Identification
- Summary
Pirbuterol is a beta-2 adrenergic agonist and bronchodilator used for the symptomatic treatment of asthma.
- Generic Name
- Pirbuterol
- DrugBank Accession Number
- DB01291
- Background
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.
- Type
- Small Molecule
- Groups
- Approved
- Structure
Structure for Pirbuterol (DB01291)
- Weight
- Average: 240.2988
Monoisotopic: 240.147392516 - Chemical Formula
- C12H20N2O3
- Synonyms
- (+/-)-pirbuterol
- Pirbuterol
- Pirbuterolum
- External IDs
- ARA-211
Pharmacology
- Indication
For the prevention and reversal of bronchospasm in patients 12 years of age and older with reversible bronchospasm including asthma.
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Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism ABeta-2 adrenergic receptor agonistHumans UBeta-1 adrenergic receptor agonistHumans - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
2 hours.
- Clearance
Not Available
- Adverse Effects
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As with all sympathomimetic aerosol medication, cardiac arrest and even death may be associated with abuse of pirbuterol.
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAcebutolol The therapeutic efficacy of Pirbuterol can be decreased when used in combination with Acebutolol. Aceclofenac The risk or severity of hypertension can be increased when Pirbuterol is combined with Aceclofenac. Acemetacin The risk or severity of hypertension can be increased when Pirbuterol is combined with Acemetacin. Acetylsalicylic acid The risk or severity of hypertension can be increased when Acetylsalicylic acid is combined with Pirbuterol. Aclidinium The risk or severity of Tachycardia can be increased when Pirbuterol is combined with Aclidinium. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Pirbuterol acetate 1EH73XKR9N 65652-44-0 QSXMZJGGEWYVCN-UHFFFAOYSA-N Pirbuterol hydrochloride GR436K4GK8 38029-10-6 GPDAJAWUGSTOSA-UHFFFAOYSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Maxair Aerosol, metered 200 ug/1 Respiratory (inhalation) 3M Company 1992-11-30 2006-12-29 US 
Maxair Aerosol, metered 200 ug/1 Respiratory (inhalation) 3M Company 1996-12-30 2006-12-29 US Maxair Aem 240mcg/aem Aerosol, metered 250 mcg / act Respiratory (inhalation) 3 M Pharmaceuticals, A Division Of 3 M Canada Company 1996-12-31 1998-08-13 Canada 
Maxair Autohaler Inhalant 200 ug/1 Respiratory (inhalation) Graceway Pharmaceuticals 2008-01-01 2014-11-30 US Maxair Autohaler Inhalant 200 ug/1 Oral Medicis Pharmaceutical Corporation 2011-11-28 2014-11-30 US
Categories
- ATC Codes
- R03CC07 — Pirbuterol
- R03CC — Selective beta-2-adrenoreceptor agonists
- R03C — ADRENERGICS FOR SYSTEMIC USE
- R03 — DRUGS FOR OBSTRUCTIVE AIRWAY DISEASES
- R — RESPIRATORY SYSTEM
- Drug Categories
- Adrenergic Agents
- Adrenergic Agonists
- Adrenergic beta-2 Receptor Agonists
- Adrenergic beta-Agonists
- Adrenergics for Systemic Use
- Adrenergics, Inhalants
- Agents producing tachycardia
- Agents that produce hypertension
- Agents to Treat Airway Disease
- Alcohols
- Amines
- Amino Alcohols
- Anti-Asthmatic Agents
- Autonomic Agents
- Bronchodilator Agents
- Cardiotonic Agents
- Cardiovascular Agents
- Compounds used in a research, industrial, or household setting
- Drugs for Obstructive Airway Diseases
- Neurotransmitter Agents
- Peripheral Nervous System Agents
- Protective Agents
- Respiratory System Agents
- Selective Beta 2-adrenergic Agonists
- Chemical TaxonomyProvided by Classyfire
- 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
- 1,2-aminoalcohol / Alcohol / Amine / Aralkylamine / Aromatic alcohol / Aromatic heteromonocyclic compound / Azacycle / Heteroaromatic compound / Hydrocarbon derivative / Hydroxypyridine
- Molecular Framework
- Aromatic heteromonocyclic compounds
- External Descriptors
- pyridines (CHEBI:8245)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- OG645J8RVW
- CAS number
- 38677-81-5
- 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
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
- 33767
- ChEBI
- 8245
- ChEMBL
- CHEMBL1094966
- Therapeutic Targets Database
- DAP000249
- PharmGKB
- PA450983
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Pirbuterol
- FDA label
- Download (260 KB)
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- 3M Health Care
- Graceway Pharmaceuticals
- Pharmedix
- Physicians Total Care Inc.
- Dosage Forms
Form Route Strength Aerosol, metered Respiratory (inhalation) Syrup Respiratory (inhalation) Aerosol, metered Respiratory (inhalation) 200 ug/1 Aerosol, metered Respiratory (inhalation) 250 mcg / act Inhalant Oral 200 ug/1 Inhalant Respiratory (inhalation) 200 ug/1 - Prices
Unit description Cost Unit Maxair Autohaler 200 mcg/inh Aerosol 14 gm Inhaler 169.99USD inhaler Maxair autohaler 0.2 mg aero 8.52USD 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
Property Value Source Water Solubility 6.22 mg/mL ALOGPS logP 0.38 ALOGPS logP -0.66 Chemaxon logS -1.6 ALOGPS pKa (Strongest Acidic) 8.79 Chemaxon pKa (Strongest Basic) 9.59 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 5 Chemaxon Hydrogen Donor Count 4 Chemaxon Polar Surface Area 85.61 Å2 Chemaxon Rotatable Bond Count 5 Chemaxon Refractivity 64.74 m3·mol-1 Chemaxon Polarizability 26.31 Å3 Chemaxon Number of Rings 1 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9563 Blood Brain Barrier - 0.9442 Caco-2 permeable - 0.6419 P-glycoprotein substrate Substrate 0.7707 P-glycoprotein inhibitor I Non-inhibitor 0.9454 P-glycoprotein inhibitor II Non-inhibitor 0.9913 Renal organic cation transporter Non-inhibitor 0.8415 CYP450 2C9 substrate Non-substrate 0.8123 CYP450 2D6 substrate Non-substrate 0.7856 CYP450 3A4 substrate Non-substrate 0.6501 CYP450 1A2 substrate Non-inhibitor 0.9045 CYP450 2C9 inhibitor Non-inhibitor 0.9071 CYP450 2D6 inhibitor Non-inhibitor 0.925 CYP450 2C19 inhibitor Non-inhibitor 0.9025 CYP450 3A4 inhibitor Non-inhibitor 0.9096 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.9293 Ames test Non AMES toxic 0.82 Carcinogenicity Non-carcinogens 0.9109 Biodegradation Not ready biodegradable 0.99 Rat acute toxicity 2.4870 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9743 hERG inhibition (predictor II) Non-inhibitor 0.9365
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Spectrum Spectrum Type Splash Key Predicted GC-MS Spectrum - GC-MS Predicted GC-MS splash10-0zn9-8930000000-28ba1967222e8cc4819f Predicted MS/MS Spectrum - 10V, Positive (Annotated) Predicted LC-MS/MS splash10-00kf-0980000000-1e20b88e36eb77078f03 Predicted MS/MS Spectrum - 10V, Negative (Annotated) Predicted LC-MS/MS splash10-000i-0090000000-25e6bbd6784154c0e575 Predicted MS/MS Spectrum - 20V, Negative (Annotated) Predicted LC-MS/MS splash10-059i-0940000000-5478cc3fc51bbdf1b840 Predicted MS/MS Spectrum - 20V, Positive (Annotated) Predicted LC-MS/MS splash10-066r-5910000000-97f4dc97ce1d3b8ee141 Predicted MS/MS Spectrum - 40V, Negative (Annotated) Predicted LC-MS/MS splash10-0aba-9800000000-fd1d85420fbf2b681043 Predicted MS/MS Spectrum - 40V, Positive (Annotated) Predicted LC-MS/MS splash10-0a4i-9600000000-b859d2637e1452c0c0a3 Predicted 1H NMR Spectrum 1D NMR Not Applicable Predicted 13C NMR Spectrum 1D NMR Not Applicable - Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 167.8991342 predictedDarkChem Lite v0.1.0 [M-H]- 161.87178 predictedDeepCCS 1.0 (2019) [M+H]+ 168.3583342 predictedDarkChem Lite v0.1.0 [M+H]+ 164.22978 predictedDeepCCS 1.0 (2019) [M+Na]+ 167.8939342 predictedDarkChem Lite v0.1.0 [M+Na]+ 170.32292 predictedDeepCCS 1.0 (2019)
Targets
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- Kind
- Protein
- Organism
- Humans
- 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
- 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. [Article]
- 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. [Article]
- 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. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Kind
- Protein
- Organism
- Humans
- 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
- van Zwieten PA: Receptor-mediated inotropic drugs. Eur Heart J. 1988 Jun;9 Suppl H:85-90. [Article]
- 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. [Article]
Drug created at June 30, 2007 14:13 / Updated at November 03, 2023 23:50