Benzonatate

Synonyms :
2-[2-[2-[2-[2-[2-[2-[2-(2-Methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-butylaminobenzoate, 2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-yl P-(butylamino)benzoate, 3,6,9,12,15,18,21,24,27-Nonaoxaoctacosyl 4-butylaminobenzoate, 4-(Butylamino)benzoic acid 3,6,9,12,15,18,21,24,27-nonaoxaoctacos-1-yl ester, Benzonatat, Benzonatate, Benzonatato, Benzonatatum, Benzononatine, Nonaethyleneglycol monomethyl ether P-N-butylaminobenzoate, P-Butylaminobenzoic acid omega-O-methylnonaethyleneglycol ester

Status : approved

Category

Antitussive Agents

Therapeutic Classification

COUGH SUPPRESSANTS, EXCL. COMBINATIONS WITH EXPECTORANTS

RESPIRATORY SYSTEM
COUGH AND COLD PREPARATIONS
COUGH SUPPRESSANTS, EXCL. COMBINATIONS WITH EXPECTORANTS

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.

Used

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.

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.

Dosage

Form Route Strength
Capsule oral 150 mg
Capsule oral 200 mg
Capsule, liquid filled oral 100 mg
Capsule, liquid filled oral 200 mg
Tablet oral 100 mg
Capsule oral 100 mg

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.

Toxic Effect

Restlessness, tremors, seizures and unconsciousness.

Metabolism

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

Half Life

3-8 hours

Chemical Classification

This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.

Benzoic acid esters

Organic compounds

Benzenoids

Benzene and substituted derivatives

Benzoic acids and derivatives

Chemical Name

2-[2-[2-[2-[2-[2-[2-[2-(2-Methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-butylaminobenzoate

Brands

name Dosage form Country
Benzonatate capsule, liquid filled US
Benzonatate capsule US
Benzonatate capsule, liquid filled US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule, liquid filled US
Benzonatate capsule, liquid filled US
Benzonatate capsule US
Benzonatate capsule, liquid filled US
Benzonatate capsule, liquid filled US
Benzonatate capsule, liquid filled US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule, liquid filled US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule, liquid filled US
Benzonatate capsule US
Benzonatate capsule, liquid filled US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate tablet US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule, liquid filled US
Benzonatate capsule, liquid filled US
Benzonatate capsule US
Benzonatate capsule, liquid filled US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule, liquid filled US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule, liquid filled US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule, liquid filled US
Benzonatate capsule US
Benzonatate capsule US
Benzonatate capsule US
Tessalon capsule US
Zonatuss capsule US

Food Interactions

  • Take without regard to meals.

Calculated Property

kind Value Source
logP 2.09 ALOGPS
logS -5.6 ALOGPS
Water Solubility 1.59e-03 g/l ALOGPS
logP 2.35 ChemAxon
IUPAC Name 2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl 4-(butylamino)benzoate ChemAxon
Traditional IUPAC Name benzonatate ChemAxon
Molecular Weight 603.7419 ChemAxon
Monoisotopic Weight 603.361861543 ChemAxon
SMILES CCCCNC1=CC=C(C=C1)C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC ChemAxon
Molecular Formula C30H53NO11 ChemAxon
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 ChemAxon
InChIKey InChIKey=MAFMQEKGGFWBAB-UHFFFAOYSA-N ChemAxon
Polar Surface Area (PSA) 121.4 ChemAxon
Refractivity 161.54 ChemAxon
Polarizability 67.87 ChemAxon
Rotatable Bond Count 33 ChemAxon
H Bond Acceptor Count 11 ChemAxon
H Bond Donor Count 1 ChemAxon
pKa (strongest basic) 3.47 ChemAxon
Physiological Charge 0 ChemAxon
Number of Rings 1 ChemAxon
Bioavailability 0 ChemAxon
Rule of Five 0 ChemAxon
Ghose Filter 0 ChemAxon
MDDR-Like Rule 0 ChemAxon

Affected organism

Humans and other mammals

Target within organism

  • Sodium channel protein type 5 subunit alpha : in Human