- Accession Number
- DB00868 (APRD00629)
- Small Molecule
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.
- 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-butylaminobenzoate
- 2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl p-(butylamino)benzoate
- 3,6,9,12,15,18,21,24,27-nonaoxaoctacosyl 4-butylaminobenzoate
- 4-(butylamino)benzoic acid 3,6,9,12,15,18,21,24,27-nonaoxaoctacos-1-yl ester
- nonaethyleneglycol monomethyl ether p-n-butylaminobenzoate
- p-butylaminobenzoic acid ω-O-methylnonaethyleneglycol ester
- External IDs
- KM 65 / KM65
- Product Images
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Benzonatate Capsule 100 mg/1 Oral Ethex Corporation 2008-12-30 Not applicable Benzonatate Capsule 200 mg/1 Oral Ethex Corporation 2008-12-30 Not applicable Tessalon Capsule 200 mg/1 Oral Pfizer Laboratories 1999-06-25 2011-02-04 Tessalon Capsule 100 mg/1 Oral Pfizer Laboratories Div Pfizer Inc 1958-02-10 Not applicable Tessalon Capsule 100 mg/1 Oral Physicians Total Care, Inc. 1958-02-10 2011-07-31
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Benzonatate Capsule 100 mg/1 Oral bryant ranch prepack 2017-03-22 Not applicable Benzonatate Capsule 200 mg/1 Oral bryant ranch prepack 2017-03-22 Not applicable Benzonatate Capsule, liquid filled 100 mg/1 Oral bryant ranch prepack 2010-06-04 Not applicable Benzonatate Capsule, liquid filled 200 mg/1 Oral bryant ranch prepack 2010-06-04 Not applicable Benzonatate Capsule 100 mg/1 Oral Cardinal Health 2015-06-01 Not applicable Benzonatate Capsule 100 mg/1 Oral Amerincan Health Packaging 2015-10-20 2018-11-30 Benzonatate Capsule 100 mg/1 Oral Nucare Pharmaceuticals,inc. 2007-04-09 Not applicable Benzonatate Capsule 100 mg/1 Oral Denton Pharma, Inc. 2018-01-02 Not applicable Benzonatate Capsule 100 mg/1 Oral bryant ranch prepack 2007-04-09 Not applicable Benzonatate Capsule 100 mg/1 Oral Remedy Repack 2013-04-02 2016-05-06
- International/Other Brands
- Exangit / Tesaperl (Novartis ) / Tessalon Perles / Ventussin
- CAS number
- Average: 603.7419
- Chemical Formula
- InChI Key
- IUPAC Name
- 2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl 4-(butylamino)benzoate
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.
- Associated Conditions
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.
- Mechanism of action
Benzonatate acts peripherally, anesthetizing the stretch receptors of vagal afferent fibers in the alveoli of the lungs, bronchi, and pleura. Since these receptors are responsible for mediating the cough reflex, anesthetizing these receptors result in the inhibiton of cough production. Benzonatate also suppresses transmission of the cough reflex at the level of the medulla where the afferent impulse is transmitted to the motor nerves. When applied locally, Benzonatate binds within the intracellular portion of voltage-gated sodium channels, decreasing the rate of membrane depolarization and increasing the threshold for electrical excitability.
Target Actions Organism USodium channel protein type 5 subunit alphaantagonist Humans
- Not Available
- Volume of distribution
- Not Available
- Protein binding
- Not Available
Benzonatate is hydrolyzed to para-aminobenzoic acid (PABA) by plasma esterases
- Route of elimination
- Not Available
- Half life
- Not Available
Restlessness, tremors, seizures and unconsciousness.
- Affected organisms
- Humans and other mammals
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.Learn more
Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.Learn more
Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.Learn more
- Synthesis Reference
Matter, M.; U.S. Patent 2,714,608; August 2, 1955; assigned to Ciba Pharmaceutical Products, Inc.
- General 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. 2011 Aug;41(2):166-71. doi: 10.1016/j.jemermed.2009.08.027. Epub 2009 Nov 5. [PubMed:19892505]
- External Links
- ATC Codes
- R05DB01 — Benzonatate
- Clinical Trials
Phase Status Purpose Conditions Count 1 Completed Basic Science Healthy Volunteers 1 3 Recruiting Treatment Coughing 1
- Banner pharmacaps inc
- Kv pharmaceutical co
- Mikart inc
- Orit laboratories llc
- Sun pharmaceutical industries inc
- The pharma network llc
- Zydus pharmaceuticals usa inc
- Forest laboratories inc
- Accucaps Industries Ltd.
- Advanced Pharmaceutical Services Inc.
- Amerisource Health Services Corp.
- Amneal Pharmaceuticals
- Apotheca Inc.
- A-S Medication Solutions LLC
- Ascend Laboratories LLC
- Atlantic Biologicals Corporation
- Atley Pharmaceuticals
- Banner Pharmacaps Inc.
- Barr Pharmaceuticals
- Bryant Ranch Prepack
- Cadila Healthcare Ltd.
- Caraco Pharmaceutical Labs
- Cardinal Health
- Catalent Pharma Solutions
- Dispensing Solutions
- Diversified Healthcare Services Inc.
- Ethex Corp.
- Forest Pharmaceuticals
- H.J. Harkins Co. Inc.
- Heartland Repack Services LLC
- Inwood Labs
- IVC Industries Inc.
- Kaiser Foundation Hospital
- KV Pharmaceutical Co.
- Lake Erie Medical and Surgical Supply
- Liberty Pharmaceuticals
- Major Pharmaceuticals
- Mallinckrodt Inc.
- Murfreesboro Pharmaceutical Nursing Supply
- Nucare Pharmaceuticals Inc.
- Palmetto Pharmaceuticals Inc.
- Patient First Corp.
- PD-Rx Pharmaceuticals Inc.
- Pharmaceutical Utilization Management Program VA Inc.
- Pharmaceutics International Inc.
- Physicians Total Care Inc.
- Pliva Inc.
- Preferred Pharmaceuticals Inc.
- Prepackage Specialists
- Prescript Pharmaceuticals
- Provident Pharmaceuticals LLC
- Rebel Distributors Corp.
- Redpharm Drug
- Remedy Repack
- Resource Optimization and Innovation LLC
- Stat Rx Usa
- Stat Scripts LLC
- Swiss Caps Ag
- United Research Laboratories Inc.
- Vangard Labs Inc.
- Zydus Pharmaceuticals
- Dosage forms
Form Route Strength Capsule Oral 100 mg/1 Capsule Oral 200 mg/1 Capsule, gelatin coated Oral 200 mg/1 Capsule, liquid filled Oral 100 mg/1 Capsule, liquid filled Oral 200 mg/1 Tablet Oral 100 mg/1 Capsule Oral 150 mg/1
Unit description Cost Unit Tessalon 200 mg capsule 2.76USD capsule Benzonatate 200 mg capsule 2.03USD capsule Tessalon Perles 100 mg capsule 1.62USD capsule Zonatuss 150 mg capsule 1.59USD capsule Tessalon perle 100 mg capsule 1.4USD capsule Benzonatate 100 mg capsule 0.85USD capsuleDrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
- Not Available
- Experimental Properties
Property Value Source water solubility Soluble in most organic solvents except aliphatic hydrocarbons Not Available logP 2.45 HANSCH,C ET AL. (1995)
- Predicted Properties
Property Value Source Water Solubility 0.00159 mg/mL ALOGPS logP 2.09 ALOGPS logP 2.35 ChemAxon logS -5.6 ALOGPS pKa (Strongest Basic) 3.47 ChemAxon Physiological Charge 0 ChemAxon Hydrogen Acceptor Count 11 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 121.4 Å2 ChemAxon Rotatable Bond Count 33 ChemAxon Refractivity 161.54 m3·mol-1 ChemAxon Polarizability 67.87 Å3 ChemAxon Number of Rings 1 ChemAxon Bioavailability 0 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule No ChemAxon MDDR-like Rule No ChemAxon
- Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9932 Blood Brain Barrier + 0.9355 Caco-2 permeable + 0.6067 P-glycoprotein substrate Substrate 0.6531 P-glycoprotein inhibitor I Non-inhibitor 0.5978 P-glycoprotein inhibitor II Non-inhibitor 0.9434 Renal organic cation transporter Non-inhibitor 0.7646 CYP450 2C9 substrate Non-substrate 0.875 CYP450 2D6 substrate Non-substrate 0.7017 CYP450 3A4 substrate Non-substrate 0.6026 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9232 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9275 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.932 Ames test Non AMES toxic 0.7269 Carcinogenicity Non-carcinogens 0.9182 Biodegradation Ready biodegradable 0.6331 Rat acute toxicity 2.2423 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9013 hERG inhibition (predictor II) Non-inhibitor 0.6129
- Mass Spec (NIST)
- Not Available
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS Not Available Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS Not Available Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS Not Available LC-MS/MS Spectrum - LC-ESI-qTof , Positive LC-MS/MS Not Available MS/MS Spectrum - , positive LC-MS/MS splash10-004i-2900000000-3718c62c83080a92ccdd
- This compound belongs to the class of organic compounds known as benzoic acid esters. These are ester derivatives of benzoic acid.
- Organic compounds
- Super Class
- Benzene and substituted derivatives
- Sub Class
- Benzoic acids and derivatives
- Direct Parent
- Benzoic acid esters
- Alternative Parents
- Aminobenzoic acids and derivatives / Phenylalkylamines / Benzoyl derivatives / Aniline and substituted anilines / Secondary alkylarylamines / Carboxylic acid esters / Amino acids and derivatives / Monocarboxylic acids and derivatives / Dialkyl ethers / Organopnictogen compoundsOrganic oxides / Hydrocarbon derivatives show 2 more
- Aminobenzoic acid or derivatives / Benzoate ester / Benzoyl / Aniline or substituted anilines / Phenylalkylamine / Secondary aliphatic/aromatic amine / Amino acid or derivatives / Carboxylic acid ester / Carboxylic acid derivative / Secondary amineDialkyl ether / Monocarboxylic acid or derivatives / Ether / Organopnictogen compound / Organonitrogen compound / Organooxygen compound / Organic nitrogen compound / Amine / Organic oxygen compound / Hydrocarbon derivative / Organic oxide / Aromatic homomonocyclic compound show 12 more
- Molecular Framework
- Aromatic homomonocyclic compounds
- External Descriptors
- substituted aniline, secondary amino compound, benzoate ester (CHEBI:3032)
- Pharmacological action
- General Function
- Voltage-gated sodium channel activity involved in sa node cell action potential
- 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 pr...
- Gene Name
- Uniprot ID
- Uniprot Name
- Sodium channel protein type 5 subunit alpha
- Molecular Weight
- 226937.475 Da
- Thimann DA, Huang CJ, Goto CS, Feng SY: Benzonatate toxicity in a teenager resulting in coma, seizures, and severe metabolic acidosis. J Pediatr Pharmacol Ther. 2012 Jul;17(3):270-3. doi: 10.5863/1551-6776-17.3.270. [PubMed:23258970]
Drug created on June 13, 2005 07:24 / Updated on April 19, 2019 19:26