ESMOLOL

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 Search

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

Description
Sources: http://www.drugbank.ca/drugs/DB00187
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Beta-1 adrenergic receptor 158 Target ID: CHEMBL213 Sources: http://www.drugbank.ca/drugs/DB00187	Antagonist 2778
sodium ion transport 14 Target ID: GO:0006814 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17235414	Inhibitor 8297		74.2 µM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Supraventricular tachycardia 8 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019386s043lbl.pdf	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 1986
Noncompensatory sinus tachycardia 3 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019386s043lbl.pdf	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 1986

C_max

Value	Dose	Analyte	Population
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

Value	Dose	Analyte	Population
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

T_1/2

Value	Dose	Analyte	Population
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

F_unbound

Value	Dose	Co-administered	Analyte	Population
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

Dose	Population	Adverse 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

AE	Significance	Dose	Population
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

Vendor/Aggregator	ID	URL
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

Title	Date	PubMed
Determination of radical yields in solid-state drugs as one technique to identify drugs that will withstand radiosterilization: radioresistance of beta blockers.	2003 Jul	12816529
[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	15446684
[Intermittent complete left bundle branch block during general anesthesia].	2004 Dec	15682804
The use of multi-frequency EPR techniques to identify the radicals produced in irradiated beta-blockers.	2004 Jan	15061654
The effect of intermittent low speed mode upon aortic valve opening in calves supported with a Jarvik 2000 axial flow device.	2005 Mar-Apr	15839437
Administration of esmolol in microlaryngeal surgery for blunting the hemodynamic response during laryngoscopy and tracheal intubation in cigarette smokers.	2007 Feb	17388233

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.

Name

Type

Language

ESMOLOL

Official Name

English

ESMOLOL [MI]

Common Name

English

(±)-METHYL P-(2-HYDROXY-3-(ISOPROPYLAMINO)PROPOXY)HYDROCINNAMATE

Common Name

English

ESMOLOL [VANDF]

Common Name

English

ASL-8052-001

Code

English

3-(4-(2-HYDROXY-3-(ISOPROPYLAMINO)PROPOXY)PHENYL)PROPIONIC ACID METHYL ESTER

Systematic Name

English

BENZENEPROPANOIC ACID, 4-(2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)-, METHYL ESTER, (±)-

Common Name

English

esmolol [INN]

Common Name

English

Esmolol [WHO-DD]

Common Name

English

BENZENEPROPANOIC ACID, 4-(2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)-, METHYL ESTER

Systematic Name

English

(±)-ESMOLOL

Common Name

English

Classification Tree Code System Code

NDF-RT

N0000000161