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Bitolterol

Bitolterol structure

CAS No:
30392-40-6
Formula:
C28H31NO5
Chemical Name:
Bitolterol
Synonyms:
Benzoic acid,4-methyl-,1,1′-[4-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-1,2-phenylene] ester;Benzoic acid,4-methyl-,4-[2-[(1,1-dimethylethyl)amino]-1-hydroxyethyl]-1,2-phenylene ester;p-Toluic acid,4-[2-(tert-butylamino)-1-hydroxyethyl]-o-phenylene ester;Bitolterol;S 1540
Categories:
Organic Chemistry > Amides

Description

Bitolterol is the di-4-toluate ester of (+-)-N-tert-butylnoradrenaline (colterol). A pro-drug for colterol, a beta2-adrenergic receptor agonist, bitolterol is used as its methanesulfonate salt for relief of bronchospasm in conditions such as asthma, chronic bronchitis and emphysema. It has a role as a bronchodilator agent, an anti-asthmatic drug, a beta-adrenergic agonist and a prodrug. It is a member of ethanolamines, a carboxylic ester, a diester, a secondary amino compound and a secondary alcohol.|Bitolterol mesylate was used to treat bronchospasms in asthma and COPD. It is a beta-2-adrenergic receptor agonist. Bitolterol was withdrawn from the market by Elan Pharmaceuticals in 2001.

Bitolterol Basic Attributes

Molecular Weight：

461.558

Exact Mass：

461.55

DSSTox ID：

DTXSID1022683

ATC Code：

R - Respiratory system

HScode：

2922509090

Characteristics

PSA：

84.9

XLogP3：

5.8

Density：

1.169g/cm3

Boiling Point：

640.5ºC at 760 mmHg

Flash Point：

341.2ºC

Refractive Index：

1.585

Drug Information

Drug Indication：

Used to dilate air passages in the lungs that have become narrowed as a result of disease or inflammation. It is used in the treatment of asthma and chronic obstructive pulmonary disease (COPD).

Pharmacology：

Bitolterol, an adrenergic bronchodilator, is a prodrug that widens constricted airways in the lungs by relaxing the smooth muscles that surround the bronchial passages. Bitolterol probably does not affect the inflammation in the lung, such as in bronchitis. Bitolterol is unique in that it is a prodrug because it must first be metabolized by the body before it becomes active.

MeSH：

Compounds bind to and activate ADRENERGIC BETA-2 RECEPTORS. (See all compounds classified as Adrenergic beta-2 Receptor Agonists.)|Agents that cause an increase in the expansion of a bronchus or bronchial tubes. (See all compounds classified as Bronchodilator Agents.)

Mechanism of Action：

Bitolterol is an adrenergic beta-2 agonist. Asthma results from a narrowing of the bronchial tubes. This narrowing is caused by muscle spasm and inflammation within the bronchial tubes. Agonism of the beta-2 adrenergic receptors by bitolterol leads to a relaxation of the smooth muscles surrounding these airway tubes which then increases the diameter and ease of air flow through the tubes.

MeSH Entry Terms：

bitolterol

Bitolterol Use and Manufacturing

Bitolterol is a is a β2-adrenergic receptor agonist used for the relief of bronchospasm in conditions such as asthma and COPD.

Computed Properties

Molecular Weight:461.5
XLogP3:5.2
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:10
Exact Mass:461.22022309
Monoisotopic Mass:461.22022309
Topological Polar Surface Area:84.9
Heavy Atom Count:34
Complexity:658
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes