benzonatate

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Tessalon Perles

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出典(authority):フリー百科事典『ウィキペディア（Wikipedia）』「2014/09/28 16:13:54」(JST)

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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 names	Tessalon
AHFS/Drugs.com	monograph
MedlinePlus	a682640
Pregnancy cat.	US: C
Legal status	?
Pharmacokinetic data
Half-life	3-8 hours
Identifiers
CAS number	104-31-4 Y
ATC code	R05DB01
PubChem	CID 7699
DrugBank	DB00868
ChemSpider	7413 Y
UNII	5P4DHS6ENR Y
KEGG	D00242 Y
ChEBI	CHEBI:3032 Y
ChEMBL	CHEMBL1374379 N
Chemical data
Formula	C30H53NO11
Mol. 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
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.

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.

References

UpToDate Contents

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• 1. 成人における亜急性および慢性咳嗽の治療 treatment of subacute and chronic cough in adults
• 2. 患者情報：成人における慢性咳嗽（詳細） chronic cough in adults beyond the basics

English Journal

• Nebulized lidocaine in the treatment of intractable cough.

• Truesdale K, Jurdi A.SourceDepartment of Family Medicine, East Tennessee State University, Kingsport, TN 37660, USA. truesdale@etsu.edu
• The American journal of hospice & palliative care.Am J Hosp Palliat Care.2013 Sep;30(6):587-9. doi: 10.1177/1049909112458577. Epub 2012 Sep 9.
• Cough is one of the most common symptoms prompting patients to be seen by health care providers in the United States. Persistent cough can disrupt daily activities such as conversation, eating, breathing, and sleeping, and it can become extremely debilitating both physically and mentally. Pharmacolo
• PMID 22964341

• Analysis of benzonatate overdoses among adults and children from 1969-2010 by the United States Food and Drug Administration.

• McLawhorn MW, Goulding MR, Gill RK, Michele TM.SourceDivision of Pharmacovigilance-I, Office of Pharmacovigilance and Epidemiology, Center for Drug Evaluation and Research, U.S. Food and Drug Administration, Silver Spring, Maryland 20993, USA. melinda.mclawhorn@fda.hhs.gov
• Pharmacotherapy.Pharmacotherapy.2013 Jan;33(1):38-43. doi: 10.1002/phar.1153.
• STUDY OBJECTIVE: To augment the December 2010 United States Food and Drug Administration (FDA) Drug Safety Communication on accidental ingestion of benzonatate in children less than 10 years old by summarizing data on emergency department visits, benzonatate exposure, and reports of benzonatate ove
• PMID 23307543

• Benzonatate toxicity in a teenager resulting in coma, seizures, and severe metabolic acidosis.

• Thimann DA, Huang CJ, Goto CS, Feng SY.SourceDivision of Emergency Medicine, Department of Pediatrics, Children's Medical Center of Dallas, Dallas, Texas  ; University of Texas Southwestern Medical Center at Dallas, Dallas, Texas.
• The journal of pediatric pharmacology and therapeutics : JPPT : the official journal of PPAG.J Pediatr Pharmacol Ther.2012 Jul;17(3):270-3. doi: 10.5863/1551-6776-17.3.270.
• We report a benzonatate overdose in a teenager resulting in life-threatening toxicity to increase awareness of this overdose, and discuss recent pediatric warnings and labeling information provided by the US Food and Drug Administration (FDA). After an overdose of benzonatate, a 13-yr-old female pre
• PMID 23258970

Japanese Journal

• PERIPHERAL EFFECTS OF MORPHINE AND CODEINE ON THE COUGH REFLEX

• YANAURA Saizo,HOSOKAWA Tomokazu,KITAGAWA Harumi,MISAWA Miwa
• The Japanese Journal of Pharmacology 31(4), 529-536, 1981
• … On the other hand, benzonatate inhibited the tracheal constriction without influencing the cough response. …
• NAID 130000835641

• 咳嗽反射時の気道血管床における反射効果

• 柳浦 才三,細川 友和,北川 晴美,三澤 美和
• 日本薬理学雑誌 78(1), 9-16, 1981
• 咳嗽反射に伴う気管気管支血管床の反応をイヌ気管血管および気管支動脈血液灌流標本を用いて，気管気管支平滑筋の反応とともに検討した．咳嗽反射は上部気管粘膜あるいは右上喉頭神経切断中枢端の電気刺激により誘発した．気管血管血液灌流標本において，上部気管粘膜の電気刺激による咳嗽反射に伴い，気管平滑筋の収縮気管血管の拡張がみられた．これらの反応に対して，atrophine 10〜300μg i.a. 適用によ …
• NAID 130000759412

Related Links

• Benzonatate - Wikipedia, the free encyclopedia

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 ...

• benzonatate (Tessalon Perles) - drug class, medical uses ...

Explains the medication benzonatate (Tessalon Perles), a drug used for relieving coughs.

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