Benzonatate

Benzonatate

Systematic (IUPAC) name
2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-yl 4-(butylamino)benzoate
Clinical data
Trade names	Tessalon
AHFS/Drugs.com	monograph
MedlinePlus	a682640
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Oral
Pharmacokinetic data
Biological half-life	3-8 hours
Identifiers
CAS Number	104-31-4 Y
ATC code	R05DB01 (WHO)
PubChem	CID: 7699
IUPHAR/BPS	7611
DrugBank	DB00868 Y
ChemSpider	7413 Y
UNII	5P4DHS6ENR Y
KEGG	D00242 Y
ChEBI	CHEBI:3032 Y
ChEMBL	CHEMBL1374379 N
Chemical data
Formula	C30H53NO11
Molecular mass	603.742 g/mol
SMILES O=C(OCCOCCOCCOCCOCCOCCOCCOCCOCCOC)c1ccc(NCCCC)cc1
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 Y Key:MAFMQEKGGFWBAB-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

Benzonatate is a non-narcotic oral cough suppressant, or antitussive, with effects that last from 6 to 8 hours. Since it is not an opioid, benzonatate is not as 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.

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.

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 producing mucus that can be spit out, or in place of treatment of the actual cause of cough, such as asthma treatment.

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.

Noted beneficial side-effect is the reduction or quieting of chronic snoring.

Dosage and administration

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.

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.

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, followed in extreme cases by convulsions and death.

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.