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Details

Stereochemistry RACEMIC
Molecular Formula C16H25NO4.H2O4S
Molecular Weight 393.4542
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESMOLOL SULFATE

SMILES

CC(C)NCC(COc1ccc(cc1)CCC(=O)OC)O.OS(=O)(=O)O

InChI

InChIKey=KHCMVWJHIZXEKF-UHFFFAOYSA-N
InChI=1S/C16H25NO4.H2O4S/c1-12(2)17-10-14(18)11-21-15-7-4-13(5-8-15)6-9-16(19)20-3;1-5(2,3)4/h4-5,7-8,12,14,17-18H,6,9-11H2,1-3H3;(H2,1,2,3,4)

HIDE SMILES / InChI

Molecular Formula H2O4S
Molecular Weight 98.0796
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Molecular Formula C16H25NO4
Molecular Weight 295.3746
Charge 0
Count
Stereochemistry RACEMIC
Additional Stereochemistry No
Defined Stereocenters 0 / 1
E/Z Centers 0
Optical Activity ( + / - )

Description
Curator's Comment:: Description was created based on several sources, including http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019386s043lbl.pdf

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

Curator's Comment:: esmolol does not cross the blood-brain barrier

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
74.2 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
BREVIBLOC

Approved Use

BREVIBLOC is a beta adrenergic blocker indicated for the short-term treatment of: Control of ventricular rate in supraventricular tachycardia including atrial fibrillation and atrial flutter and control of heart rate in noncompensatory sinus tachycardia Control of perioperative tachycardia and hypertension

Launch Date

5.36284791E11
Primary
BREVIBLOC

Approved Use

BREVIBLOC is a beta adrenergic blocker indicated for the short-term treatment of: Control of ventricular rate in supraventricular tachycardia including atrial fibrillation and atrial flutter and control of heart rate in noncompensatory sinus tachycardia Control of perioperative tachycardia and hypertension

Launch Date

5.36284791E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.22 μg/mL
0.5 mg/kg single, intravenous
dose: 0.5 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ESMOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.56 μg/mL
1 mg/kg single, intravenous
dose: 1 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ESMOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.96 μg/mL
1.5 mg single, intravenous
dose: 1.5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ESMOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
0.02 μg × h/mL
0.5 mg/kg single, intravenous
dose: 0.5 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ESMOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.03 μg × h/mL
1 mg/kg single, intravenous
dose: 1 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ESMOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
0.06 μg × h/mL
1.5 mg single, intravenous
dose: 1.5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ESMOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.65 min
0.5 mg/kg single, intravenous
dose: 0.5 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ESMOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
4.77 min
1 mg/kg single, intravenous
dose: 1 mg/kg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ESMOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
4.76 min
1.5 mg single, intravenous
dose: 1.5 mg
route of administration: Intravenous
experiment type: SINGLE
co-administered:
ESMOLOL plasma
Homo sapiens
population: HEALTHY
age: ADULT
sex: FEMALE / MALE
food status: UNKNOWN
Funbound

Funbound

ValueDoseCo-administeredAnalytePopulation
45%
ESMOLOL plasma
Homo sapiens
population: UNKNOWN
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
400 ug/kg/min single, intravenous
Dose: 400 ug/kg/min
Route: intravenous
Route: single
Dose: 400 ug/kg/min
Sources:
unhealthy, 15 years
n = 1
Health Status: unhealthy
Condition: hypertrophic cardiomyopathy
Age Group: 15 years
Sex: M
Population Size: 1
Sources:
Disc. AE: Delirium...
AEs leading to
discontinuation/dose reduction:
Delirium (1 patient)
Sources:
500 ug/kg single, intravenous (mean)
Recommended
Dose: 500 ug/kg
Route: intravenous
Route: single
Dose: 500 ug/kg
Sources:
unhealthy, adult
n = 369
Health Status: unhealthy
Condition: supraventricular tachycardia
Age Group: adult
Sex: unknown
Population Size: 369
Sources:
Other AEs: Hypotension asymptomatic, Hypotension symptomatic...
Other AEs:
Hypotension asymptomatic (25%)
Hypotension symptomatic (12%)
Infusion site reactions (8%)
Nausea (7%)
Dizziness (3%)
Somnolence (3%)
Sources:
500 ug/kg single, intravenous (mean)
Recommended
Dose: 500 ug/kg
Route: intravenous
Route: single
Dose: 500 ug/kg
Sources:
unhealthy, mean 44 years
n = 20
Health Status: unhealthy
Condition: ASA physical status I-III
Age Group: mean 44 years
Population Size: 20
Sources:
500 ug/kg single, intravenous
Recommended
Dose: 500 ug/kg
Route: intravenous
Route: single
Dose: 500 ug/kg
Sources:
unhealthy, mean 58 years
n = 16
Health Status: unhealthy
Condition: out-of-hospital cardiac arrest
Age Group: mean 58 years
Sex: M+F
Population Size: 16
Sources:
AEs

AEs

AESignificanceDosePopulation
Delirium 1 patient
Disc. AE
400 ug/kg/min single, intravenous
Dose: 400 ug/kg/min
Route: intravenous
Route: single
Dose: 400 ug/kg/min
Sources:
unhealthy, 15 years
n = 1
Health Status: unhealthy
Condition: hypertrophic cardiomyopathy
Age Group: 15 years
Sex: M
Population Size: 1
Sources:
Hypotension symptomatic 12%
500 ug/kg single, intravenous (mean)
Recommended
Dose: 500 ug/kg
Route: intravenous
Route: single
Dose: 500 ug/kg
Sources:
unhealthy, adult
n = 369
Health Status: unhealthy
Condition: supraventricular tachycardia
Age Group: adult
Sex: unknown
Population Size: 369
Sources:
Hypotension asymptomatic 25%
500 ug/kg single, intravenous (mean)
Recommended
Dose: 500 ug/kg
Route: intravenous
Route: single
Dose: 500 ug/kg
Sources:
unhealthy, adult
n = 369
Health Status: unhealthy
Condition: supraventricular tachycardia
Age Group: adult
Sex: unknown
Population Size: 369
Sources:
Dizziness 3%
500 ug/kg single, intravenous (mean)
Recommended
Dose: 500 ug/kg
Route: intravenous
Route: single
Dose: 500 ug/kg
Sources:
unhealthy, adult
n = 369
Health Status: unhealthy
Condition: supraventricular tachycardia
Age Group: adult
Sex: unknown
Population Size: 369
Sources:
Somnolence 3%
500 ug/kg single, intravenous (mean)
Recommended
Dose: 500 ug/kg
Route: intravenous
Route: single
Dose: 500 ug/kg
Sources:
unhealthy, adult
n = 369
Health Status: unhealthy
Condition: supraventricular tachycardia
Age Group: adult
Sex: unknown
Population Size: 369
Sources:
Nausea 7%
500 ug/kg single, intravenous (mean)
Recommended
Dose: 500 ug/kg
Route: intravenous
Route: single
Dose: 500 ug/kg
Sources:
unhealthy, adult
n = 369
Health Status: unhealthy
Condition: supraventricular tachycardia
Age Group: adult
Sex: unknown
Population Size: 369
Sources:
Infusion site reactions 8%
500 ug/kg single, intravenous (mean)
Recommended
Dose: 500 ug/kg
Route: intravenous
Route: single
Dose: 500 ug/kg
Sources:
unhealthy, adult
n = 369
Health Status: unhealthy
Condition: supraventricular tachycardia
Age Group: adult
Sex: unknown
Population Size: 369
Sources:
Sourcing

Sourcing

Vendor/AggregatorIDURL
PubMed

PubMed

TitleDatePubMed
[Successful control of rapid heart rate with atrial flutter by intravenous administration of esmolol in a patient after total correction of the tetralogy of Fallot].
2004 Aug
[Intermittent complete left bundle branch block during general anesthesia].
2004 Dec
Patents

Patents

Sample Use Guides

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 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
Created
by admin
on Sat Jun 26 09:44:30 UTC 2021
Edited
by admin
on Sat Jun 26 09:44:30 UTC 2021
Record UNII
4FAM116LV3
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ESMOLOL SULFATE
Common Name English
BENZENEPROPANOIC ACID, 4-(2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)-, METHYL ESTER, SULFATE (2:1) (SALT)
Systematic Name English
Code System Code Type Description
FDA UNII
4FAM116LV3
Created by admin on Sat Jun 26 09:44:30 UTC 2021 , Edited by admin on Sat Jun 26 09:44:30 UTC 2021
PRIMARY
CAS
81147-93-5
Created by admin on Sat Jun 26 09:44:30 UTC 2021 , Edited by admin on Sat Jun 26 09:44:30 UTC 2021
PRIMARY
PUBCHEM
126961356
Created by admin on Sat Jun 26 09:44:30 UTC 2021 , Edited by admin on Sat Jun 26 09:44:30 UTC 2021
PRIMARY
Related Record Type Details
PARENT -> SALT/SOLVATE
Related Record Type Details
ACTIVE MOIETY