Details
Stereochemistry | RACEMIC |
Molecular Formula | C16H25NO4.ClH |
Molecular Weight | 331.835 |
Optical Activity | ( + / - ) |
Defined Stereocenters | 0 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cl.COC(=O)CCC1=CC=C(OCC(O)CNC(C)C)C=C1
InChI
InChIKey=GEKNCWBANDDJJL-UHFFFAOYSA-N
InChI=1S/C16H25NO4.ClH/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;1H
DescriptionSources: http://www.drugbank.ca/drugs/DB00187Curator's Comment: Description was created based on several sources, including
http://www.accessdata.fda.gov/drugsatfda_docs/label/2012/019386s043lbl.pdf
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
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20877697
Curator's Comment: esmolol does not cross the blood-brain barrier
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL213 Sources: http://www.drugbank.ca/drugs/DB00187 |
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Target ID: GO:0006814 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17235414 |
74.2 µM [IC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | BREVIBLOC Approved UseBREVIBLOC 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 Date1986 |
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Primary | BREVIBLOC Approved UseBREVIBLOC 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 Date1986 |
Cmax
Value | Dose | Co-administered | 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 | Co-administered | 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 |
T1/2
Value | Dose | Co-administered | 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 |
Funbound
Value | Dose | Co-administered | Analyte | Population |
---|---|---|---|---|
45% |
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: |
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%) Sources: Hypotension symptomatic (12%) Infusion site reactions (8%) Nausea (7%) Dizziness (3%) Somnolence (3%) |
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
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: |
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: |
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 |
|
Administration of esmolol in microlaryngeal surgery for blunting the hemodynamic response during laryngoscopy and tracheal intubation in cigarette smokers. | 2007 Feb |
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 Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/20176816
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.
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NCI_THESAURUS |
C29576
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C47519
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ACTIVE MOIETY
SUBSTANCE RECORD