U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C30H53NO11
Molecular Weight 603.7431
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BENZONATATE

SMILES

CCCCNC1=CC=C(C=C1)C(=O)OCCOCCOCCOCCOCCOCCOCCOCCOCCOC

InChI

InChIKey=MAFMQEKGGFWBAB-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C30H53NO11
Molecular Weight 603.7431
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description
Curator's Comment: description was created based on several sources, including: https://www.drugs.com/pro/benzonatate.html | http://www.wikidoc.org/index.php/Benzonatate | http://www.rxlist.com/tessalon-drug.htm

Benzonatate is an antitussive that is FDA approved for the symptomatic relief of cough. It acts peripherally by anesthetizing the stretch receptors located in the respiratory passages, lungs, and pleura by dampening their activity and thereby reducing the cough reflex at its source. Common adverse reactions include nausea, oral hypoesthesia, throat symptom, numbness, dizziness, headache, sedation, somnolence. 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.

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
TESSALON

Approved Use

Benzonatate USP is indicated for the symptomatic relief of cough.

Launch Date

1958
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
1063 ng/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BENZONATATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
1111 ng × h/mL
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BENZONATATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
1.01 h
100 mg single, oral
dose: 100 mg
route of administration: Oral
experiment type: SINGLE
co-administered:
BENZONATATE plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: FASTED
Doses

Doses

DosePopulationAdverse events​
50.9 mg/kg single, oral
Overdose
Dose: 50.9 mg/kg
Route: oral
Route: single
Dose: 50.9 mg/kg
Sources:
healthy, ADOLESCENT
Health Status: healthy
Age Group: ADOLESCENT
Sex: F
Food Status: UNKNOWN
Sources:
Disc. AE: Consciousness loss, Cyanosis...
AEs leading to
discontinuation/dose reduction:
Consciousness loss
Cyanosis
Polymorphic ventricular tachycardia
Torsades de pointes
Cardiac arrest
Sources:
5200 mg single, oral
Overdose
Dose: 5200 mg
Route: oral
Route: single
Dose: 5200 mg
Sources:
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Disc. AE: Status epilepticus, Cardiac arrest...
AEs leading to
discontinuation/dose reduction:
Status epilepticus
Cardiac arrest
Tachycardia
Hypotension
Brain death
Encephalopathy
Brain injury
Sources:
10000 mg single, oral
Overdose
Dose: 10000 mg
Route: oral
Route: single
Dose: 10000 mg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: F
Food Status: UNKNOWN
Sources:
Disc. AE: Seizure, Cardiac arrest...
AEs leading to
discontinuation/dose reduction:
Seizure
Cardiac arrest
Tachycardia
Sources:
200 mg 3 times / day multiple, oral
Recommended
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources:
unhealthy, CHILD|ADOLESCENT|ADULT
Health Status: unhealthy
Age Group: CHILD|ADOLESCENT|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Disc. AE: Hypersensitivity reaction, Mental confusion...
AEs leading to
discontinuation/dose reduction:
Hypersensitivity reaction
Mental confusion
Visual hallucinations
Sources:
3600 mg single, oral
Overdose
Dose: 3600 mg
Route: oral
Route: single
Dose: 3600 mg
Sources:
healthy
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Sources:
Disc. AE: Grand mal seizure, Ventricular tachycardia...
AEs leading to
discontinuation/dose reduction:
Grand mal seizure
Ventricular tachycardia
Sinus tachycardia
Mental confusion
Sources:
AEs

AEs

AESignificanceDosePopulation
Cardiac arrest Disc. AE
50.9 mg/kg single, oral
Overdose
Dose: 50.9 mg/kg
Route: oral
Route: single
Dose: 50.9 mg/kg
Sources:
healthy, ADOLESCENT
Health Status: healthy
Age Group: ADOLESCENT
Sex: F
Food Status: UNKNOWN
Sources:
Consciousness loss Disc. AE
50.9 mg/kg single, oral
Overdose
Dose: 50.9 mg/kg
Route: oral
Route: single
Dose: 50.9 mg/kg
Sources:
healthy, ADOLESCENT
Health Status: healthy
Age Group: ADOLESCENT
Sex: F
Food Status: UNKNOWN
Sources:
Cyanosis Disc. AE
50.9 mg/kg single, oral
Overdose
Dose: 50.9 mg/kg
Route: oral
Route: single
Dose: 50.9 mg/kg
Sources:
healthy, ADOLESCENT
Health Status: healthy
Age Group: ADOLESCENT
Sex: F
Food Status: UNKNOWN
Sources:
Polymorphic ventricular tachycardia Disc. AE
50.9 mg/kg single, oral
Overdose
Dose: 50.9 mg/kg
Route: oral
Route: single
Dose: 50.9 mg/kg
Sources:
healthy, ADOLESCENT
Health Status: healthy
Age Group: ADOLESCENT
Sex: F
Food Status: UNKNOWN
Sources:
Torsades de pointes Disc. AE
50.9 mg/kg single, oral
Overdose
Dose: 50.9 mg/kg
Route: oral
Route: single
Dose: 50.9 mg/kg
Sources:
healthy, ADOLESCENT
Health Status: healthy
Age Group: ADOLESCENT
Sex: F
Food Status: UNKNOWN
Sources:
Brain death Disc. AE
5200 mg single, oral
Overdose
Dose: 5200 mg
Route: oral
Route: single
Dose: 5200 mg
Sources:
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Brain injury Disc. AE
5200 mg single, oral
Overdose
Dose: 5200 mg
Route: oral
Route: single
Dose: 5200 mg
Sources:
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Cardiac arrest Disc. AE
5200 mg single, oral
Overdose
Dose: 5200 mg
Route: oral
Route: single
Dose: 5200 mg
Sources:
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Encephalopathy Disc. AE
5200 mg single, oral
Overdose
Dose: 5200 mg
Route: oral
Route: single
Dose: 5200 mg
Sources:
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Hypotension Disc. AE
5200 mg single, oral
Overdose
Dose: 5200 mg
Route: oral
Route: single
Dose: 5200 mg
Sources:
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Status epilepticus Disc. AE
5200 mg single, oral
Overdose
Dose: 5200 mg
Route: oral
Route: single
Dose: 5200 mg
Sources:
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Tachycardia Disc. AE
5200 mg single, oral
Overdose
Dose: 5200 mg
Route: oral
Route: single
Dose: 5200 mg
Sources:
unknown, ADULT
Health Status: unknown
Age Group: ADULT
Sex: F
Food Status: UNKNOWN
Sources:
Cardiac arrest Disc. AE
10000 mg single, oral
Overdose
Dose: 10000 mg
Route: oral
Route: single
Dose: 10000 mg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: F
Food Status: UNKNOWN
Sources:
Seizure Disc. AE
10000 mg single, oral
Overdose
Dose: 10000 mg
Route: oral
Route: single
Dose: 10000 mg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: F
Food Status: UNKNOWN
Sources:
Tachycardia Disc. AE
10000 mg single, oral
Overdose
Dose: 10000 mg
Route: oral
Route: single
Dose: 10000 mg
Sources:
healthy, CHILD
Health Status: healthy
Age Group: CHILD
Sex: F
Food Status: UNKNOWN
Sources:
Hypersensitivity reaction Disc. AE
200 mg 3 times / day multiple, oral
Recommended
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources:
unhealthy, CHILD|ADOLESCENT|ADULT
Health Status: unhealthy
Age Group: CHILD|ADOLESCENT|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Mental confusion Disc. AE
200 mg 3 times / day multiple, oral
Recommended
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources:
unhealthy, CHILD|ADOLESCENT|ADULT
Health Status: unhealthy
Age Group: CHILD|ADOLESCENT|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Visual hallucinations Disc. AE
200 mg 3 times / day multiple, oral
Recommended
Dose: 200 mg, 3 times / day
Route: oral
Route: multiple
Dose: 200 mg, 3 times / day
Sources:
unhealthy, CHILD|ADOLESCENT|ADULT
Health Status: unhealthy
Age Group: CHILD|ADOLESCENT|ADULT
Sex: M+F
Food Status: UNKNOWN
Sources:
Grand mal seizure Disc. AE
3600 mg single, oral
Overdose
Dose: 3600 mg
Route: oral
Route: single
Dose: 3600 mg
Sources:
healthy
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Sources:
Mental confusion Disc. AE
3600 mg single, oral
Overdose
Dose: 3600 mg
Route: oral
Route: single
Dose: 3600 mg
Sources:
healthy
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Sources:
Sinus tachycardia Disc. AE
3600 mg single, oral
Overdose
Dose: 3600 mg
Route: oral
Route: single
Dose: 3600 mg
Sources:
healthy
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Sources:
Ventricular tachycardia Disc. AE
3600 mg single, oral
Overdose
Dose: 3600 mg
Route: oral
Route: single
Dose: 3600 mg
Sources:
healthy
Health Status: healthy
Sex: M
Food Status: UNKNOWN
Sources:
PubMed

PubMed

TitleDatePubMed
Cardiac arrest with residual blindness after overdose of Tessalon® (benzonatate) perles.
2011-08
Benzonatate Ingestion Reported to the National Poison Center Database System (NPDS).
2010-12
Clinical expert guidelines for the management of cough in lung cancer: report of a UK task group on cough.
2010-10-06
Acute cough: a diagnostic and therapeutic challenge.
2009-12-16
Inhibition of cough-reflex sensitivity by benzonatate and guaifenesin in acute viral cough.
2009-06
The cough from hell: diazepam for intractable cough in a patient with renal cell carcinoma.
2008-11
Rasagiline in treatment of Parkinson's disease.
2008-02
Management of cough in advanced cancer.
2005-11-24
Important drugs for cough in advanced cancer.
2001-11
Subanesthetic concentrations of lidocaine selectively inhibit a nociceptive response in the isolated rat spinal cord.
1995-02
Patents

Sample Use Guides

Usual dose is one 100 mg or 200 mg capsule three times a day. If necessary to control cough, up to 600 mg daily in three divided doses may be given.
Route of Administration: Oral
The IC50 for Na+ current block by benzonatate in CAD cells was 5.9 mM at 100 mV but considerably less, 1.4 mM, at 70 mV.
Substance Class Chemical
Created
by admin
on Wed Apr 02 17:21:37 GMT 2025
Edited
by admin
on Wed Apr 02 17:21:37 GMT 2025
Record UNII
5P4DHS6ENR
Record Status FAILED
Record Version
  • Download
Name Type Language
BENZONATATE
INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official Name English
TESSALON PERLES
Preferred Name English
BENZONATATE [MART.]
Common Name English
BENZONATATE [USP MONOGRAPH]
Common Name English
Benzonatate [WHO-DD]
Common Name English
BENZONATATE [ORANGE BOOK]
Common Name English
NSC-760128
Code English
BENZOIC ACID, 4-(BUTYLAMINO)-, 2,5,8,11,14,17,20,23,26-NONAOXAOCTACOS-28-YL ESTER
Common Name English
BENZONATATE [USP-RS]
Common Name English
POLY(OXY-1,2-ETHANEDIYL), .ALPHA.-(4-(BUTYLAMINO)BENZOYL)-.OMEGA.-METHOXY-
Systematic Name English
BENZONATATE [MI]
Common Name English
TESSALON
Brand Name English
BENZONATATE [VANDF]
Common Name English
benzonatate [INN]
Common Name English
2,5,8,11,14,17,20,23,26-NONAOXAOCTACOSAN-28-YL P-(BUTYLAMINO)BENZOATE
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C66917
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
NDF-RT N0000175796
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
WHO-VATC QR05DB01
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
WHO-ATC R05DB01
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
NDF-RT N0000009010
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
Code System Code Type Description
CAS
32760-16-0
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY
CHEBI
3032
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY
EPA CompTox
DTXSID9022655
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY
INN
651
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY
NCI_THESAURUS
C28863
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY
ECHA (EC/EINECS)
203-194-7
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY
DRUG BANK
DB00868
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY
IUPHAR
7611
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY
NSC
760128
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY
RS_ITEM_NUM
1056005
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY
RXCUI
18993
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY RxNorm
EVMPD
SUB05760MIG
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY
MESH
C029755
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY
FDA UNII
5P4DHS6ENR
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY
SMS_ID
100000086389
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY
DAILYMED
5P4DHS6ENR
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY
DRUG CENTRAL
326
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY
PUBCHEM
7699
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY
HSDB
7933
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY
ChEMBL
CHEMBL1374379
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY
WIKIPEDIA
BENZONATATE
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY
MERCK INDEX
m2368
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
PRIMARY Merck Index
CAS
104-31-4
Created by admin on Wed Apr 02 17:21:37 GMT 2025 , Edited by admin on Wed Apr 02 17:21:37 GMT 2025
MAJOR COMPONENT STRUCTURE/SEQUENCE
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