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Identification
NameBenzocaine
Accession NumberDB01086  (APRD00539)
Typesmall molecule
Groupsapproved
Description

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

Structure
Thumb
Synonyms
SynonymLanguageCode
4-aminobenzoic acid ethyl esterNot AvailableNot Available
Amben ethyl esterNot AvailableNot Available
BenzocainaNot AvailableNot Available
BenzocaineNot AvailableNot Available
BenzocainumNot AvailableNot Available
Ethyl AminobenzoateNot AvailableNot Available
Ethyl p-AminobenzoateNot AvailableNot Available
Ethyl p-AminophenylcarboxylateNot AvailableNot Available
p-(Ethoxycarbonyl)anilineNot AvailableNot Available
p-CarbethoxyanilineNot AvailableNot Available
p-Ethoxycarboxylic AnilineNot AvailableNot Available
SaltsNot Available
Brand names
NameCompany
AmericaineNot Available
AnacaineNot Available
AnaesthesinNot Available
Anbesol BabyNot Available
DermoplastNot Available
Brand mixtures
Brand NameIngredients
Anbesol GelBenzocaine + Phenol
Anbesol LiquidBenzocaine + Camphor + Menthol + Phenol
AnivyBenzocaine + Chlorphenesin + Titanium Dioxide + Zinc Oxide
AppedrineBenzocaine + Iron (Ferrous Fumarate) + Nicotinamide + Thiamine Hydrochloride + Vitamin a (Vitamin a Acetate) + Vitamin B2 + Vitamin C (Sodium Ascorbate) + Vitamin D
ArkodyneBenzalkonium Chloride + Benzocaine + Oxyquinoline Sulfate
AuralganAntipyrine + Benzocaine
Burn O Sol SprayBenzocaine + Chlorhexidine Acetate
CepacolBenzocaine + Cetylpyridinium Chloride
CetacaineBenzocaine + Butamben + Tetracaine Hydrochloride
ChlorasepticBenzocaine + Menthol
EndosprayBenzocaine + Tetracaine Hydrochloride
Extra Strength LanacaneBenzocaine + Resorcinol
Extra Strength VagisilBenzocaine + Resorcinol
Lanacane Anti-Bacterial First Aid SprayBenzethonium Chloride + Benzocaine
Lanacane CreamBenzocaine + Resorcinol
OnrectalBenzocaine + Bismuth Subcarbonate (Oxycarbonate) + Bismuth Subgallate + Hamamelis Virginiana + Naphazoline Hydrochloride + Zinc Oxide
Orajel Denture PlusBenzocaine + Menthol
Orajel Mouth Sore MedicineBenzocaine + Zinc Chloride
Orajel Mouth-AidBenzalkonium Chloride + Benzocaine + Zinc Chloride
Orajel Multi-Action Cold Sore MedicineAllantoin + Benzocaine + Camphor + Dimethicone + Menthol + White Petrolatum
Orajel Ultra Canker Sore MedicineBenzocaine + Menthol
RectogelBenzocaine + Zinc Sulfate
SolarcaineBenzocaine + Triclosan
Sting EzeBenzocaine + Phenol
Categories
CAS number94-09-7
WeightAverage: 165.1891
Monoisotopic: 165.078978601
Chemical FormulaC9H11NO2
InChI KeyBLFLLBZGZJTVJG-UHFFFAOYSA-N
InChI
InChI=1S/C9H11NO2/c1-2-12-9(11)7-3-5-8(10)6-4-7/h3-6H,2,10H2,1H3
IUPAC Name
ethyl 4-aminobenzoate
SMILES
CCOC(=O)C1=CC=C(N)C=C1
Mass Specshow(7.74 KB)
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassBenzoic Acid and Derivatives
Direct parentBenzoic Acid Esters
Alternative parentsAminobenzoic Acid Derivatives; Benzylethers; Benzoyl Derivatives; Anilines; Primary Aromatic Amines; Carboxylic Acid Esters; Enolates; Polyamines; Dialkyl Ethers
Substituentsbenzoyl; aniline; primary aromatic amine; carboxylic acid ester; polyamine; enolate; ether; dialkyl ether; carboxylic acid derivative; primary amine; amine; organonitrogen compound
Classification descriptionThis compound belongs to the benzoic acid esters. These are ester derivatives of benzoic acid.
Pharmacology
IndicationFor 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.
PharmacodynamicsBenzocaine 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 actionBenzocaine 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.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism
Route of eliminationNot Available
Half lifeNot Available
ClearanceNot Available
ToxicityLD50=3040 mg/kg (rat, oral)
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
Property Value Probability
Human Intestinal Absorption + 0.9963
Blood Brain Barrier + 0.9609
Caco-2 permeable + 0.7814
P-glycoprotein substrate Non-substrate 0.8329
P-glycoprotein inhibitor I Non-inhibitor 0.9589
P-glycoprotein inhibitor II Non-inhibitor 0.9612
Renal organic cation transporter Non-inhibitor 0.8818
CYP450 2C9 substrate Non-substrate 0.8426
CYP450 2D6 substrate Non-substrate 0.7934
CYP450 3A4 substrate Non-substrate 0.7513
CYP450 1A2 substrate Inhibitor 0.9107
CYP450 2C9 substrate Non-inhibitor 0.9071
CYP450 2D6 substrate Non-inhibitor 0.9231
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.937
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7883
Ames test Non AMES toxic 0.8825
Carcinogenicity Carcinogens 0.513
Biodegradation Ready biodegradable 0.7718
Rat acute toxicity 1.7665 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9721
hERG inhibition (predictor II) Non-inhibitor 0.9668
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
AerosolBuccal
AerosolDental
GelDental
GelOral
GelTopical
LiquidOral
LiquidTopical
OintmentTopical
PasteDental
PasteOral
SwabOral
SwabTopical
Prices
Unit descriptionCostUnit
Americaine Anesthetic 20% Gel 28 gm Tube22.99USDtube
Americaine 20% ear drops1.26USDml
Oticaine 20% ear drops0.83USDml
Americaine lubricant0.71USDg
Hurricaine 20% liquid swab0.6USDswab
Hurricaine 20% spray0.52USDml
Anbesol baby 7.5% gel0.41USDg
Cepacol 6 mg fizzlers tablet0.39USDtablet
Benzocaine powder0.09USDg
Dermoplast pain relieving spry0.07USDml
Dermoplast spray0.07USDml
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Statesolid
Experimental Properties
PropertyValueSource
melting point92 °CPhysProp
boiling point310 °CPhysProp
water solubility1310 mg/L (at 30 °C)YALKOWSKY,SH & HE,Y (2003)
logP1.86HANSCH,C ET AL. (1995)
pKa2.51 (at 25 °C)PERRIN,DD (1965)
Predicted Properties
PropertyValueSource
water solubility2.85e+00 g/lALOGPS
logP2.2ALOGPS
logP1.5ChemAxon
logS-1.8ALOGPS
pKa (strongest basic)2.78ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count2ChemAxon
hydrogen donor count1ChemAxon
polar surface area52.32ChemAxon
rotatable bond count3ChemAxon
refractivity47.53ChemAxon
polarizability17.46ChemAxon
number of rings1ChemAxon
bioavailability1ChemAxon
rule of fiveYesChemAxon
Ghose filterYesChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraGC-MSMS/MSLC-MS1D NMR2D NMR
References
Synthesis ReferenceNot Available
General ReferenceNot Available
External Links
ResourceLink
KEGG DrugD00552
KEGG CompoundC07527
PubChem Compound2337
PubChem Substance46508891
ChemSpider13854242
ChEBI116735
ChEMBLCHEMBL278172
Therapeutic Targets DatabaseDAP001234
PharmGKBPA448576
Drug Product Database2223805
RxListhttp://www.rxlist.com/cgi/generic3/americaine.htm
Drugs.comhttp://www.drugs.com/cdi/benzocaine-drops.html
WikipediaBenzocaine
ATC CodesC05AD03D04AB04N01BA05R02AD01
AHFS Codes
  • 52:16.00
  • 84:08.00
PDB EntriesNot Available
FDA labelNot Available
MSDSshow(73.3 KB)
Interactions
Drug InteractionsSearched, but no interactions found.
Food InteractionsNot Available

Targets

1. Sodium channel protein type 10 subunit alpha

Kind: protein

Organism: Human

Pharmacological action: yes

Actions: inhibitor

Components

Name UniProt ID Details
Sodium channel protein type 10 subunit alpha Q9Y5Y9 Details

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

Enzymes

1. Liver carboxylesterase 1

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Liver carboxylesterase 1 P23141 Details

References:

  1. 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

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: inhibitor

Components

Name UniProt ID Details
Multidrug resistance protein 1 P08183 Details

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
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Drug created on June 13, 2005 07:24 / Updated on September 16, 2013 17:13