benzonatate   Click here for help

GtoPdb Ligand ID: 7611

Synonyms: Tessalon® | Zonatuss®
Approved drug
benzonatate is an approved drug (FDA (1958))
Compound class: Synthetic organic
Comment: Benzonatate is a non-narcotic antitussive. It is classified as a butylamine compound, and has structural similatities to ester type local anesthetics (e.g. Procaine and tetracaine). It has reduced abuse potential compared to opioid-like antitussives.
2D Structure
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2D Structure

An image of the ligand's 2D structure. For small molecules with SMILES these are drawn using the NCI/CADD Chemical Identifier Resolver. Click on the image to access the chemical structure search tool with the ligand pre-loaded in the structure editor. For other types of ligands, e.g. longer nucleotides and peptides, a manually drawn representation of the molecule may be provided.

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Physico-chemical Properties
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Physico-chemical Properties

Calculated molecular properties are available for small molecules and natural products (not peptides). Properties were generated using the CDK toolkit. All properties were selected to enable the prediction of the Lipinski Rule-of-Five profile or ‘druglikeness’ for each ligand. For more info on each category see the help pages.

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Hydrogen bond acceptors 12
Hydrogen bond donors 1
Rotatable bonds 33
Topological polar surface area 121.4
Molecular weight 603.36
XLogP 1.24
No. Lipinski's rules broken 2
SMILES / InChI / InChIKey
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SMILES / InChI / InChIKey

SMILES (Simplified Molecular Input Line Entry Specification) A specification for unambiguously describing the structure of chemical molecules using short ASCII strings. Canonical SMILES specify a unique representation of the 2D structure without chiral or isotopic specifications. Isomeric SMILES include chiral specification and isotopes.

Standard InChI (IUPAC International Chemical Identifier) and InChIKey InChI is a non-proprietary, standard, textual identifier for chemical substances designed to facilitate linking of information and database searching. An InChIKey is a simplified version of a full InChI, designed for easier web searching.

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Canonical SMILES COCCOCCOCCOCCOCCOCCOCCOCCOCCOC(=O)c1ccc(cc1)NCCCC
Isomeric SMILES COCCOCCOCCOCCOCCOCCOCCOCCOCCOC(=O)c1ccc(cc1)NCCCC
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
InChI Key MAFMQEKGGFWBAB-UHFFFAOYSA-N
No information available.
Summary of Clinical Use Click here for help
Benzonatate is a non-narcotic oral antitussive used to reduce coughing in respiratory conditions including bronchitis, emphysema, influenza, and pneumonia.
Mechanism Of Action and Pharmacodynamic Effects Click here for help
Benzonatate is believed to anesthetise stretch sensors in the lungs, activation of which is responsible for the cough reflex. However, the precise protein structure of these receptors remains elusive, but they appear to be protein complexes likely to contain voltage-gated sodium channels.
External links Click here for help
For extended ADME data see the following:

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