Orciprenaline Other names Metaproterenol (USAN US ) AHFS /Drugs.com Monograph MedlinePlus a682084 Pregnancy category Routes of administration Inhalation (MDI ) and tablets ATC code Legal status
AU : S4 (Prescription only)
US : ℞-only
Bioavailability 3% if inhaled, 40% if taken orally Metabolism Gastrointestinal and hepatic Elimination half-life 6 hours
(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 Formula C 11 H 17 N O 3 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
Y Key:LMOINURANNBYCM-UHFFFAOYSA-N
Y
N Y (what is this?)
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 [ ]
^ 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 .
^ 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 .
Drugs for obstructive airway diseases : asthma /COPD (R03 )
Adrenergics , inhalants
Short-acting β2 agonists Long-acting β2 agonists Ultra-long-acting β2 agonists
Abediterol
Carmoterol
Indacaterol
Olodaterol
Vilanterol
Other
Glucocorticoids Anticholinergics /muscarinic antagonist Mast cell stabilizers Xanthines
Acefylline
Ambuphylline
Aminophylline
Bamifylline
Choline theophyllinate
Doxofylline
Enprofylline
Etamiphylline
Proxyphylline
Theophylline
Eicosanoid inhibition
Leukotriene antagonists Arachidonate 5-lipoxygenase inhibitors Thromboxane receptor antagonists Non-xanthine PDE4 inhibitors
Others/unknown
Amlexanox
Eprozinol
Fenspiride ‡
Omalizumab
Combination products
# WHO-EM
‡ Withdrawn from market
Clinical trials :
† Phase III
§ Never to phase III
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See also: Receptor/signaling modulators
Dopaminergics
Serotonergics
Monoamine reuptake inhibitors
Monoamine releasing agents
Monoamine metabolism modulators
Monoamine neurotoxins