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Identification
Name Benzonatate
Accession Number DB00868 (APRD00629)
Type small molecule
Groups approved
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
Download: MOL | SDF | SMILES | InChI
Display: 2D Structure | 3D Structure
Synonyms
Benzonatato [INN-Spanish]
Benzonatatum [INN-Latin]
Benzononatine
Salts Not Available
Brand names
Name Company
Benzononantin
Exangit
Tesalon
Tessalin
Tessalon
Tessalon Perles
Tessalon-Ciba
Ventussin
Ventussin-Loz
Brand mixtures Not Available
Categories
  • Antitussives
CAS number 104-31-4
Weight Average: 603.7419
Monoisotopic: 603.361861543
Chemical Formula C30H53NO11
InChI Key InChIKey=MAFMQEKGGFWBAB-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
Plain Text
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
Plain Text
Mass Spec Not Available
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 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.
Pharmacodynamics Benzonatate, 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 action Benzonatate 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.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Benzonatate is hydrolyzed to para-aminobenzoic acid (PABA) by plasma esterases
Route of elimination Not Available
Half life 3-8 hours
Clearance Not Available
Toxicity Restlessness, tremors, seizures and unconsciousness.
Affected organisms
  • Humans and other mammals
Pathways Not Available
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
Form Route Strength
Capsule Oral
Prices
Unit description Cost Unit
Tessalon 200 mg capsule 2.76 USD capsule
Benzonatate 200 mg capsule 2.03 USD capsule
Tessalon Perles 100 mg capsule 1.62 USD capsule
Zonatuss 150 mg capsule 1.59 USD capsule
Tessalon perle 100 mg capsule 1.4 USD capsule
Benzonatate 100 mg capsule 0.85 USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents Not Available
Properties
State liquid
Experimental Properties
Property Value Source
water solubility Soluble in most organic solvents except aliphatic hydrocarbons Not Available
logP 2.45 HANSCH,C ET AL. (1995)
Predicted Properties
Property Value Source
water solubility 1.59e-03 g/l ALOGPS
logP 2.09 ALOGPS
logP 2.35 ChemAxon
logS -5.6 ALOGPS
pKa (strongest basic) 3.47 ChemAxon
physiological charge 0 ChemAxon
hydrogen acceptor count 11 ChemAxon
hydrogen donor count 1 ChemAxon
polar surface area 121.4 ChemAxon
rotatable bond count 33 ChemAxon
refractivity 161.54 ChemAxon
polarizability 67.87 ChemAxon
References
Synthesis Reference Not Available
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
Resource Link
KEGG Drug D00242 Link_out
PubChem Compound 7699 Link_out
PubChem Substance 46506376 Link_out
ChemSpider 7413 Link_out
ChEBI 3032 Link_out
ChEMBL 3032 Link_out
Therapeutic Targets Database DAP000514 Link_out
PharmGKB PA164745459 Link_out
RxList http://www.rxlist.com/cgi/generic/benzon.htm Link_out
Drugs.com http://www.drugs.com/cdi/benzonatate.html Link_out
Wikipedia http://en.wikipedia.org/wiki/Benzonatate Link_out
ATC Codes
  • R05DB01
AHFS Codes Not Available
PDB Entries Not Available
FDA label Not Available
MSDS Not Available
Interactions
Drug Interactions Searched, but no interactions found.
Food Interactions
  • Take without regard to meals.
Targets

1. Sodium channel protein type 5 subunit alpha

Pharmacological action: unknown
Actions: antagonist

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 Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram

Organism class: human
UniProt ID: Q14524 Link_out
Gene: SCN5A Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

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