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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H22N2O3
Molecular Weight 266.3361
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ESATENOLOL

SMILES

CC(C)NC[C@H](O)COC1=CC=C(CC(N)=O)C=C1

InChI

InChIKey=METKIMKYRPQLGS-LBPRGKRZSA-N
InChI=1S/C14H22N2O3/c1-10(2)16-8-12(17)9-19-13-5-3-11(4-6-13)7-14(15)18/h3-6,10,12,16-17H,7-9H2,1-2H3,(H2,15,18)/t12-/m0/s1

HIDE SMILES / InChI
Molecular Formula C14H22N2O3
Molecular Weight 266.3361
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description

Esatenolol is the (S) enantiomer of atenolol, a beta1-adrenergic receptor antagonist. Only (S)-atenolol, but not (R)-atenolol, contributes to the beta-blocking effect of currently used racemic atenolol since the same effect can be elicited with the (S)-enantiomer alone. Pure (S)-atenolol has been launched in India for the treatment of hypertension and angina pectoris.

CNS Activity

Originator

Sepracor
11
Curator's Comment: originally atenolol was discovered by ICI http://www.world-medicinehistory.com/2014/08/discovery-of-atenolol.html

Approval Year

Unknown
149124
Targets

Targets

Primary TargetPharmacologyConditionPotency
Antagonist
2849
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Approved
8583
ADBETA

Approved Use

This medication is used to treat high blood pressure (hypertension). Lowering high blood pressure helps prevent strokes, heart attacks, and kidney problems. This medication is also used to treat chest pain (angina) and to improve survival after a heart attack.
Primary
Approved
8583
ADBETA

Approved Use

This medication is used to treat high blood pressure (hypertension). Lowering high blood pressure helps prevent strokes, heart attacks, and kidney problems. This medication is also used to treat chest pain (angina) and to improve survival after a heart attack.
Primary
Approved
8583
ADBETA

Approved Use

This medication is used to treat high blood pressure (hypertension). Lowering high blood pressure helps prevent strokes, heart attacks, and kidney problems. This medication is also used to treat chest pain (angina) and to improve survival after a heart attack.
PubMed

PubMed

TitleDatePubMed
3-[4-(2-Amino-2-oxoeth-yl)phen-oxy]-2-hy-droxy-N-isopropyl-propanaminium 1,1'-binaphthyl-2,2'-diyl phosphate.
2010-12-11
A comparative study of nebivolol and (S) atenolol on blood pressure and heart rate on essential hypertensive patients.
2010-12
Spectrophotometric method for simultaneous estimation of atenolol in combination with losartan potassium and hydrochlorothiazide in bulk and tablet formulation.
2010-10
Influence of plasma protein binding on pharmacodynamics: Estimation of in vivo receptor affinities of beta blockers using a new mechanism-based PK-PD modelling approach.
2009-10
Clinical pharmacology.
2008-10
Mechanism-based pharmacodynamic modeling of S(-)-atenolol: estimation of in vivo affinity for the beta1-adrenoceptor with an agonist-antagonist interaction model.
2008-03
Infrared spectroscopy of racemic and enantiomeric forms of atenolol.
2007-08
Pharmacokinetic-pharmacodynamic modelling of S(-)-atenolol in rats: reduction of isoprenaline-induced tachycardia as a continuous pharmacodynamic endpoint.
2007-06
The future lies in chiral purity: a perspective.
2007-04
Direct enantiomeric resolution of betaxolol with application to analysis of pharmaceutical products.
2007-02-06
Enantioanalysis of bisoprolol in human plasma with a macrocyclic antibiotic HPLC chiral column using fluorescence detection and solid phase extraction.
2007-02
Development of safer molecules through chirality.
2006-10
Insights into cyclodextrin interactions during sample stacking using capillary isotachophoresis with on-line microcoil NMR detection.
2005-09
An efficient asymmetric synthesis of (S)-atenolol: using hydrolytic kinetic resolution.
2005-02-01
Binding of (-)-[3H]-CGP12177 at two sites in recombinant human beta 1-adrenoceptors and interaction with beta-blockers.
2004-05
Enantioselective determination of (R)- and (S)-sotalol in human plasma by on-line coupling of a restricted-access material precolumn to a cellobiohydrolase I-based chiral stationary phase.
2002-08-05
An improved HPLC-fluorescence stereoselective method for analysis of (+)-S- and (-)-R-sotalol enantiomers in plasma sample.
2002-02-02
Low-molecular-weight chiral cation exchangers: novel chiral stationary phases and their application for enantioseparation of chiral bases by nonaqueous capillary electrochromatography.
2002-02
Patents

Patents

EP0519925A1
1
JP2001503394A
2
JP2002541233A
406
JP2005516940A
28
JP2009526755A
475
JP2011510954A
147
JP2011529101A
67
JP4800219B2
66
JPH01272519A
1
JPH0767692A
1
JPH08310946A
1
JPS6440425A
3
WO1991007175
1

Sample Use Guides

In Vivo Use Guide
12.5-100 mg once daily. The dosing regimen of Esatenolol is set individually. he maximum dose for adults for oral administration is 200 mg/day in 1 or 2 doses.
Route of Administration: Oral
In Vitro Use Guide
Unknown
Substance Class Chemical
Created
by admin
on Mon Mar 31 18:22:33 GMT 2025
Edited
by admin
on Mon Mar 31 18:22:33 GMT 2025
Record UNII
DPF757BOSR
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
(-)-ATENOLOL
Preferred Name English
ESATENOLOL
INN   JAN   MART.   WHO-DD  
INN  
Official Name English
4-((2S)-2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)BENZENEACETAMIDE
Systematic Name English
ATENOLOL, (-)-
Common Name English
ESATENOLOL [MART.]
Common Name English
BENZENEACETAMIDE, 4-((2S)-2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)-
Systematic Name English
S-ATENOLOL
Common Name English
(S)-ATENOLOL
Common Name English
2-(P-((2S)-2-HYDROXY-3-(ISOPROPYLAMINO)PROPOXY)PHENYL)ACETAMIDE
Common Name English
ESATENOLOL [JAN]
Common Name English
BENZENEACETAMIDE, 4-(2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)-, (S)-
Systematic Name English
ATENOLOL, (S)-
Common Name English
esatenolol [INN]
Common Name English
Esatenolol [WHO-DD]
Common Name English
Classification Tree Code System Code
WHO-VATC QC07AB11
Created by admin on Mon Mar 31 18:22:33 GMT 2025 , Edited by admin on Mon Mar 31 18:22:33 GMT 2025
WHO-ATC C07AB11
Created by admin on Mon Mar 31 18:22:33 GMT 2025 , Edited by admin on Mon Mar 31 18:22:33 GMT 2025
NCI_THESAURUS C29576
Created by admin on Mon Mar 31 18:22:33 GMT 2025 , Edited by admin on Mon Mar 31 18:22:33 GMT 2025
Code System Code Type Description
CHEBI
31556
Created by admin on Mon Mar 31 18:22:33 GMT 2025 , Edited by admin on Mon Mar 31 18:22:33 GMT 2025
PRIMARY
PUBCHEM
175540
Created by admin on Mon Mar 31 18:22:33 GMT 2025 , Edited by admin on Mon Mar 31 18:22:33 GMT 2025
PRIMARY
EPA CompTox
DTXSID10239405
Created by admin on Mon Mar 31 18:22:33 GMT 2025 , Edited by admin on Mon Mar 31 18:22:33 GMT 2025
PRIMARY
CAS
93379-54-5
Created by admin on Mon Mar 31 18:22:33 GMT 2025 , Edited by admin on Mon Mar 31 18:22:33 GMT 2025
PRIMARY
SMS_ID
100000084564
Created by admin on Mon Mar 31 18:22:33 GMT 2025 , Edited by admin on Mon Mar 31 18:22:33 GMT 2025
PRIMARY
INN
7337
Created by admin on Mon Mar 31 18:22:33 GMT 2025 , Edited by admin on Mon Mar 31 18:22:33 GMT 2025
PRIMARY
FDA UNII
DPF757BOSR
Created by admin on Mon Mar 31 18:22:33 GMT 2025 , Edited by admin on Mon Mar 31 18:22:33 GMT 2025
PRIMARY
DRUG CENTRAL
4702
Created by admin on Mon Mar 31 18:22:33 GMT 2025 , Edited by admin on Mon Mar 31 18:22:33 GMT 2025
PRIMARY
EVMPD
SUB06608MIG
Created by admin on Mon Mar 31 18:22:33 GMT 2025 , Edited by admin on Mon Mar 31 18:22:33 GMT 2025
PRIMARY
ChEMBL
CHEMBL343633
Created by admin on Mon Mar 31 18:22:33 GMT 2025 , Edited by admin on Mon Mar 31 18:22:33 GMT 2025
PRIMARY
DRUG BANK
DB13443
Created by admin on Mon Mar 31 18:22:33 GMT 2025 , Edited by admin on Mon Mar 31 18:22:33 GMT 2025
PRIMARY
NCI_THESAURUS
C81661
Created by admin on Mon Mar 31 18:22:33 GMT 2025 , Edited by admin on Mon Mar 31 18:22:33 GMT 2025
PRIMARY
Related Record Type Details
Structure of ATENOLOL, (+)-
ENANTIOMER -> ENANTIOMER
Structure of ATENOLOL
RACEMATE -> ENANTIOMER
BETA-1 ADRENERGIC RECEPTOR
TARGET -> INHIBITOR
Related Record Type Details
Structure of ESATENOLOL
ACTIVE MOIETY
NIH
NCATS
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