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    Benzonatate

    ACTIVE PHARMA INGREDIENTS

    FINISHED DOSAGE FORMULATIONS

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    $ API Ref.Price (USD/KG) : 109Xls

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    2D Structure
    Also known as: 104-31-4, Benzononatine, Tessalon, Benzononantin, Exangit, Ventussin
    Molecular Formula
    C30H53NO11
    Molecular Weight
    603.7  g/mol
    InChI Key
    MAFMQEKGGFWBAB-UHFFFAOYSA-N
    Benzonatate is an oral antitussive drug used in the relief and suppression of cough in patients older than ten years of age. Currently, benzonatate is the only non-narcotic antitussive available as a prescription drug. It works to reduce the activity of cough reflex by desensitizing the tissues of the lungs and pleura involved in the cough reflex. Benzonatate was approved by the FDA in 1958 under the market name Tessalon Perles. Because its chemical structure resembles that of the anesthetic agents in the para-amino-benzoic acid class (such as [procaine] and [tetracaine]), benzonatate exhibits anesthetic or numbing action. Although it not prone to drug misuse or abuse, benzonatate is associated with a risk for severe toxicity and overdose, especially in children.
    1 2D Structure

    2D Structure

    2 Identification
    2.1 Computed Descriptors
    2.1.1 IUPAC Name
    2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-(butylamino)benzoate
    2.1.2 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
    2.1.3 InChI Key
    MAFMQEKGGFWBAB-UHFFFAOYSA-N
    2.1.4 Canonical SMILES
    CCCCNC1=CC=C(C=C1)C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC
    2.2 Synonyms
    2.2.1 MeSH Synonyms

    1. Tessalon

    2.2.2 Depositor-Supplied Synonyms

    1. 104-31-4

    2. Benzononatine

    3. Tessalon

    4. Benzononantin

    5. Exangit

    6. Ventussin

    7. Benzonatatum

    8. Tessalon-ciba

    9. Ventussin-loz

    10. Benzonatato

    11. Tessalin

    12. Zonatuss

    13. Benzonatatum [inn-latin]

    14. Benzonatato [inn-spanish]

    15. Km65

    16. 2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl P-(butylamino)benzoate

    17. P-(n)-butylaminobenzoesaeure-(nonaaethylenglykol-monomethylaether)-ester

    18. 2,5,8,11,14,17,20,23,26-nonaoxaoctacosan-28-yl 4-(butylamino)benzoate

    19. Benzoic Acid, 4-(butylamino)-, 3,6,9,12,15,18,21,24,27-nonaoxaoctacos-1-yl Ester

    20. Chebi:3032

    21. Nonaethyleneglycol Monomethyl Ether P-n-butylaminobenzoate

    22. Tesalon

    23. 4-(butylamino)benzoic Acid 3,6,9,12,15,18,21,24,27-nonaoxaoctacos-1-yl Ester

    24. Benzoic Acid, 4-(butylamino)-, 2,5,8,11,14,17,20,23,26-nonaoxaoctacos-28-yl Ester

    25. Nsc-760128

    26. 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-butylaminobenzoate

    27. Benzoic Acid, P-(butylamino)-, 2-(2-(2-(2-(2-(2-(2-(2-(2-methoxyethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethoxy)ethyl Ester

    28. Ncgc00016362-01

    29. Cas-104-31-4

    30. P-butylaminobenzoic Acid Omega-o-methylnonaethyleneglycol Ester

    31. 3,6,9,12,15,18,21,24,27-nonaoxaoctacosyl 4-butylaminobenzoate

    32. Dsstox_cid_2655

    33. Dsstox_rid_76676

    34. Dsstox_gsid_22655

    35. 3,6,9,12,15,18,21,24,27-nonaoxaoctacosyl-4-butylaminobenzoate;3,6,9,12,15,18,21,24,27-nonaoxaoctacosyl-4-butylaminobenzoate

    36. Tessalon Perles (tn)

    37. Benzonatate (usp/inn)

    38. Einecs 203-194-7

    39. Polyethyleneglycol-p-n-butylaminobenzoate Methyl Ester

    40. Benzonatate [usp:inn:ban]

    41. Hsdb 7933

    42. P-(n)-butylaminobenzoesaeure-(nonaaethylenglykol-monomethylaether)-ester [german]

    43. Prestwick0_000012

    44. Prestwick1_000012

    45. Prestwick2_000012

    46. Prestwick3_000012

    47. Schembl28366

    48. Bspbio_000043

    49. 2-[2-[2-[2-[2-[2-[2-[2-(2-methoxyethoxy)ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethoxy]ethyl 4-(butylamino)benzoate

    50. Mls002154171

    51. Spbio_001964

    52. Bpbio1_000049

    53. Gtpl7611

    54. Chembl1374379

    55. Dtxsid9022655

    56. Hms1568c05

    57. Hms2095c05

    58. Hms2230m19

    59. Hms3373i11

    60. Hms3712c05

    61. Km-65

    62. Pharmakon1600-01503864

    63. Hy-b1551

    64. Zinc3830276

    65. Tox21_110398

    66. Nsc760128

    67. 3,6,9,12,15,18,21,24,27-nonaoxaoctacos-1-yl 4-(butylamino)benzoate

    68. Akos015891366

    69. Tox21_110398_1

    70. Ccg-213706

    71. Db00868

    72. Nsc 760128

    73. Ncgc00016362-02

    74. Ncgc00016362-03

    75. Ncgc00016362-05

    76. Smr001233469

    77. Ab00513795

    78. Cs-0013413

    79. Ft-0622718

    80. D00242

    81. Ab00513795_06

    82. Sr-01000841197

    83. J-001145

    84. Q2070778

    85. Sr-01000841197-2

    86. Nonaethyleneglycol-p-n-butylaminobenzoate Methyl Ester

    87. 3,6,9,12,15,18,21,24,27-nonaoxaoctacos-1-yl 4-(butylamino)benzoate #

    2.3 Create Date
    2005-03-27
    3 Chemical and Physical Properties
    Molecular Weight 603.7 g/mol
    Molecular Formula C30H53NO11
    XLogP32.4
    Hydrogen Bond Donor Count1
    Hydrogen Bond Acceptor Count12
    Rotatable Bond Count33
    Exact Mass603.36186151 g/mol
    Monoisotopic Mass603.36186151 g/mol
    Topological Polar Surface Area121 Ų
    Heavy Atom Count42
    Formal Charge0
    Complexity565
    Isotope Atom Count0
    Defined Atom Stereocenter Count0
    Undefined Atom Stereocenter Count0
    Defined Bond Stereocenter Count0
    Undefined Bond Stereocenter Count0
    Covalently Bonded Unit Count1
    4 Drug and Medication Information
    4.1 Drug Information
    1 of 4  
    Drug NameBenzonatate
    PubMed HealthBenzonatate (By mouth)
    Drug ClassesAntitussive
    Drug LabelBenzonatate, a non-narcotic oral antitussive agent, is 2, 5, 8, 11, 14, 17, 20, 23, 26-nonaoxaoctacosan-28-yl p-(butylamino) benzoate; with a molecular weight of 603.7.Each soft gelatin capsule, for oral administration, contains 100 mg or 200 mg of b...
    Active IngredientBenzonatate
    Dosage FormCapsule
    RouteOral
    Strength200mg; 100mg; 150mg
    Market StatusPrescription
    CompanyThepharmanetwork; Orit Labs; Sun Pharm Inds; Zydus Pharms Usa; The Pharma Network; Banner Pharmacaps; Mikart

    2 of 4  
    Drug NameTessalon
    PubMed HealthBenzonatate (By mouth)
    Drug ClassesAntitussive
    Drug LabelTESSALON, a non-narcotic oral antitussive agent, is 2, 5, 8, 11, 14, 17, 20, 23, 26-nonaoxaoctacosan-28-yl p-(butylamino) benzoate; with a molecular weight of 603.7.Each TESSALON Perle contains:Benzonatate, USP 100 mgTESSALON Perles (capsules) also c...
    Active IngredientBenzonatate
    Dosage FormCapsule
    RouteOral
    Strength200mg; 100mg
    Market StatusPrescription
    CompanyPfizer

    3 of 4  
    Drug NameBenzonatate
    PubMed HealthBenzonatate (By mouth)
    Drug ClassesAntitussive
    Drug LabelBenzonatate, a non-narcotic oral antitussive agent, is 2, 5, 8, 11, 14, 17, 20, 23, 26-nonaoxaoctacosan-28-yl p-(butylamino) benzoate; with a molecular weight of 603.7.Each soft gelatin capsule, for oral administration, contains 100 mg or 200 mg of b...
    Active IngredientBenzonatate
    Dosage FormCapsule
    RouteOral
    Strength200mg; 100mg; 150mg
    Market StatusPrescription
    CompanyThepharmanetwork; Orit Labs; Sun Pharm Inds; Zydus Pharms Usa; The Pharma Network; Banner Pharmacaps; Mikart

    4 of 4  
    Drug NameTessalon
    PubMed HealthBenzonatate (By mouth)
    Drug ClassesAntitussive
    Drug LabelTESSALON, a non-narcotic oral antitussive agent, is 2, 5, 8, 11, 14, 17, 20, 23, 26-nonaoxaoctacosan-28-yl p-(butylamino) benzoate; with a molecular weight of 603.7.Each TESSALON Perle contains:Benzonatate, USP 100 mgTESSALON Perles (capsules) also c...
    Active IngredientBenzonatate
    Dosage FormCapsule
    RouteOral
    Strength200mg; 100mg
    Market StatusPrescription
    CompanyPfizer

    4.2 Therapeutic Uses

    Antitussive Agents

    National Library of Medicine's Medical Subject Headings online file (MeSH, 2011)

    Tessalon is indicated for the symptomatic relief of cough. /Included in US product label/

    US Natl Inst Health; DailyMed. Current Medication Information for TESSALON (benzonatate) capsule (February 2011). Available from, as of July 7, 2011: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=benzonatate

    4.3 Drug Warning

    Accidental ingestion of Tessalon resulting in death has been reported in children below age 10. Signs and symptoms of overdose have been reported within 15-20 minutes and death has been reported within one hour of ingestion. If accidental ingestion occurs, seek medical attention immediately

    US Natl Inst Health; DailyMed. Current Medication Information for TESSALON (benzonatate) capsule (February 2011). Available from, as of July 7, 2011: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=benzonatate

    Safety and effectiveness in children below the age of 10 have not been established. Accidental ingestion resulting in death has been reported in children below age 10. Keep out of reach of children.

    US Natl Inst Health; DailyMed. Current Medication Information for TESSALON (benzonatate) capsule (February 2011). Available from, as of July 7, 2011: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=benzonatate

    Severe hypersensitivity reactions (including bronchospasm, laryngospasm and cardiovascular collapse) have been reported which are possibly related to local anesthesia from sucking or chewing the capsule instead of swallowing it. Severe reactions have required intervention with vasopressor agents and supportive measures.

    US Natl Inst Health; DailyMed. Current Medication Information for TESSALON (benzonatate) capsule (February 2011). Available from, as of July 7, 2011: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=benzonatate

    Benzonatate is chemically related to anesthetic agents of the para-amino-benzoic acid class (e.g. procaine; tetracaine) and has been associated with adverse CNS effects possibly related to a prior sensitivity to related agents or interaction with concomitant medication.

    US Natl Inst Health; DailyMed. Current Medication Information for TESSALON (benzonatate) capsule (February 2011). Available from, as of July 7, 2011: https://dailymed.nlm.nih.gov/dailymed/search.cfm?startswith=benzonatate

    For more Drug Warnings (Complete) data for Benzonatate (8 total), please visit the HSDB record page.

    4.4 Drug Indication

    Benzonatate is indicated for the symptomatic relief of cough.

    5 Pharmacology and Biochemistry
    5.1 Pharmacology

    Benzonatate suppresses cough associated with both acute and chronic respiratory conditions. Its works by desensitizing the pulmonary stretch receptors involved in the cough reflex. There are limited clinical trials of benzonatate; however, earlier studies demonstrated inhibition of experimentally-induced cough and subjectively-measured pathological cough by benzonatate. Benzonatate has no inhibitory effects on the respiratory center in recommended dosage. Its onset of action is within 15 to 20 minutes following administration and its duration of effect is about 3 to 8 hours.

    5.2 MeSH Pharmacological Classification

    Antitussive Agents

    Agents that suppress cough. They act centrally on the medullary cough center. EXPECTORANTS, also used in the treatment of cough, act locally. (See all compounds classified as Antitussive Agents.)

    5.3 FDA Pharmacological Classification
    5.3.1 Pharmacological Classes
    Non-narcotic Antitussive [EPC]; Decreased Tracheobronchial Stretch Receptor Activity [PE]
    5.4 ATC Code

    R - Respiratory system

    R05 - Cough and cold preparations

    R05D - Cough suppressants, excl. combinations with expectorants

    R05DB - Other cough suppressants

    R05DB01 - Benzonatate

    5.5 Absorption, Distribution and Excretion

    Absorption

    Following oral administration, benzonatate enters the systemic circulation via gastrointestinal absorption. The Cmax of benzonatate following oral administration of 100 mg in healthy Chinese volunteers was 1063 460 ng/mL.

    Route of Elimination

    There is limited information on the route of elimination of benzonatate.

    Volume of Distribution

    There is limited information on the volume of distribution of benzonatate.

    Clearance

    There is limited information on the clearance of benzonatate.

    5.6 Metabolism/Metabolites

    Benzonatate is hydrolyzed to the major metabolite 4-(butylamino)benzoic acid (BABA) by plasma butyrylcholinesterase (BChE).

    5.7 Biological Half-Life

    The half life of benzonatate following oral administration of 100 mg in healthy Chinese volunteers was 1.01 0.41 h.

    5.8 Mechanism of Action

    Benzonatate is a local anesthetic drug that acts peripherally by anesthetizing and reducing the activity of vagal stretch receptors or nerve fibres located in the respiratory passages, lungs, and pleura. Once the stretch receptors are stimulated, they send impulses to the cough centre located in the medulla via an afferent pathway consisting of sensory nerve fibres or the vagus nerve. The efferent signal is then generated that sends impulses to the expiratory muscles to produce a cough. Anesthetizing these receptors by benzonatate results in the inhibition of the cough reflex activity and cough production. Benzonatate also inhibits the transmission of impulses of the cough reflex in the vagal nuclei of the medulla. There are several proposed mechanisms of benzonatate; it is also a potent voltage-gated sodium channel inhibitor.

    Benzonatate apparently inhibits cough production by anesthetizing stretch receptors of vagal afferent fibers in the bronchi, alveoli, and pleura that mediate the cough reflex; the drug also suppresses transmission of the cough reflex at the level of the medulla where the afferent impulse is transmitted to the motor nerves. The relationship between local anesthetic action and peripheral action on sensory nerve endings is not clear.

    American Society of Health-System Pharmacists 2011; Drug Information 2011. Bethesda, MD. 2011