Details
Stereochemistry | ACHIRAL |
Molecular Formula | C30H53NO11 |
Molecular Weight | 603.7419 |
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
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 |
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Target ID: CHEMBL4296 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26386152 |
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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 |
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Palliative | TESSALON Approved UseBenzonatate USP is indicated for the symptomatic relief of cough. Launch Date1958 |
PubMed
Title | Date | PubMed |
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Subanesthetic concentrations of lidocaine selectively inhibit a nociceptive response in the isolated rat spinal cord. | 1995 Feb |
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Management of cough in advanced cancer. | 2004 Nov-Dec |
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The cough from hell: diazepam for intractable cough in a patient with renal cell carcinoma. | 2008 Nov |
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Inhibition of cough-reflex sensitivity by benzonatate and guaifenesin in acute viral cough. | 2009 Jun |
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Clinical expert guidelines for the management of cough in lung cancer: report of a UK task group on cough. | 2010 Oct 6 |
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.
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Classification Tree | Code System | Code | ||
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NCI_THESAURUS |
C66917
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NDF-RT |
N0000175796
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WHO-VATC |
QR05DB01
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WHO-ATC |
R05DB01
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NDF-RT |
N0000009010
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SUB05760MIG
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C029755
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100000086389
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CHEMBL1374379
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BENZONATATE
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m2368
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104-31-4
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MAJOR COMPONENT STRUCTURE/SEQUENCE |
ACTIVE MOIETY
METABOLITE (PARENT)