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.

benzonatate is commercially available from our sponsors

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 Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/). 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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
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.

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)

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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

Generated using the Chemistry Development Kit (CDK) (Willighagen EL et al. Journal of Cheminformatics vol. 9:33. 2017, doi:10.1186/s13321-017-0220-4; https://cdk.github.io/)
Classification Click here for help
Compound class Synthetic organic
Approved drug? Yes. FDA (1958)
IUPAC Name Click here for help
2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-butylaminobenzoate
International Nonproprietary Names Click here for help
INN number INN
651 benzonatate
Synonyms Click here for help
Tessalon® | Zonatuss®
Database Links Click here for help
CAS Registry No. 104-31-4
ChEBI CHEBI:3032
ChEMBL Ligand CHEMBL1374379
DrugBank Ligand DB00868
GtoPdb PubChem SID 223365946
PubChem CID 7699
Search Google for chemical match using the InChIKey MAFMQEKGGFWBAB-UHFFFAOYSA-N
Search Google for chemicals with the same backbone MAFMQEKGGFWBAB
Search PubMed clinical trials benzonatate
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UniChem Compound Search for chemical match using the InChIKey MAFMQEKGGFWBAB-UHFFFAOYSA-N
UniChem Connectivity Search for chemical match using the InChIKey MAFMQEKGGFWBAB-UHFFFAOYSA-N
Wikipedia Benzonatate

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MedChemExpress
Benzonatate (links to external site)
Cat. No. HY-B1551