Isoprenaline

Isoprenaline
Clinical data
Trade namesIsuprel, others[1][2]
Other namesIsoproterenol; Isopropylnorepinephrine; Isopropylnoradrenaline; Isopropydine; WIN-5162
AHFS/Drugs.comMonograph
MedlinePlusa601236
Pregnancy
category
  • AU: A
Routes of
administration		Intravenous, intramuscular, subcutaneous, intracardiac, inhalation, sublingual, rectal[3][4]
ATC code
Legal status
Legal status
  • AU: S4 (Prescription only)
  • In general: ℞ (Prescription only)
Pharmacokinetic data
BioavailabilityOral: Very low[5][6]
Protein binding69% (mostly to albumin)[3]
MetabolismMethylation (COMTTooltip Catechol O-methyltransferase), conjugation (sulfation)[7][3]
Metabolites• 3-O-Methylisoprenaline[3]
• Sulfate conjugates[7]
Onset of actionInhalation: 2–5 min[8]
Elimination half-lifeIVTooltip Intravenous infusion: 2.5–5 min[3]
Oral: 40 min[3]
Duration of actionInhalation: 0.5–2 hours[8]
ExcretionUrine: 59–107%[3]
Feces: 12–27%[3]
Identifiers
IUPAC name
  • 4-[1-hydroxy-2-(isopropylamino)ethyl]benzene-1,2-diol
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.028.807
Chemical and physical data
FormulaC11H17NO3
Molar mass211.261 g·mol−1
3D model (JSmol)
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 Y
  • Key:JWZZKOKVBUJMES-UHFFFAOYSA-N Y
  (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.[9] 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.[3][4]

Side effects of isoprenaline include rapid heart beat, heart palpitations, and arrhythmias, among others.[9] Isoprenaline is a selective agonist of the β-adrenergic receptors, including both the β1- and β2-adrenergic receptors.[9] By activating these receptors, it increases heart rate and the force of heart contractions.[10] Chemically, isoprenaline is a synthetic catecholamine and is the N-isopropyl analogue of norepinephrine (noradrenaline) and epinephrine (adrenaline).[11][3][12][13]

Isoprenaline was one of the first synthetic sympathomimetic amines and was the first selective β-adrenergic receptor agonist.[7][14] The medication was discovered in 1940[5] and was introduced for medical use in 1947.[15]

  1. ^ Cite error: The named reference IndexNominum2004 was invoked but never defined (see the help page).
  2. ^ Cite error: The named reference Drugs.com was invoked but never defined (see the help page).
  3. ^ a b c d e f g h i j "Isoprenaline: Uses, Interactions, Mechanism of Action". DrugBank Online. 19 February 1948. Retrieved 31 July 2024.
  4. ^ a b "Drugs@FDA: FDA-Approved Drugs". accessdata.fda.gov. Archived from the original on November 4, 2016. Retrieved 31 July 2024.
  5. ^ a b Cite error: The named reference Waldeck2002 was invoked but never defined (see the help page).
  6. ^ Cite error: The named reference ConollyDaviesDollery1972 was invoked but never defined (see the help page).
  7. ^ a b c Cite error: The named reference Morgan1990 was invoked but never defined (see the help page).
  8. ^ a b Cite error: The named reference Sterling1995 was invoked but never defined (see the help page).
  9. ^ a b c "Label: Isoproterenol hydrochloride injection, solution". NIH DailyMed. September 10, 2013. Retrieved June 21, 2017.
  10. ^ Motwani SK, Saunders H (2024). "Inotropes". Anaesthesia & Intensive Care Medicine. 25 (3): 185–191. doi:10.1016/j.mpaic.2023.11.019.
  11. ^ Cite error: The named reference PubChem was invoked but never defined (see the help page).
  12. ^ Cite error: The named reference ChemSpider was invoked but never defined (see the help page).
  13. ^ Cite error: The named reference Konzett1981 was invoked but never defined (see the help page).
  14. ^ Cite error: The named reference RuženaJindraRenáta2020 was invoked but never defined (see the help page).
  15. ^ Cite error: The named reference MozayaniRaymon2003 was invoked but never defined (see the help page).
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