U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C9H11NO2
Molecular Weight 165.1891
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZOCAINE

SMILES

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

InChI

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

HIDE SMILES / InChI

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
The optimization test in the guinea-pig. A method for the predictive evaluation of the contact allergenicity of chemicals.
1975 May
Contact dermatitis in students practicing sports: incidence of rubber sensitisation.
2001 Apr
Pharmacological regulation of gastric acid secretion in the apical membrane of parietal cells; a new target for antisecretory drugs.
2001 Dec
Drug-induced methemoglobinemia during thoracoscopic lung biopsy.
2001 Feb
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
Comparison of topical EMLA 5% oral adhesive to benzocaine 20% on the pain experienced during palatal anesthetic infiltration in children.
2001 Jan-Feb
Effects of pelargonidine and a benzocaine analogue p-diethylaminoethyl benzoate on mitochondrial K(ATP) channel.
2001 Jul
Benzocaine-induced methemoglobinemia accompanying adult respiratory distress syndrome and sepsis syndrome: case report.
2001 Jun
Modified short-term guinea pig sensitization tests for detecting contact allergens as an alternative to the conventional test.
2001 Mar
Disappearing and reappearing polymorphs. The benzocaine:picric acid system.
2001 Mar 7
Inhibition of m3 muscarinic acetylcholine receptors by local anaesthetics.
2001 May
Allergic contact dermatitis to cinchocaine.
2001 May
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
[The killing of aquarium fish by owners: a commentary].
2001 Sep 1
Effects of four anaesthetics on the innate immune response of gilthead seabream (Sparus aurata L.).
2002 Jan
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
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
[Photocontact dermatitis due to ketoprofen and photosensitization to tetrachlorosalicylanide and to Fenticlor(R)].
2002 Oct
Methemoglobinemia induced by topical benzocaine: a warning for the endoscopist.
2002 Sep
Inhibition of tetrodotoxin (TTX)-resistant and TTX-sensitive neuronal Na(+) channels by the secretolytic ambroxol.
2002 Sep
Two cases of methemoglobinemia from the use of topical anesthetics.
2003 Apr
Dangerous in small amounts: ten nondrug substances that cause harm.
2003 Aug
Lipid-protein interactions and effect of local anesthetics in acetylcholine receptor-rich membranes from Torpedo marmorata electric organ.
2003 Aug 5
Benzocaine-induced methemoglobinemia: experience from a high-volume transesophageal echocardiography laboratory.
2003 Feb
Evolution of sugars in cider brandy aged in oak barrels: a contribution to its characterization.
2003 Feb 12
Quinoxaline chemistry. Part 15. 4-[2-Quinoxalylmethylenimino]-benzoylglutamates and -benzoates, 4-[2-quinoxalylmethyl-N-methylamino]-benzoylglutamates as analogues of classical antifolate agents. Synthesis, elucidation of structures and in vitro evaluation of antifolate and anticancer activities.
2003 Jan
Children's preference of benzocaine gel versus the lidocaine patch.
2003 Jul-Aug
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
Respiratory failure secondary to methemoglobinemia induced by benzocaine: a case report.
2004 Apr
Effects of the local anesthetic benzocaine on the human erythrocyte membrane and molecular models.
2004 Apr 1
Detection of apple juice concentrate in the manufacture of natural and sparkling cider by means of HPLC chemometric sugar analyses.
2004 Jan 28
Prospective randomized study of viscous lidocaine versus benzocaine in a GI cocktail for dyspepsia.
2004 Jul
Reported adverse event cases of methemoglobinemia associated with benzocaine products.
2004 Jun 14
Methemoglobinemia: an unusual cause of postoperative cyanosis.
2004 Mar
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.
Name Type Language
BENZOCAINE
EP   HSDB   INN   MART.   MI   USP   USP-RS   VANDF   WHO-DD   WHO-IP  
INN  
Official Name English
ETHYL PABA
INCI  
INCI  
Official Name English
ETHYL PABA [INCI]
Common Name English
BENZOCAINE [VANDF]
Common Name English
AMINOBENZOIC ACID IMPURITY B [EP IMPURITY]
Common Name English
SUBCUTIN
Brand Name English
BENZOCAINE [USP-RS]
Common Name English
Ethyl 4-aminobenzoate
Systematic Name English
BENZOCAINUM [WHO-IP LATIN]
Common Name English
BENZOCAINE [HSDB]
Common Name English
NSC-4688
Code English
BABY ANBESOL
Brand Name English
BENZOCAINE [EP MONOGRAPH]
Common Name English
AR-01
Code English
NORCAINE
Brand Name English
BENZOCAINE [WHO-IP]
Common Name English
PARATHESINE
Common Name English
Benzocaine [WHO-DD]
Common Name English
FLAVAMED
Brand Name English
BENZOIC ACID, 4-AMINO-, ETHYL ESTER
Common Name English
ETHYL AMINOBENZOATE
Systematic Name English
AR01
Code English
BENZOCAINE [USP MONOGRAPH]
Common Name English
AMERICAINE
Brand Name English
NSC-41531
Code English
PARATHESIN
Brand Name English
BENZOCAINE [MI]
Common Name English
4-AMINOBENZOIC ACID ETHYL ESTER
Systematic Name English
ETHYL P-AMINOBENZOATE
Common Name English
ETHYL AMINOBENZOATE [JAN]
Common Name English
ANAESTHESIN
Brand Name English
BENZOCAINE [MART.]
Common Name English
benzocaine [INN]
Common Name English
Classification Tree Code System Code
CFR 21 CFR 346.10
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
CFR 21 CFR 310.531
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
EPA PESTICIDE CODE 97001
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
WHO-VATC QN01AX92
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
WHO-ATC D04AB04
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
NDF-RT N0000185508
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WHO-VATC QN01BA05
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WHO-ATC R02AD01
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CFR 21 CFR 348.10
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
WHO-ATC C05AD03
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
CFR 21 CFR 310.538
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
WHO-ATC N01BA05
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
WHO-VATC QR02AD01
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WHO-VATC QC05AD03
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WHO-VATC QD04AB04
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NCI_THESAURUS C245
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Code System Code Type Description
MESH
D001566
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
PRIMARY
SMS_ID
100000089829
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
PRIMARY
NDF-RT
N0000175629
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
PRIMARY Increased Histamine Release [PE]
FDA UNII
U3RSY48JW5
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
PRIMARY
NDF-RT
N0000171131
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
PRIMARY Allergens [Chemical/Ingredient]
NDF-RT
N0000184306
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
PRIMARY Cell-mediated Immunity [PE]
CHEBI
116735
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
PRIMARY
ChEMBL
CHEMBL278172
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PRIMARY
MERCK INDEX
m2358
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
PRIMARY Merck Index
ECHA (EC/EINECS)
202-303-5
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PRIMARY
RXCUI
1399
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
PRIMARY RxNorm
CAS
94-09-7
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PRIMARY
NCI_THESAURUS
C28923
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
BENZOCAINE
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
PRIMARY Description: Colourless crystals or a white, crystalline powder; odourless. Solubility: Very slightly soluble in water; soluble in 6 parts of ethanol (~750 g/l) TS and 5.5 parts of ether R. Category: Local anaesthetic. Storage: Benzocaine should be kept in a well-closed container, protected from light. Additional information: Benzocaine causes local numbness after being placed on the tongue. Definition: Benzocaine contains not less than 98.0% and not more than 101.0% of C9H11NO2, calculated with reference to the dried substance.
EPA CompTox
DTXSID8021804
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
PRIMARY
DRUG CENTRAL
323
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PRIMARY
NSC
4688
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PRIMARY
RS_ITEM_NUM
1054000
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PRIMARY
NSC
41531
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
PRIMARY
WIKIPEDIA
BENZOCAINE
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
PRIMARY
INN
3953
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PRIMARY
PUBCHEM
2337
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
PRIMARY
HSDB
7225
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
PRIMARY
LACTMED
Benzocaine
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
PRIMARY
DRUG BANK
DB01086
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PRIMARY
DAILYMED
U3RSY48JW5
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PRIMARY
EVMPD
SUB05755MIG
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PRIMARY