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Details

Stereochemistry RACEMIC
Molecular Formula C16H25NO4
Molecular Weight 295.374
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESMOLOL

SMILES

COC(=O)CCC1=CC=C(OCC(O)CNC(C)C)C=C1

InChI

InChIKey=AQNDDEOPVVGCPG-UHFFFAOYSA-N
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

HIDE SMILES / InChI

Molecular Formula C16H25NO4
Molecular Weight 295.374
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description

Esmolol (trade name Brevibloc) is a cardioselective beta1 receptor blocker with rapid onset, a very short duration of action, and no significant intrinsic sympathomimetic or membrane stabilizing activity at therapeutic dosages. 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. Esmolol predominantly blocks the beta-1 receptors in cardiac tissue. Used for the rapid control of ventricular rate in patients with atrial fibrillation or atrial flutter in perioperative, postoperative, or other emergent circumstances where short term control of ventricular rate with a short-acting agent is desirable. Also used in noncompensatory sinus tachycardia where the rapid heart rate requires specific intervention.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
74.2 µM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BREVIBLOC
Primary
BREVIBLOC

Cmax

ValueDoseCo-administeredAnalytePopulation
0.22 μg/mL
0.5 mg/kg single, intravenous
ESMOLOL plasma
Homo sapiens
0.56 μg/mL
1 mg/kg single, intravenous
ESMOLOL plasma
Homo sapiens
0.96 μg/mL
1.5 mg single, intravenous
ESMOLOL plasma
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
0.02 μg × h/mL
0.5 mg/kg single, intravenous
ESMOLOL plasma
Homo sapiens
0.03 μg × h/mL
1 mg/kg single, intravenous
ESMOLOL plasma
Homo sapiens
0.06 μg × h/mL
1.5 mg single, intravenous
ESMOLOL plasma
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
3.65 min
0.5 mg/kg single, intravenous
ESMOLOL plasma
Homo sapiens
4.77 min
1 mg/kg single, intravenous
ESMOLOL plasma
Homo sapiens
4.76 min
1.5 mg single, intravenous
ESMOLOL plasma
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
45%
ESMOLOL plasma
Homo sapiens

Doses

AEs

PubMed

Patents

Sample Use Guides

In Vivo Use Guide
Supraventricular tachycardia (SVT) or noncompensatory sinus tachycardia Optional loading dose: 500 mcg per kg infused over one minute Then 50 mcg per kg per minute for the next 4 minutes Adjust dose as needed to a maximum of 200 mcg per kg per minute Additional loading doses may be administered
Route of Administration: Intravenous
In Vitro Use Guide
In unpaced Langendorff-perfused rat hearts, esmolol (0.03-3 mmol/L) had a profound negative inotropic effect resulting in diastolic arrest at 1 mmol/L and above.
Substance Class Chemical
Record UNII
MDY902UXSR
Record Status Validated (UNII)
Record Version