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Details

Stereochemistry ACHIRAL
Molecular Formula C9H11NO2.ClH
Molecular Weight 201.65
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZOCAINE HYDROCHLORIDE

SMILES

Cl.CCOC(=O)C1=CC=C(N)C=C1

InChI

InChIKey=JAADDQHUJDUAKW-UHFFFAOYSA-N
InChI=1S/C9H11NO2.ClH/c1-2-12-9(11)7-3-5-8(10)6-4-7;/h3-6H,2,10H2,1H3;1H

HIDE SMILES / InChI

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

Molecular Formula C9H11NO2
Molecular Weight 165.1891
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 https://www.fda.gov/drugs/drugsafety/ucm250024.htm

Benzocaine is a local anesthetic. It acts by blocking voltage-gated sodium ion channels in nerve endings. Benzocaine is available over-the counter for local anesthesia of oral and pharyngeal mucous membranes (sore throat, cold sores, mouth ulcers, toothache, sore gums, denture irritation), otic pain, and as a local anesthetic for surgical or diagnostic procedures. As a spray, benzocaine is used for temporary relief of pain and itching associated with minor burns, sunburn, minor cuts or scrapes, insect bites, or minor skin irritations. Topical application of benzocaine to gums or mouth may cause rare, but serious and potentially fatal adverse effect methemoglobinemia.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Target ID: Q9Y5Y9
Gene ID: 6336.0
Gene Symbol: SCN10A
Target Organism: Homo sapiens (Human)
0.32 mM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
CEPACOL

Approved Use

Benzocaine lozenges are used to relieve pain and irritation caused by sore throat, sore mouth, or canker sores.
Palliative
CEPACOL

Approved Use

Benzocaine lozenges are used to relieve pain and irritation caused by sore throat, sore mouth, or canker sores.
Palliative
CEPACOL

Approved Use

Benzocaine lozenges are used to relieve pain and irritation caused by sore throat, sore mouth, or canker sores.
Palliative
AMERICAINE

Approved Use

Self-medication for temporary relief of pain and itching associated with minor burns, sunburn, minor cuts or scrapes, insect bites, or minor skin irritations.
Palliative
AMERICAINE HEMORRHOIDAL

Approved Use

Self-medication for temporary relief of pain and itching associated with hemorrhoids
Palliative
OTOCAINE DROPS

Approved Use

Relieving pain and itching in the ear caused by ear infections.
Doses

Doses

DosePopulationAdverse events​
20 % single, topical
Dose: 20 %
Route: topical
Route: single
Dose: 20 %
Sources:
unhealthy, 17-71 years
n = 2
Health Status: unhealthy
Age Group: 17-71 years
Sex: F
Population Size: 2
Sources:
Other AEs: Methaemoglobinaemia...
8 mg 1 times / 2 hours multiple, oral
Dose: 8 mg, 1 times / 2 hours
Route: oral
Route: multiple
Dose: 8 mg, 1 times / 2 hours
Sources:
unhealthy, 49.4 years (range: 18–74 years)
n = 246
Health Status: unhealthy
Age Group: 49.4 years (range: 18–74 years)
Sex: M+F
Population Size: 246
Sources:
AEs

AEs

AESignificanceDosePopulation
Methaemoglobinaemia 2 patients
20 % single, topical
Dose: 20 %
Route: topical
Route: single
Dose: 20 %
Sources:
unhealthy, 17-71 years
n = 2
Health Status: unhealthy
Age Group: 17-71 years
Sex: F
Population Size: 2
Sources:
Overview

Overview

CYP3A4CYP2C9CYP2D6hERG


OverviewOther

Drug as perpetrator​

Drug as perpetrator​

TargetModalityActivityMetaboliteClinical evidence
yes
Drug as victim
PubMed

PubMed

TitleDatePubMed
Contact dermatitis in students practicing sports: incidence of rubber sensitisation.
2001 Apr
From cocaine to ropivacaine: the history of local anesthetic drugs.
2001 Aug
Canister tip orientation and residual volume have significant impact on the dose of benzocaine delivered by Hurricaine spray.
2001 Feb
Analgesia for colposcopy: double-masked, randomized comparison of ibuprofen and benzocaine gel.
2001 Jan
Modulation of gastric distension-induced sensations by small intestinal receptors.
2001 Jan
Reducing children's injection pain: lidocaine patches versus topical benzocaine gel.
2001 Jan-Feb
Comparison of topical EMLA 5% oral adhesive to benzocaine 20% on the pain experienced during palatal anesthetic infiltration in children.
2001 Jan-Feb
Evaluation of an acetic acid ester of monoglyceride as a suppository base with unique properties.
2001 Jul 17
Controlled release from an electrorheological fluid dosage form: experimental results for a prototype system.
2001 Jul-Aug
A potentially fatal effect of topical anesthesia.
2001 Jun 15
Severe methemoglobinemia on reexposure to benzocaine.
2001 Mar
Modified short-term guinea pig sensitization tests for detecting contact allergens as an alternative to the conventional test.
2001 Mar
Allergic contact dermatitis to cinchocaine.
2001 May
Diaminodiphenylmethane (DDM): frequency of sensitization, clinical relevance and concomitant positive reactions.
2001 May
Fluorescent labeling of drugs and simple organic compounds containing amine functional groups, utilizing dansyl chloride in Na(2)CO(3) buffer.
2001 May-Jun
A survey of local and topical anesthesia use by pediatric dentists in the United States.
2001 May-Jun
The treatment of oral aphthous ulceration or erosive lichen planus with topical clobetasol propionate in three preparations: a clinical and pilot study on 54 patients.
2001 Nov
Methemoglobinemia as a cause of respiratory failure.
2002 Apr
The role of fat and cholecystokinin in functional dyspepsia.
2002 Jul
[Photocontact dermatitis due to ketoprofen and photosensitization to tetrachlorosalicylanide and to Fenticlor(R)].
2002 Oct
Effective topical anesthetic agents and techniques.
2002 Oct
Efficacy of a wax containing benzocaine in the relief of oral mucosal pain caused by orthodontic appliances.
2002 Oct
Putative binding sites for benzocaine on a human cardiac cloned channel (Kv1.5).
2002 Oct
A study of release mechanisms of different ophthalmic drugs from erodible ocular inserts based on poly(ethylene oxide).
2002 Sep
Effectiveness of 20% benzocaine as a topical anesthetic for intraoral injections.
2003
Spectrophotometric determination of labetalol in pharmaceutical preparations and spiked human urine.
2003 Apr
The association between ambient air conditions (temperature and absolute humidity), irritant sodium lauryl sulfate patch test reactions and patch test reactivity to standard allergens.
2003 Aug
Lipid-protein interactions and effect of local anesthetics in acetylcholine receptor-rich membranes from Torpedo marmorata electric organ.
2003 Aug 5
Patch testing with the irritant sodium lauryl sulfate (SLS) is useful in interpreting weak reactions to contact allergens as allergic or irritant.
2003 Feb
Benzocaine-induced methemoglobinemia: experience from a high-volume transesophageal echocardiography laboratory.
2003 Feb
Anesthesia of fish with benzocaine does not interfere with comet assay results.
2003 Jan 10
Bye-bye benzocaine?
2003 Jul
Preparation and evaluation of bioadhesive benzocaine gels for enhanced local anesthetic effects.
2003 Jul 9
Benzocaine-induced methemoglobinemia.
2003 Mar
Thermodynamics of partitioning of benzocaine in some organic solvent/buffer and liposome systems.
2003 Mar
Severe methemoglobinemia after transesophageal echocardiography.
2003 May-Jun
Colorimetric determination of benzocaine, lignocaine and procaine hydrochlorides in pure form and in pharmaceutical formulations using p-benzoquinone.
2003 Oct
Analgesic synergy between topical morphine and butamben in mice.
2003 Oct
Respiratory failure secondary to methemoglobinemia induced by benzocaine: a case report.
2004 Apr
Critical rebound methemoglobinemia after methylene blue treatment: case report.
2004 Apr
Tongue entrapment in an aluminum juice can.
2004 Apr
Effects of the local anesthetic benzocaine on the human erythrocyte membrane and molecular models.
2004 Apr 1
Contact dermatitis and other skin conditions in instrumental musicians.
2004 Apr 16
George Crile, Harvey Cushing, and the Ambulance Americaine: military medical preparedness in World War I.
2004 Jun
The need for caution with topical anesthesia during endoscopic procedures, as liberal use may result in methemoglobinemia.
2004 Mar
A high prevalence of sensitization still persists in leg ulcer patients: a retrospective series of 106 patients tested between 2001 and 2002 and a meta-analysis of 1975-2003 data.
2004 May
Iatrogenic methemoglobinemia from benzocaine spray in trauma.
2004 May
Acute methemoglobinemia after endoscopy.
2004 May-Jun
Patents

Sample Use Guides

Apply topically to the skin as an aerosol spray, cream, lotion, ointment, or solution.
Route of Administration: Other
Benzocaine produced voltage-sensor inhibition in voltage-gated Na+ channel (Nav1.5) expressed in HEK293 cells, and caused large leftward shifts in the V1/2 of the steady-state availability curves aswell as a reduction in Imax with an ED50 of 0.32 mM.
Substance Class Chemical
Created
by admin
on Fri Dec 15 15:15:17 GMT 2023
Edited
by admin
on Fri Dec 15 15:15:17 GMT 2023
Record UNII
OG625Z9LEO
Record Status Validated (UNII)
Record Version
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Name Type Language
BENZOCAINE HYDROCHLORIDE
WHO-DD  
Common Name English
NSC-122792
Code English
AMBEN ETHYL ESTER HYDROCHLORIDE
Common Name English
BENZOIC ACID, 4-AMINO-, ETHYL ESTER, HYDROCHLORIDE (1:1)
Common Name English
Benzocaine hydrochloride [WHO-DD]
Common Name English
ETHYL P-AMINOBENZOATE HYDROCHLORIDE
Common Name English
BENZOIC ACID, P-AMINO-, ETHYL ESTER, HYDROCHLORIDE
Common Name English
4-(ETHOXYCARBONYL)ANILINIUM CHLORIDE
Systematic Name English
BENZOIC ACID, 4-AMINO-, ETHYL ESTER, HYDROCHLORIDE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C245
Created by admin on Fri Dec 15 15:15:17 GMT 2023 , Edited by admin on Fri Dec 15 15:15:17 GMT 2023
Code System Code Type Description
NCI_THESAURUS
C97306
Created by admin on Fri Dec 15 15:15:17 GMT 2023 , Edited by admin on Fri Dec 15 15:15:17 GMT 2023
PRIMARY
CAS
23239-88-5
Created by admin on Fri Dec 15 15:15:17 GMT 2023 , Edited by admin on Fri Dec 15 15:15:17 GMT 2023
PRIMARY
RXCUI
1049105
Created by admin on Fri Dec 15 15:15:17 GMT 2023 , Edited by admin on Fri Dec 15 15:15:17 GMT 2023
PRIMARY RxNorm
FDA UNII
OG625Z9LEO
Created by admin on Fri Dec 15 15:15:17 GMT 2023 , Edited by admin on Fri Dec 15 15:15:17 GMT 2023
PRIMARY
EPA CompTox
DTXSID50177812
Created by admin on Fri Dec 15 15:15:17 GMT 2023 , Edited by admin on Fri Dec 15 15:15:17 GMT 2023
PRIMARY
NSC
122792
Created by admin on Fri Dec 15 15:15:17 GMT 2023 , Edited by admin on Fri Dec 15 15:15:17 GMT 2023
PRIMARY
SMS_ID
100000178151
Created by admin on Fri Dec 15 15:15:17 GMT 2023 , Edited by admin on Fri Dec 15 15:15:17 GMT 2023
PRIMARY
PUBCHEM
10214462
Created by admin on Fri Dec 15 15:15:17 GMT 2023 , Edited by admin on Fri Dec 15 15:15:17 GMT 2023
PRIMARY
DRUG BANK
DBSALT001560
Created by admin on Fri Dec 15 15:15:17 GMT 2023 , Edited by admin on Fri Dec 15 15:15:17 GMT 2023
PRIMARY
DAILYMED
OG625Z9LEO
Created by admin on Fri Dec 15 15:15:17 GMT 2023 , Edited by admin on Fri Dec 15 15:15:17 GMT 2023
PRIMARY
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ACTIVE MOIETY