Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C30H53NO11 |
| Molecular Weight | 603.7431 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCNC1=CC=C(C=C1)C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC
InChI
InChIKey=MAFMQEKGGFWBAB-UHFFFAOYSA-N
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
| Molecular Formula | C30H53NO11 |
| Molecular Weight | 603.7431 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/benzonatate.html | http://www.wikidoc.org/index.php/Benzonatate | http://www.rxlist.com/tessalon-drug.htm
Curator's Comment: description was created based on several sources, including:
https://www.drugs.com/pro/benzonatate.html | http://www.wikidoc.org/index.php/Benzonatate | http://www.rxlist.com/tessalon-drug.htm
Benzonatate is an antitussive that is FDA approved for the symptomatic relief of cough. It acts peripherally by anesthetizing the stretch receptors located in the respiratory passages, lungs, and pleura by dampening their activity and thereby reducing the cough reflex at its source. Common adverse reactions include nausea, oral hypoesthesia, throat symptom, numbness, dizziness, headache, sedation, somnolence. Benzonatate is chemically related to anesthetic agents of the para-amino-benzoic acid class (e.g. procaine; tetracaine) and has been associated with adverse CNS effects possibly related to a prior sensitivity to related agents or interaction with concomitant medication.
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL4296 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26386152 |
|||
Target ID: CHEMBL5163 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26386152 |
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Target ID: CHEMBL2364682 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Palliative | TESSALON Approved UseBenzonatate USP is indicated for the symptomatic relief of cough. Launch Date1958 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1063 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31129533/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENZONATATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1111 ng × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31129533/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENZONATATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
1.01 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/31129533/ |
100 mg single, oral dose: 100 mg route of administration: Oral experiment type: SINGLE co-administered: |
BENZONATATE plasma | Homo sapiens population: HEALTHY age: ADULT sex: FEMALE / MALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
50.9 mg/kg single, oral Overdose Dose: 50.9 mg/kg Route: oral Route: single Dose: 50.9 mg/kg Sources: |
healthy, ADOLESCENT Health Status: healthy Age Group: ADOLESCENT Sex: F Food Status: UNKNOWN Sources: |
Disc. AE: Consciousness loss, Cyanosis... AEs leading to discontinuation/dose reduction: Consciousness loss Sources: Cyanosis Polymorphic ventricular tachycardia Torsades de pointes Cardiac arrest |
5200 mg single, oral Overdose Dose: 5200 mg Route: oral Route: single Dose: 5200 mg Sources: |
unknown, ADULT Health Status: unknown Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
Disc. AE: Status epilepticus, Cardiac arrest... AEs leading to discontinuation/dose reduction: Status epilepticus Sources: Cardiac arrest Tachycardia Hypotension Brain death Encephalopathy Brain injury |
10000 mg single, oral Overdose Dose: 10000 mg Route: oral Route: single Dose: 10000 mg Sources: |
healthy, CHILD Health Status: healthy Age Group: CHILD Sex: F Food Status: UNKNOWN Sources: |
Disc. AE: Seizure, Cardiac arrest... AEs leading to discontinuation/dose reduction: Seizure Sources: Cardiac arrest Tachycardia |
200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: |
unhealthy, CHILD|ADOLESCENT|ADULT Health Status: unhealthy Age Group: CHILD|ADOLESCENT|ADULT Sex: M+F Food Status: UNKNOWN Sources: |
Disc. AE: Hypersensitivity reaction, Mental confusion... AEs leading to discontinuation/dose reduction: Hypersensitivity reaction Sources: Mental confusion Visual hallucinations |
3600 mg single, oral Overdose |
healthy |
Disc. AE: Grand mal seizure, Ventricular tachycardia... AEs leading to discontinuation/dose reduction: Grand mal seizure Sources: Ventricular tachycardia Sinus tachycardia Mental confusion |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Cardiac arrest | Disc. AE | 50.9 mg/kg single, oral Overdose Dose: 50.9 mg/kg Route: oral Route: single Dose: 50.9 mg/kg Sources: |
healthy, ADOLESCENT Health Status: healthy Age Group: ADOLESCENT Sex: F Food Status: UNKNOWN Sources: |
| Consciousness loss | Disc. AE | 50.9 mg/kg single, oral Overdose Dose: 50.9 mg/kg Route: oral Route: single Dose: 50.9 mg/kg Sources: |
healthy, ADOLESCENT Health Status: healthy Age Group: ADOLESCENT Sex: F Food Status: UNKNOWN Sources: |
| Cyanosis | Disc. AE | 50.9 mg/kg single, oral Overdose Dose: 50.9 mg/kg Route: oral Route: single Dose: 50.9 mg/kg Sources: |
healthy, ADOLESCENT Health Status: healthy Age Group: ADOLESCENT Sex: F Food Status: UNKNOWN Sources: |
| Polymorphic ventricular tachycardia | Disc. AE | 50.9 mg/kg single, oral Overdose Dose: 50.9 mg/kg Route: oral Route: single Dose: 50.9 mg/kg Sources: |
healthy, ADOLESCENT Health Status: healthy Age Group: ADOLESCENT Sex: F Food Status: UNKNOWN Sources: |
| Torsades de pointes | Disc. AE | 50.9 mg/kg single, oral Overdose Dose: 50.9 mg/kg Route: oral Route: single Dose: 50.9 mg/kg Sources: |
healthy, ADOLESCENT Health Status: healthy Age Group: ADOLESCENT Sex: F Food Status: UNKNOWN Sources: |
| Brain death | Disc. AE | 5200 mg single, oral Overdose Dose: 5200 mg Route: oral Route: single Dose: 5200 mg Sources: |
unknown, ADULT Health Status: unknown Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Brain injury | Disc. AE | 5200 mg single, oral Overdose Dose: 5200 mg Route: oral Route: single Dose: 5200 mg Sources: |
unknown, ADULT Health Status: unknown Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Cardiac arrest | Disc. AE | 5200 mg single, oral Overdose Dose: 5200 mg Route: oral Route: single Dose: 5200 mg Sources: |
unknown, ADULT Health Status: unknown Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Encephalopathy | Disc. AE | 5200 mg single, oral Overdose Dose: 5200 mg Route: oral Route: single Dose: 5200 mg Sources: |
unknown, ADULT Health Status: unknown Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Hypotension | Disc. AE | 5200 mg single, oral Overdose Dose: 5200 mg Route: oral Route: single Dose: 5200 mg Sources: |
unknown, ADULT Health Status: unknown Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Status epilepticus | Disc. AE | 5200 mg single, oral Overdose Dose: 5200 mg Route: oral Route: single Dose: 5200 mg Sources: |
unknown, ADULT Health Status: unknown Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Tachycardia | Disc. AE | 5200 mg single, oral Overdose Dose: 5200 mg Route: oral Route: single Dose: 5200 mg Sources: |
unknown, ADULT Health Status: unknown Age Group: ADULT Sex: F Food Status: UNKNOWN Sources: |
| Cardiac arrest | Disc. AE | 10000 mg single, oral Overdose Dose: 10000 mg Route: oral Route: single Dose: 10000 mg Sources: |
healthy, CHILD Health Status: healthy Age Group: CHILD Sex: F Food Status: UNKNOWN Sources: |
| Seizure | Disc. AE | 10000 mg single, oral Overdose Dose: 10000 mg Route: oral Route: single Dose: 10000 mg Sources: |
healthy, CHILD Health Status: healthy Age Group: CHILD Sex: F Food Status: UNKNOWN Sources: |
| Tachycardia | Disc. AE | 10000 mg single, oral Overdose Dose: 10000 mg Route: oral Route: single Dose: 10000 mg Sources: |
healthy, CHILD Health Status: healthy Age Group: CHILD Sex: F Food Status: UNKNOWN Sources: |
| Hypersensitivity reaction | Disc. AE | 200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: |
unhealthy, CHILD|ADOLESCENT|ADULT Health Status: unhealthy Age Group: CHILD|ADOLESCENT|ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Mental confusion | Disc. AE | 200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: |
unhealthy, CHILD|ADOLESCENT|ADULT Health Status: unhealthy Age Group: CHILD|ADOLESCENT|ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Visual hallucinations | Disc. AE | 200 mg 3 times / day multiple, oral Recommended Dose: 200 mg, 3 times / day Route: oral Route: multiple Dose: 200 mg, 3 times / day Sources: |
unhealthy, CHILD|ADOLESCENT|ADULT Health Status: unhealthy Age Group: CHILD|ADOLESCENT|ADULT Sex: M+F Food Status: UNKNOWN Sources: |
| Grand mal seizure | Disc. AE | 3600 mg single, oral Overdose |
healthy |
| Mental confusion | Disc. AE | 3600 mg single, oral Overdose |
healthy |
| Sinus tachycardia | Disc. AE | 3600 mg single, oral Overdose |
healthy |
| Ventricular tachycardia | Disc. AE | 3600 mg single, oral Overdose |
healthy |
PubMed
| Title | Date | PubMed |
|---|---|---|
| Cardiac arrest with residual blindness after overdose of Tessalon® (benzonatate) perles. | 2011-08 |
|
| Benzonatate Ingestion Reported to the National Poison Center Database System (NPDS). | 2010-12 |
|
| Clinical expert guidelines for the management of cough in lung cancer: report of a UK task group on cough. | 2010-10-06 |
|
| Acute cough: a diagnostic and therapeutic challenge. | 2009-12-16 |
|
| Inhibition of cough-reflex sensitivity by benzonatate and guaifenesin in acute viral cough. | 2009-06 |
|
| The cough from hell: diazepam for intractable cough in a patient with renal cell carcinoma. | 2008-11 |
|
| Rasagiline in treatment of Parkinson's disease. | 2008-02 |
|
| Management of cough in advanced cancer. | 2005-11-24 |
|
| Important drugs for cough in advanced cancer. | 2001-11 |
|
| Subanesthetic concentrations of lidocaine selectively inhibit a nociceptive response in the isolated rat spinal cord. | 1995-02 |
Patents
Sample Use Guides
Usual dose is one 100 mg or 200 mg capsule three times a day. If necessary to control cough, up to 600 mg daily in three divided doses may be given.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26386152
The IC50 for Na+ current block by benzonatate in CAD cells was 5.9 mM at 100 mV but considerably less, 1.4 mM, at 70 mV.
| Substance Class |
Chemical
Created
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| Record UNII |
5P4DHS6ENR
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| Record Status |
FAILED
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NCI_THESAURUS |
C66917
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N0000175796
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R05DB01
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N0000009010
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BENZONATATE
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104-31-4
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