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Details

Stereochemistry RACEMIC
Molecular Formula C16H25NO4.H2O4S
Molecular Weight 393.452
Optical Activity ( + / - )
Defined Stereocenters 0 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESMOLOL SULFATE

SMILES

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

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 98.078
Charge 0
Count
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE
Molecular Formula C16H25NO4
Molecular Weight 295.374
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

CNS Non-penetrant
1014
Curator's Comment: esmolol does not cross the blood-brain barrier

Originator

Approval Year

1986
103
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2778
Inhibitor
8297
 74.2 µM [IC50]
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8429
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
Approved
8429
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28091703
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28091703
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28091703
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28091703
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28091703
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28091703
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28091703
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28091703
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
EXPERIMENT
https://pubmed.ncbi.nlm.nih.gov/28091703
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%
DRUG LABEL
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205703s000lbl.pdf
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:
https://pubmed.ncbi.nlm.nih.gov/24687543/
unhealthy, 15 years
n = 1
Health Status: unhealthy
Condition: hypertrophic cardiomyopathy
Age Group: 15 years
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/24687543/
Disc. AE: Delirium...
AEs leading to
discontinuation/dose reduction:
Delirium (1 patient)
Sources:
https://pubmed.ncbi.nlm.nih.gov/24687543/
500 ug/kg single, intravenous (mean)
Recommended
Dose: 500 ug/kg
Route: intravenous
Route: single
Dose: 500 ug/kg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205703s000lbl.pdf
unhealthy, adult
n = 369
Health Status: unhealthy
Condition: supraventricular tachycardia
Age Group: adult
Sex: unknown
Population Size: 369
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205703s000lbl.pdf
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:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205703s000lbl.pdf
500 ug/kg single, intravenous (mean)
Recommended
Dose: 500 ug/kg
Route: intravenous
Route: single
Dose: 500 ug/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/1358003/
unhealthy, mean 44 years
n = 20
Health Status: unhealthy
Condition: ASA physical status I-III
Age Group: mean 44 years
Population Size: 20
Sources:
https://pubmed.ncbi.nlm.nih.gov/1358003/
Sources:
https://pubmed.ncbi.nlm.nih.gov/1358003/
500 ug/kg single, intravenous
Recommended
Dose: 500 ug/kg
Route: intravenous
Route: single
Dose: 500 ug/kg
Sources:
https://pubmed.ncbi.nlm.nih.gov/27523955/
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:
https://pubmed.ncbi.nlm.nih.gov/27523955/
Sources:
https://pubmed.ncbi.nlm.nih.gov/27523955/
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:
https://pubmed.ncbi.nlm.nih.gov/24687543/
unhealthy, 15 years
n = 1
Health Status: unhealthy
Condition: hypertrophic cardiomyopathy
Age Group: 15 years
Sex: M
Population Size: 1
Sources:
https://pubmed.ncbi.nlm.nih.gov/24687543/
Hypotension symptomatic 12%
500 ug/kg single, intravenous (mean)
Recommended
Dose: 500 ug/kg
Route: intravenous
Route: single
Dose: 500 ug/kg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205703s000lbl.pdf
unhealthy, adult
n = 369
Health Status: unhealthy
Condition: supraventricular tachycardia
Age Group: adult
Sex: unknown
Population Size: 369
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205703s000lbl.pdf
Hypotension asymptomatic 25%
500 ug/kg single, intravenous (mean)
Recommended
Dose: 500 ug/kg
Route: intravenous
Route: single
Dose: 500 ug/kg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205703s000lbl.pdf
unhealthy, adult
n = 369
Health Status: unhealthy
Condition: supraventricular tachycardia
Age Group: adult
Sex: unknown
Population Size: 369
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205703s000lbl.pdf
Dizziness 3%
500 ug/kg single, intravenous (mean)
Recommended
Dose: 500 ug/kg
Route: intravenous
Route: single
Dose: 500 ug/kg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205703s000lbl.pdf
unhealthy, adult
n = 369
Health Status: unhealthy
Condition: supraventricular tachycardia
Age Group: adult
Sex: unknown
Population Size: 369
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205703s000lbl.pdf
Somnolence 3%
500 ug/kg single, intravenous (mean)
Recommended
Dose: 500 ug/kg
Route: intravenous
Route: single
Dose: 500 ug/kg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205703s000lbl.pdf
unhealthy, adult
n = 369
Health Status: unhealthy
Condition: supraventricular tachycardia
Age Group: adult
Sex: unknown
Population Size: 369
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205703s000lbl.pdf
Nausea 7%
500 ug/kg single, intravenous (mean)
Recommended
Dose: 500 ug/kg
Route: intravenous
Route: single
Dose: 500 ug/kg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205703s000lbl.pdf
unhealthy, adult
n = 369
Health Status: unhealthy
Condition: supraventricular tachycardia
Age Group: adult
Sex: unknown
Population Size: 369
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205703s000lbl.pdf
Infusion site reactions 8%
500 ug/kg single, intravenous (mean)
Recommended
Dose: 500 ug/kg
Route: intravenous
Route: single
Dose: 500 ug/kg
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205703s000lbl.pdf
unhealthy, adult
n = 369
Health Status: unhealthy
Condition: supraventricular tachycardia
Age Group: adult
Sex: unknown
Population Size: 369
Sources:
https://www.accessdata.fda.gov/drugsatfda_docs/label/2016/205703s000lbl.pdf
Sourcing

Sourcing

Vendor/AggregatorIDURL
001 Chemical
DY572840
https://www.001chemical.com/chem/81147-92-4
AHH Chemical co.,ltd
MT-50834
http://www.ahhchemical.com/product/MT-50834.html
AK Scientific, Inc. (AKSCI)
K444
http://www.aksci.com/item_detail.php?cat=K444
Angene
AGN-PC-0WH7EC
http://www.angenechemical.com/productshow/AGN-PC-0WH7EC.html
AvaChem Scientific
1690B
http://www.avachem.com/productSearch.asp?1690B
ChemMol
30101870
http://www.chemmol.com/chemmol/30101870.html
ChemMol
49421725
http://www.chemmol.com/chemmol/49421725.html
ChemMol
49422815
http://www.chemmol.com/chemmol/49422815.html
ChemMol
99171669
http://www.chemmol.com/chemmol/99171669.html
Clearsynth
CS-BV-00039
https://www.clearsynth.com/en/CSBV00039.html
DC Chemicals
DC36783
http://www.dcchemicals.com//product_show-Esmolol.html
Debye Scientific
DB-015362
http://www.debyesci.com/cas_103598-03-4.html
Finetech
FT-0630886
http://www.finetechnology-ind.com/prod/detail/pub/81147-92-4.html
Glentham Life Sciences
GP0641
http://www.glentham.com/products/product/GP0641/
Hairui
HR123893
http://www.hairuichem.com/en/product/81147-92-4.html
Molcore
MC572840
https://www.molcore.com/product/81147-92-4
OChem
9337
http://www.ocheminc.com/index.php?act=psearch&pid=147E924
Parchem
28880
http://www.parchem.com/chemical-supplier-distributor/Esmolol-018880.aspx
Parchem
87652
https://www.parchem.com/chemical-supplier-distributor/Esmolol-087652.aspx
Smolecule
S527432
http://www.smolecule.com/products/s527432
TCI (Tokyo Chemical Industry)
E1106
http://www.tcichemicals.com/eshop/en/us/commodity/E1106/index.html
THE BioTek
bt-267747
https://www.thebiotek.com/product/inhibitors/bt-267747
TripleBond
CE0048
http://www.triplebond-canada.com/prod/1304/
Yuhao Chemical
LT5536
http://www.chemyuhao.com/103598-03-4.html
abcr GmbH
AB505801
http://www.abcr.com/shop/en/AB505801
PubMed

PubMed

TitleDatePubMed
Determination of radical yields in solid-state drugs as one technique to identify drugs that will withstand radiosterilization: radioresistance of beta blockers.
2003 Jul
[Intermittent complete left bundle branch block during general anesthesia].
2004 Dec
The use of multi-frequency EPR techniques to identify the radicals produced in irradiated beta-blockers.
2004 Jan
Administration of esmolol in microlaryngeal surgery for blunting the hemodynamic response during laryngoscopy and tracheal intubation in cigarette smokers.
2007 Feb
Patents

Patents

JP2001513495A
14

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
Created
by admin
on Sat Dec 16 01:55:04 UTC 2023
Edited
by admin
on Sat Dec 16 01:55:04 UTC 2023
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 Dec 16 01:55:04 UTC 2023 , Edited by admin on Sat Dec 16 01:55:04 UTC 2023
PRIMARY
CAS
81147-93-5
Created by admin on Sat Dec 16 01:55:04 UTC 2023 , Edited by admin on Sat Dec 16 01:55:04 UTC 2023
PRIMARY
PUBCHEM
126961356
Created by admin on Sat Dec 16 01:55:04 UTC 2023 , Edited by admin on Sat Dec 16 01:55:04 UTC 2023
PRIMARY
Related Record Type Details
Structure of ESMOLOL
PARENT -> SALT/SOLVATE
Related Record Type Details
Structure of ESMOLOL
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