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CHEBI:3032 - benzonatate

ChEBI IDCHEBI:3032
ChEBI Namebenzonatate
Stars
DefinitionThe 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.
Last Modified25 February 2016
DownloadsMolfile
FormulaC30H53NO11
Net Charge0
Average Mass603.750
Monoisotopic Mass603.36186
SMILESCCCCNc1ccc(C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC)cc1
InChIInChI=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
InChIKeyMAFMQEKGGFWBAB-UHFFFAOYSA-N
Wikipedia
Roles Classification
Chemical Role:
Bronsted base  A molecular entity capable of accepting a hydron from a donor (Brønsted acid).
Applications:
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.
anaesthetic  Substance which produces loss of feeling or sensation.
ChEBI Ontology
Outgoing Relation(s)
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  Source
benzonatatoDrugBank
benzonatateKEGG DRUG
benzonatatumDrugBank
Synonyms  Source
2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl p-(butylamino)benzoateChEBI
2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-butylaminobenzoateDrugBank
4-(butylamino)benzoic acid 3,6,9,12,15,18,21,24,27-nonaoxaoctacos-1-yl esterChEBI
nonaethyleneglycol monomethyl ether p-n-butylaminobenzoateChEBI
p-butylaminobenzoic acid ω-O-methylnonaethyleneglycol esterChEBI
benzononatineChemIDplus
Manual XrefsDatabases
DB00868DrugBank
D00242KEGG DRUG
US2714608Patent
BenzonatateWikipedia
HMDB0015006HMDB
WO2012054067Patent
LSM-4052LINCS
Registry NumbersSources
Reaxys:6897154Reaxys
CAS:104-31-4KEGG DRUG
CAS:104-31-4ChemIDplus
Citations