CHEBI:3032 - benzonatate

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ChEBI Name benzonatate
ChEBI ID CHEBI:3032
Definition The ester obtained by formal condensation of 4-butylaminobenzoic acid with nonaethylene glycol monomethyl ether. Structurally related to procaine and benzocaine, it has an anaesthetic effect on the stretch sensors in the lungs, and is used as a non-narcotic cough suppressant.
Stars This entity has been manually annotated by the ChEBI Team.
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Formula C30H53NO11
Net Charge 0
Average Mass 603.74190
Monoisotopic Mass 603.36186
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
InChIKey MAFMQEKGGFWBAB-UHFFFAOYSA-N
SMILES CCCCNc1ccc(cc1)C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC
Roles Classification
Chemical Role(s): Bronsted base
A molecular entity capable of accepting a hydron from a donor (Bronsted acid).
(via organic amino compound )
Application(s): anaesthetic
Substance which produces loss of feeling or sensation.
antitussive
An agent that suppresses cough. Antitussives have a central or a peripheral action on the cough reflex, or a combination of both. Compare with expectorants, which are considered to increase the volume of secretions in the respiratory tract, so facilitating their removal by ciliary action and coughing, and mucolytics, which decrease the viscosity of mucus, facilitating its removal by ciliary action and expectoration.
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ChEBI Ontology
Outgoing benzonatate (CHEBI:3032) has functional parent 4-(butylamino)benzoic acid (CHEBI:521021)
benzonatate (CHEBI:3032) has functional parent nonaethylene glycol monomethyl ether (CHEBI:59168)
benzonatate (CHEBI:3032) has role anaesthetic (CHEBI:38867)
benzonatate (CHEBI:3032) has role antitussive (CHEBI:51177)
benzonatate (CHEBI:3032) is a benzoate ester (CHEBI:36054)
benzonatate (CHEBI:3032) is a secondary amino compound (CHEBI:50995)
benzonatate (CHEBI:3032) is a substituted aniline (CHEBI:48975)
IUPAC Name
2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl 4-(butylamino)benzoate
INNs Sources
benzonatate KEGG DRUG
benzonatato DrugBank
benzonatatum DrugBank
Synonyms Sources
2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl p-(butylamino)benzoate ChEBI
2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-butylaminobenzoate DrugBank
3,6,9,12,15,18,21,24,27-nonaoxaoctacosyl 4-butylaminobenzoate ChEBI
4-(butylamino)benzoic acid 3,6,9,12,15,18,21,24,27-nonaoxaoctacos-1-yl ester ChEBI
benzononatine ChemIDplus
nonaethyleneglycol monomethyl ether p-n-butylaminobenzoate ChEBI
p-butylaminobenzoic acid ω-O-methylnonaethyleneglycol ester ChEBI
Manual Xrefs Databases
Benzonatate Wikipedia
D00242 KEGG DRUG
DB00868 DrugBank
HMDB0015006 HMDB
LSM-4052 LINCS
US2714608 Patent
WO2012054067 Patent
View more database links
Registry Numbers Types Sources
104-31-4 CAS Registry Number KEGG DRUG
104-31-4 CAS Registry Number ChemIDplus
6897154 Beilstein Registry Number Beilstein
6897154 Reaxys Registry Number Reaxys
Citations Waiting for Citations Types Sources
15445814 PubMed citation Europe PMC
19121573 PubMed citation Europe PMC
21673569 PubMed citation Europe PMC
7223452 PubMed citation Europe PMC
Last Modified
25 February 2016