Orciprenaline

Orciprenaline

Systematic (IUPAC) name
(RS)-5-[1-hydroxy-2-(isopropylamino)ethyl]benzene-1,3-diol
Clinical data
AHFS/Drugs.com	monograph
MedlinePlus	a682084
Pregnancy category	AU: A US: C (Risk not ruled out)
Legal status	US: ℞-only
Routes of administration	Inhalation / tablets
Pharmacokinetic data
Bioavailability	3% if inhaled, 40% if taken orally
Metabolism	Gastrointestinal and hepatic
Biological half-life	6 hours
Identifiers
CAS Number	586-06-1 Y
ATC code	R03AB03 (WHO) R03CB03 R03CB53
PubChem	CID: 4086
IUPHAR/BPS	7250
DrugBank	DB00816 N
ChemSpider	3944 Y
UNII	53QOG569E0 Y
KEGG	D08300 Y
ChEBI	CHEBI:82719 N
ChEMBL	CHEMBL776 Y
Chemical data
Formula	C11H17NO3
Molecular mass	211.258 g/mol
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
Physical data
Solubility in water	9.7 mg/mL (20 °C)
NY (what is this?)  (verify)

Orciprenaline (INN), also known as metaproterenol (USAN), is a bronchodilator used in the treatment of asthma. Orciprenaline is a moderately selective beta₂-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 alpha-adrenergic receptors. The pharmacologic effects of beta adrenergic agonist drugs, such as orciprenaline, are at least in part attributable to stimulation through beta adrenergic receptors of intracellular adenyl 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