My watch list

Orciprenaline


Orciprenaline
Systematic (IUPAC) name
5-[1-hydroxy-2-(1-methylethylamino)ethyl]benzene-1,3-diol
Identifiers
CAS number	586-06-1
ATC code	R03AB03 R03CB03 R03CB53
PubChem	4086
Chemical data
Formula	C₁₁H₁₇N O₃
Mol. mass	211.258 g/mol
SMILES	search in eMolecules, PubChem
Physical data
Solubility in water	9.7 mg/mL (20 °C)
Pharmacokinetic data
Bioavailability	3% if inhaled, 40% if taken orally
Metabolism	Gastrointestinal and hepatic
Half life	6 hours
Excretion	?
Therapeutic considerations
Pregnancy cat.	A(AU) C(US)
Legal status	℞-only(US)
Routes	Inhalation / tablets

Orciprenaline (INN, also known as metaproterenol) 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.

Additional recommended knowledge

Brand names

Brand names for orciprenaline include Alotec, Alupent, Metaprel and Novasmasol.

v • d • e Adrenergic agonists
Direct Acting	Albuterol · Clonidine · Dobutamine · Dopamine · Epinephrine · Formoterol · Isoproterenol · Metaproterenol · Methoxamine · Norepinephrine - Phenylephrine · Piruterol · Salmeterol · Tamsulosin · Terbutaline
Indirect Acting	Amphetamine · Tyramine
Mixed Action	Ephedrine

v • d • e Drugs for obstructive airway diseases: asthma/COPD (R03)
Adrenergics, inhalants	Short acting β₂-agonists: Salbutamol/Levosalbutamol • Fenoterol • Terbutaline Long acting β₂-agonists (LABA): Bambuterol • Clenbuterol • Formoterol • Salmeterol other: Epinephrine • Isoproterenol • Orciprenaline
Glucocorticoids	Beclometasone • Budesonide • Ciclesonide • Fluticasone • Mometasone
Anticholinergics	Ipratropium • Tiotropium
Mast cell stabilizers	Cromoglicate • Nedocromil
Xanthines	Aminophylline • Theobromine • Theophylline
Leukotriene antagonists	Montelukast • Pranlukast • Zafirlukast
Combination products	Budesonide/formoterol • Fluticasone/salmeterol • Ipratropium/salbutamol