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
Maxair Aem 240mcg/aemAerosol, metered250 mcgRespiratory (inhalation)3 M Pharmaceuticals, A Division Of 3 M Canada Company1996-12-311998-08-13Canada
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.

Structured Indications
Not Available
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
DrugInteractionDrug group
7,8-Dichloro-1,2,3,4-tetrahydroisoquinolineThe risk or severity of adverse effects can be increased when 7,8-Dichloro-1,2,3,4-tetrahydroisoquinoline is combined with Pirbuterol.Experimental
AcebutololAcebutolol may decrease the bronchodilatory activities of Pirbuterol.Approved
AlfuzosinAlfuzosin may decrease the vasoconstricting activities of Pirbuterol.Approved, Investigational
AlprenololAlprenolol may decrease the bronchodilatory activities of Pirbuterol.Approved, Withdrawn
AmineptineThe risk or severity of adverse effects can be increased when Amineptine is combined with Pirbuterol.Illicit, Withdrawn
AmitriptylineThe risk or severity of adverse effects can be increased when Amitriptyline is combined with Pirbuterol.Approved
AmoxapineThe risk or severity of adverse effects can be increased when Amoxapine is combined with Pirbuterol.Approved
AmphetamineThe risk or severity of adverse effects can be increased when Amphetamine is combined with Pirbuterol.Approved, Illicit
AtenololAtenolol may decrease the bronchodilatory activities of Pirbuterol.Approved
AtomoxetineAtomoxetine may increase the tachycardic activities of Pirbuterol.Approved
AtosibanThe risk or severity of adverse effects can be increased when Pirbuterol is combined with Atosiban.Approved, Investigational
BendroflumethiazidePirbuterol may increase the hypokalemic activities of Bendroflumethiazide.Approved
BenmoxinThe risk or severity of adverse effects can be increased when Benmoxin is combined with Pirbuterol.Withdrawn
Benzylpenicilloyl PolylysinePirbuterol may decrease effectiveness of Benzylpenicilloyl Polylysine as a diagnostic agent.Approved
BetahistineThe therapeutic efficacy of Pirbuterol can be decreased when used in combination with Betahistine.Approved
BetaxololBetaxolol may decrease the bronchodilatory activities of Pirbuterol.Approved
BisoprololBisoprolol may decrease the bronchodilatory activities of Pirbuterol.Approved
BopindololBopindolol may decrease the bronchodilatory activities of Pirbuterol.Approved
BrofaromineThe risk or severity of adverse effects can be increased when Brofaromine is combined with Pirbuterol.Experimental
BromocriptineBromocriptine may increase the hypertensive activities of Pirbuterol.Approved, Investigational
BucindololBucindolol may decrease the vasoconstricting activities of Pirbuterol.Investigational
BumetanidePirbuterol may increase the hypokalemic activities of Bumetanide.Approved
BunazosinBunazosin may decrease the vasoconstricting activities of Pirbuterol.Investigational
BupranololBupranolol may decrease the bronchodilatory activities of Pirbuterol.Approved
CabergolineCabergoline may increase the hypertensive activities of Pirbuterol.Approved
CaroxazoneThe risk or severity of adverse effects can be increased when Caroxazone is combined with Pirbuterol.Withdrawn
CarteololCarteolol may decrease the bronchodilatory activities of Pirbuterol.Approved
CarvedilolCarvedilol may decrease the vasoconstricting activities of Pirbuterol.Approved, Investigational
CeliprololCeliprolol may decrease the bronchodilatory activities of Pirbuterol.Approved, Investigational
ChlorothiazidePirbuterol may increase the hypokalemic activities of Chlorothiazide.Approved, Vet Approved
ChlorthalidonePirbuterol may increase the hypokalemic activities of Chlorthalidone.Approved
ClomipramineThe risk or severity of adverse effects can be increased when Clomipramine is combined with Pirbuterol.Approved, Vet Approved
CloranololCloranolol may decrease the bronchodilatory activities of Pirbuterol.Experimental
CyclobenzaprineThe risk or severity of adverse effects can be increased when Cyclobenzaprine is combined with Pirbuterol.Approved
CyclopenthiazidePirbuterol may increase the hypokalemic activities of Cyclopenthiazide.Experimental
DesipramineThe risk or severity of adverse effects can be increased when Desipramine is combined with Pirbuterol.Approved
DesvenlafaxineDesvenlafaxine may increase the tachycardic activities of Pirbuterol.Approved
DibenzepinThe risk or severity of adverse effects can be increased when Dibenzepin is combined with Pirbuterol.Experimental
DihydroergotamineDihydroergotamine may increase the hypertensive activities of Pirbuterol.Approved
DosulepinThe risk or severity of adverse effects can be increased when Dosulepin is combined with Pirbuterol.Approved
DoxazosinDoxazosin may decrease the vasoconstricting activities of Pirbuterol.Approved
DoxepinThe risk or severity of adverse effects can be increased when Doxepin is combined with Pirbuterol.Approved
DuloxetineDuloxetine may increase the tachycardic activities of Pirbuterol.Approved
Ergoloid mesylateErgoloid mesylate may increase the hypertensive activities of Pirbuterol.Approved
ErgonovineErgonovine may increase the hypertensive activities of Pirbuterol.Approved
ErgotamineErgotamine may increase the hypertensive activities of Pirbuterol.Approved
EsmirtazapineThe risk or severity of adverse effects can be increased when Esmirtazapine is combined with Pirbuterol.Investigational
EsmololEsmolol may decrease the bronchodilatory activities of Pirbuterol.Approved
Etacrynic acidPirbuterol may increase the hypokalemic activities of Etacrynic acid.Approved
FurazolidoneThe risk or severity of adverse effects can be increased when Furazolidone is combined with Pirbuterol.Approved, Investigational, Vet Approved
FurosemidePirbuterol may increase the hypokalemic activities of Furosemide.Approved, Vet Approved
HarmalineThe risk or severity of adverse effects can be increased when Harmaline is combined with Pirbuterol.Experimental
HydracarbazineThe risk or severity of adverse effects can be increased when Hydracarbazine is combined with Pirbuterol.Experimental
HydrochlorothiazidePirbuterol may increase the hypokalemic activities of Hydrochlorothiazide.Approved, Vet Approved
HydroflumethiazidePirbuterol may increase the hypokalemic activities of Hydroflumethiazide.Approved, Investigational
ImipramineThe risk or severity of adverse effects can be increased when Imipramine is combined with Pirbuterol.Approved
IndapamidePirbuterol may increase the hypokalemic activities of Indapamide.Approved
IndoraminIndoramin may decrease the vasoconstricting activities of Pirbuterol.Withdrawn
IprindoleThe risk or severity of adverse effects can be increased when Iprindole is combined with Pirbuterol.Experimental
IproclozideThe risk or severity of adverse effects can be increased when Iproclozide is combined with Pirbuterol.Withdrawn
IproniazidThe risk or severity of adverse effects can be increased when Iproniazid is combined with Pirbuterol.Withdrawn
IsocarboxazidThe risk or severity of adverse effects can be increased when Isocarboxazid is combined with Pirbuterol.Approved
LabetalolLabetalol may decrease the vasoconstricting activities of Pirbuterol.Approved
LevomilnacipranLevomilnacipran may increase the tachycardic activities of Pirbuterol.Approved
LofepramineThe risk or severity of adverse effects can be increased when Lofepramine is combined with Pirbuterol.Experimental
LoxapineThe risk or severity of adverse effects can be increased when Pirbuterol is combined with Loxapine.Approved
MebanazineThe risk or severity of adverse effects can be increased when Mebanazine is combined with Pirbuterol.Withdrawn
MepindololMepindolol may decrease the bronchodilatory activities of Pirbuterol.Experimental
MethyclothiazidePirbuterol may increase the hypokalemic activities of Methyclothiazide.Approved
Methylene blueThe risk or severity of adverse effects can be increased when Methylene blue is combined with Pirbuterol.Approved, Investigational
MethylergometrineMethylergometrine may increase the hypertensive activities of Pirbuterol.Approved
MetolazonePirbuterol may increase the hypokalemic activities of Metolazone.Approved
MetoprololMetoprolol may decrease the bronchodilatory activities of Pirbuterol.Approved, Investigational
MilnacipranMilnacipran may increase the tachycardic activities of Pirbuterol.Approved
MinaprineThe risk or severity of adverse effects can be increased when Minaprine is combined with Pirbuterol.Approved
MirtazapineThe risk or severity of adverse effects can be increased when Mirtazapine is combined with Pirbuterol.Approved
MoclobemideThe risk or severity of adverse effects can be increased when Moclobemide is combined with Pirbuterol.Approved
NebivololNebivolol may decrease the bronchodilatory activities of Pirbuterol.Approved, Investigational
NialamideThe risk or severity of adverse effects can be increased when Nialamide is combined with Pirbuterol.Withdrawn
NortriptylineThe risk or severity of adverse effects can be increased when Nortriptyline is combined with Pirbuterol.Approved
OctamoxinThe risk or severity of adverse effects can be increased when Octamoxin is combined with Pirbuterol.Withdrawn
OpipramolThe risk or severity of adverse effects can be increased when Opipramol is combined with Pirbuterol.Investigational
OxprenololOxprenolol may decrease the bronchodilatory activities of Pirbuterol.Approved
PargylineThe risk or severity of adverse effects can be increased when Pargyline is combined with Pirbuterol.Approved
PenbutololPenbutolol may decrease the bronchodilatory activities of Pirbuterol.Approved, Investigational
PhenelzineThe risk or severity of adverse effects can be increased when Phenelzine is combined with Pirbuterol.Approved
PheniprazineThe risk or severity of adverse effects can be increased when Pheniprazine is combined with Pirbuterol.Withdrawn
PhenoxypropazineThe risk or severity of adverse effects can be increased when Phenoxypropazine is combined with Pirbuterol.Withdrawn
PiretanidePirbuterol may increase the hypokalemic activities of Piretanide.Experimental
PirlindoleThe risk or severity of adverse effects can be increased when Pirlindole is combined with Pirbuterol.Approved
PivhydrazineThe risk or severity of adverse effects can be increased when Pivhydrazine is combined with Pirbuterol.Withdrawn
PolythiazidePirbuterol may increase the hypokalemic activities of Polythiazide.Approved
PrazosinPrazosin may decrease the vasoconstricting activities of Pirbuterol.Approved
ProcarbazineThe risk or severity of adverse effects can be increased when Procarbazine is combined with Pirbuterol.Approved
ProtriptylineThe risk or severity of adverse effects can be increased when Protriptyline is combined with Pirbuterol.Approved
QuinethazonePirbuterol may increase the hypokalemic activities of Quinethazone.Approved
RasagilineThe risk or severity of adverse effects can be increased when Rasagiline is combined with Pirbuterol.Approved
SafrazineThe risk or severity of adverse effects can be increased when Safrazine is combined with Pirbuterol.Withdrawn
SelegilineThe risk or severity of adverse effects can be increased when Selegiline is combined with Pirbuterol.Approved, Investigational, Vet Approved
SilodosinSilodosin may decrease the vasoconstricting activities of Pirbuterol.Approved
SotalolSotalol may decrease the bronchodilatory activities of Pirbuterol.Approved
SpironolactoneSpironolactone may decrease the vasoconstricting activities of Pirbuterol.Approved
TamsulosinTamsulosin may decrease the vasoconstricting activities of Pirbuterol.Approved, Investigational
TerazosinTerazosin may decrease the vasoconstricting activities of Pirbuterol.Approved
TertatololTertatolol may decrease the bronchodilatory activities of Pirbuterol.Experimental
TianeptineThe risk or severity of adverse effects can be increased when Tianeptine is combined with Pirbuterol.Approved, Investigational
ToloxatoneThe risk or severity of adverse effects can be increased when Toloxatone is combined with Pirbuterol.Approved
TorasemidePirbuterol may increase the hypokalemic activities of Torasemide.Approved
Trans-2-PhenylcyclopropylamineThe risk or severity of adverse effects can be increased when Trans-2-Phenylcyclopropylamine is combined with Pirbuterol.Experimental
TranylcypromineThe risk or severity of adverse effects can be increased when Tranylcypromine is combined with Pirbuterol.Approved
TrichlormethiazidePirbuterol may increase the hypokalemic activities of Trichlormethiazide.Approved, Vet Approved
TrimazosinTrimazosin may decrease the vasoconstricting activities of Pirbuterol.Experimental
TrimipramineThe risk or severity of adverse effects can be increased when Trimipramine is combined with Pirbuterol.Approved
UrapidilUrapidil may decrease the vasoconstricting activities of Pirbuterol.Investigational
VemurafenibThe risk or severity of QTc prolongation can be increased when Vemurafenib is combined with Pirbuterol.Approved
VenlafaxineVenlafaxine may increase the tachycardic activities of Pirbuterol.Approved
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
HMDB15407
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
ATC Codes
R03AC08 — PirbuterolR03CC07 — Pirbuterol
FDA label
Download (260 KB)

Clinical Trials

Clinical Trials
Not Available

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Dosage forms
FormRouteStrength
Aerosol, meteredRespiratory (inhalation)250 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.
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 December 01, 2017 17:16