benzonatate   

GtoPdb Ligand ID: 7611

Synonyms: Tessalon® | Zonatuss®
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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Physico-chemical Properties
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
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
Classification
Compound class Synthetic organic
Approved drug? Yes (FDA (1958))
IUPAC Name
2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-butylaminobenzoate
International Nonproprietary Names
INN number INN
651 benzonatate
Synonyms
Tessalon® | Zonatuss®
Database Links
CAS Registry No. 104-31-4
ChEBI CHEBI:3032
ChEMBL Ligand CHEMBL1374379
DrugBank Ligand DB00868
GtoPdb PubChem SID 223365946
PubChem CID 7699
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Wikipedia Benzonatate