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Details

Stereochemistry ACHIRAL
Molecular Formula C9H11NO2.ClH
Molecular Weight 201.6504
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZOCAINE HYDROCHLORIDE

SMILES

CCOC(=O)c1ccc(cc1)N.Cl

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 36.4609
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C9H11NO2
Molecular Weight 165.1895
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
Clinical evaluation and comparison of 2 topical anesthetics for pain caused by needle sticks and scaling and root planing.
2001 Apr
Pediatric anesthesia in dermatologic surgery: when hand-holding is not enough.
2001 Dec
Placement of the esophageal Doppler ultrasound monitor probe in awake patients.
2001 Jan
Modulation of gastric distension-induced sensations by small intestinal receptors.
2001 Jan
Effects of pelargonidine and a benzocaine analogue p-diethylaminoethyl benzoate on mitochondrial K(ATP) channel.
2001 Jul
Local anesthetic effects on priming and activation of human neutrophils.
2001 Jul
[The killing of aquarium fish by their owners].
2001 Jul 15-Aug 1
Benzocaine-induced methemoglobinemia accompanying adult respiratory distress syndrome and sepsis syndrome: case report.
2001 Jun
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
Fluorescent labeling of drugs and simple organic compounds containing amine functional groups, utilizing dansyl chloride in Na(2)CO(3) buffer.
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
Local lymph node assay with non-radioisotope alternative endpoints.
2002 Aug
Effects of four anaesthetics on the innate immune response of gilthead seabream (Sparus aurata L.).
2002 Jan
Analysis of N-glycosylation of phospholipase A2 from venom of individual bees by microbore high-performance liquid chromatography-electrospray mass spectrometry using an ion trap mass spectrometer.
2002 Jan 25
The role of fat and cholecystokinin in functional dyspepsia.
2002 Jul
The antinociceptive and histologic effect of sciatic nerve blocks with 5% butamben suspension in rats.
2002 Mar
Effects of anaesthesia on blood gases, acid-base status and ions in the toad Bufo marinus.
2002 Mar
Managing patients with local anesthetic complications using alternative methods.
2002 May-Jun
Granuloma gluteale adultorum associated with use of topical benzocaine preparations: case report and literature review.
2002 May-Jun
The use of lubricants to achieve tracheal intubation in neonates and infants.
2002 Oct
Efficacy of a wax containing benzocaine in the relief of oral mucosal pain caused by orthodontic appliances.
2002 Oct
Methemoglobinemia induced by topical benzocaine: a warning for the endoscopist.
2002 Sep
Should a mucoadhesive patch (DentiPatch) be used for gingival anesthesia in children?
2002 Winter
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
Kv1.1 channels of dorsal root ganglion neurons are inhibited by n-butyl-p-aminobenzoate, a promising anesthetic for the treatment of chronic pain.
2003 Feb
Children's preference of benzocaine gel versus the lidocaine patch.
2003 Jul-Aug
Effects of isoeugenol on in vitro neuromuscular blockade of rat phrenic nerve-diaphragm preparations.
2003 Jun
Respiratory failure secondary to methemoglobinemia induced by benzocaine: a case report.
2004 Apr
Inhibition of cell growth, induction of apoptosis and mechanism of action of the novel platinum compound cis-diaminechloro-[2-(diethylamino) ethyl 4-amino-benzoate, N(4)]-chloride platinum (II) monohydrochloride monohydrate.
2004 Jan
Reported adverse event cases of methemoglobinemia associated with benzocaine products.
2004 Jun 14
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 Sat Jun 26 10:40:56 UTC 2021
Edited
by admin
on Sat Jun 26 10:40:56 UTC 2021
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
ETHYL P-AMINOBENZOATE HYDROCHLORIDE
Common Name English
BENZOIC ACID, P-AMINO-, ETHYL ESTER, HYDROCHLORIDE
Common Name English
BENZOCAINE HYDROCHLORIDE [WHO-DD]
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 Sat Jun 26 10:40:56 UTC 2021 , Edited by admin on Sat Jun 26 10:40:56 UTC 2021
Code System Code Type Description
NCI_THESAURUS
C97306
Created by admin on Sat Jun 26 10:40:56 UTC 2021 , Edited by admin on Sat Jun 26 10:40:56 UTC 2021
PRIMARY
CAS
23239-88-5
Created by admin on Sat Jun 26 10:40:56 UTC 2021 , Edited by admin on Sat Jun 26 10:40:56 UTC 2021
PRIMARY
RXCUI
1049105
Created by admin on Sat Jun 26 10:40:56 UTC 2021 , Edited by admin on Sat Jun 26 10:40:56 UTC 2021
PRIMARY RxNorm
FDA UNII
OG625Z9LEO
Created by admin on Sat Jun 26 10:40:56 UTC 2021 , Edited by admin on Sat Jun 26 10:40:56 UTC 2021
PRIMARY
EPA CompTox
23239-88-5
Created by admin on Sat Jun 26 10:40:56 UTC 2021 , Edited by admin on Sat Jun 26 10:40:56 UTC 2021
PRIMARY
PUBCHEM
10214462
Created by admin on Sat Jun 26 10:40:56 UTC 2021 , Edited by admin on Sat Jun 26 10:40:56 UTC 2021
PRIMARY
DRUG BANK
DBSALT001560
Created by admin on Sat Jun 26 10:40:56 UTC 2021 , Edited by admin on Sat Jun 26 10:40:56 UTC 2021
PRIMARY
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