Orciprenaline

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.

Orciprenaline
Clinical data
Other namesMetaproterenol (USAN US)
AHFS/Drugs.comMonograph
MedlinePlusa682084
Pregnancy
category
  • AU: A
Routes of
administration		Inhalation (MDI) and tablets
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • US: ℞-only
Pharmacokinetic data
Bioavailability3% if inhaled, 40% if taken orally
MetabolismGastrointestinal and hepatic
Elimination half-life6 hours
Identifiers
IUPAC name
  • (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
Chemical and physical data
FormulaC11H17NO3
Molar mass211.261 g·mol−1
3D model (JSmol)
ChiralityRacemic mixture
Solubility in water9.7 mg/mL (20 °C)
SMILES
  • Oc1cc(cc(O)c1)C(O)CNC(C)C
InChI
  • 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 Y
  • Key:LMOINURANNBYCM-UHFFFAOYSA-N Y
 NY (what is this?)  (verify)

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

References
  1. Knox C, Law V, Jewison T, Liu P, Ly S, Frolkis A, Pon A, Banco K, Mak C, Neveu V, Djoumbou Y, Eisner R, Guo AC, Wishart DS (2011). "DrugBank 3.0: a comprehensive resource for omics research on drugs". Nucleic Acids Res. 39 (Database issue): D1035-41. doi:10.1093/nar/gkq1126. PMC 3013709. PMID 21059682.
  2. Wishart DS, Knox C, Guo AC, Cheng D, Shrivastava S, Tzur D, Gautam B, Hassanali M (2008). "DrugBank: a knowledgebase for drugs, drug actions and drug targets". Nucleic Acids Res. 36 (Database issue): D901-6. doi:10.1093/nar/gkm958. PMC 2238889. PMID 18048412.
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