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Orciprenaline

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Orciprenaline
Orciprenaline.svg
Clinical data
Other names Metaproterenol (USAN US)
AHFS/Drugs.com Monograph
MedlinePlus a682084
Pregnancy
category
  • AU: A
Routes of
administration
Inhalation (MDI) and tablets
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability 3% if inhaled, 40% if taken orally
Metabolism Gastrointestinal and hepatic
Elimination half-life 6 hours
Identifiers
  • (RS)-5-[1-hydroxy-2-(isopropylamino)ethyl]benzene-1,3-diol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard 100.008.701
Chemical and physical data
Formula C11H17NO3
Molar mass 211.261 g·mol−1
3D model (JSmol)
Chirality Racemic mixture
Solubility in water 9.7 mg/mL (20 °C)
  • Oc1cc(cc(O)c1)C(O)CNC(C)C
  • InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-9(13)5-10(14)4-8/h3-5,7,11-15H,6H2,1-2H3 checkY
  • Key:LMOINURANNBYCM-UHFFFAOYSA-N checkY
 ☒NcheckY (what is this?)  (verify)

Orciprenaline, also known as metaproterenol, is a bronchodilator used in the treatment of asthma. Orciprenaline is a moderately selective β2 adrenergic receptor agonist that stimulates receptors of the smooth muscle in the lungs, uterus, and vasculature supplying skeletal muscle, with minimal or no effect on α adrenergic receptors. The pharmacologic effects of β adrenergic agonist drugs, such as orciprenaline, are at least in part attributable to stimulation through β adrenergic receptors of intracellular adenylyl cyclase, the enzyme which catalyzes the conversion of ATP to cAMP. Increased cAMP levels are associated with relaxation of bronchial smooth muscle and inhibition of release of mediators of immediate hypersensitivity from many cells, especially from mast cells.

Possible side effects

  • tremor
  • nervousness
  • dizziness
  • weakness
  • headache
  • nausea
  • tachycardia
Rare side effects that could be life-threatening
  • increased difficulty breathing
  • rapid or increased heart rate
  • irregular heartbeat
  • chest pain or discomfort

Brand names

  • Alupent
  • Metaprel
  • Orcibest

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