Isoprenaline

Isoprenaline
Clinical data
Trade names	Isuprel, others
Other names	Isoproterenol; Isopropylnorepinephrine; Isopropylnoradrenaline; Isopropydine; WIN-5162
AHFS/Drugs.com	Monograph
MedlinePlus	a601236
Pregnancy; category	AU: A;
Routes of; administration	Intravenous, intramuscular, subcutaneous, intracardiac, inhalation, sublingual, rectal
ATC code	C01CA02 (WHO) R03AB02 (WHO); R03CB01 (WHO);
Legal status
Legal status	AU: S4 (Prescription only); In general: ℞ (Prescription only);
Pharmacokinetic data
Bioavailability	Oral: Very low
Protein binding	69% (mostly to albumin)
Metabolism	Methylation (COMTTooltip Catechol O-methyltransferase), conjugation (sulfation)
Metabolites	• 3-O-Methylisoprenaline; • Sulfate conjugates
Onset of action	Inhalation: 2–5 min
Elimination half-life	IVTooltip Intravenous infusion: 2.5–5 min; Oral: 40 min
Duration of action	Inhalation: 0.5–2 hours
Excretion	Urine: 59–107%; Feces: 12–27%
Identifiers
	IUPAC name 4-[1-hydroxy-2-(isopropylamino)ethyl]benzene-1,2-diol;
CAS Number	7683-59-2 ;
PubChem CID	3779;
IUPHAR/BPS	536;
DrugBank	DB01064 ;
ChemSpider	3647 ;
UNII	L628TT009W;
KEGG	D08090 ;
ChEMBL	ChEMBL434 ;
CompTox Dashboard (EPA)	DTXSID4023175 ;
ECHA InfoCard	100.028.807
Chemical and physical data
Formula	C11H17NO3
Molar mass	211.261 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC(C)NCC(O)c1cc(O)c(O)cc1;
	InChI InChI=1S/C11H17NO3/c1-7(2)12-6-11(15)8-3-4-9(13)10(14)5-8/h3-5,7,11-15H,6H2,1-2H3 ; Key:JWZZKOKVBUJMES-UHFFFAOYSA-N ;
	(verify)

Isoprenaline, also known as isoproterenol and sold under the brand name Isuprel among others, is a sympathomimetic medication which is used in the treatment of acute bradycardia (slow heart rate), heart block, and rarely for asthma, among other indications. It is used by injection into a vein, muscle, fat, or the heart, by inhalation, and in the past under the tongue or into the rectum.

Side effects of isoprenaline include rapid heart beat, heart palpitations, and arrhythmias, among others. Isoprenaline is a selective agonist of the β-adrenergic receptors, including both the β₁- and β₂-adrenergic receptors. By activating these receptors, it increases heart rate and the force of heart contractions. Chemically, isoprenaline is a synthetic catecholamine and is the N-isopropyl analogue of norepinephrine (noradrenaline) and epinephrine (adrenaline).

Isoprenaline was one of the first synthetic sympathomimetic amines and was the first selective β-adrenergic receptor agonist. The medication was discovered in 1940 and was introduced for medical use in 1947.