DrugBank: Benzocaine (DB01086)

targets (1) enzymes (1) transporters (1)

Identification

Name

Benzocaine

Accession Number

DB01086 (APRD00539)

Type

small molecule

Groups

approved

Description

A surface anesthetic that acts by preventing transmission of impulses along nerve fibers and at nerve endings. [PubChem]

Structure

Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure

Synonyms

Ethyl Aminobenzoate
Ethyl P-Aminobenzoate
Ethyl P-Aminophenylcarboxylate
Ethylester Kyseliny P-Aminobenzoove
P-Aminobenzoic Acid, Ethyl Ester
P-Carbethoxyaniline
P-Ethoxycarboxylic Aniline

Salts

Not Available

Brand names

Name	Company
Aethoform
Amben Ethyl Ester
Americaine
Anaesthan-Syngala
Anaesthesin
Anaesthin
Anestezin
Anesthesin
Anesthesine
Anesthone
Baby Anbesol
Dermoplast
Ethoform
Hurricaine
Identhesin
Keloform
Norcain
Norcaine
Ora-Jel
Orthesin
Parathesin
Parathesine
Solu H
Topcaine

Brand mixtures

Brand Name	Ingredients
Anbesol Gel	Benzocaine + Phenol
Anbesol Liquid	Benzocaine + Camphor + Menthol + Phenol
Anbesol Maximum Strength Liquid	Benzocaine + Camphor + Menthol + Phenol
Anivy	Benzocaine + Chlorphenesin + Titanium Dioxide + Zinc Oxide
Antibiotic Cold Sore Ointment	Benzocaine + Camphor + Menthol + Polymyxin B + Tyrothricin
Antibiotic Lozenges	Benzocaine + Cetylpyridinium Chloride + Polymyxin B Sulfate + Tyrothricin
Appedrine	Benzocaine + Iron (Ferrous Fumarate) + Nicotinamide + Thiamine Hydrochloride + Vitamin a (Vitamin a Acetate) + Vitamin B2 + Vitamin C (Sodium Ascorbate) + Vitamin D
Arkodyne	Benzalkonium Chloride + Benzocaine + Oxyquinoline Sulfate
Auralgan Eardrops	Antipyrine + Benzocaine
Auralgan Solution	Antipyrine + Benzocaine
Aurisan Dps	Benzocaine + Camphor + Chlorobutanol
Balminil Loz	Benzocaine + Cetylpyridinium Chloride
Balsaris Ont	Allantoin + Benzocaine + Phenol
Balzarol Ont	Allantoin + Benzocaine + Phenol
Bionet Lozenge	Benzocaine + Cetalkonium Chloride
Bite Relief	Benzocaine + Camphor + Menthol + Phenol
Boil Ease Drawing Salve Ont	Benzocaine + Camphor + Ichthammol + Juniper Tar + Phenol + Sulfur + Thymol + Zinc Oxide
Burn O Sol Spray	Benzocaine + Chlorhexidine Acetate
Burncare Kit	Benzocaine + Lidocaine Hydrochloride
Bye Bye Bite Lot	Benzocaine + Diphenhydramine Hydrochloride + Menthol
Bye Bye Burn Lot	Allantoin + Benzocaine + Cetrimonium Bromide + Vitamin E
Canoids Cap	Aloin + Areca Catechu + Arecoline Hbr + Benzocaine + Piperazine Citrate + Santonin
Cepacol Citrus Extra Strength Lozenges	Benzocaine + Cetylpyridinium Chloride
Cepacol Extra Strength Lozenge	Benzocaine + Cetylpyridinium Chloride
Cepacol Extra Strength Orange Citrus Lozenge	Benzocaine + Cetylpyridinium Chloride
Cepacol Sore Throat Extra Strength Sucrose-Free Lozenge	Cherry Flavour) (Benzocaine + Cetylpyridinium Chloride
Cetacaine Liquid	Benzocaine + Butamben + Tetracaine Hydrochloride
Cetacaine Spray	Benzocaine + Butamben + Tetracaine Hydrochloride
Chloraseptic Sore Throat Lozenges - Cherry	Benzocaine + Menthol
Chloraseptic Sore Throat Lozenges - Menthol	Benzocaine + Menthol
Chloraseptic Sore Throat Relief Strips	Benzocaine + Menthol
Cold Sore Lotion	Benzocaine + Benzoin + Camphor + Menthol + Myrrh
Cora Caine	Benzocaine + Methyl Heptyl Colamino Formylmethyl Pyridinium Chl
Dentalgar Liq	Benzocaine + Camphor + Clove Oil + Guaiacol + Menthol
Denti-Care Topical Anesthetic Gel	Benzocaine + Tetracaine Hydrochloride
Denti-Care Topical Anesthetic Liquid Spray	Benzocaine + Tetracaine Hydrochloride
Denture Orajel Gel	Benzocaine + Benzyl Alcohol + Clove Oil
Dermaphy Ont	Benzocaine + Phenol
Dermoplast	Benzocaine + Menthol
Dermoplast Aer	Benzethonium Chloride + Benzocaine + Menthol + Methylparaben + Oxyquinoline Benzoate
Dermoplast Aerosol Spray	Benzethonium Chloride + Benzocaine + Menthol + Oxyquinoline Benzoate
Dexatrim Tablets	Benzocaine + Iron (Ferrous Fumarate) + Nicotinamide + Thiamine Hydrochloride + Vitamin a (Vitamin a Acetate) + Vitamin B2 + Vitamin C (Sodium Ascorbate) + Vitamin D (Vitamin D3)
Ear Clear	Benzocaine + Chlordan(E) + Dichlorophene + Methapyrilene Hcl. + Propylene Glycol
Emercol Loz	Benzocaine + Cetalkonium Chloride + Cetylpyridinium Chloride
Emercreme No4 Ont Efa	Bacitracin + Benzocaine + Cetylpyridinium Chloride + Diphenylpyraline Hydrochloride + Tyrothricin
Endospray	Benzocaine + Tetracaine Hydrochloride
Extra Strength Lanacane	Benzocaine + Resorcinol
Extra Strength Vagisil	Benzocaine + Resorcinol
Feloids Tab	Aloin + Areca Catechu + Arecoline Hbr + Benzocaine + Piperazine Citrate + Santonin
Foille Ont	Benzocaine + Benzyl Alcohol
Freezex Ont	Benzocaine + Menthol + Methyl Salicylate
Gercillin	Bacitracin + Benzocaine + Polymyxin B Sulfate + Tyrothricin
Gouttes Dentaires	Benzocaine + Camphor + Clove Oil + Guaiacol + Menthol
Gouttes Pour Mal d'Oreilles	Benzocaine + Camphor + Chlorobutanol
Hemorro-Dol Ont	Allantoin + Belladonna + Benzocaine + Bismuth Subcarbonate (Oxycarbonate) + Bismuth Subnitrate + Ephedrine Sulfate + Peruvian Balsam + Zinc Oxide
Hemorro-Dol Sup	Belladonna + Benzocaine + Bismuth Subcarbonate (Oxycarbonate) + Bismuth Subnitrate + Boric Acid + Ephedrine Sulfate + Peruvian Balsam + Zinc Oxide
Jiffy Toothache Drops	Benzocaine + Eugenol
Kama Sutra Pleasure Balm	Benzocaine + Camphor + Menthol
Kank-a Liq	Benzocaine + Cetylpyridinium Chloride
Lanacane Anti-Bacterial First Aid Spray	Benzethonium Chloride + Benzocaine
Lanacane Crm Medication	Benzocaine + Resorcinol
Laryngets Loz	Benzocaine + Cetylpyridinium Chloride + Polymyxin B Sulfate + Tyrothricin
Mites Out	Solution for Dogs and Cats) (Benzocaine + Docusate Sodium + Hydrocortisone + Piperonyl Butoxide + Pyrethrins + Tyrothricin
Noivy Ont	Benzocaine + Calamine + Camphor + Menthol
Onrectal	Benzocaine + Bismuth Subcarbonate (Oxycarbonate) + Bismuth Subgallate + Hamamelis Virginiana + Naphazoline Hydrochloride + Zinc Oxide
Orajel Denture Plus	Benzocaine + Menthol
Orajel Mouth Sore Medicine	Benzocaine + Zinc Chloride
Orajel Mouth-Aid	Benzalkonium Chloride + Benzocaine + Zinc Chloride
Orajel Multi-Action Cold Sore Medicine	Allantoin + Benzocaine + Camphor + Dimethicone + Menthol + White Petrolatum
Orajel Ultra Canker Sore Medicine	Benzocaine + Menthol
Oralgar Dps	Benzocaine + Camphor + Chlorobutanol
Osmopak Plus	Benzocaine + Magnesium Sulfate
Oti Cal	Antipyrine + Benzocaine
Oxipor Lotion	Benzocaine + Coal Tar + Salicylic Acid
Panocaine Gel	Benzocaine + Tetracaine Hydrochloride
Pastilles Antiseptiques Jener	Benzocaine + Cetylpyridinium Chloride
Pastilles Merol	Benzocaine + Cetylpyridinium Chloride
Permathene-12 - Caplet	Benzocaine + Iron (Ferrous Fumarate) + Nicotinamide + Thiamine Hydrochloride + Vitamin a + Vitamin B2 + Vitamin C (Sodium Ascorbate) + Vitamin D
Pommade Midy	Aesculus Hippocastanum + Amylocaine Hydrochloride + Benzocaine + Hamamelis Virginiana
Pulmosirum Pastille	Benzocaine + Cetylpyridinium Chloride + Polymyxin B Sulfate + Tyrothricin
Rectogel Hc	Benzocaine + Hydrocortisone Acetate + Zinc Sulfate
Rectogel Ont	Benzocaine + Zinc Sulfate
Slim-Mint Gum	Benzocaine + Methylcellulose
Solarcaine First Aid Cream	Benzocaine + Triclosan
Solarcaine First Aid Spray	Benzocaine + Triclosan
Solarcaine Medicated First Aid Lotion	Benzocaine + Triclosan
Sore Throat Lozenges Menthol Flavour	Benzocaine + Menthol
Sore Throat Lozenges with Benzocaine and Menthol	Benzocaine + Menthol
Sting Eze	Benzocaine + Phenol
Sting Kure - Liq	Benzocaine + Camphor + Diphenhydramine Hydrochloride + Phenol
Sting-Eze-Liq	Benzocaine + Camphor + Diphenhydramine Hydrochloride + Phenol
Tanac Liquid	Benzalkonium Chloride + Benzocaine + Tannic Acid
Thermo-Gel	Benzocaine + Camphor + Menthol + Thymol
Throat Lozenges	Benzocaine + Cetylpyridinium Chloride
Thunas Pile Sup	Benzocaine + Bismuth Subcarbonate (Oxycarbonate) + Ephedrine Sulfate + Zinc Oxide
Topicale Gel Pump Pina Colada	Benzalkonium Chloride + Benzocaine
Udder Ointment with Lanolin	Benzocaine + Camphor + Eucalyptol + Lanolin + Methyl Salicylate + Phenol
Vagisil Crm Medication	Benzocaine + Resorcinol
Zap Liquid	Benzocaine + Tetracaine Hydrochloride
Zap Topical Anesthetic Gel Cool Mint	Benzocaine + Tetracaine Hydrochloride
Zap Topical Anesthetic Spray	Benzocaine + Tetracaine Hydrochloride

Categories

Antipruritics
Anesthetics
Local Anesthetics
Anesthetics, Local

CAS number

94-09-7

Weight

Average: 165.1891
Monoisotopic: 165.078978601

Chemical Formula

C₉H₁₁NO₂

InChI Key

InChIKey=BLFLLBZGZJTVJG-UHFFFAOYSA-N

InChI

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

Plain Text

IUPAC Name

ethyl 4-aminobenzoate

SMILES

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

Plain Text

Mass Spec

show (7.74 KB)

Taxonomy

Kingdom

Organic

Classes

Aminobenzoates

Substructures

Aminobenzoates
Carboxylic Acids and Derivatives
Benzyl Alcohols and Derivatives
Acetates
Benzoates
Aliphatic and Aryl Amines
Ethers
Benzene and Derivatives
Aromatic compounds
Benzoyl Derivatives
Anilines

Pharmacology

Indication

For general use as a lubricant and topical anesthetic on esophagus, larynx, mouth, nasal cavity, rectum, respiratory tract or trachea, urinary tract, vagina. It is also used to suppress gag reflex.

Pharmacodynamics

Benzocaine is a local anesthetic commonly used as a topical pain reliever. It is the active ingredient in many over-the-counter analgesic ointments. It is also indicated for general use as a lubricant and topical anesthetic on intratracheal catheters and pharyngeal and nasal airways to obtund the pharyngeal and tracheal reflexes; on nasogastric and endoscopic tubes; urinary catheters; laryngoscopes; proctoscopes; sigmoidoscopes and vaginal specula.

Mechanism of action

Benzocaine binds to sodium channels and reversibly stabilizes the neuronal membrane which decreases its permeability to sodium ions. Depolarization of the neuronal membrane is inhibited thereby blocking the initiation and conduction of nerve impulses.

Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism

Not Available

Route of elimination

Not Available

Half life

Not Available

Clearance

Not Available

Toxicity

LD₅₀=3040 mg/kg (rat, oral)

Affected organisms

Humans and other mammals

Pathways

Pathway	Name	SMPDB ID
	Benzocaine Pathway	SMP00392

Pharmacoeconomics

Manufacturers

Not Available

Packagers

Dosage forms

Form	Route	Strength
Aerosol	Buccal
Aerosol	Dental
Gel	Dental
Gel	Oral
Gel	Topical
Liquid	Oral
Liquid	Topical
Ointment	Topical
Paste	Dental
Paste	Oral
Swab	Oral
Swab	Topical

Prices

Unit description	Cost	Unit
Americaine Anesthetic 20% Gel 28 gm Tube	22.99 USD	tube
Americaine 20% ear drops	1.26 USD	ml
Oticaine 20% ear drops	0.83 USD	ml
Americaine lubricant	0.71 USD	g
Hurricaine 20% liquid swab	0.6 USD	swab
Hurricaine 20% spray	0.52 USD	ml
Anbesol baby 7.5% gel	0.41 USD	g
Cepacol 6 mg fizzlers tablet	0.39 USD	tablet
Benzocaine powder	0.09 USD	g
Dermoplast pain relieving spry	0.07 USD	ml
Dermoplast spray	0.07 USD	ml

DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.

Patents

Not Available

Properties

State

solid

Experimental Properties

Property	Value	Source
melting point	92 °C	PhysProp
boiling point	310 °C	PhysProp
water solubility	1310 mg/L (at 30 °C)	YALKOWSKY,SH & HE,Y (2003)
logP	1.86	HANSCH,C ET AL. (1995)
pKa	2.51 (at 25 °C)	PERRIN,DD (1965)

Predicted Properties

Property	Value	Source
water solubility	2.85e+00 g/l	ALOGPS
logP	2.2	ALOGPS
logP	1.5	ChemAxon
logS	-1.8	ALOGPS
pKa (strongest basic)	2.78	ChemAxon
physiological charge	0	ChemAxon
hydrogen acceptor count	2	ChemAxon
hydrogen donor count	1	ChemAxon
polar surface area	52.32	ChemAxon
rotatable bond count	3	ChemAxon
refractivity	47.53	ChemAxon
polarizability	17.46	ChemAxon

References

Synthesis Reference

Not Available

General Reference

Not Available

External Links

Resource	Link
KEGG Drug	D00552
KEGG Compound	C07527
PubChem Compound	2337
PubChem Substance	46508891
ChemSpider	13854242
ChEBI	116735
ChEMBL	116735
Therapeutic Targets Database	DAP001234
PharmGKB	PA448576
Drug Product Database	2223805
RxList	http://www.rxlist.com/cgi/generic3/americaine.htm
Drugs.com	http://www.drugs.com/cdi/benzocaine-drops.html
Wikipedia	http://en.wikipedia.org/wiki/Benzocaine

ATC Codes

C05AD03
D04AB04
N01BA05
R02AD01
A01AD11

AHFS Codes

52:16.00
84:08.00

PDB Entries

Not Available

FDA label

Not Available

MSDS

show (73.3 KB)

Interactions

Drug Interactions

Searched, but no interactions found.

Food Interactions

Not Available

Targets
1. Sodium channel protein type 10 subunit alpha Pharmacological action: yes Actions: inhibitor This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms Organism class: human UniProt ID: Q9Y5Y9 Gene: SCN10A Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed Ahern CA, Eastwood AL, Dougherty DA, Horn R: Electrostatic contributions of aromatic residues in the local anesthetic receptor of voltage-gated sodium channels. Circ Res. 2008 Jan 4;102(1):86-94. Epub 2007 Oct 25. Pubmed Hanck DA, Nikitina E, McNulty MM, Fozzard HA, Lipkind GM, Sheets MF: Using lidocaine and benzocaine to link sodium channel molecular conformations to state-dependent antiarrhythmic drug affinity. Circ Res. 2009 Aug 28;105(5):492-9. Epub 2009 Aug 6. Pubmed Lipkind GM, Fozzard HA: Molecular modeling of local anesthetic drug binding by voltage-gated sodium channels. Mol Pharmacol. 2005 Dec;68(6):1611-22. Epub 2005 Sep 20. Pubmed

Targets

1. Sodium channel protein type 10 subunit alpha

Pharmacological action: yes
Actions: inhibitor

This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which sodium ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant sodium channel isoform. Its electrophysiological properties vary depending on the type of the associated beta subunits (in vitro). Plays a role in neuropathic pain mechanisms

Organism class: human
UniProt ID: Q9Y5Y9 Link_out

Gene: SCN10A Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. Pubmed
Ahern CA, Eastwood AL, Dougherty DA, Horn R: Electrostatic contributions of aromatic residues in the local anesthetic receptor of voltage-gated sodium channels. Circ Res. 2008 Jan 4;102(1):86-94. Epub 2007 Oct 25. Pubmed
Hanck DA, Nikitina E, McNulty MM, Fozzard HA, Lipkind GM, Sheets MF: Using lidocaine and benzocaine to link sodium channel molecular conformations to state-dependent antiarrhythmic drug affinity. Circ Res. 2009 Aug 28;105(5):492-9. Epub 2009 Aug 6. Pubmed
Lipkind GM, Fozzard HA: Molecular modeling of local anesthetic drug binding by voltage-gated sodium channels. Mol Pharmacol. 2005 Dec;68(6):1611-22. Epub 2005 Sep 20. Pubmed

Enzymes
1. Liver carboxylesterase 1 Actions: inhibitor Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl CoA ester UniProt ID: P23141 Gene: CES1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Bell FP: The effect of local anesthetics on arterial lipid metabolism. Inhibition of sterol esterification in vitro. Atherosclerosis. 1981 Jan-Feb;38(1-2):81-8. Pubmed

Enzymes

1. Liver carboxylesterase 1

Actions: inhibitor

Involved in the detoxification of xenobiotics and in the activation of ester and amide prodrugs. Hydrolyzes aromatic and aliphatic esters, but has no catalytic activity toward amides or a fatty acyl CoA ester

UniProt ID: P23141 Link_out

Gene: CES1
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Bell FP: The effect of local anesthetics on arterial lipid metabolism. Inhibition of sterol esterification in vitro. Atherosclerosis. 1981 Jan-Feb;38(1-2):81-8. Pubmed

Transporters
1. Multidrug resistance protein 1 Actions: inhibitor Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells UniProt ID: P08183 Gene: ABCB1 Protein Sequence: FASTA Gene Sequence: FASTA SNPs: SNPJam Report References: Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. Pubmed

Transporters

1. Multidrug resistance protein 1

Actions: inhibitor

Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells

UniProt ID: P08183 Link_out

Gene: ABCB1 Link_out

Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:

Nagy H, Goda K, Fenyvesi F, Bacso Z, Szilasi M, Kappelmayer J, Lustyik G, Cianfriglia M, Szabo G Jr: Distinct groups of multidrug resistance modulating agents are distinguished by competition of P-glycoprotein-specific antibodies. Biochem Biophys Res Commun. 2004 Mar 19;315(4):942-9. Pubmed

Comments

Drug created on June 13, 2005 07:24 / Updated on February 08, 2013 16:19