL) + Benzethonium chloride (0.2 mg/9mL) Liquid Topical AmerisourceBergen Drug Corporation 2017-12-21 Not applicable US 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 US 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 US Benzethonium chloride Plus Dyclonine hydrochloride Dyclonine hydrochloride (0.75 mg/9mL) + Benzethonium chloride (0.2 mg/9mL) Liquid Topical Chain Drug Marketing Association 2017-12-19 Not applicable US 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 US
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)
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
- External Links
- Human Metabolome Database
- HMDB0014783
- KEGG Compound
- C07881
- PubChem Compound
- 3180
- PubChem Substance
- 46506697
- ChemSpider
- 3068
- BindingDB
- 50240047
- 23744
- ChEBI
- 4724
- ChEMBL
- CHEMBL1201217
- ZINC
- ZINC000001530940
- Therapeutic Targets Database
- DAP000509
- PharmGKB
- PA164748037
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- 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
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
Targets
- 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 August 14, 2020 04:24
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