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Identification
NameBenzonatate
Accession NumberDB00868  (APRD00629)
Typesmall molecule
Groupsapproved
Description

Benzonatate is a non-narcotic oral antitussive (cough suppressant) drug which works by anesthetizing the tissues of the lungs and pleura responsible for the cough reflex. It is chemically related to other ester anesthetics such as procaine. It has an anesthetic (numbing) action similar to that of benzocaine and “numbs” the stretch sensors in the lungs. It is the stretching of these sensors with breathing that causes the cough. It was approved by the FDA in 1958.

Structure
Thumb
Synonyms
SynonymLanguageCode
BenzonatatGermanINN
BenzonatateFrenchBAN
BenzonatatoSpanishINN
BenzonatatumLatinINN
SaltsNot Available
Brand names
NameCompany
TesaperlNovartis
TessalonForest Laboratories
ZonatussAtley Pharmaceuticals
Brand mixtures
Brand NameIngredients
CelltiusBenzonatate and Ambroxol
Categories
CAS number104-31-4
WeightAverage: 603.7419
Monoisotopic: 603.361861543
Chemical FormulaC30H53NO11
InChI KeyMAFMQEKGGFWBAB-UHFFFAOYSA-N
InChI
InChI=1S/C30H53NO11/c1-3-4-9-31-29-7-5-28(6-8-29)30(32)42-27-26-41-25-24-40-23-22-39-21-20-38-19-18-37-17-16-36-15-14-35-13-12-34-11-10-33-2/h5-8,31H,3-4,9-27H2,1-2H3
IUPAC Name
2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl 4-(butylamino)benzoate
SMILES
CCCCNC1=CC=C(C=C1)C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC
Mass SpecNot Available
Taxonomy
KingdomOrganic Compounds
SuperclassBenzenoids
ClassBenzene and Substituted Derivatives
SubclassBenzoic Acid and Derivatives
Direct parentBenzoic Acid Esters
Alternative parentsAminobenzoic Acid Derivatives; Benzylethers; Benzoyl Derivatives; Carboxylic Acid Esters; Dialkyl Ethers; Enolates; Polyamines; Secondary Amines
Substituentsbenzoyl; carboxylic acid ester; polyamine; dialkyl ether; secondary amine; ether; carboxylic acid derivative; enolate; amine; organonitrogen compound
Classification descriptionThis compound belongs to the benzoic acid esters. These are ester derivatives of benzoic acid.
Pharmacology
IndicationFor the symptomatic relief of cough. Has also been applied locally in the oral cavity in adults by releasing the drug from the liquid-filled capsules to provide oropharyngeal anesthesia for conscious intubation.
PharmacodynamicsBenzonatate, a non-narcotic antitussive agent chemically related to tetracaine and other ester-type local anesthetics, is used to suppress cough associated with both acute and chronic respiratory conditions. The drug acts peripherally by anesthetizing the stretch receptors located in the respiratory passages, lungs, and pleura through the dampening of their activity, which reduces the cough reflex.
Mechanism of actionBenzonatate acts peripherally, anesthetizing the stretch receptors of vagal afferent fibers in the alveoli of the lungs, bronchi, and pleura. Since these receptors are responsible for mediating the cough reflex, anesthetizing these receptors result in the inhibiton of cough production. Benzonatate also suppresses transmission of the cough reflex at the level of the medulla where the afferent impulse is transmitted to the motor nerves. When applied locally, Benzonatate binds within the intracellular portion of voltage-gated sodium channels, decreasing the rate of membrane depolarization and increasing the threshold for electrical excitability.
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Benzonatate is hydrolyzed to para-aminobenzoic acid (PABA) by plasma esterases

Route of eliminationNot Available
Half life3-8 hours
ClearanceNot Available
ToxicityRestlessness, tremors, seizures and unconsciousness.
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 + 0.9932
Blood Brain Barrier + 0.9355
Caco-2 permeable + 0.6067
P-glycoprotein substrate Substrate 0.6531
P-glycoprotein inhibitor I Non-inhibitor 0.5978
P-glycoprotein inhibitor II Non-inhibitor 0.9434
Renal organic cation transporter Non-inhibitor 0.7646
CYP450 2C9 substrate Non-substrate 0.875
CYP450 2D6 substrate Non-substrate 0.7017
CYP450 3A4 substrate Non-substrate 0.6026
CYP450 1A2 substrate Non-inhibitor 0.9045
CYP450 2C9 substrate Non-inhibitor 0.907
CYP450 2D6 substrate Non-inhibitor 0.9232
CYP450 2C19 substrate Non-inhibitor 0.9025
CYP450 3A4 substrate Non-inhibitor 0.9275
CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.932
Ames test Non AMES toxic 0.7269
Carcinogenicity Non-carcinogens 0.9182
Biodegradation Ready biodegradable 0.6331
Rat acute toxicity 2.2423 LD50, mol/kg Not applicable
hERG inhibition (predictor I) Weak inhibitor 0.9013
hERG inhibition (predictor II) Non-inhibitor 0.6129
Pharmacoeconomics
Manufacturers
  • Banner pharmacaps inc
  • Kv pharmaceutical co
  • Mikart inc
  • Orit laboratories llc
  • Sun pharmaceutical industries inc
  • The pharma network llc
  • Zydus pharmaceuticals usa inc
  • Forest laboratories inc
Packagers
Dosage forms
FormRouteStrength
CapsuleOral
Prices
Unit descriptionCostUnit
Tessalon 200 mg capsule2.76USDcapsule
Benzonatate 200 mg capsule2.03USDcapsule
Tessalon Perles 100 mg capsule1.62USDcapsule
Zonatuss 150 mg capsule1.59USDcapsule
Tessalon perle 100 mg capsule1.4USDcapsule
Benzonatate 100 mg capsule0.85USDcapsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
Stateliquid
Experimental Properties
PropertyValueSource
water solubilitySoluble in most organic solvents except aliphatic hydrocarbonsNot Available
logP2.45HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
water solubility1.59e-03 g/lALOGPS
logP2.09ALOGPS
logP2.35ChemAxon
logS-5.6ALOGPS
pKa (strongest basic)3.47ChemAxon
physiological charge0ChemAxon
hydrogen acceptor count11ChemAxon
hydrogen donor count1ChemAxon
polar surface area121.4ChemAxon
rotatable bond count33ChemAxon
refractivity161.54ChemAxon
polarizability67.87ChemAxon
number of rings1ChemAxon
bioavailability0ChemAxon
rule of fiveNoChemAxon
Ghose filterNoChemAxon
Veber's ruleNoChemAxon
MDDR-like ruleNoChemAxon
Spectra
SpectraNot Available
References
Synthesis Reference

Matter, M.; U.S. Patent 2,714,608; August 2, 1955; assigned to Ciba Pharmaceutical Products, Inc.

General Reference
  1. Cohen V, Jellinek SP, Stansfield L, Truong H, Baseluos C, Marshall JP: Cardiac arrest with residual blindness after overdose of tessalon® (benzonatate) perles. J Emerg Med. 2009 Nov 4. Pubmed
External Links
ResourceLink
KEGG DrugD00242
PubChem Compound7699
PubChem Substance46506376
ChemSpider7413
ChEBI3032
ChEMBLCHEMBL1200369
Therapeutic Targets DatabaseDAP000514
PharmGKBPA164745459
RxListhttp://www.rxlist.com/cgi/generic/benzon.htm
Drugs.comhttp://www.drugs.com/cdi/benzonatate.html
WikipediaBenzonatate
ATC CodesR05DB01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsSearched, but no interactions found.
Food InteractionsNot Available

Targets

1. Sodium channel protein type 5 subunit alpha

Kind: protein

Organism: Human

Pharmacological action: unknown

Actions: antagonist

Components

Name UniProt ID Details
Sodium channel protein type 5 subunit alpha Q14524 Details

References:

  1. Thimann DA, Huang CJ, Goto CS, Feng SY: Benzonatate toxicity in a teenager resulting in coma, seizures, and severe metabolic acidosis. J Pediatr Pharmacol Ther. 2012 Jul;17(3):270-3. doi: 10.5863/1551-6776-17.3.270. Pubmed

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Drug created on June 13, 2005 07:24 / Updated on March 31, 2014 15:07