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Identification
NameBenzonatate
Accession NumberDB00868  (APRD00629)
TypeSmall Molecule
GroupsApproved
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.

Structure
Thumb
Synonyms
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
Benzonatat
Benzonatate
Benzonatato
Benzonatatum
Benzononatine
Nonaethyleneglycol monomethyl ether P-N-butylaminobenzoate
P-Butylaminobenzoic acid omega-O-methylnonaethyleneglycol ester
External Identifiers
  • KM 65
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Tessaloncapsule100 mg/1oralPfizer Laboratories1958-02-102016-04-23Us
Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Benzonatatecapsule100 mg/1oralGolden State Medical Supply, Inc.2007-07-252016-04-05Us
Benzonatatecapsule100 mg/1oralRed Pharm Drug Inc.2007-07-252016-04-05Us
Benzonatatecapsule200 mg/1oralStrides Arcolab Limited2015-07-302016-04-05Us
Benzonatatecapsule200 mg/1oralProficient Rx LP2015-08-102016-04-05Us
Benzonatatecapsule200 mg/1oralZydus Pharmaceuticals (USA) Inc.2007-09-042016-04-05Us
Benzonatatecapsule200 mg/1oralNorthwind Pharmaceuticals2015-01-152016-04-05Us
Benzonatatecapsule200 mg/1oralMikart, Inc.2009-11-092016-04-05Us
Benzonatatecapsule100 mg/1oralAidarex Pharmaceuticals LLC2007-07-252016-04-05Us
Benzonatatecapsule200 mg/1oralRebel Distributors Corp2007-07-252016-04-05Us
Benzonatatecapsule200 mg/1oralMajor Pharmaceuticals Inc2007-07-252016-04-05Us
Benzonatatecapsule100 mg/1oralKAISER FOUNDATION HOSPITALS2010-06-212016-04-23Us
Benzonatatecapsule200 mg/1oralClinical Solutions Wholesale2007-07-252016-04-05Us
Benzonatatecapsule200 mg/1oralPhysicians Total Care, Inc.2001-04-042016-04-05Us
Benzonatatecapsule100 mg/1oralStrides Arcolab Limited2015-07-302016-04-05Us
Benzonatatecapsule, liquid filled100 mg/1oralNorthwind Pharmaceuticals, LLC2015-03-122016-04-05Us
Benzonatatecapsule200 mg/1oralDIRECT RX2014-01-012016-04-05Us
Benzonatatecapsule100 mg/1oralZydus Pharmaceuticals (USA) Inc.2007-09-042016-04-05Us
Benzonatatecapsule200 mg/1oralNorthwind Pharmaceuticals, LLC2014-07-252016-04-05Us
Benzonatatecapsule150 mg/1oralMikart, Inc.2009-11-092016-04-05Us
Benzonatatecapsule100 mg/1oralRebel Distributors Corp2007-07-252016-04-05Us
Benzonatatecapsule100 mg/1oralMajor Pharmaceuticals Inc2007-07-252016-04-05Us
Benzonatatecapsule100 mg/1oralClinical Solutions Wholesale2007-07-252016-04-05Us
Benzonatatecapsule100 mg/1oralPhysicians Total Care, Inc.1995-12-272016-04-05Us
Benzonatatecapsule, liquid filled100 mg/1oralReady Meds2010-06-042016-04-05Us
Benzonatatecapsule, liquid filled100 mg/1oralDIRECT RX2015-01-012016-04-05Us
Benzonatatecapsule, liquid filled100 mg/1oralCarilion Materials Management2010-06-042016-04-05Us
Benzonatatecapsule, liquid filled100 mg/1oralRed Pharm Drug Inc.2010-01-132016-04-05Us
Benzonatatecapsule, liquid filled200 mg/1oralAv Kare, Inc.2016-03-152016-04-05Us
Benzonatatecapsule100 mg/1oralLife Line Home Care Services, Inc.2012-01-122016-04-05Us
Benzonatatecapsule100 mg/1oralStat Rx USA2007-07-302016-04-05Us
Benzonatatecapsule100 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2007-07-252016-04-23Us
Benzonatatecapsule200 mg/1oralSun Pharmaceutical Industries, Inc.2008-04-072016-04-05Us
Benzonatatecapsule100 mg/1oralH.J. Harkins Company, Inc.2007-07-252016-04-05Us
Benzonatatecapsule200 mg/1oralbryant ranch prepack2007-07-252016-04-05Us
Benzonatatecapsule200 mg/1oralDIRECT RX2015-01-012016-04-05Us
Benzonatatecapsule100 mg/1oralAmerican Health Packaging2011-10-032016-06-30Us
Benzonatatecapsule200 mg/1oralMed Vantx, Inc.2008-01-252016-04-05Us
Benzonatatecapsule, liquid filled100 mg/1oralAv Kare, Inc.2016-03-152016-04-05Us
Benzonatatecapsule200 mg/1oralBanner Life Sciences Llc.2015-06-012016-04-05Us
Benzonatatetablet100 mg/1oralNorthwind Pharmaceuticals, LLC2014-12-082016-04-05Us
Benzonatatecapsule100 mg/1oralMikart, Inc.2009-11-092016-04-05Us
Benzonatatecapsule, liquid filled100 mg/1oralApotheca Inc.2010-06-042016-04-05Us
Benzonatatecapsule100 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2007-09-042016-04-23Us
Benzonatatecapsule100 mg/1oralSun Pharmaceutical Industries, Inc.2008-04-072016-04-05Us
Benzonatatecapsule200 mg/1oralH.J. Harkins Company, Inc.2007-07-252016-04-05Us
Benzonatatecapsule100 mg/1oralbryant ranch prepack1993-04-012016-04-05Us
Benzonatatecapsule100 mg/1oralDIRECT RX2014-01-012016-04-05Us
Benzonatatecapsule, liquid filled200 mg/1oralMed Vantx, Inc.2010-06-042016-04-05Us
Benzonatatecapsule, liquid filled100 mg/1oralA S Medication Solutions2010-06-042016-04-05Us
Benzonatatecapsule100 mg/1oralBanner Life Sciences Llc.2015-06-012016-04-05Us
Benzonatatecapsule200 mg/1oralTAGI Pharma, Inc.2015-08-102016-04-05Us
Benzonatatecapsule100 mg/1oralPd Rx Pharmaceuticals, Inc.2007-07-252016-04-05Us
Benzonatatecapsule200 mg/1oralPd Rx Pharmaceuticals, Inc.2007-07-252016-04-05Us
Benzonatatecapsule, liquid filled100 mg/1oralREMEDYREPACK INC.2014-06-162016-04-05Us
Benzonatatecapsule200 mg/1oralProficient Rx LP2008-04-072016-04-05Us
Benzonatatecapsule, liquid filled100 mg/1oralREMEDYREPACK INC.2014-10-022016-04-05Us
Benzonatatecapsule150 mg/1oralAscend Laboratories LLC2015-02-092016-04-05Us
Benzonatatecapsule200 mg/1oralCadila Healthcare Limited2007-09-042016-04-05Us
Benzonatatecapsule100 mg/1oralAvera Mc Kennan Hospital2015-03-052016-04-05Us
Benzonatatecapsule, liquid filled100 mg/1oralPreferred Pharmaceuticals, Inc.2012-04-052016-04-05Us
Benzonatatecapsule200 mg/1oralUnit Dose Services2007-07-252016-04-05Us
Benzonatatecapsule100 mg/1oralPd Rx Pharmaceuticals, Inc.2007-07-252016-04-05Us
Benzonatatecapsule100 mg/1oralBlenheim Pharmacal, Inc.2010-11-012016-04-05Us
Benzonatatecapsule100 mg/1oralNcs Health Care Of Ky, Inc Dba Vangard Labs2010-11-142016-04-23Us
Benzonatatecapsule100 mg/1oralPd Rx Pharmaceuticals, Inc.2007-07-252016-04-05Us
Benzonatatecapsule100 mg/1oralREMEDYREPACK INC.2013-05-292016-04-05Us
Benzonatatecapsule200 mg/1oralProficient Rx LP2007-07-252016-04-05Us
Benzonatatecapsule100 mg/1oralSt Marys Medical Park Pharmacy2007-07-252016-04-05Us
Benzonatatecapsule200 mg/1oralAscend Laboratories LLC2007-07-252016-04-05Us
Benzonatatecapsule100 mg/1oralCadila Healthcare Limited2007-09-042016-04-05Us
Benzonatatecapsule100 mg/1oralPreferred Pharmaceuticals Inc.2016-03-012016-04-05Us
Benzonatatecapsule200 mg/1oralPreferred Pharmaceuticals, Inc.2014-08-012016-04-05Us
Benzonatatecapsule100 mg/1oralUnit Dose Services2007-07-252016-04-05Us
Benzonatatecapsule, liquid filled100 mg/1oralRebel Distributors Corp2010-01-132016-04-05Us
Benzonatatecapsule200 mg/1oralBlenheim Pharmacal, Inc.2013-07-102016-04-05Us
Benzonatatecapsule200 mg/1oralLiberty Pharmaceuticals, Inc.2007-07-252016-04-23Us
Benzonatatecapsule100 mg/1oralCardinal Health2010-11-142016-04-05Us
Benzonatatecapsule100 mg/1oralREMEDYREPACK INC.2013-05-222016-04-05Us
Benzonatatecapsule, liquid filled100 mg/1oralProficient Rx LP2010-06-042016-04-05Us
Benzonatatecapsule100 mg/1oralAmerican Health Packaging2015-06-012016-04-05Us
Benzonatatecapsule100 mg/1oralAscend Laboratories LLC2007-07-252016-04-05Us
Benzonatatecapsule, liquid filled200 mg/1oralAmneal Pharmaceuticals of NY LLC2010-06-042016-04-05Us
Benzonatatecapsule100 mg/1oralMajor Pharmaceuticals, Inc.2007-09-042016-04-05Us
Benzonatatecapsule100 mg/1oralPreferred Pharmaceuticals, Inc.2008-04-072016-04-05Us
Benzonatatecapsule200 mg/1oralLake Erie Medical DBA Quality Care Products LLC2007-07-252016-04-05Us
Benzonatatecapsule, liquid filled100 mg/1oralLake Erie Medical DBA Quality Care Products LLC2010-06-042016-04-05Us
Benzonatatecapsule100 mg/1oralBlenheim Pharmacal, Inc.2013-01-142016-04-05Us
Benzonatatecapsule100 mg/1oralLiberty Pharmaceuticals, Inc.2007-07-252016-04-23Us
Benzonatatecapsule100 mg/1oralCardinal Health2007-09-042016-04-05Us
Benzonatatecapsule, liquid filled200 mg/1oralNorthwind Pharmaceuticals2015-03-122016-04-05Us
Benzonatatecapsule100 mg/1oralProficient Rx LP2007-07-252016-04-05Us
Benzonatatecapsule200 mg/1oralGolden State Medical Supply, Inc.2007-07-252016-04-05Us
Benzonatatecapsule200 mg/1oralRed Pharm Drug Inc.2007-07-252016-04-05Us
Benzonatatecapsule, liquid filled100 mg/1oralAmneal Pharmaceuticals of NY LLC2010-06-042016-04-05Us
Benzonatatecapsule, gelatin coated200 mg/1oralDIRECT RX2016-02-152016-04-05Us
Benzonatatecapsule100 mg/1oralPreferred Pharmaceuticlas Inc.2016-01-042016-04-05Us
Benzonatatecapsule100 mg/1oralLake Erie Medical & Surgical Supply DBA Quality Care Products LLC2007-07-252016-04-05Us
Benzonatatecapsule200 mg/1oralAidarex Pharmaceuticals LLC2007-07-252016-04-05Us
Benzonatatecapsule, liquid filled200 mg/1oralMajor Pharmaceuticals2010-06-042016-04-05Us
Benzonatatecapsule100 mg/1oralLiberty Pharmaceuticals, Inc.2007-07-252016-04-23Us
Zonatusscapsule150 mg/1oralVertical Pharmaceuticals, Inc.2011-11-012016-04-05Us
Over the Counter ProductsNot Available
International Brands
NameCompany
TesaperlNovartis
Brand mixturesNot Available
SaltsNot Available
Categories
UNII5P4DHS6ENR
CAS number104-31-4
WeightAverage: 603.7419
Monoisotopic: 603.361861543
Chemical FormulaC30H53NO11
InChI KeyInChIKey=MAFMQEKGGFWBAB-UHFFFAOYSA-N
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
IUPAC Name
2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl 4-(butylamino)benzoate
SMILES
CCCCNC1=CC=C(C=C1)C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC
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
Pharmacology
IndicationFor 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.
PharmacodynamicsBenzonatate, 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 actionBenzonatate 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Benzonatate is hydrolyzed to para-aminobenzoic acid (PABA) by plasma esterases

Route of eliminationNot Available
Half life3-8 hours
ClearanceNot Available
ToxicityRestlessness, tremors, seizures and unconsciousness.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9932
Blood Brain Barrier+0.9355
Caco-2 permeable+0.6067
P-glycoprotein substrateSubstrate0.6531
P-glycoprotein inhibitor INon-inhibitor0.5978
P-glycoprotein inhibitor IINon-inhibitor0.9434
Renal organic cation transporterNon-inhibitor0.7646
CYP450 2C9 substrateNon-substrate0.875
CYP450 2D6 substrateNon-substrate0.7017
CYP450 3A4 substrateNon-substrate0.6026
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.907
CYP450 2D6 inhibitorNon-inhibitor0.9232
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9275
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.932
Ames testNon AMES toxic0.7269
CarcinogenicityNon-carcinogens0.9182
BiodegradationReady biodegradable0.6331
Rat acute toxicity2.2423 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9013
hERG inhibition (predictor II)Non-inhibitor0.6129
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • 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
Packagers
Dosage forms
FormRouteStrength
Capsuleoral150 mg/1
Capsuleoral200 mg/1
Capsule, gelatin coatedoral200 mg/1
Capsule, liquid filledoral100 mg/1
Capsule, liquid filledoral200 mg/1
Tabletoral100 mg/1
Capsuleoral100 mg/1
Prices
Unit descriptionCostUnit
Tessalon 200 mg capsule2.76USD capsule
Benzonatate 200 mg capsule2.03USD capsule
Tessalon Perles 100 mg capsule1.62USD capsule
Zonatuss 150 mg capsule1.59USD capsule
Tessalon perle 100 mg capsule1.4USD capsule
Benzonatate 100 mg capsule0.85USD capsule
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
PatentsNot Available
Properties
StateLiquid
Experimental Properties
PropertyValueSource
water solubilitySoluble in most organic solvents except aliphatic hydrocarbonsNot Available
logP2.45HANSCH,C ET AL. (1995)
Predicted Properties
PropertyValueSource
Water Solubility0.00159 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
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

Matter, M.; U.S. Patent 2,714,608; August 2, 1955; assigned to Ciba Pharmaceutical Products, Inc.

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. [PubMed:19892505 ]
External Links
ATC CodesR05DB01
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelNot Available
MSDSNot Available
Interactions
Drug InteractionsNo interactions found.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
antagonist
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 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 respon...
Gene Name:
SCN5A
Uniprot ID:
Q14524
Molecular Weight:
226937.475 Da
References
  1. 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 ]
Comments
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Drug created on June 13, 2005 07:24 / Updated on March 31, 2014 15:07