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Record Information
Version3.6
Creation Date2012-09-06 15:16:51 UTC
Update Date2016-02-11 01:30:57 UTC
HMDB IDHMDB15006
Secondary Accession NumbersNone
Metabolite Identification
Common NameBenzonatate
DescriptionBenzonatate is a non-narcotic oral antitussive (cough suppressant) drug which works by anesthetizing the tissues of the lungs and pleura responsible for the cough reflex. It is chemically related to other ester anesthetics such as procaine. It has an anesthetic (numbing) action similar to that of benzocaine and 'numbs' the stretch sensors in the lungs. It is the stretching of these sensors with breathing that causes the cough. It was approved by the FDA in 1958.
Structure
Thumb
Synonyms
ValueSource
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-butylaminobenzoateChEBI
3,6,9,12,15,18,21,24,27-Nonaoxaoctacosyl 4-butylaminobenzoateChEBI
4-(butylamino)Benzoic acid 3,6,9,12,15,18,21,24,27-nonaoxaoctacos-1-yl esterChEBI
BenzonatatoChEBI
BenzonatatumChEBI
BenzononatineChEBI
Nonaethyleneglycol monomethyl ether P-N-butylaminobenzoateChEBI
P-Butylaminobenzoic acid omega-O-methylnonaethyleneglycol esterChEBI
2,5,8,11,14,17,20,23,26-Nonaoxaoctacosan-28-yl P-(butylamino)benzoic acidGenerator
Benzonatic acidGenerator
Chemical FormulaC30H53NO11
Average Molecular Weight603.7419
Monoisotopic Molecular Weight603.361861543
IUPAC Name2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl 4-(butylamino)benzoate
Traditional Namebenzonatate
CAS Registry Number104-31-4
SMILES
CCCCNC1=CC=C(C=C1)C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC
InChI Identifier
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 KeyInChIKey=MAFMQEKGGFWBAB-UHFFFAOYSA-N
Chemical Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
KingdomOrganic compounds
Super ClassBenzenoids
ClassBenzene and substituted derivatives
Sub ClassBenzoic acids and derivatives
Direct ParentBenzoic acid esters
Alternative Parents
Substituents
  • Benzoate ester
  • Aminobenzoic acid or derivatives
  • Benzylether
  • Phenylalkylamine
  • Substituted aniline
  • Benzoyl
  • Secondary aliphatic/aromatic amine
  • Aniline
  • Carboxylic acid ester
  • Secondary amine
  • Monocarboxylic acid or derivatives
  • Ether
  • Dialkyl ether
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Organonitrogen compound
  • Carbonyl group
  • Amine
  • Aromatic homomonocyclic compound
Molecular FrameworkAromatic homomonocyclic compounds
External Descriptors
Ontology
StatusExpected but not Quantified
Origin
  • Drug
Biofunction
  • Antitussives
Application
  • Pharmaceutical
Cellular locations
  • Membrane
Physical Properties
StateLiquid
Experimental Properties
PropertyValueReference
Melting PointNot AvailableNot Available
Boiling PointNot AvailableNot Available
Water Solubility1.59e-03 g/LNot Available
LogP1.2Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.0016 mg/mLALOGPS
logP2.09ALOGPS
logP2.35ChemAxon
logS-5.6ALOGPS
pKa (Strongest Basic)3.47ChemAxon
Physiological Charge0ChemAxon
Hydrogen Acceptor Count11ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area121.4 Å2ChemAxon
Rotatable Bond Count33ChemAxon
Refractivity161.54 m3·mol-1ChemAxon
Polarizability67.87 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability0ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
SpectraNot Available
Biological Properties
Cellular Locations
  • Membrane
Biofluid Locations
  • Blood
  • Urine
Tissue LocationNot Available
PathwaysNot Available
Normal Concentrations
BiofluidStatusValueAgeSexConditionReferenceDetails
BloodExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00868
  • Not Applicable
details
UrineExpected but not QuantifiedNot ApplicableNot AvailableNot AvailableTaking drug identified by DrugBank entry DB00868
  • Not Applicable
details
Abnormal Concentrations
Not Available
Associated Disorders and Diseases
Disease ReferencesNone
Associated OMIM IDsNone
DrugBank IDDB00868
DrugBank Metabolite IDNot Available
Phenol Explorer Compound IDNot Available
Phenol Explorer Metabolite IDNot Available
FoodDB IDNot Available
KNApSAcK IDNot Available
Chemspider ID7413
KEGG Compound IDNot Available
BioCyc IDNot Available
BiGG IDNot Available
Wikipedia LinkBenzonatate
NuGOwiki LinkHMDB15006
Metagene LinkHMDB15006
METLIN IDNot Available
PubChem Compound7699
PDB IDNot Available
ChEBI ID3032
References
Synthesis ReferenceNot Available
Material Safety Data Sheet (MSDS)Not Available
General References
  1. Cohen V, Jellinek SP, Stansfield L, Truong H, Baseluos C, Marshall JP: Cardiac arrest with residual blindness after overdose of Tessalon(R) (benzonatate) perles. J Emerg Med. 2011 Aug;41(2):166-71. doi: 10.1016/j.jemermed.2009.08.027. Epub 2009 Nov 5. [19892505 ]

Enzymes

General function:
Involved in ion channel activity
Specific function:
This protein mediates the voltage-dependent sodium ion permeability of excitable membranes. Assuming opened or closed conformations in response to the voltage difference across the membrane, the protein forms a sodium-selective channel through which Na(+) ions may pass in accordance with their electrochemical gradient. It is a tetrodotoxin-resistant Na(+) channel isoform. This channel is responsible for the initial upstroke of the action potential in the electrocardiogram
Gene Name:
SCN5A
Uniprot ID:
Q14524
Molecular weight:
226937.5
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [17016423 ]
  3. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [11752352 ]