Esmolol

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Class II antiarrhythmic drug

title: "Esmolol" type: doc version: 1 created: 2026-02-28 author: "Wikipedia contributors" status: active scope: public tags: ["beta-blockers", "n-isopropyl-phenoxypropanolamines", "carboxylate-esters", "diseases-of-the-aorta", "methyl-esters", "peripherally-selective-drugs"] description: "Class II antiarrhythmic drug" topic_path: "general/beta-blockers" source: "https://en.wikipedia.org/wiki/Esmolol" license: "CC BY-SA 4.0" wikipedia_page_id: 0 wikipedia_revision_id: 0

::summary Class II antiarrhythmic drug ::

| Verifiedfields = changed | Watchedfields = changed | verifiedrevid = 412885041 | image = Esmolol structure.svg | image_class = skin-invert-image

| tradename = Brevibloc | Drugs.com = | pregnancy_AU = C | pregnancy_category = | routes_of_administration = Intravenous | ATC_prefix = C07 | ATC_suffix = AB09

| legal_AU = S4 | legal_AU_comment = | legal_BR = | legal_BR_comment = | legal_CA = | legal_CA_comment = | legal_DE = | legal_DE_comment = | legal_NZ = | legal_NZ_comment = | legal_UK = | legal_UK_comment = | legal_US = | legal_US_comment = | legal_EU = | legal_EU_comment = | legal_UN = | legal_UN_comment = | legal_status =

| bioavailability = | protein_bound = 60% | metabolism = Red blood cell (erythrocytic) | elimination_half-life = 9 minutes | excretion = Kidney

| IUPHAR_ligand = 7178 | CAS_number_Ref = | CAS_number = 81147-92-4 | PubChem = 59768 | DrugBank_Ref = | DrugBank = DB00187 | ChemSpiderID_Ref = | ChemSpiderID = 53916 | UNII_Ref = | UNII = MDY902UXSR | KEGG_Ref = | KEGG = D07916 | ChEBI_Ref = | ChEBI = 4856 | ChEMBL_Ref = | ChEMBL = 768

| IUPAC_name = methyl (RS)-3-{4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl}propanoate | C=16 | H=25 | N=1 | O=4 | SMILES = O=C(OC)CCc1ccc(OCC(O)CNC(C)C)cc1 | StdInChI_Ref = | StdInChI = 1S/C16H25NO4/c1-12(2)17-10-14(18)11-21-15-7-4-13(5-8-15)6-9-16(19)20-3/h4-5,7-8,12,14,17-18H,6,9-11H2,1-3H3 | StdInChIKey_Ref = | StdInChIKey = AQNDDEOPVVGCPG-UHFFFAOYSA-N Esmolol, sold under the brand name Brevibloc, is a cardio selective beta1 receptor blocker with rapid onset, a very short duration of action, and no significant intrinsic sympathomimetic or membrane stabilising activity at therapeutic dosages.

It is a class II antiarrhythmic. Esmolol decreases the force and rate of heart contractions by blocking beta-adrenergic receptors of the sympathetic nervous system, which are found in the heart and other organs of the body. Esmolol prevents the action of two naturally occurring substances: epinephrine and norepinephrine.

It was patented in 1980 and approved for medical use in 1987.

Medical uses

To terminate supraventricular tachycardia,

Episodic atrial fibrillation or flutter,

Arrhythmia during anaesthesia,

To reduce HR and BP during and after cardiac surgery, and

In early treatment of myocardial infarction.

Esmolol is also used in blunting the hemodynamic response to laryngoscopy and intubation.

Pharmacology

Pharmacodynamics

Esmolol is a beta blocker, or an antagonist of the β-adrenergic receptors. It is selective for the β1-adrenergic receptor and has no intrinsic sympathomimetic activity.

Pharmacokinetics

Esmolol is considered a soft drug, one that is rapidly metabolized to an inactive form. Esmolol is rapidly metabolized by hydrolysis of the ester linkage, chiefly by the esterases in the cytosol of red blood cells and not by plasma cholinesterases or red cell membrane acetylcholinesterase. Total body clearance in man was found to be about 20 L/kg/hr, which is greater than cardiac output; thus the metabolism of esmolol is not limited by the rate of blood flow to metabolizing tissues such as the liver or affected by hepatic or renal blood flow. Esmolol's short duration of action is based on the ester-methyl side chain which allows for quick hydrolysis. Esmolol's structure is reflected in its name, es-molol as in ester-methyl. Plasma cholinesterases and red cell membrane acetylcholinesterase do not have any action. This metabolism results in the formation of a free acid and methanol. The amount of methanol produced is similar to endogenous methanol production. Esmolol has a rapid distribution half-life of about two minutes and an elimination half-life of about nine minutes.

Esmolol is classified as a beta blocker with moderate lipophilicity and hence moderate potential for crossing the blood–brain barrier. As such, esmolol may produce effects in the central nervous system and have a risk of neuropsychiatric side effects.

Chemistry

The experimental log P is 1.7 and its predicted log P ranges from 1.82 to 2.02. It is a moderately lipophilic beta blocker.

References

References

  1. (26 May 2022). "Brevibloc esmolol hydrochloride 2.5 g powder for injection for infusion vial (310943)".
  2. (13 January 2023). "Esmolol Juno (Juno Pharmaceuticals Pty Ltd)".
  3. (December 2006). "Esmolol inhibits Na+ current in rat ventricular myocytes". Methods and Findings in Experimental and Clinical Pharmacology.
  4. (December 1989). "Recent antiarrhythmic drugs". The American Journal of Cardiology.
  5. "Essentials of Medical Pharmacology".
  6. (2006). "Analogue-based Drug Discovery". John Wiley & Sons.
  7. (2018). "Comparison of Esmolol and Dexmedetomidine for Suppression of Hemodynamic Response to Laryngoscopy and Endotracheal Intubation in Adult Patients Undergoing Elective General Surgery: A Prospective, Randomized Controlled Double-blinded Study". Anesthesia: Essays and Researches.
  8. (2000). "Soft drug design: General principles and recent applications". Medicinal Research Reviews.
  9. (February 2021). "Neuropsychiatric Consequences of Lipophilic Beta-Blockers". Medicina (Kaunas).
  10. "Esmolol".
  11. (31 December 1986). "Esmolol: Uses, Interactions, Mechanism of Action".
  12. (10 June 2024). "C16H25NO4".
  13. (September 2014). "Pharmacokinetics of selective β1-adrenergic blocking agents: prescribing implications". Expert Opin Drug Metab Toxicol.
  14. (February 2005). "The impact of lipophilicity in drug research: a case report on beta-blockers". Mini Rev Med Chem.

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beta-blockersn-isopropyl-phenoxypropanolaminescarboxylate-estersdiseases-of-the-aortamethyl-estersperipherally-selective-drugs