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Benzonatate

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Synopsis

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Chemistry

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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

Benzonatate

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 Formula	C₃₀H₅₃NO₁₁
Molecular Weight	603.7 g/mol
XLogP3	2.4
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	12
Rotatable Bond Count	33
Exact Mass	603.36186151 g/mol
Monoisotopic Mass	603.36186151 g/mol
Topological Polar Surface Area	121 Å²
Heavy Atom Count	42
Formal Charge	0
Complexity	565
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Drug and Medication Information

4.1 Drug Information

1 of 4
Drug Name	Benzonatate
PubMed Health	Benzonatate (By mouth)
Drug Classes	Antitussive
Drug Label	Benzonatate, 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 Ingredient	Benzonatate
Dosage Form	Capsule
Route	Oral
Strength	200mg; 100mg; 150mg
Market Status	Prescription
Company	Thepharmanetwork; Orit Labs; Sun Pharm Inds; Zydus Pharms Usa; The Pharma Network; Banner Pharmacaps; Mikart

2 of 4
Drug Name	Tessalon
PubMed Health	Benzonatate (By mouth)
Drug Classes	Antitussive
Drug Label	TESSALON, 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 Ingredient	Benzonatate
Dosage Form	Capsule
Route	Oral
Strength	200mg; 100mg
Market Status	Prescription
Company	Pfizer

3 of 4
Drug Name	Benzonatate
PubMed Health	Benzonatate (By mouth)
Drug Classes	Antitussive
Drug Label	Benzonatate, 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 Ingredient	Benzonatate
Dosage Form	Capsule
Route	Oral
Strength	200mg; 100mg; 150mg
Market Status	Prescription
Company	Thepharmanetwork; Orit Labs; Sun Pharm Inds; Zydus Pharms Usa; The Pharma Network; Banner Pharmacaps; Mikart

4 of 4
Drug Name	Tessalon
PubMed Health	Benzonatate (By mouth)
Drug Classes	Antitussive
Drug Label	TESSALON, 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 Ingredient	Benzonatate
Dosage Form	Capsule
Route	Oral
Strength	200mg; 100mg
Market Status	Prescription
Company	Pfizer

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

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.

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.

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.

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

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LIMITED","customerCountry":"INDIA","quantity":"1229.22","actualQuantity":"1229.22","unit":"KGS","unitRateFc":"110","totalValueFC":"136543.3","currency":"USD","unitRateINR":"9273","date":"17-Jun-2024","totalValueINR":"11398557.06","totalValueInUsd":"136543.3","indian_port":"JNPT","hs_no":"29420090","bill_no":"4042235","productDescription":"API","marketType":"REGULATED MARKET","country":"TAIWAN","selfForZScoreResived":"Pharma Grade","supplierPort":"KAOHSIUNG","supplierAddress":"36 HOPING STREET, LOUCHU, TAOYUAN 33842 Taoyuan, , TaiwanSDNF Taiwan","customerAddress":"ZYDUS TOWER, SARKHEJ-GANDHINAGAR,H"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q2","strtotime":1719340200,"product":"BENZONATATE USP","address":"206, DEVAVRATA,","city":"NAVI MUMBAI, MAHARASHTRA.","supplier":"FORMOSA LABORATORIES","supplierCountry":"TAIWAN","foreign_port":"KAOHSIUNG","customer":"STRIDES PHARMA 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PLOT NO 27 PONNU GREEN FARMS, Samy Apartments Ponnu Green Form Padur ,? CHENNAI , ?KANCHIPURAM ,? TAMIL NADU,? 603103","city":"","supplier":"CHEMISTRY & HEALTH FZ-LLC","supplierCountry":"TAIWAN","foreign_port":"KAOHSIUNG","customer":"ESJAY PHARMA PRIVATE LIMITED","customerCountry":"INDIA","quantity":"2447.44","actualQuantity":"2447.44","unit":"KGS","unitRateFc":"105","totalValueFC":"260350.7","currency":"USD","unitRateINR":"8914.5","date":"19-Sep-2024","totalValueINR":"21817703.88","totalValueInUsd":"260350.7","indian_port":"Madras Sea","hs_no":"29163190","bill_no":"5679210","productDescription":"API","marketType":"REGULATED MARKET","country":"TAIWAN","selfForZScoreResived":"Pharma Grade","supplierPort":"KAOHSIUNG","supplierAddress":"P.O. BOX 452820 DUBAI SCEIENCE PARK DUBAI DUBAI","customerAddress":"FIRST FLOOR, SF NO 534 42AB FLAT NO 102 ,? PLOT NO 27 PONNU GREEN FARMS, Samy Apartments Ponnu Green Form Padur ,? CHENNAI , ?KANCHIPURAM ,? TAMIL NADU,? 603103"},{"dataSource":"API Import","activeIngredients":"","year":"2024","qtr":"Q3","strtotime":1727375400,"product":"BENZONATATE USP","address":"206, DEVAVRATA,","city":"NAVI MUMBAI, MAHARASHTRA.","supplier":"FORMOSA LABORATORIES","supplierCountry":"TAIWAN","foreign_port":"KAOHSIUNG","customer":"STRIDES PHARMA SCIENCE","customerCountry":"INDIA","quantity":"4894.95","actualQuantity":"4894.95","unit":"KGS","unitRateFc":"105","totalValueFC":"518868.8","currency":"USD","unitRateINR":"8883","date":"27-Sep-2024","totalValueINR":"43481840.85","totalValueInUsd":"518868.8","indian_port":"Madras Sea","hs_no":"29224990","bill_no":"5838801","productDescription":"API","marketType":"REGULATED MARKET","country":"TAIWAN","selfForZScoreResived":"Pharma Grade","supplierPort":"KAOHSIUNG","supplierAddress":"36 HOPING STREET, LOUCHU, TAOYUAN 33842 , TAIWAN","customerAddress":"206, DEVAVRATA,"}]

Number of Transactions

Total Quantity (KGS)

Total Value (USD)

Quantity (KGS) & Unit rate (USD/KGS) over time

API Imports and Exports

Importing Country	Total Quantity (KGS)	Average Price (USD/KGS)	Number of Transactions

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DOSAGE - CAPSULE;ORAL - 100MG

USFDA APPLICATION NUMBER - 11210

DOSAGE - CAPSULE;ORAL - 200MG **Federal Regis...DOSAGE - CAPSULE;ORAL - 200MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

USFDA APPLICATION NUMBER - 11210

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ACTIVE PHARMA INGREDIENTS

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7 USDMF

1 EU WC

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$ API Reference Price

FINISHED DOSAGE FORMULATIONS

40 FDF Dossiers

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DRUG PRODUCT COMPOSITIONS

CAPSULE;ORAL - 100MG

CAPSULE;ORAL - 200MG **Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons**

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EXCIPIENTS BY APPLICATIONS

25 Fillers, Diluents & Binders

16 Direct Compression

15 Thickeners and Stabilizers

14 Disintegrants & Superdisintegrants

13 Film Formers & Plasticizers

11 Coating Systems & Additives

9 Co-Processed Excipients

8 Empty Capsules

7 Taste Masking

7 Granulation

6 Parenteral

5 Topical

5 Controlled & Modified Release

4 Chewable & Orodispersible Aids

3 Solubilizers

3 Emulsifying Agents

3 Lubricants & Glidants

2 Coloring Agents

2 Rheology Modifiers

1 Soft Gelatin

1 API Stability Enhancers

DIGITAL CONTENT

7 NEWS #PharmaBuzz

GLOBAL SALES INFORMATION

1 US Medicaid Prescriptions

4 Finished Drug Prices

MARKET PLACE

CAPSULE;ORAL - 200MG Federal Register determination that product was not discontinued or withdrawn for safety or effectiveness reasons