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Identification
NamePirbuterol
Accession NumberDB01291
TypeSmall Molecule
GroupsApproved
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
Maxair autohaler
Pirbuterol
Pirbuterolum
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Maxair Aem 240mcg/aemmetered-dose aerosol250 mcginhalation3 M Pharmaceuticals, A Division Of 3 M Canada Company1996-12-311998-08-13Canada
Approved Generic Prescription ProductsNot Available
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
MaxairNot Available
Brand mixturesNot Available
Salts
Name/CASStructureProperties
Pirbuterol acetate
Thumb
  • InChI Key: QSXMZJGGEWYVCN-UHFFFAOYNA-N
  • Monoisotopic Mass: 300.168521888
  • Average Mass: 300.3508
DBSALT000799
Pirbuterol hydrochloride
Thumb
  • InChI Key: GPDAJAWUGSTOSA-UHFFFAOYNA-N
  • Monoisotopic Mass: 276.124070255
  • Average Mass: 276.76
DBSALT000798
Categories
UNIIOG645J8RVW
CAS number38677-81-5
WeightAverage: 240.2988
Monoisotopic: 240.147392516
Chemical FormulaC12H20N2O3
InChI KeyInChIKey=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
Taxonomy
DescriptionThis 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.
KingdomOrganic compounds
Super ClassOrganoheterocyclic compounds
ClassPyridines and derivatives
Sub ClassHydroxypyridines
Direct ParentHydroxypyridines
Alternative Parents
Substituents
  • Hydroxypyridine
  • Aralkylamine
  • Heteroaromatic compound
  • Secondary alcohol
  • 1,2-aminoalcohol
  • Azacycle
  • Secondary amine
  • Secondary aliphatic amine
  • Hydrocarbon derivative
  • Aromatic alcohol
  • Primary alcohol
  • Organooxygen compound
  • Organonitrogen compound
  • Amine
  • Alcohol
  • Aromatic heteromonocyclic compound
Molecular FrameworkAromatic heteromonocyclic compounds
External DescriptorsNot Available
Pharmacology
IndicationFor the prevention and reversal of bronchospasm in patients 12 years of age and older with reversible bronchospasm including asthma.
PharmacodynamicsPirbuterol 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 actionThe 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.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein bindingNot Available
MetabolismNot Available
Route of eliminationNot Available
Half lifeThe plasma half-life measured after oral administration is about two hours.
ClearanceNot Available
ToxicityAs with all sympathomimetic aerosol medication, cardiac arrest and even death may be associated with abuse of pirbuterol.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
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 )
Pharmacoeconomics
ManufacturersNot Available
Packagers
Dosage forms
FormRouteStrength
Metered-dose aerosolinhalation250 mcg
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.
PatentsNot Available
Properties
StateSolid
Experimental PropertiesNot 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 FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot 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 ReferencesNot Available
External Links
ATC CodesR03AC08R03CC07
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (260 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AcebutololThe risk or severity of adverse effects can be increased when Acebutolol is combined with Pirbuterol.
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Pirbuterol.
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Pirbuterol.
AtomoxetineAtomoxetine may increase the tachycardic activities of Pirbuterol.
AtosibanThe risk or severity of adverse effects can be increased when Pirbuterol is combined with Atosiban.
BenzphetamineThe risk or severity of adverse effects can be increased when Benzphetamine is combined with Pirbuterol.
BetahistineThe therapeutic efficacy of Pirbuterol can be decreased when used in combination with Betahistine.
ChlorphentermineThe risk or severity of adverse effects can be increased when Chlorphentermine is combined with Pirbuterol.
ClenbuterolThe risk or severity of adverse effects can be increased when Clenbuterol is combined with Pirbuterol.
DobutamineThe risk or severity of adverse effects can be increased when Dobutamine is combined with Pirbuterol.
DopamineThe risk or severity of adverse effects can be increased when Dopamine is combined with Pirbuterol.
DoxofyllineThe risk or severity of adverse effects can be increased when Pirbuterol is combined with Doxofylline.
DronabinolDronabinol may increase the tachycardic activities of Pirbuterol.
EpinephrineThe risk or severity of adverse effects can be increased when Epinephrine is combined with Pirbuterol.
EsmololEsmolol may decrease the activities of Pirbuterol.
FenoterolThe risk or severity of adverse effects can be increased when Fenoterol is combined with Pirbuterol.
FormoterolThe risk or severity of adverse effects can be increased when Formoterol is combined with Pirbuterol.
IobenguaneThe therapeutic efficacy of Iobenguane can be decreased when used in combination with Pirbuterol.
IsoprenalineThe risk or severity of adverse effects can be increased when Isoprenaline is combined with Pirbuterol.
LabetalolThe risk or severity of adverse effects can be increased when Labetalol is combined with Pirbuterol.
LinezolidLinezolid may increase the hypertensive activities of Pirbuterol.
LoxapineThe risk or severity of adverse effects can be increased when Pirbuterol is combined with Loxapine.
MephentermineThe risk or severity of adverse effects can be increased when Mephentermine is combined with Pirbuterol.
MetaraminolThe risk or severity of adverse effects can be increased when Metaraminol is combined with Pirbuterol.
MethamphetamineThe risk or severity of adverse effects can be increased when Methamphetamine is combined with Pirbuterol.
MethoxamineThe risk or severity of adverse effects can be increased when Methoxamine is combined with Pirbuterol.
MidodrineThe risk or severity of adverse effects can be increased when Midodrine is combined with Pirbuterol.
NadololNadolol may decrease the activities of Pirbuterol.
NaphazolineThe risk or severity of adverse effects can be increased when Naphazoline is combined with Pirbuterol.
NorepinephrineThe risk or severity of adverse effects can be increased when Norepinephrine is combined with Pirbuterol.
OrciprenalineThe risk or severity of adverse effects can be increased when Orciprenaline is combined with Pirbuterol.
OxymetazolineThe risk or severity of adverse effects can be increased when Oxymetazoline is combined with Pirbuterol.
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Pirbuterol.
PhenmetrazineThe risk or severity of adverse effects can be increased when Phenmetrazine is combined with Pirbuterol.
PhentermineThe risk or severity of adverse effects can be increased when Phentermine is combined with Pirbuterol.
PhenylephrineThe risk or severity of adverse effects can be increased when Phenylephrine is combined with Pirbuterol.
PhenylpropanolamineThe risk or severity of adverse effects can be increased when Phenylpropanolamine is combined with Pirbuterol.
RitodrineThe risk or severity of adverse effects can be increased when Ritodrine is combined with Pirbuterol.
SalmeterolThe risk or severity of adverse effects can be increased when Salmeterol is combined with Pirbuterol.
Tedizolid PhosphateTedizolid Phosphate may increase the hypertensive activities of Pirbuterol.
TerbutalineThe risk or severity of adverse effects can be increased when Terbutaline is combined with Pirbuterol.
TorasemidePirbuterol may increase the hypokalemic activities of Torasemide.
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Pirbuterol.
TrichlormethiazidePirbuterol may increase the hypokalemic activities of Trichlormethiazide.
Food InteractionsNot Available

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 30-fold greater affinity than it does norepinephrine.
Gene Name:
ADRB2
Uniprot ID:
P07550
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 equal affinity. Mediates Ras activation through G(s)-alpha- and cAMP-mediated signaling.
Gene Name:
ADRB1
Uniprot ID:
P08588
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 ]
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Drug created on June 30, 2007 08:13 / Updated on September 16, 2013 17:14