BENZOCAINE HYDROCHLORIDE

US Approved OTC

First marketed in 1895

Details

Stereochemistry	ACHIRAL
Molecular Formula	C9H11NO2.ClH
Molecular Weight	201.65
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=JAADDQHUJDUAKW-UHFFFAOYSA-N

InChI=1S/C9H11NO2.ClH/c1-2-12-9(11)7-3-5-8(10)6-4-7;/h3-6H,2,10H2,1H3;1H

HIDE SMILES / InChI

Molecular Formula	ClH
Molecular Weight	36.461
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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 534		0.32 mM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Sore mouth 2 Sources: https://www.ncbi.nlm.nih.gov/pubmedhealth/PMHT0009234/	Palliative	Approved 8360	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 8360	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 8360	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 8360	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 8360	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 8360	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 1010	substrate 1193

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
voltage-gated Na channels 2	CYP1A1 348 CYP1A2 1032 CYP2B6 660 CYP2C19 985 CYP2E1 648 UGT 187

Drug as perpetrator

Target	Modality	Activity	Metabolite	Clinical evidence
voltage-gated Na channels 2	inhibitor 3240 Sources: https://pubmed.ncbi.nlm.nih.gov/19661462/ Page: -	yes

Drug as victim

Target	Modality	Activity
CYP1A1 348	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
CYP1A2 1032	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
CYP2B6 660	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
CYP2C19 985	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
CYP2C9 1010	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
CYP2D6 1193	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
CYP2E1 648	substrate 3326 Sources: https://pubmed.ncbi.nlm.nih.gov/25010377/ Page: -	yes
UGT 187	substrate 3326 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
Clinical evaluation and comparison of 2 topical anesthetics for pain caused by needle sticks and scaling and root planing.	2001 Apr	11338300
Pharmacological regulation of gastric acid secretion in the apical membrane of parietal cells; a new target for antisecretory drugs.	2001 Dec	11787764
Modulation of gastric distension-induced sensations by small intestinal receptors.	2001 Jan	11123197
[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
Controlled release from an electrorheological fluid dosage form: experimental results for a prototype system.	2001 Jul-Aug	11505558
Benzocaine-induced methemoglobinemia accompanying adult respiratory distress syndrome and sepsis syndrome: case report.	2001 Jun	11426135
Disappearing and reappearing polymorphs. The benzocaine:picric acid system.	2001 Mar 7	11456802
Inhibition of m3 muscarinic acetylcholine receptors by local anaesthetics.	2001 May	11325812
Allergic contact dermatitis to cinchocaine.	2001 May	11309035
Fluorescent labeling of drugs and simple organic compounds containing amine functional groups, utilizing dansyl chloride in Na(2)CO(3) buffer.	2001 May-Jun	11755390
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
Methemoglobinemia as a cause of respiratory failure.	2002 Apr	11956408
Local lymph node assay with non-radioisotope alternative endpoints.	2002 Aug	12238144
General solution for diffusion-controlled dissolution of spherical particles. 2. Evaluation of experimental data.	2002 Feb	11835211
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
Perioperatively acquired methaemoglobinaemia in a preterm infant.	2002 Mar	11903945
Topical anesthesia for minor gynecological procedures: a review.	2002 Mar	11889416
[Photocontact dermatitis due to ketoprofen and photosensitization to tetrachlorosalicylanide and to Fenticlor(R)].	2002 Oct	12442124
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
Spectrophotometric determination of labetalol in pharmaceutical preparations and spiked human urine.	2003 Apr	12727538
Two cases of methemoglobinemia from the use of topical anesthetics.	2003 Apr	12660690
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
Patch testing with the irritant sodium lauryl sulfate (SLS) is useful in interpreting weak reactions to contact allergens as allergic or irritant.	2003 Feb	12694214
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
Effect of prolonged exposure to low antigen concentration for sensitization.	2003 Feb 14	12505373
Methemoglobinemia and topical pharyngeal anesthesia.	2003 Jan 2	12510055
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
Critical rebound methemoglobinemia after methylene blue treatment: case report.	2004 Apr	15098811
Tongue entrapment in an aluminum juice can.	2004 Apr	15057180
Effects of the local anesthetic benzocaine on the human erythrocyte membrane and molecular models.	2004 Apr 1	15059670
Contact dermatitis and other skin conditions in instrumental musicians.	2004 Apr 16	15090069
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	15111272
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
Detection of apple juice concentrate in the manufacture of natural and sparkling cider by means of HPLC chemometric sugar analyses.	2004 Jan 28	14733495
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
Reported adverse event cases of methemoglobinemia associated with benzocaine products.	2004 Jun 14	15197044
Methemoglobinemia: an unusual cause of postoperative cyanosis.	2004 Mar	14981472
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	15149505

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 Jul 05 22:46:35 UTC 2023` Edited by `admin` on `Wed Jul 05 22:46:35 UTC 2023`
Record UNII	OG625Z9LEO
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

BENZOCAINE HYDROCHLORIDE

Common Name

English

NSC-122792

Code

English

AMBEN ETHYL ESTER HYDROCHLORIDE

Common Name

English

BENZOIC ACID, 4-AMINO-, ETHYL ESTER, HYDROCHLORIDE (1:1)

Common Name

English

Benzocaine hydrochloride [WHO-DD]

Common Name

English

ETHYL P-AMINOBENZOATE HYDROCHLORIDE

Common Name

English

BENZOIC ACID, P-AMINO-, ETHYL ESTER, HYDROCHLORIDE

Common Name

English

4-(ETHOXYCARBONYL)ANILINIUM CHLORIDE

Systematic Name

English

BENZOIC ACID, 4-AMINO-, ETHYL ESTER, HYDROCHLORIDE

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C245