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Details

Stereochemistry ACHIRAL
Molecular Formula C18H27NO2.ClH
Molecular Weight 325.873
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of DYCLONINE HYDROCHLORIDE

SMILES

Cl.CCCCOC1=CC=C(C=C1)C(=O)CCN2CCCCC2

InChI

InChIKey=KNZADIMHVBBPOA-UHFFFAOYSA-N
InChI=1S/C18H27NO2.ClH/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;1H

HIDE SMILES / InChI

Molecular Formula C18H27NO2
Molecular Weight 289.4125
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula ClH
Molecular Weight 36.461
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: Description was created based on several sources, including http://www.sucrets.com/sore-throat-remedies | https://www.ncbi.nlm.nih.gov/pubmed/25113747 | https://www.drugs.com/monograph/dyclonine-hydrochloride.html | https://www.ncbi.nlm.nih.gov/pubmed/19148544 | https://www.ncbi.nlm.nih.gov/pubmed/25174315 | https://www.ncbi.nlm.nih.gov/pubmed/25113747

Dyclonine is an local anesthetic used to provide topical anesthesia to mucous membranes through sodium channel inhibition. It is the active ingredient in Sucrets, an over-the-counter throat lozenge. It has been used as a local anesthetic agent prior to laryngoscopy, bronchoscopy, esophagoscopy, or endotracheal intubation. However, oral solutions no longer are commercially available in the US. Recently, additional activities of dyclonine have been discovered. Dyclonine represents a novel therapeutic strategy that can potentially be repurposed for the treatment of Friedreich's ataxia. Dyclonine enhances the cytotoxic effect of proteasome inhibitors on cancer and multiple myeloma cells.

Originator

Sources: Pofft, Chem. Tech. (Berlin) 4, 241 (1952)
Curator's Comment: reference retrieved from http://www.druglead.com/cds/Dyclonine.html

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
SUCRETS

Approved Use

temporarily relieves: occasional minor irritation, pain, sore throat and sore mouth cough associated with a cold or inhaled irritants
Primary
Unknown

Approved Use

Unknown
Primary
DYCLONE

Approved Use

Has been used as a local anesthetic agent prior to laryngoscopy, bronchoscopy, esophagoscopy, or endotracheal intubation. However, oral solutions no longer are commercially available in the US.
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
42.17 ng/mL
20 μg/cm² single, topical
dose: 20 μg/cm²
route of administration: Topical
experiment type: SINGLE
co-administered:
DYCLONINE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
152.81 ng × h/mL
20 μg/cm² single, topical
dose: 20 μg/cm²
route of administration: Topical
experiment type: SINGLE
co-administered:
DYCLONINE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
5.85 h
20 μg/cm² single, topical
dose: 20 μg/cm²
route of administration: Topical
experiment type: SINGLE
co-administered:
DYCLONINE plasma
Rattus norvegicus
population: HEALTHY
age: ADULT
sex: MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
8 mg single, oral
Recommended
Dose: 8 mg
Route: oral
Route: single
Dose: 8 mg
Sources:
healthy, adult
n = 10
Health Status: healthy
Age Group: adult
Sex: unknown
Population Size: 10
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG

OverviewOther

Other InhibitorOther SubstrateOther Inducer

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
PubMed

PubMed

TitleDatePubMed
Applications of microarray technology in breast cancer research.
2001
Airway anesthesia alone does not explain attenuation of histamine-induced bronchospasm by local anesthetics: a comparison of lidocaine, ropivacaine, and dyclonine.
2001 Mar
Enigmatic pain referred to the teeth and jaws.
2001 Mar-Apr
Both local anesthetics and salbutamol pretreatment affect reflex bronchoconstriction in volunteers with asthma undergoing awake fiberoptic intubation.
2002 Dec
Chemical genomics in yeast.
2004
The uses of genome-wide yeast mutant collections.
2004
Solid-state characterization of falicaine hydrochloride and isomorphic dyclonine hydrochloride. Part IV. Crystal polymorphism of local anaesthetic drugs.
2005 Jul-Aug
Genome-wide fitness test and mechanism-of-action studies of inhibitory compounds in Candida albicans.
2007 Jun
Lidocaine exerts its effect on induced bronchospasm by mitigating reflexes, rather than by attenuation of smooth muscle contraction.
2007 Mar
[The use of 1% dyclonine and local cryoanesthesia plus pulp vitality test agent in taking dental X-ray film].
2008 Feb
Dyclonine and alverine citrate enhance the cytotoxic effects of proteasome inhibitor MG132 on breast cancer cells.
2009 Feb
Best drugs for what ails you: the brands to buy--and those to skip.
2009 Sep
Functional toxicogenomics: mechanism-centered toxicology.
2010
Microneedle pretreatment improves efficacy of cutaneous topical anesthesia.
2010 Feb
Profiling of a prescription drug library for potential renal drug-drug interactions mediated by the organic cation transporter 2.
2011 Jul 14
Patents

Sample Use Guides

Oral/Throat Pain 1 lozenge (1.2, 2, or 3 mg); repeat after 2 hours if necessary Usual Dosage Use the lowest dose needed to provide effective anesthesia Mouth sores: 5-10 mL of 0.5% or 1% to oral mucosa (swab or swish and then spit) 3-4 times/day as needed; maximum single dose: 200 mg (40 mL of 0.5% solution or 20 mL of 1% solution) Bronchoscopy: Use 2 mL of the 1% solution or 4 mL of the 0.5% solution sprayed onto the larynx and trachea every 5 minutes until the reflex has been abolished
Route of Administration: Topical
Dyclonine enhances the cytotoxic effects of proteasome inhibitor MG132 on breast cancer cells in low micromolar range
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:02:41 UTC 2023
Edited
by admin
on Fri Dec 15 15:02:41 UTC 2023
Record UNII
ZEC193879Q
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
DYCLONINE HYDROCHLORIDE
MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
Common Name English
4-N-BUTOXY-.BETA.-PIPERIDONOPROPIOPHENONE HYDROCHLORIDE
Systematic Name English
DYCLONINE HYDROCHLORIDE [ORANGE BOOK]
Common Name English
DYCLONE
Brand Name English
DYCLONINE HYDROCHLORIDE [USP-RS]
Common Name English
Dyclonine hydrochloride [WHO-DD]
Common Name English
4'-BUTOXY-3-PIPERIDINOPROPIOPHENONE HYDROCHLORIDE
Systematic Name English
4’-Butoxy-3-piperidinopropiophenone hydrochloride
Systematic Name English
DYCLONINE HCL
Common Name English
DYCLONINE HYDROCHLORIDE [VANDF]
Common Name English
1-PROPANONE, 1-(4-BUTOXYPHENYL)-3-(1-PIPERIDINYL)HYDROCHLORIDE
Common Name English
DYCLONINE HYDROCHLORIDE [MI]
Common Name English
NSC-23018
Code English
DYCLONINE HYDROCHLORIDE [USP MONOGRAPH]
Common Name English
DYCLONINE HYDROCHLORIDE [MART.]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 346.10
Created by admin on Fri Dec 15 15:02:41 UTC 2023 , Edited by admin on Fri Dec 15 15:02:41 UTC 2023
NCI_THESAURUS C245
Created by admin on Fri Dec 15 15:02:41 UTC 2023 , Edited by admin on Fri Dec 15 15:02:41 UTC 2023
CFR 21 CFR 310.201
Created by admin on Fri Dec 15 15:02:41 UTC 2023 , Edited by admin on Fri Dec 15 15:02:41 UTC 2023
Code System Code Type Description
CHEBI
4725
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PRIMARY
DRUG BANK
DBSALT000651
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PRIMARY
EPA CompTox
DTXSID6045323
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PRIMARY
RXCUI
91188
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PRIMARY RxNorm
FDA UNII
ZEC193879Q
Created by admin on Fri Dec 15 15:02:41 UTC 2023 , Edited by admin on Fri Dec 15 15:02:41 UTC 2023
PRIMARY
CAS
536-43-6
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PRIMARY
PUBCHEM
68304
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PRIMARY
NSC
23018
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PRIMARY
ECHA (EC/EINECS)
208-633-6
Created by admin on Fri Dec 15 15:02:41 UTC 2023 , Edited by admin on Fri Dec 15 15:02:41 UTC 2023
PRIMARY
ChEMBL
CHEMBL1201217
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PRIMARY
SMS_ID
100000088125
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PRIMARY
NCI_THESAURUS
C66875
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PRIMARY
DAILYMED
ZEC193879Q
Created by admin on Fri Dec 15 15:02:41 UTC 2023 , Edited by admin on Fri Dec 15 15:02:41 UTC 2023
PRIMARY
EVMPD
SUB01848MIG
Created by admin on Fri Dec 15 15:02:41 UTC 2023 , Edited by admin on Fri Dec 15 15:02:41 UTC 2023
PRIMARY
MERCK INDEX
m4790
Created by admin on Fri Dec 15 15:02:41 UTC 2023 , Edited by admin on Fri Dec 15 15:02:41 UTC 2023
PRIMARY Merck Index
RS_ITEM_NUM
1230000
Created by admin on Fri Dec 15 15:02:41 UTC 2023 , Edited by admin on Fri Dec 15 15:02:41 UTC 2023
PRIMARY
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ACTIVE MOIETY