Benzonatate

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Benzonatate
Systematic (IUPAC) name
2-[2-[2-[2-[2-[2-[2-[2- (2-methoxyethoxy) ethoxy] ethoxy] ethoxy] ethoxy] ethoxy] ethoxy] ethoxy] ethyl4-butylaminobenzoate
Clinical data
Trade namesTessalon
AHFS/Drugs.commonograph
MedlinePlusa682640
Pregnancy cat.C (US)
Legal status ?
Pharmacokinetic data
Half-life3-8 hours
Identifiers
CAS number104-31-4 YesY
ATC codeR05DB01
PubChemCID 7699
DrugBankDB00868
ChemSpider7413 YesY
UNII5P4DHS6ENR YesY
KEGGD00242 YesY
ChEBICHEBI:3032 YesY
ChEMBLCHEMBL1200369 N
Chemical data
FormulaC30H53NO11 
Mol. mass603.742 g/mol
 N (what is this?)  (verify)
 
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Benzonatate
Systematic (IUPAC) name
2-[2-[2-[2-[2-[2-[2-[2- (2-methoxyethoxy) ethoxy] ethoxy] ethoxy] ethoxy] ethoxy] ethoxy] ethoxy] ethyl4-butylaminobenzoate
Clinical data
Trade namesTessalon
AHFS/Drugs.commonograph
MedlinePlusa682640
Pregnancy cat.C (US)
Legal status ?
Pharmacokinetic data
Half-life3-8 hours
Identifiers
CAS number104-31-4 YesY
ATC codeR05DB01
PubChemCID 7699
DrugBankDB00868
ChemSpider7413 YesY
UNII5P4DHS6ENR YesY
KEGGD00242 YesY
ChEBICHEBI:3032 YesY
ChEMBLCHEMBL1200369 N
Chemical data
FormulaC30H53NO11 
Mol. mass603.742 g/mol
 N (what is this?)  (verify)

Benzonatate is a non-narcotic oral cough suppressant, or antitussive, with effects that last from 6 to 8 hours. Its formal name is 2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl para-butylaminobenzoate. Since it is not an opioid, benzonatate is not prone to abuse like some other cough medications such as codeine. Benzonatate was approved by the U.S. Food and Drug Administration (FDA) in 1958.[1]

Contents

Chemical structure

Benzonatate is a butylamine, chemically related to other ester local anesthetics such as procaine and tetracaine.

Pharmacologic mechanisms of action

Benzonatate is thought to act as a local anesthetic, decreasing the sensitivity of stretch receptors in the lower airway and lung, thereby reducing the drive to cough after taking a deep breath.[2]

Indications

An antitussive, benzonatate is employed to reduce coughing in various respiratory conditions such as bronchitis, emphysema, influenza, and pneumonia. It should never be used to suppress a productive cough or in place of treatment of the actual cause of cough, such as asthma treatment. [2]

It has been used in small doses as a topical anesthetic for mouth or pharyngeal pain. This practice is not recommended, because the oropharyngeal anesthesia may result in pulmonary aspiration.[3]

Dosage and administration

100mg generic Benzonatate capsules.
100mg generic Benzonatate capsules.

Benzonatate is sold as yellow or blue 100 mg and 200 mg softgel capsules. Initial dose is one 100 mg perle (gelcap) by mouth, 3 times a day. Dosage may be increased as necessary, up to a maximum of 600 mg per day.[1]

Due to its potency and potential toxicity, the capsules must be swallowed intact in order to allow slower release of the medication.

Adverse reactions

Reported side effects include drowsiness, dizziness, and dysphagia. There are numerous reports of death related to overdose of benzonatate, mostly in children.

Para-aminobenzoic acid (PABA) is a metabolite of the ester class of local anesthetics, which includes benzonatate, as well as procaine and tetracaine. Severe allergic reactions have been reported in patients who are allergic to PABA. Severe sensitivity reactions to benzonatate have resulted in respiratory side effects such as bronchospasm, laryngospasm and cardiac arrest.[4]

Excessive absorption of benzonatate (a local anesthetic) in the oral mucosa will result in the rapid development of numbness of the mouth and throat. In extreme cases, the mouth and pharynx may become so numb that pulmonary aspiration may occur.

Excessive absorption of benzonatate will occur if the gelcaps are chewed or allowed to dissolve in the mouth. This may lead to an overdose of the drug. Overdose of benzonatate may manifest as central nervous system side effects, such as mental confusion and hallucination, restlessness and tremors,[citation needed] followed in extreme cases by convulsions and death.[5]

Brand names

It is sold in the USA generically or under the brand name Tessalon Perles (gelcaps), Zonatuss or Tessalon Capsules. It is sold in other countries under various brand names, including Benzonatato, Benzonatatum, Benzononantin, Benzononatine, Exangit, Tesalon, Tessalin, and Ventussin.

References

  1. ^ a b MedicineNet.com: Benzonatate
  2. ^ a b Medicalook.com: Benzonatate
  3. ^ Medline Plus: Benzonatate
  4. ^ Crouch, B. I.; Knick, K. A.; Crouch, D. J.; Matsumura, K. S.; Rollins, D. E. (1998). "Benzonatate overdose associated with seizures and arrhythmias". Journal of toxicology. Clinical toxicology 36 (7): 713–718. PMID 9865240. edit
  5. ^ Cohan, J. A.; Manning, T. J.; Lukash, L.; Long, C.; Ziminski, K. R.; Conradi, S. E. (1986). "Two fatalities resulting from Tessalon (benzonatate)". Veterinary and human toxicology 28 (6): 543–544. PMID 3788039. edit