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 537		0.32 mM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Sore mouth 2 Sources: https://www.ncbi.nlm.nih.gov/pubmedhealth/PMHT0009234/	Palliative	Approved 8429	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 8429	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 8429	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 8429	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 8429	AMERICAINE HEMORRHOIDAL Approved Use Self-medication for temporary relief of pain and itching associated with hemorrhoids
Otitis media 41 Sources: https://www.drugs.com/cdi/benzocaine-drops.html	Palliative	Approved 8429	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 n = 2 Health Status: unhealthy Age Group: 17-71 years Sex: F Population Size: 2 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) n = 246 Health Status: unhealthy Age Group: 49.4 years (range: 18–74 years) Sex: M+F Population Size: 246 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 n = 2 Health Status: unhealthy Age Group: 17-71 years Sex: F Population Size: 2 Sources: https://pubmed.ncbi.nlm.nih.gov/18971079 https://pubmed.ncbi.nlm.nih.gov/17694687

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
	substrate 1037	substrate 1217

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
voltage-gated Na channels 2	CYP1A1 349 CYP1A2 1054 CYP2B6 664 CYP2C19 991 CYP2E1 667 UGT 192

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
voltage-gated Na channels 2	inhibitor 3277 Sources: https://pubmed.ncbi.nlm.nih.gov/19661462/ Page: -	yes

Drug as victim

Target	Modality	Activity
CYP1A1 349	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
CYP1A2 1054	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
CYP2B6 664	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
CYP2C19 991	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
CYP2C9 1037	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
CYP2D6 1217	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
CYP2E1 667	substrate 3367 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
UGT 192	substrate 3367 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
MolPort	MolPort-000-871-526	https://www.molport.com/shop/molecule-link/MolPort-000-871-526
ZINC	ZINC000012358719	http://zinc15.docking.org/substances/ZINC000012358719
eMolecules	476470	https://www.emolecules.com/cgi-bin/more?vid=476470

PubMed

Title	Date	PubMed
The optimization test in the guinea-pig. A method for the predictive evaluation of the contact allergenicity of chemicals.	1975 May	1155304
Clinical evaluation and comparison of 2 topical anesthetics for pain caused by needle sticks and scaling and root planing.	2001 Apr	11338300
Contact dermatitis in students practicing sports: incidence of rubber sensitisation.	2001 Apr	11273970
From cocaine to ropivacaine: the history of local anesthetic drugs.	2001 Aug	11895133
Reducing children's injection pain: lidocaine patches versus topical benzocaine gel.	2001 Jan-Feb	11242725
[The killing of aquarium fish by their owners].	2001 Jul 15-Aug 1	11510375
Evaluation of an acetic acid ester of monoglyceride as a suppository base with unique properties.	2001 Jul 17	14727872
Benzocaine-induced methemoglobinemia accompanying adult respiratory distress syndrome and sepsis syndrome: case report.	2001 Jun	11426135
Severe methemoglobinemia on reexposure to benzocaine.	2001 Mar	11331174
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	11722711
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	11824812
The role of fat and cholecystokinin in functional dyspepsia.	2002 Jul	12077066
Perioperatively acquired methaemoglobinaemia in a preterm infant.	2002 Mar	11903945
The antinociceptive and histologic effect of sciatic nerve blocks with 5% butamben suspension in rats.	2002 Mar	11867403
Effects of anaesthesia on blood gases, acid-base status and ions in the toad Bufo marinus.	2002 Mar	11867289
Determination of linkages of linear and branched oligosaccharides using closed-ring chromophore labeling and negative ion trap mass spectrometry.	2002 Nov	12443023
Benzoate X receptors alpha and beta are pharmacologically distinct and do not function as xenobiotic receptors.	2002 Nov 15	12198127
The use of lubricants to achieve tracheal intubation in neonates and infants.	2002 Oct	12472715
[Photocontact dermatitis due to ketoprofen and photosensitization to tetrachlorosalicylanide and to Fenticlor(R)].	2002 Oct	12442124
Effective topical anesthetic agents and techniques.	2002 Oct	12436830
Putative binding sites for benzocaine on a human cardiac cloned channel (Kv1.5).	2002 Oct	12237171
Methemoglobinemia induced by topical benzocaine: a warning for the endoscopist.	2002 Sep	12195332
Should a mucoadhesive patch (DentiPatch) be used for gingival anesthesia in children?	2002 Winter	12779107
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
Spectrophotometric determination of labetalol in pharmaceutical preparations and spiked human urine.	2003 Apr	12727538
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	14641358
Dangerous in small amounts: ten nondrug substances that cause harm.	2003 Aug	12874566
Angioedema as a complication of upper endoscopy.	2003 Aug 5	12899608
Lipid-protein interactions and effect of local anesthetics in acetylcholine receptor-rich membranes from Torpedo marmorata electric organ.	2003 Aug 5	12885251
Black henna tattoo reaction in a person with sulfonamide and benzocaine drug allergies.	2003 Feb	12582412
Benzocaine-induced methemoglobinemia: experience from a high-volume transesophageal echocardiography laboratory.	2003 Feb	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 Feb	12538804
Evolution of sugars in cider brandy aged in oak barrels: a contribution to its characterization.	2003 Feb 12	12568550
Bye-bye benzocaine?	2003 Jul	12862005
Preparation and evaluation of bioadhesive benzocaine gels for enhanced local anesthetic effects.	2003 Jul 9	12818812
Influence of site preparation methods on the pain reported during palatal infiltration using the Wand Local Anesthetic System.	2003 Jun	12967069
Effects of isoeugenol on in vitro neuromuscular blockade of rat phrenic nerve-diaphragm preparations.	2003 Jun	12828253
Thermodynamics of partitioning of benzocaine in some organic solvent/buffer and liposome systems.	2003 Mar	12612403
Severe methemoglobinemia after transesophageal echocardiography.	2003 May-Jun	12756430
Colorimetric determination of benzocaine, lignocaine and procaine hydrochlorides in pure form and in pharmaceutical formulations using p-benzoquinone.	2003 Oct	14596417
Analgesic synergy between topical morphine and butamben in mice.	2003 Oct	14500165
Critical rebound methemoglobinemia after methylene blue treatment: case report.	2004 Apr	15098811
Tongue entrapment in an aluminum juice can.	2004 Apr	15057180
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	14707490
Prospective randomized study of viscous lidocaine versus benzocaine in a GI cocktail for dyspepsia.	2004 Jul	15219296
George Crile, Harvey Cushing, and the Ambulance Americaine: military medical preparedness in World War I.	2004 Jun	15197098
The need for caution with topical anesthesia during endoscopic procedures, as liberal use may result in methemoglobinemia.	2004 Mar	15128067
Acute methemoglobinemia after endoscopy.	2004 May-Jun	15226289

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 `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

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Name

Type

Language

BENZOCAINE

Official Name

English

ETHYL PABA

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