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

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
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
Canister tip orientation and residual volume have significant impact on the dose of benzocaine delivered by Hurricaine spray.
2001 Feb
Placement of the esophageal Doppler ultrasound monitor probe in awake patients.
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
Local anesthetic effects on priming and activation of human neutrophils.
2001 Jul
Benzocaine-induced methemoglobinemia accompanying adult respiratory distress syndrome and sepsis syndrome: case report.
2001 Jun
A potentially fatal effect of topical anesthesia.
2001 Jun 15
Severe methemoglobinemia on reexposure to benzocaine.
2001 Mar
Disappearing and reappearing polymorphs. The benzocaine:picric acid system.
2001 Mar 7
Allergic contact dermatitis to cinchocaine.
2001 May
Methemoglobinemia as a cause of respiratory failure.
2002 Apr
The role of fat and cholecystokinin in functional dyspepsia.
2002 Jul
Perioperatively acquired methaemoglobinaemia in a preterm infant.
2002 Mar
Topical anesthesia for minor gynecological procedures: a review.
2002 Mar
Benzoate X receptors alpha and beta are pharmacologically distinct and do not function as xenobiotic receptors.
2002 Nov 15
[Photocontact dermatitis due to ketoprofen and photosensitization to tetrachlorosalicylanide and to Fenticlor(R)].
2002 Oct
Effective topical anesthetic agents and techniques.
2002 Oct
Methemoglobinemia induced by topical benzocaine: a warning for the endoscopist.
2002 Sep
Two cases of methemoglobinemia from the use of topical anesthetics.
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
Patch testing with the irritant sodium lauryl sulfate (SLS) is useful in interpreting weak reactions to contact allergens as allergic or irritant.
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
Effects of isoeugenol on in vitro neuromuscular blockade of rat phrenic nerve-diaphragm preparations.
2003 Jun
Thermodynamics of partitioning of benzocaine in some organic solvent/buffer and liposome systems.
2003 Mar
Severe methemoglobinemia after transesophageal echocardiography.
2003 May-Jun
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
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
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 Dec 16 20:21:19 GMT 2023
Edited
by admin
on Sat Dec 16 20:21:19 GMT 2023
Record UNII
U3RSY48JW5
Record Status Validated (UNII)
Record Version
  • Download
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
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 QN01BA05
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 R02AD01
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 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
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 QC05AD03
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 QD04AB04
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
NCI_THESAURUS C245
Created by admin on Sat Dec 16 20:21:20 GMT 2023 , Edited by admin on Sat Dec 16 20:21:20 GMT 2023
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
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
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
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
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
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
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
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
NSC
4688
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
RS_ITEM_NUM
1054000
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
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
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
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
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
DAILYMED
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
EVMPD
SUB05755MIG
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
Related Record Type Details
SALT/SOLVATE -> PARENT
Related Record Type Details
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
Related Record Type Details
ACTIVE MOIETY
http://apps.who.int/phint/pdf/b/Jb.6.1.48.pdf