Drug Details

General Information of the Drug (ID: DR6219)
Name
Esmolol
Synonyms
ESMOLOL; 81147-92-4; 103598-03-4; Brevibloc; ASL 8052-001; Methyl 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)benzenepropanoate; Benzenepropanoic acid, 4-(2-hydroxy-3-((1-methylethyl)amino)propoxy)-, methyl ester; CHEBI:88206; (+-)-Esmolol; Esmolol [INN:BAN]; Esmolol (INN); NCGC00185766-01; BRN 5287174; SR-01000763706; Benzenepropanoic acid, 4-[2-hydroxy-3-[(1-methylethyl)amino]propoxy]-, methyl ester; (+/-)-esmolol; CHEMBL768; SCHEMBL3605; GTPL7178; DTXSID4022995; HMS2090P06; HMS3743M15; HMS3886F03; methyl p-(2-hydroxy-3-(isopropylamino)propoxy)hydrocinnamate; BDBM50404796; CE0048; methyl 3-(4-(2-hydroxy-3-(isopropylamino)propoxy)phenyl)propanoate; methyl 3-{4-[2-hydroxy-3-(propan-2-ylamino)propoxy]phenyl}propanoate; MFCD00864566; s5778; AKOS015960734; methyl 3-(4-{2-hydroxy-3-[(propan-2-yl)amino]propoxy}phenyl)propanoate; methyl 3-[4-({2-hydroxy-3-[(1-methylethyl)amino]propyl}oxy)phenyl]propanoate; DB00187; SL-8052; MRF-0000253; NCGC00185766-02; NCGC00185766-05; AC-12058; ASL-8052-001; DB-015362; E1106; FT-0630886; C06980; D07916; AB00698516-07; AB00698516-09; AB00698516_10; 147E924; L001332; Q418139; SR-01000763706-3; (+/-)-methyl p-(2-hydroxy-3-(isopropylamino)propoxy)hydrocinnamate; Methyl 3-[4-[2-Hydroxy-3-(isopropylamino)propoxy]phenyl]propionate; 3-[4-(2-Hydroxy-3-isopropylamino-propoxy)-phenyl]-propionic acid methyl ester; 3-[4-[2-Hydroxy-3-(isopropylamino)propoxy]phenyl]propionic Acid Methyl Ester; Methyl 3-[4-[2-Hydroxy-3-(isopropylamino)propoxy]phenyl]propionate / 3-[4-[2-Hydroxy-3-(isopropylamino)propoxy]phenyl]propionic Acid Methyl Ester
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Molecular Type
Small molecule
Disease Supraventricular tachyarrhythmia [ICD-11: BC81] Approved [1]
Structure
Click to Download Mol
2D MOL

3D MOL

ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 1: high solubility and high permeability
Clearance
The clearance of drug is 20 L/h/kg in Men
Elimination
0.5% of drug is excreted from urine in the unchanged form
Half-life
The concentration or amount of drug in body reduced by one-half in 3.7 hours
Metabolism
The drug is metabolized via the esterases
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.67709 micromolar/kg/day
Unbound Fraction
The unbound fraction of drug in plasma is 0.59%
Vd
Fluid volume that would be required to contain the amount of drug present in the body at the same concentration as in the plasma 1.2 L/kg
Water Solubility
The ability of drug to dissolve in water is measured as 20 mg/mL
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    Click to Show/Hide the Molecular Information and External Link(s) of This Natural Product
Formula
C16H25NO4
PubChem CID
59768
Canonical SMILES
CC(C)NCC(COC1=CC=C(C=C1)CCC(=O)OC)O
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
InChIKey
AQNDDEOPVVGCPG-UHFFFAOYSA-N
CAS Number
CAS 81147-92-4
ChEBI ID
CHEBI:88206
TTD Drug ID
D03XTC
DrugBank ID
DB00187
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Epinephrine      Ephedra sinica     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation		 Down-regulation Expression TNNI3  Molecule Info 
Pathway MAP
                    Biological
                    Regulation		 Increase 24-hour survival rate
Down-regulation Lactate level
Up-regulation Mean aortic pressure
Up-regulation Oxygen consumption
Up-regulation Oxygen delivery
                    In-vivo Model Twenty-four inbred Wuzhishan miniature pigs (12-14 months of age, 30+/-2 kg) were used in this study.
                    Experimental
                    Result(s)		 Combination of epinephrine with esmolol attenuates post-resuscitation myocardial dysfunction in a porcine model of cardiac arrest.
    β. A List of Natural Product(s) Able to Decrease the Adverse Effect of This Drug
          Levosimendan      Homo sapiens     Click to Show/Hide the Molecular Data of This NP
                 Decreasing Adverse Drug Reaction     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [3]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    In-vivo Model A case report
                    Experimental
                    Result(s)		 levosimendan in combination with a beta-adrenergic antagonist may have beneficial effects in patients with cardiogenic shock who exhibit tachycardia in response to inotropic agents.
Target and Pathway
Target(s) Adrenergic receptor beta-1 (ADRB1)  Molecule Info  [4]
KEGG Pathway Calcium signaling pathway Click to Show/Hide
2 cGMP-PKG signaling pathway
3 cAMP signaling pathway
4 Neuroactive ligand-receptor interaction
5 Endocytosis
6 Adrenergic signaling in cardiomyocytes
7 Gap junction
8 Salivary secretion
9 Dilated cardiomyopathy
Panther Pathway Heterotrimeric G-protein signaling pathway-Gi alpha and Gs alpha mediated pathway Click to Show/Hide
2 Beta1 adrenergic receptor signaling pathway
Pathwhiz Pathway Muscle/Heart Contraction Click to Show/Hide
Reactome Adrenoceptors Click to Show/Hide
2 G alpha (s) signalling events
WikiPathways Monoamine GPCRs Click to Show/Hide
2 Calcium Regulation in the Cardiac Cell
3 GPCRs, Class A Rhodopsin-like
4 Endothelin Pathways
5 GPCR ligand binding
6 GPCR downstream signaling
References
Reference 1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 7178).
Reference 2 Combination of epinephrine with esmolol attenuates post-resuscitation myocardial dysfunction in a porcine model of cardiac arrest. PLoS One. 2013 Dec 18;8(12):e82677.
Reference 3 Treatment of cardiogenic shock with levosimendan in combination with beta-adrenergic antagonists. Br J Anaesth. 2005 Nov;95(5):648-50.
Reference 4 Beta-1 selective adrenergic antagonist landiolol and esmolol can be safely used in patients with airway hyperreactivity. Heart Lung. 2009 Jan-Feb;38(1):48-55.
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