Orciprenaline

Chemical compound From Wikipedia, the free encyclopedia

Orciprenaline, also known as metaproterenol, is a bronchodilator used in the treatment of asthma.[1][2] 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.

Trade namesAlupent, Metaprel, Orcibest
Other namesMetaproterenol (USAN US)
Quick facts Clinical data, Trade names ...
Orciprenaline
Clinical data
Trade namesAlupent, Metaprel, Orcibest
Other namesMetaproterenol (USAN US)
AHFS/Drugs.comMonograph
MedlinePlusa682084
Pregnancy
category
  • AU: A
Routes of
administration
By mouth, inhalation
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability3% if inhaled, 40% if taken orally
MetabolismGastrointestinal and hepatic
Elimination half-life6 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 InfoCard100.008.701 Edit this at Wikidata
Chemical and physical data
FormulaC11H17NO3
Molar mass211.261 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
Solubility in water9.7 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)
Close

Adverse effects

More common side effects of metaproterenol include tachycardia and nervousness.[3][4] Additional side effects with >1% incidence include headache, nausea, and tremor.[3] A non-exhaustive list of rare side effects includes other cardiovascular symptoms, dizziness, fatigue, etc.[3][4]

References

Related Articles

Wikiwand AI