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Identification
Name Pirbuterol
Accession Number DB01291
Type small molecule
Groups approved
Description

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.
Structure Thumb
Download: MOL | SDF | SMILES | InChI
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Synonyms
  • Pirbuterol hydrochloride
  • Pirbuterolum [inn-latin]
Synonyms
Pirbuterol hydrochloride
Pirbuterolum [inn-latin]
Salts Not Available
Brand names
Name Company
Maxair
Brand mixtures Not Available
Categories
  • Bronchodilator Agents
  • Adrenergic beta-Agonists
  • Cardiotonic Agents
CAS number 38677-81-5
Weight Average: 240.2988
Monoisotopic: 240.147392516
Chemical Formula C12H20N2O3
InChI Key InChIKey=VQDBNKDJNJQRDG-UHFFFAOYSA-N
InChI
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
Plain Text
IUPAC Name
6-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)pyridin-3-ol
SMILES
CC(C)(C)NCC(O)C1=NC(CO)=C(O)C=C1
Plain Text
Mass Spec Not Available
Taxonomy
Kingdom Organic
Classes
  • Phenols and Derivatives
Substructures
  • Hydroxy Compounds
  • Aliphatic and Aryl Amines
  • Pyridines and Derivatives
  • Alcohols and Polyols
  • Amino Alcohols
  • Heterocyclic compounds
  • Aromatic compounds
  • Imines
  • Phenols and Derivatives
Pharmacology
Indication For the prevention and reversal of bronchospasm in patients 12 years of age and older with reversible bronchospasm including asthma.
Pharmacodynamics 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.
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.
Absorption Not Available
Volume of distribution Not Available
Protein binding Not Available
Metabolism Not Available
Route of elimination Not Available
Half life The plasma half-life measured after oral administration is about two hours.
Clearance Not Available
Toxicity As with all sympathomimetic aerosol medication, cardiac arrest and even death may be associated with abuse of pirbuterol.
Affected organisms
  • Humans and other mammals
Pathways Not Available
Pharmacoeconomics
Manufacturers
  • Graceway pharmaceuticals llc
Packagers
Dosage forms
Form Route Strength
Aerosol Respiratory (inhalation)
Prices
Unit description Cost Unit
Maxair Autohaler 200 mcg/inh Aerosol 14 gm Inhaler 169.99 USD inhaler
Maxair autohaler 0.2 mg aero 8.52 USD g
Patents Not Available
Properties
State solid
Melting point Not Available
Experimental Properties Not Available
Predicted Properties
Property Value Source
water solubility 6.22e+00 g/l ALOGPS
logP 0.38 ALOGPS
logP -0.66 ChemAxon Molconvert
logS -1.6 ALOGPS
pKa 13.49 ChemAxon Molconvert
hydrogen acceptor count 5 ChemAxon Molconvert
hydrogen donor count 4 ChemAxon Molconvert
polar surface area 85.61 ChemAxon Molconvert
rotatable bond count 5 ChemAxon Molconvert
refractivity 64.74 ChemAxon Molconvert
polarizability 26.31 ChemAxon Molconvert
References
Synthesis Reference Not Available
General Reference Not Available
External Links
Resource Link
KEGG Compound C07807 Link_out
PubChem Compound 4845 Link_out
PubChem Substance 46506379 Link_out
ChemSpider 4679 Link_out
Therapeutic Targets Database DAP000249 Link_out
PharmGKB PA450983 Link_out
RxList http://www.rxlist.com/cgi/generic/pirbu.htm Link_out
Drugs.com http://www.drugs.com/cdi/pirbuterol.html Link_out
ATC Codes
  • R03AC08
  • R03CC07
AHFS Codes Not Available
PDB Entries Not Available
FDA label show (260 KB)
MSDS Not Available
Interactions
Drug Interactions
Drug Interaction
Acebutolol Antagonism
Amitriptyline The tricyclic antidepressant, amitriptyline, increases the sympathomimetic effect of pirbuterol.
Amoxapine The tricyclic antidepressant, amoxapine, increases the sympathomimetic effect of pirbuterol.
Atenolol Antagonism
Bisoprolol Antagonism
Carvedilol Antagonism
Clomipramine The tricyclic antidepressant, clomipramine, increases the sympathomimetic effect of pirbuterol.
Desipramine The tricyclic antidepressant, desipramine, increases the sympathomimetic effect of pirbuterol.
Doxepin The tricyclic antidepressant, doxepin, increases the sympathomimetic effect of pirbuterol.
Esmolol Antagonism
Imipramine The tricyclic antidepressant, imipramine, increases the sympathomimetic effect of pirbuterol.
Isocarboxazid Increased arterial pressure
Labetalol Antagonism
Linezolid Possible increase of arterial pressure
Methyldopa Increased arterial pressure
Metoprolol Antagonism
Midodrine Increased arterial pressure
Moclobemide Moclobemide increases the sympathomimetic effect of pirbuterol.
Nadolol Antagonism
Nortriptyline The tricyclic antidepressant, nortriptyline, increases the sympathomimetic effect of pirbuterol.
Oxprenolol Antagonism
Phenelzine Increased arterial pressure
Pindolol Antagonism
Propranolol Antagonism
Rasagiline Increased arterial pressure
Reserpine Increased arterial pressure
Timolol Antagonism
Food Interactions Not Available
Targets

1. Beta-2 adrenergic receptor

Pharmacological action: yes
Actions: agonist

Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. The beta-2-adrenergic receptor binds epinephrine with an approximately 30-fold greater affinity than it does norepinephrine

Organism class: human
UniProt ID: P07550 Link_out
Gene: ADRB2 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. Carie AE, Sebti SM: A chemical biology approach identifies a beta-2 adrenergic receptor agonist that causes human tumor regression by blocking the Raf-1/Mek-1/Erk1/2 pathway. Oncogene. 2007 May 31;26(26):3777-88. Epub 2007 Jan 29. Pubmed
  2. Leier CV, Nelson S, Huss P, Bianchine JR, Olukotun AY, Taylor CR, Salzburg DS: Intravenous pirbuterol. Clin Pharmacol Ther. 1982 Jan;31(1):89-94. Pubmed
  3. Hamdad N, Ming Z, Parent R, Lavallee M: Beta 2-adrenergic dilation of conductance coronary arteries involves flow-dependent NO formation in conscious dogs. Am J Physiol. 1996 Nov;271(5 Pt 2):H1926-37. Pubmed
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. Pubmed

2. Beta-1 adrenergic receptor

Pharmacological action: unknown
Actions: agonist

Beta-adrenergic receptors mediate the catecholamine- induced activation of adenylate cyclase through the action of G proteins. This receptor binds epinephrine and norepinephrine with approximately equal affinity

Organism class: human
UniProt ID: P08588 Link_out
Gene: ADRB1 Link_out
Protein Sequence: FASTA
Gene Sequence: FASTA
SNPs: SNPJam Report Link_out

References:
  1. van Zwieten PA: Receptor-mediated inotropic drugs. Eur Heart J. 1988 Jun;9 Suppl H:85-90. Pubmed
  2. Kenakin TP, Beek D: Relative efficacy of prenalterol and pirbuterol for beta-1 adrenoceptors: measurement of agonist affinity by alteration of receptor number. J Pharmacol Exp Ther. 1984 May;229(2):340-5. Pubmed
Comments
Drug created on June 30, 2007 08:13 / Updated on February 14, 2012 11:46