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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 Thumb
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
Brand names
  • 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 name mixtures
  • 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 (7.7 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
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
Smp00392 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
Patents Not Available
Properties
State solid
Melting point 92 oC
Experimental Properties
Property Value Source
water solubility 1310 mg/L PhysProp
logP 1.6 PhysProp
pKa 2.51 Various sources
Predicted Properties
Property Value Source
water solubility 2.85e+00 g/l ALOGPS
logP 2.20 ALOGPS
logP 1.50 ChemAxon Molconvert
logS -1.76 ALOGPS
pKa ChemAxon Molconvert
hydrogen acceptor count 2 ChemAxon Molconvert
hydrogen donor count 1 ChemAxon Molconvert
polar surface area 52.32 ChemAxon Molconvert
rotatable bond count 3 ChemAxon Molconvert
refractivity 47.53 ChemAxon Molconvert
polarizability 17.44 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Drug D00552 Link_out
KEGG Compound C07527 Link_out
PubChem Compound 2337 Link_out
PubChem Substance 46508891 Link_out
ChemSpider 13854242 Link_out
ChEBI 116735 Link_out
ChEMBL 116735 Link_out
Therapeutic Targets Database DAP001234 Link_out
PharmGKB PA448576 Link_out
Drug Product Database 2223805 Link_out
RxList http://www.rxlist.com/cgi/generic3/americaine.htm Link_out
Drugs.com http://www.drugs.com/cdi/benzocaine-drops.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Benzocaine Link_out
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
Drug Interaction
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 Link_out
Gene: SCN10A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. Pubmed
  2. 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
  3. 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
  4. 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
  5. 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
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:
  1. 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 July 23, 2011 21:32

This project is supported by Genome Alberta & Genome Canada, a not-for-profit organization that is leading Canada's national genomics strategy with $600 million in funding from the federal government. This project is also supported in part by GenomeQuest, Inc., an enterprise genomic information company serving the life science community.