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

Details

Stereochemistry RACEMIC
Molecular Formula C12H20N2O3
Molecular Weight 240.2988
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PIRBUTEROL

SMILES

CC(C)(C)NCC(O)C1=NC(CO)=C(O)C=C1

InChI

InChIKey=VQDBNKDJNJQRDG-UHFFFAOYSA-N
InChI=1S/C12H20N2O3/c1-12(2,3)13-6-11(17)8-4-5-10(16)9(7-15)14-8/h4-5,11,13,15-17H,6-7H2,1-3H3

HIDE SMILES / InChI

Molecular Formula C12H20N2O3
Molecular Weight 240.2988
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Pirbuterol (trade name Maxair) is a short-acting β2 adrenoreceptor agonist with bronchodilating action used in the treatment of asthma. 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 (ATP) to cyclic-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 is used in asthma for reversal of acute bronchospasm, and also as a maintenance medication to prevent future attacks. It should be used in patients 12 years of age and older with or without concurrent theophylline and/or inhaled corticosteroid. After inhalation of doses up to 800 μg (twice the maximum recommended dose) systemic blood levels of pirbuterol are below the limit of assay sensitivity (2–5 ng/ml). A mean of 51% of the dose is recovered in urine as pirbuterol plus its sulfate conjugate following administration by aerosol. Pirbuterol is not metabolized by catechol-O-methyltransferase.

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MAXAIR

Cmax

ValueDoseCo-administeredAnalytePopulation
6.2 μg/L
10 mg single, oral
PIRBUTEROL plasma
Homo sapiens
9.8 μg/L
15 mg single, oral
PIRBUTEROL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
2 h
10 mg single, oral
PIRBUTEROL plasma
Homo sapiens

Doses

Sourcing

PubMed

Sample Use Guides

In Vivo Use Guide
Bronchospasm, prevention and treatment: Inhalation: 1 to 2 inhalations (200mcg) every 4 to 6 hours; not to exceed 12 inhalations daily. Patients should be advised to promptly consult healthcare provider or seek medical attention if no relief from acute treatment
Route of Administration: Respiratory
In Vitro Use Guide
MDA-MB-231, SF-539, ACHN, A-549, HCT-116, SNB-19 were used for activity evaluation. Cells (1x10^5) were plated in 60mm dishes and treated with various doses of ARA-211 (Pirbuterol) or vehicle for 48 h. Apoptosis was analysed using the Cell Death Detection ELISA (Roche, Indianapolis, IN, USA) measuring cytoplasmic histoneassociated mono- and oligonucleosome DNA fragments.
Substance Class Chemical
Record UNII
OG645J8RVW
Record Status Validated (UNII)
Record Version