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(±)-Pirbuterol

(±)-Pirbuterol structure

CAS No:
38677-81-5
Formula:
C12H20N2O3
Chemical Name:
(±)-Pirbuterol
Synonyms:
2,6-Pyridinedimethanol,α6-[[(1,1-dimethylethyl)amino]methyl]-3-hydroxy-;α6-[[(1,1-Dimethylethyl)amino]methyl]-3-hydroxy-2,6-pyridinedimethanol;Pirbuterol;(±)-Pirbuterol;ARA 211;77145-72-3
Categories:
Organic Chemistry > Amides

Description

Solid

Pirbuterol is a member of pyridines.|Pirbuterol is a beta-2 adrenergic bronchodilator. In vitro studies and in vivo pharmacologic studies have demonstrated that pirbuterol has a preferential effect on beta-2 Adrenergic receptors compared with isoproterenol. While it is recognized that beta-2 adrenergic receptors are the predominant receptors in bronchial smooth muscle, data indicate that there is a population of beta-2 receptors in the human heart, existing in a concentration between 10-50%. The precise function of these receptors has not been established. The pharmacologic effects of beta adrenergic agonist drugs, including pirbuterol, are at least in proof attributable to stimulation through beta adrenergic receptors of intracellular adenyl cyclase, the enzyme which catalyzes the conversion of adenosine triphosphate (AlP) to cyclic-3† ,5†-adenosine monophosphate (c-AMP). Increased c-AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells.

(±)-Pirbuterol Basic Attributes

Molecular Weight：

240.303

Exact Mass：

240.30

EC Number：

253-751-3

DSSTox ID：

DTXSID0046937

ATC Code：

R - Respiratory system

Characteristics

PSA：

85.6

XLogP3：

-0.1

Appearance：

Solid

Density：

1.196±0.06 g/cm3(Predicted)

Water Solubility：

6.22e+00 g/L

Toxicity

Toxicity Summary：

As with all sympathomimetic aerosol medication, cardiac arrest and even death may be associated with abuse of pirbuterol.

Drug Information

Drug Indication：

For the prevention and reversal of bronchospasm in patients 12 years of age and older with reversible bronchospasm including asthma.|FDA Label

Pharmacology：

Pirbuterol is a beta-2 adrenergic bronchodilator. In vitro studies and in vivo pharmacologic studies have demonstrated that pirbuterol has a preferential effect on beta-2 adrenergic receptors compared with isoproterenol. While it is recognized that beta-2 adrenergic receptors are the predominant receptors in bronchial smooth muscle, data indicate that there is a population of beta-2 receptors in the human heart, existing in a concentration between 10-50%. The precise function of these receptors has not been established.

MeSH：

Agents that have a strengthening effect on the heart or that can increase cardiac output. They may be CARDIAC GLYCOSIDES; SYMPATHOMIMETICS; or other drugs. They are used after MYOCARDIAL INFARCT; CARDIAC SURGICAL PROCEDURES; in SHOCK; or in congestive heart failure (HEART FAILURE). (See all compounds classified as Cardiotonic Agents.)|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.)

Biological Half-Life：

2 hours.

Mechanism of Action：

The pharmacologic effects of beta adrenergic agonist drugs, including pirbuterol, are at least in proof attributable to stimulation through beta adrenergic receptors of intracellular adenyl cyclase, the enzyme which catalyzes the conversion of adenosine triphosphate (AlP) to cyclic-3† ,5†-adenosine monophosphate (c-AMP). Increased c-AMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from cells, especially from mast cells.

MeSH Entry Terms：

2-hydroxymethyl-3-hydroxy-6-(1-hydroxy-2-tert-butylamino ethyl)pyridine, dihydrochloride

(±)-Pirbuterol Use and Manufacturing

Uses

Bronchodilator.

Use Classification：

Human Drugs -> FDA Approved Drug Products with Therapeutic Equivalence Evaluations (Orange Book) -> Active Ingredients|Pharmaceuticals

Computed Properties

Molecular Weight:240.30
XLogP3:-0.1
Hydrogen Bond Donor Count:4
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:5
Exact Mass:240.14739250
Monoisotopic Mass:240.14739250
Topological Polar Surface Area:85.6
Heavy Atom Count:17
Complexity:230
Undefined Atom Stereocenter Count:1
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes