Pirbuterol
Pirbuterol.svg
Clinical data
Trade namesMaxair
AHFS/Drugs.comConsumer Drug Information
MedlinePlusa601096
Pregnancy
category
  • C
Routes of
administration
Inhalational (MDI)
ATC code
Legal status
Legal status
Identifiers
  • (RS)-6-[2-(tert-butylamino)-1-hydroxyethyl]-2-(hydroxymethyl)pyridin-3-ol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC12H20N2O3
Molar mass240.303 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
  • Oc1ccc(nc1CO)C(O)CNC(C)(C)C
  • 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 checkY
  • Key:VQDBNKDJNJQRDG-UHFFFAOYSA-N checkY
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Pirbuterol (trade name Maxair) is a short-acting β2 adrenoreceptor agonist with bronchodilating action used in the treatment of asthma, available (as pirbuterol acetate) as a breath-activated metered-dose inhaler.

It was patented in 1971 and came into medical use in 1983.[1]

Medical use

Pirbuterol is used in asthma for reversal of acute bronchospasm, and also as a maintenance medication to prevent future attacks. It should be used in patients 12 years of age and older with or without concurrent theophylline and/or inhaled corticosteroid.[2][3]

Mode of action

Further information: Beta2-adrenergic agonist

Pharmacokinetics

After inhalation of doses up to 800 μg (twice the maximum recommended dose) systemic blood levels of pirbuterol are below the limit of assay sensitivity (2–5 ng/ml). A mean of 51% of the dose is recovered in urine as pirbuterol plus its sulfate conjugate following administration by aerosol. Pirbuterol is not metabolized by catechol-O-methyltransferase. The plasma half-life measured after oral administration is about two hours.[2]

Adverse effects

Further information: Beta2-adrenergic agonist

References

  1. ^ Fischer J, Ganellin CR (2006). Analogue-based Drug Discovery. John Wiley & Sons. p. 543. ISBN 9783527607495.
  2. ^ a b "Maxair Autohaler (pirbuterol acetate inhalation aerosol) For Oral Inhalation Only. U.S. Full Prescribing Information". 3M Pharmaceuticals. Northridge, CA 91324. Archived from the original on 20 September 2018. Retrieved 7 March 2016.
  3. ^ Bianchi M, Clavenna A, Bonati M (September 2010). "Inter-country variations in anti-asthmatic drug prescriptions for children. Systematic review of studies published during the 2000-2009 period" (PDF). European Journal of Clinical Pharmacology. 66 (9): 929–36. doi:10.1007/s00228-010-0845-y. PMID 20533030. S2CID 21834280.