BENZOCAINE

US Approved OTC

First marketed in 1895

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 Search

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
Sources: https://www.drugs.com/monograph/benzocaine-topical.html
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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Sodium channel protein type 10 subunit alpha 3 Target ID: Q9Y5Y9 Gene ID: 6336.0 Gene Symbol: SCN10A Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19661462	Blocker 555		0.32 mM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Sore mouth 2 Sources: https://www.ncbi.nlm.nih.gov/pubmedhealth/PMHT0009234/	Palliative	Approved 8583	CEPACOL Approved Use Benzocaine lozenges are used to relieve pain and irritation caused by sore throat, sore mouth, or canker sores.
Sore throat 18 Sources: https://www.ncbi.nlm.nih.gov/pubmedhealth/PMHT0009234/	Palliative	Approved 8583	CEPACOL Approved Use Benzocaine lozenges are used to relieve pain and irritation caused by sore throat, sore mouth, or canker sores.
Canker sores 2 Sources: https://www.ncbi.nlm.nih.gov/pubmedhealth/PMHT0009234/	Palliative	Approved 8583	CEPACOL Approved Use Benzocaine lozenges are used to relieve pain and irritation caused by sore throat, sore mouth, or canker sores.
Burn 40 Sources: https://www.drugs.com/monograph/benzocaine-topical.html	Palliative	Approved 8583	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.
Hemorrhoids 4 Sources: https://www.drugs.com/monograph/benzocaine-topical.html	Palliative	Approved 8583	AMERICAINE HEMORRHOIDAL Approved Use Self-medication for temporary relief of pain and itching associated with hemorrhoids
Otitis media 42 Sources: https://www.drugs.com/cdi/benzocaine-drops.html	Palliative	Approved 8583	OTOCAINE DROPS Approved Use Relieving pain and itching in the ear caused by ear infections.

Doses

Dose	Population	Adverse events
20 % single, topical Dose: 20 % Route: topical Route: single Dose: 20 % Sources: https://pubmed.ncbi.nlm.nih.gov/18971079 https://pubmed.ncbi.nlm.nih.gov/17694687	unhealthy, 17-71 years Health Status: unhealthy Age Group: 17-71 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/18971079 https://pubmed.ncbi.nlm.nih.gov/17694687	Other AEs: Methaemoglobinaemia... Other AEs: Methaemoglobinaemia (2 patients) Sources: https://pubmed.ncbi.nlm.nih.gov/18971079 https://pubmed.ncbi.nlm.nih.gov/17694687
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: https://pubmed.ncbi.nlm.nih.gov/20533760	unhealthy, 49.4 years (range: 18–74 years) Health Status: unhealthy Age Group: 49.4 years (range: 18–74 years) Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/20533760	Sources: https://pubmed.ncbi.nlm.nih.gov/20533760

AEs

AE	Significance	Dose	Population
Methaemoglobinaemia	2 patients	20 % single, topical Dose: 20 % Route: topical Route: single Dose: 20 % Sources: https://pubmed.ncbi.nlm.nih.gov/18971079 https://pubmed.ncbi.nlm.nih.gov/17694687	unhealthy, 17-71 years Health Status: unhealthy Age Group: 17-71 years Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/18971079 https://pubmed.ncbi.nlm.nih.gov/17694687

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	substrate 1193	substrate 1388

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
voltage-gated Na channels 2	CYP1A1 389 CYP1A2 1197 CYP2B6 776 CYP2C19 1119 CYP2E1 729 UGT 219

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
voltage-gated Na channels 2	inhibitor 4027 Sources: https://pubmed.ncbi.nlm.nih.gov/19661462/ Page: -	yes

Drug as victim

Target	Modality	Activity
CYP1A1 389	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
CYP1A2 1197	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
CYP2B6 776	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
CYP2C19 1119	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
CYP2C9 1193	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
CYP2D6 1388	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
CYP2E1 729	substrate 4014 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
UGT 219	substrate 4014 Sources: https://dmd.aspetjournals.org/content/47/3/271 Page: -	yes

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:116735	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:116735
ChemicalBook	CB1217951	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB1217951
ChemicalBook	CB9339022	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9339022
eMolecules	476470	https://www.emolecules.com/cgi-bin/more?vid=476470
MolPort	MolPort-000-871-526	https://www.molport.com/shop/molecule-link/MolPort-000-871-526
ZINC	ZINC000012358719	http://zinc15.docking.org/substances/ZINC000012358719

PubMed

Title	Date	PubMed
Acute methemoglobinemia after endoscopy.	2004-07-01	15226289
Prospective randomized study of viscous lidocaine versus benzocaine in a GI cocktail for dyspepsia.	2004-07	15219296
Reported adverse event cases of methemoglobinemia associated with benzocaine products.	2004-06-14	15197044
George Crile, Harvey Cushing, and the Ambulance Americaine: military medical preparedness in World War I.	2004-06	15197098
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.	2004-05	15149505
Iatrogenic methemoglobinemia from benzocaine spray in trauma.	2004-05	15138963
Contact dermatitis and other skin conditions in instrumental musicians.	2004-04-16	15090069
Effects of the local anesthetic benzocaine on the human erythrocyte membrane and molecular models.	2004-04-01	15059670
Respiratory failure secondary to methemoglobinemia induced by benzocaine: a case report.	2004-04	15119100
Critical rebound methemoglobinemia after methylene blue treatment: case report.	2004-04	15098811
Tongue entrapment in an aluminum juice can.	2004-04	15057180
The need for caution with topical anesthesia during endoscopic procedures, as liberal use may result in methemoglobinemia.	2004-03	15128067
Methemoglobinemia: an unusual cause of postoperative cyanosis.	2004-03	14981472
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.	2004-02-17	15111272
Detection of apple juice concentrate in the manufacture of natural and sparkling cider by means of HPLC chemometric sugar analyses.	2004-01-28	14733495
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.	2004-01	14707490
Colorimetric determination of benzocaine, lignocaine and procaine hydrochlorides in pure form and in pharmaceutical formulations using p-benzoquinone.	2003-10	14596417
Analgesic synergy between topical morphine and butamben in mice.	2003-10	14500165
Children's preference of benzocaine gel versus the lidocaine patch.	2003-09-19	13678108
Angioedema as a complication of upper endoscopy.	2003-08-05	12899608
Lipid-protein interactions and effect of local anesthetics in acetylcholine receptor-rich membranes from Torpedo marmorata electric organ.	2003-08-05	12885251
The association between ambient air conditions (temperature and absolute humidity), irritant sodium lauryl sulfate patch test reactions and patch test reactivity to standard allergens.	2003-08	14641358
Dangerous in small amounts: ten nondrug substances that cause harm.	2003-08	12874566
Preparation and evaluation of bioadhesive benzocaine gels for enhanced local anesthetic effects.	2003-07-09	12818812
Bye-bye benzocaine?	2003-07	12862005
Influence of site preparation methods on the pain reported during palatal infiltration using the Wand Local Anesthetic System.	2003-06	12967069
Effects of isoeugenol on in vitro neuromuscular blockade of rat phrenic nerve-diaphragm preparations.	2003-06	12828253
Severe methemoglobinemia after transesophageal echocardiography.	2003-05-21	12756430
Suspected methemoglobinemia following awake intubation: one possible effect of benzocaine topical anesthesia--a case report.	2003-04	12776639
Spectrophotometric determination of labetalol in pharmaceutical preparations and spiked human urine.	2003-04	12727538
Two cases of methemoglobinemia from the use of topical anesthetics.	2003-04	12660690
Benzocaine-induced methemoglobinemia.	2003-03	12629296
Thermodynamics of partitioning of benzocaine in some organic solvent/buffer and liposome systems.	2003-03	12612403
Effect of prolonged exposure to low antigen concentration for sensitization.	2003-02-14	12505373
Evolution of sugars in cider brandy aged in oak barrels: a contribution to its characterization.	2003-02-12	12568550
Patch testing with the irritant sodium lauryl sulfate (SLS) is useful in interpreting weak reactions to contact allergens as allergic or irritant.	2003-02	12694214
Black henna tattoo reaction in a person with sulfonamide and benzocaine drug allergies.	2003-02	12582412
Benzocaine-induced methemoglobinemia: experience from a high-volume transesophageal echocardiography laboratory.	2003-02	12574744
Kv1.1 channels of dorsal root ganglion neurons are inhibited by n-butyl-p-aminobenzoate, a promising anesthetic for the treatment of chronic pain.	2003-02	12538804
Anesthesia of fish with benzocaine does not interfere with comet assay results.	2003-01-10	12504765
Methemoglobinemia and topical pharyngeal anesthesia.	2003-01-02	12510055
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.	2003-01	12595037
Effectiveness of 20% benzocaine as a topical anesthetic for intraoral injections.	2003	14959903
Benzocaine-induced methemoglobinemia: a potentially fatal complication of transesophageal echocardiography.	2003	14677742
Efficacy and tolerability of an intraoral benzocaine patch in the relief of spontaneous toothache pain.	2003	12619262
Determination of linkages of linear and branched oligosaccharides using closed-ring chromophore labeling and negative ion trap mass spectrometry.	2002-11	12443023
The use of lubricants to achieve tracheal intubation in neonates and infants.	2002-10	12472715
[Photocontact dermatitis due to ketoprofen and photosensitization to tetrachlorosalicylanide and to Fenticlor(R)].	2002-10	12442124
Should a mucoadhesive patch (DentiPatch) be used for gingival anesthesia in children?	2002	12779107
Evaluation of an acetic acid ester of monoglyceride as a suppository base with unique properties.	2001-07-17	14727872

Patents

Sample Use Guides

In Vivo Use Guide

Apply topically to the skin as an aerosol spray, cream, lotion, ointment, or solution.

Route of Administration: Other

In Vitro Use Guide

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 `Wed Apr 02 18:52:36 GMT 2025` Edited by `admin` on `Wed Apr 02 18:52:36 GMT 2025`
Record UNII	U3RSY48JW5
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ETHYL PABA

Preferred Name

English

BENZOCAINE

Official 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

ETHYL PARA-AMINO BENZOATE

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