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
Synonyms
  • (+/-)-pirbuterol
  • Pirbuterolum
External IDs
ARA-211
Product Ingredients
IngredientUNIICASInChI Key
Pirbuterol acetate1EH73XKR9N65652-44-0QSXMZJGGEWYVCN-UHFFFAOYSA-N
Pirbuterol hydrochlorideJ6793T658K38029-10-6GPDAJAWUGSTOSA-UHFFFAOYSA-N
Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
MaxairAerosol, metered200 ug/1Respiratory (inhalation)3M Company1996-12-302006-12-29Us
MaxairAerosol, metered200 ug/1Respiratory (inhalation)3M Company1992-11-302006-12-29Us
Maxair Aem 240mcg/aemAerosol, metered250 mcgRespiratory (inhalation)3 M Pharmaceuticals, A Division Of 3 M Canada Company1996-12-311998-08-13Canada
Maxair AutohalerInhalant200 ug/1OralMedicis Pharmaceutical Corporation2011-11-282014-11-30Us
Maxair AutohalerInhalant200 ug/1OralPhysicians Total Care, Inc.2011-11-282012-06-30Us
Maxair AutohalerInhalant200 ug/1Respiratory (inhalation)Graceway Pharmaceuticals2008-01-012014-11-30Us
International/Other Brands
Maxair / Maxair autohaler
Categories
UNII
OG645J8RVW
CAS number
38677-81-5
Weight
Average: 240.2988
Monoisotopic: 240.147392516
Chemical Formula
C12H20N2O3
InChI Key
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
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

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.

TargetActionsOrganism
ABeta-2 adrenergic receptor
agonist
Human
UBeta-1 adrenergic receptor
agonist
Human
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
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
DrugInteraction
AbediterolThe risk or severity of adverse effects can be increased when Pirbuterol is combined with Abediterol.
AcebutololThe therapeutic efficacy of Pirbuterol can be decreased when used in combination with Acebutolol.
AcepromazineThe therapeutic efficacy of Pirbuterol can be decreased when used in combination with Acepromazine.
AldosteroneThe risk or severity of hypokalemia can be increased when Aldosterone is combined with Pirbuterol.
AlfuzosinThe therapeutic efficacy of Pirbuterol can be decreased when used in combination with Alfuzosin.
AlprenololAlprenolol may decrease the bronchodilatory activities of Pirbuterol.
AmineptineThe risk or severity of hypertension can be increased when Amineptine is combined with Pirbuterol.
AmitriptylineThe risk or severity of hypertension can be increased when Amitriptyline is combined with Pirbuterol.
AmitriptylinoxideThe risk or severity of hypertension can be increased when Amitriptylinoxide is combined with Pirbuterol.
AmoxapineThe risk or severity of hypertension can be increased when Amoxapine is combined with Pirbuterol.
Food Interactions
Not Available

References

Synthesis Reference

Berkeley W. Cue, Stephen S. Massett, "Intermediates for preparing pirbuterol and analogs." U.S. Patent US4632992, issued June, 1977.

US4632992
General References
Not Available
External Links
Human Metabolome Database
HMDB0015407
KEGG Compound
C07807
PubChem Compound
4845
PubChem Substance
46506379
ChemSpider
4679
ChEBI
8245
ChEMBL
CHEMBL1094966
Therapeutic Targets Database
DAP000249
PharmGKB
PA450983
RxList
RxList Drug Page
Drugs.com
Drugs.com Drug Page
Wikipedia
Pirbuterol
ATC Codes
R03CC07 — PirbuterolR03AC08 — Pirbuterol
FDA label
Download (260 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
  • 3M Health Care
  • Graceway Pharmaceuticals
  • Pharmedix
  • Physicians Total Care Inc.
Dosage forms
FormRouteStrength
Aerosol, meteredRespiratory (inhalation)200 ug/1
Aerosol, meteredRespiratory (inhalation)250 mcg
InhalantOral200 ug/1
InhalantRespiratory (inhalation)200 ug/1
Prices
Unit descriptionCostUnit
Maxair Autohaler 200 mcg/inh Aerosol 14 gm Inhaler169.99USD inhaler
Maxair autohaler 0.2 mg aero8.52USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility6.22 mg/mLALOGPS
logP0.38ALOGPS
logP-0.66ChemAxon
logS-1.6ALOGPS
pKa (Strongest Acidic)8.79ChemAxon
pKa (Strongest Basic)9.59ChemAxon
Physiological Charge1ChemAxon
Hydrogen Acceptor Count5ChemAxon
Hydrogen Donor Count4ChemAxon
Polar Surface Area85.61 Å2ChemAxon
Rotatable Bond Count5ChemAxon
Refractivity64.74 m3·mol-1ChemAxon
Polarizability26.31 Å3ChemAxon
Number of Rings1ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterNoChemAxon
Veber's RuleNoChemAxon
MDDR-like RuleNoChemAxon
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+0.9563
Blood Brain Barrier-0.9442
Caco-2 permeable-0.6419
P-glycoprotein substrateSubstrate0.7707
P-glycoprotein inhibitor INon-inhibitor0.9454
P-glycoprotein inhibitor IINon-inhibitor0.9913
Renal organic cation transporterNon-inhibitor0.8415
CYP450 2C9 substrateNon-substrate0.8123
CYP450 2D6 substrateNon-substrate0.7856
CYP450 3A4 substrateNon-substrate0.6501
CYP450 1A2 substrateNon-inhibitor0.9045
CYP450 2C9 inhibitorNon-inhibitor0.9071
CYP450 2D6 inhibitorNon-inhibitor0.925
CYP450 2C19 inhibitorNon-inhibitor0.9025
CYP450 3A4 inhibitorNon-inhibitor0.9096
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.9293
Ames testNon AMES toxic0.82
CarcinogenicityNon-carcinogens0.9109
BiodegradationNot ready biodegradable0.99
Rat acute toxicity2.4870 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9743
hERG inhibition (predictor II)Non-inhibitor0.9365
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted GC-MS Spectrum - GC-MSPredicted GC-MSNot Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSNot Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSNot Available

Taxonomy

Description
This compound belongs to the class of organic compounds known as hydroxypyridines. These are organic compounds containing a pyridine ring substituted at one or more positions by a hydroxyl group.
Kingdom
Organic compounds
Super Class
Organoheterocyclic compounds
Class
Pyridines and derivatives
Sub Class
Hydroxypyridines
Direct Parent
Hydroxypyridines
Alternative Parents
Aralkylamines / Heteroaromatic compounds / Secondary alcohols / 1,2-aminoalcohols / Dialkylamines / Azacyclic compounds / Primary alcohols / Organopnictogen compounds / Hydrocarbon derivatives / Aromatic alcohols
Substituents
Aralkylamine / Hydroxypyridine / Heteroaromatic compound / 1,2-aminoalcohol / Secondary alcohol / Secondary aliphatic amine / Secondary amine / Azacycle / Aromatic alcohol / Alcohol
Molecular Framework
Aromatic heteromonocyclic compounds
External Descriptors
pyridines (CHEBI:8245)

Targets

Kind
Protein
Organism
Human
Pharmacological action
Yes
Actions
Agonist
General Function
Protein homodimerization activity
Specific Function
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 ...
Gene Name
ADRB2
Uniprot ID
P07550
Uniprot Name
Beta-2 adrenergic receptor
Molecular Weight
46458.32 Da
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:17260025]
  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:7053311]
  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:8945911]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352]
Kind
Protein
Organism
Human
Pharmacological action
Unknown
Actions
Agonist
General Function
Receptor signaling protein activity
Specific Function
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 e...
Gene Name
ADRB1
Uniprot ID
P08588
Uniprot Name
Beta-1 adrenergic receptor
Molecular Weight
51322.1 Da
References
  1. van Zwieten PA: Receptor-mediated inotropic drugs. Eur Heart J. 1988 Jun;9 Suppl H:85-90. [PubMed:2901958]
  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:6143816]

Drug created on June 30, 2007 08:13 / Updated on November 02, 2018 08:41