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Details

Stereochemistry ACHIRAL
Molecular Formula C30H53NO11
Molecular Weight 603.7419
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

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

-3.75235215E11
PubMed

PubMed

TitleDatePubMed
Subanesthetic concentrations of lidocaine selectively inhibit a nociceptive response in the isolated rat spinal cord.
1995 Feb
Management of cough in advanced cancer.
2004 Nov-Dec
Inhibition of cough-reflex sensitivity by benzonatate and guaifenesin in acute viral cough.
2009 Jun
Benzonatate Ingestion Reported to the National Poison Center Database System (NPDS).
2010 Dec
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.
Name Type Language
BENZONATATE
INN   MART.   MI   ORANGE BOOK   USP   USP-RS   VANDF   WHO-DD  
INN  
Official 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
TESSALON PERLES
Brand 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 Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
NDF-RT N0000175796
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
WHO-VATC QR05DB01
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
WHO-ATC R05DB01
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
NDF-RT N0000009010
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
Code System Code Type Description
CAS
32760-16-0
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY
CHEBI
3032
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY
EPA CompTox
DTXSID9022655
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY
INN
651
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY
NCI_THESAURUS
C28863
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY
ECHA (EC/EINECS)
203-194-7
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY
DRUG BANK
DB00868
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY
IUPHAR
7611
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY
NSC
760128
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY
RS_ITEM_NUM
1056005
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY
RXCUI
18993
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY RxNorm
EVMPD
SUB05760MIG
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY
MESH
C029755
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY
FDA UNII
5P4DHS6ENR
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY
SMS_ID
100000086389
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY
DAILYMED
5P4DHS6ENR
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY
DRUG CENTRAL
326
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY
PUBCHEM
7699
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY
HSDB
7933
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY
ChEMBL
CHEMBL1374379
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY
WIKIPEDIA
BENZONATATE
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY
MERCK INDEX
m2368
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
PRIMARY Merck Index
CAS
104-31-4
Created by admin on Sat Dec 16 19:49:34 UTC 2023 , Edited by admin on Sat Dec 16 19:49:34 UTC 2023
MAJOR COMPONENT STRUCTURE/SEQUENCE