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

Details

Stereochemistry ACHIRAL
Molecular Formula C30H53NO11
Molecular Weight 603.7419
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

Molecular Formula C30H53NO11
Molecular Weight 603.7419
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

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.

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Palliative
TESSALON

PubMed

Sample Use Guides

In Vivo Use Guide
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
In Vitro Use Guide
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
Record UNII
5P4DHS6ENR
Record Status Validated (UNII)
Record Version