2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl 4-(butylamino)benzoate

• ChemBase ID: 746
• Molecular Formular: C30H53NO11
• Molecular Mass: 603.74192
• Monoisotopic Mass: 603.36186152
• SMILES: O(CCOCCOCCOCCOCCOC)CCOCCOCCOCCOC(=O)c1ccc(NCCCC)cc1
• Canonical 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
• InChIKey: MAFMQEKGGFWBAB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl 4-(butylamino)benzoate
• IUPAC Traditional name: @benzonatate
• Brand Name: Benzononantin; Exangit; Tesalon; Tessalin; Tessalon; Tessalon Perles; Tessalon-Ciba; Ventussin; Ventussin-Loz
• Synonyms: Benzonatato [INN-Spanish]; Benzonatatum [INN-Latin]; Benzononatine; Benzonatate

Database IDs

• CAS Number: 104-31-4
• PubChem SID: 160964209; 46506376
• PubChem CID: 7699

CALCULATED PROPERTIES

JChem

• H Acceptors: 11
• H Donor: 1
• LogD (pH = 5.5): 2.3465576
• LogD (pH = 7.4): 2.350569
• Log P: 2.3506203
• Molar Refractivity: 161.5422 cm^3
• Polarizability: 62.730156 Å^3
• Polar Surface Area: 121.4 Å^2
• Rotatable Bonds: 33
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: 2.09
• LOG S: -5.58
• Solubility (Water): 1.59e-03 g/l

PROPERTIES

Physical Property

• Solubility: Soluble in most organic solvents except aliphatic hydrocarbons
• Hydrophobicity(logP): 1.2

DETAILS

DrugBank - DB00868

• Drug Groups: approved
• Description: Benzonatate 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.
• Indication: For the symptomatic relief of cough. Has also been applied locally in the oral cavity in adults by releasing the drug from the liquid-filled capsules to provide oropharyngeal anesthesia for conscious intubation.
• Pharmacology: Benzonatate, a non-narcotic antitussive agent chemically related to tetracaine and other ester-type local anesthetics, is used to suppress cough associated with both acute and chronic respiratory conditions. The drug acts peripherally by anesthetizing the stretch receptors located in the respiratory passages, lungs, and pleura through the dampening of their activity, which reduces the cough reflex.
• Toxicity: Restlessness, tremors, seizures and unconsciousness.
• Affected Organisms: Humans and other mammals
• Biotransformation: Benzonatate is hydrolyzed to para-aminobenzoic acid (PABA) by plasma esterases
• Half Life: 3-8 hours
• References: 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. 2009 Nov 4. [Pubmed]
• External Links: Wikipedia; RxList; Drugs.com

REFERENCES

• 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. 2009 Nov 4. Pubmed