Benzonatate (104-31-4)

Benzonatate Chemical Structure

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What is Benzonatate?

Chemically, Benzonatate is a benzoate ester, a substituted aniline and a secondary amino compound, structurally related to procaine and benzocaine. It exhibits anti-tussive properties and is used as a non-narcotic cough suppressant and for the symptomatic treatment of hiccups. However, It is not suggested for children under the age of ten.

Benzonatate, commonly sold under the brand name Tessalon, was approved for medical use in the United States in 1958 and is available as a generic medication.

The product is currently under development. Samples are available from R&D.
PRODUCT SPECIFICATIONS
Name of Product Benzonatate
IUPAC Name 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]
ethoxy]ethoxy]ethyl 4-(butylamino)benzoate
Synonyms Benzononatine; Tessalon; Benzononantin; Exangit;
Ventussin; Benzonatato; Benzonatatum; Zonatuss
CAS No 104-31-4
Molecular Formula C30H53NO11
Molecular Weight 603.7 g/mol
Pubchem CID 7699

Chemical Properties

SR. No Criteria Limit/Specification
1 Appearance (Form) Liquid
2 Appearance (Colour) Colorless to faintly yellow oil
3 Solubility Soluble in most organic solvents except aliphatic hydrocarbons
4 LogP 2.45

Mechanism of Action

Benzonatate is a strong voltage-gated sodium channel inhibitor. It works as a local anaesthetic in the respiratory tract after absorption and circulation, lowering the sensitivity of vagal afferent fibres and stretch receptors in the bronchi, alveoli, and pleura in the lower airway and lung. This lowers their activity and decreases the cough reflex.

Benzonatate also has central antitussive activity on the cough center in the central nervous system at the medulla level. However, at therapeutic doses, there is little inhibition of the respiratory center.

Uses

  • Benzonatate is used for the symptomatic treatment of coughing due to colds or influenza (flu).
  • It has been reported to alleviate cough in a range of respiratory disorders, including asthma, bronchitis, pneumonia, tuberculosis, pneumothorax, opiate-resistant cough in lung cancer, and emphysema.
  • It has also been demonstrated to be useful in the treatment of hiccups and their suppression.
  • Benzonatate has an anaesthetic effect on the immediate area.

Side effects

Common side effects associated with the use of Benzonatate are-

  • Headache, Dizziness
  • Nausea, upset stomach
  • Constipation
  • Itching, rash
  • Stuffy nose

Other side effects include-

  • Burning sensation in the eyes
  • Sensation of chills
  • Allergic reactions (symptoms include trouble breathing, swelling or tightness in your throat, low blood pressure causing dizziness)
  • Confusion and hallucinations (seeing or hearing something that isn’t there)

FAQs

Q. Is benzonatate a steroid ?

Benzonatate is a non-narcotic cough medicine and it works by numbing the throat and lungs, making the cough reflex less active, thus is used to relieve coughing.

Q. Is benzonatate an antibiotic ?

Benzonatate is an antitussive drug (cough suppressants).

Q. Does benzonatate make you sleepy?

Drowsiness and dizziness may occur upon the use of Benzonatate.

Q. How long does benzonatate stay in your system?

Benzonatate relieves coughing for three to eight hours after ingesting a capsule. The half-life, or the period of time it takes for half the drug amount to be removed from the body, is around 1 hour.

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