Orciprenaline

Chemical compound
  • AU: A
Routes of
administrationInhalation (MDI) and tabletsATC code
  • R03AB03 (WHO) R03CB03 (WHO)
    R03CB53 (WHO)
Legal statusLegal status
  • AU: S4 (Prescription only)
  • US: ℞-only
Pharmacokinetic dataBioavailability3% if inhaled, 40% if taken orallyMetabolismGastrointestinal and hepaticElimination half-life6 hoursIdentifiers
  • (RS)-5-[1-hydroxy-2-(isopropylamino)ethyl]benzene-1,3-diol
CAS Number
  • 586-06-1 checkY
PubChem CID
  • 4086
IUPHAR/BPS
  • 7250
DrugBank
  • DB00816 ☒N
ChemSpider
  • 3944 checkY
UNII
  • 53QOG569E0
KEGG
  • D08300 checkY
ChEBI
  • CHEBI:82719 ☒N
ChEMBL
  • ChEMBL776 checkY
CompTox Dashboard (EPA)
  • DTXSID8048529 Edit this at Wikidata
ECHA InfoCard100.008.701 Edit this at WikidataChemical and physical dataFormulaC11H17NO3Molar mass211.261 g·mol−13D model (JSmol)
  • Interactive image
ChiralityRacemic mixtureSolubility 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)

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.

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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Adrenergics, inhalants
Short-acting β2 agonists
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  • See also: Receptor/signaling modulators
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Phenethylamines


Stimulants: Phenylethanolamine

Amphetamines
Phentermines
Cathinones
Phenylisobutylamines
Phenylalkylpyrrolidines
Catecholamines
(and close relatives)
Miscellaneous
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