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

Details

Stereochemistry ACHIRAL
Molecular Formula C9H11NO2
Molecular Weight 165.1895
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZOCAINE

SMILES

CCOC(=O)c1ccc(cc1)N

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 165.1895
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
The optimization test in the guinea-pig. A method for the predictive evaluation of the contact allergenicity of chemicals.
1975 May
Redox properties of local anesthetics: A structural determinant of closed channel blockers in BTX-modified Na+ channels.
2001
Pharmacological regulation of gastric acid secretion in the apical membrane of parietal cells; a new target for antisecretory drugs.
2001 Dec
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
Benzocaine-induced methemoglobinemia accompanying adult respiratory distress syndrome and sepsis syndrome: case report.
2001 Jun
Disappearing and reappearing polymorphs. The benzocaine:picric acid system.
2001 Mar 7
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
[The killing of aquarium fish by owners: a commentary].
2001 Sep 1
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
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
Determination of linkages of linear and branched oligosaccharides using closed-ring chromophore labeling and negative ion trap mass spectrometry.
2002 Nov
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
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
Efficacy and tolerability of an intraoral benzocaine patch in the relief of spontaneous toothache pain.
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
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
Evolution of sugars in cider brandy aged in oak barrels: a contribution to its characterization.
2003 Feb 12
Effect of prolonged exposure to low antigen concentration for sensitization.
2003 Feb 14
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
Anesthesia of fish with benzocaine does not interfere with comet assay results.
2003 Jan 10
Methemoglobinemia and topical pharyngeal anesthesia.
2003 Jan 2
Bye-bye benzocaine?
2003 Jul
Preparation and evaluation of bioadhesive benzocaine gels for enhanced local anesthetic effects.
2003 Jul 9
Children's preference of benzocaine gel versus the lidocaine patch.
2003 Jul-Aug
Influence of site preparation methods on the pain reported during palatal infiltration using the Wand Local Anesthetic System.
2003 Jun
Thermodynamics of partitioning of benzocaine in some organic solvent/buffer and liposome systems.
2003 Mar
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
Tongue entrapment in an aluminum juice can.
2004 Apr
Contact dermatitis and other skin conditions in instrumental musicians.
2004 Apr 16
Can clinical trials requiring frequent participant contact be conducted over the Internet? Results from an online randomized controlled trial evaluating a topical ointment for herpes labialis.
2004 Feb 17
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
Prospective randomized study of viscous lidocaine versus benzocaine in a GI cocktail for dyspepsia.
2004 Jul
George Crile, Harvey Cushing, and the Ambulance Americaine: military medical preparedness in World War I.
2004 Jun
Reported adverse event cases of methemoglobinemia associated with benzocaine products.
2004 Jun 14
Methemoglobinemia: an unusual cause of postoperative cyanosis.
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 Jun 25 21:19:54 UTC 2021
Edited
by admin
on Fri Jun 25 21:19:54 UTC 2021
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
SUBCUTIN
Brand Name English
AMINOBENZOIC ACID IMPURITY B [EP]
Common 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
FLAVAMED
Brand Name English
BENZOIC ACID, 4-AMINO-, ETHYL ESTER
Common Name English
ETHYL AMINOBENZOATE
Systematic Name English
AR01
Code English
BENZOCAINE [WHO-DD]
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
BENZOCAINE [USP]
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 Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
CFR 21 CFR 310.531
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
EPA PESTICIDE CODE 97001
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
WHO-VATC QN01AX92
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
WHO-ATC D04AB04
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
NDF-RT N0000185508
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
WHO-VATC QN01BA05
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
WHO-ATC R02AD01
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
CFR 21 CFR 348.10
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
WHO-ATC C05AD03
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
CFR 21 CFR 310.538
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
WHO-ATC N01BA05
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
WHO-VATC QR02AD01
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
WHO-VATC QC05AD03
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
WHO-VATC QD04AB04
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
NCI_THESAURUS C245
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
Code System Code Type Description
MESH
D001566
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
PRIMARY
NDF-RT
N0000175629
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
PRIMARY Increased Histamine Release [PE]
FDA UNII
U3RSY48JW5
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
PRIMARY
NDF-RT
N0000171131
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
PRIMARY Allergens [Chemical/Ingredient]
NDF-RT
N0000184306
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
PRIMARY Cell-mediated Immunity [PE]
ChEMBL
CHEMBL278172
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
PRIMARY
MERCK INDEX
M2358
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
PRIMARY Merck Index
ECHA (EC/EINECS)
202-303-5
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
PRIMARY
RXCUI
1399
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
PRIMARY RxNorm
CAS
94-09-7
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
PRIMARY
NCI_THESAURUS
C28923
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
PRIMARY
WHO INTERNATIONAL PHARMACOPEIA
BENZOCAINE
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
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
94-09-7
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
PRIMARY
DRUG CENTRAL
323
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
PRIMARY
WIKIPEDIA
BENZOCAINE
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
PRIMARY
INN
3953
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
PRIMARY
PUBCHEM
2337
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
PRIMARY
HSDB
7225
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
PRIMARY
LACTMED
Benzocaine
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
PRIMARY
DRUG BANK
DB01086
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
PRIMARY
USP_CATALOG
1054000
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
PRIMARY USP-RS
EVMPD
SUB05755MIG
Created by admin on Fri Jun 25 21:19:54 UTC 2021 , Edited by admin on Fri Jun 25 21:19:54 UTC 2021
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