Esmolol

Esmolol, sold under the brand name Brevibloc, is a cardio selective beta₁ receptor blocker with rapid onset,^[3] a very short duration of action, and no significant intrinsic sympathomimetic or membrane stabilising activity at therapeutic dosages.

Esmolol

Clinical data
Trade names	Brevibloc
AHFS/Drugs.com	Monograph
Pregnancy category	AU: C
Routes of administration	Intravenous
ATC code	C07AB09 (WHO)
Legal status
Legal status	AU: S4 (Prescription only)[1][2]
Pharmacokinetic data
Protein binding	60%
Metabolism	Red blood cell (erythrocytic)
Elimination half-life	9 minutes
Excretion	Kidney
Identifiers
IUPAC name methyl (RS)-3-{4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl}propanoate
CAS Number	81147-92-4 N
PubChem CID	59768
IUPHAR/BPS	7178
DrugBank	DB00187 N
ChemSpider	53916 Y
UNII	MDY902UXSR
KEGG	D07916 Y
ChEBI	CHEBI:4856 N
ChEMBL	ChEMBL768 Y
CompTox Dashboard (EPA)	DTXSID4022995
Chemical and physical data
Formula	C16H25NO4
Molar mass	295.379 g·mol−1
3D model (JSmol)	Interactive image
SMILES O=C(OC)CCc1ccc(OCC(O)CNC(C)C)cc1
InChI InChI=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 Y Key:AQNDDEOPVVGCPG-UHFFFAOYSA-N Y
NY (what is this?)  (verify)

It is a class II antiarrhythmic.^[4] 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.^[5]

It was patented in 1980 and approved for medical use in 1987.^[6]

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.^[7]

Pharmacology

Pharmacodynamics

Esmolol is a beta blocker, or an antagonist of the β-adrenergic receptors.^[8] It is selective for the β₁-adrenergic receptor and has no intrinsic sympathomimetic activity.^[8]

Pharmacokinetics

Esmolol is considered a soft drug,^[9] 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.^{[citation needed]}

Esmolol is classified as a beta blocker with low lipophilicity and hence lower potential for crossing the blood–brain barrier.^[8] This in turn may result in fewer effects in the central nervous system as well as a lower risk of neuropsychiatric side effects.^[8]