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Details

Stereochemistry ABSOLUTE
Molecular Formula C14H22N2O3
Molecular Weight 266.3366
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of ATENOLOL, (-)-

SMILES

CC(C)NC[C@@]([H])(COc1ccc(cc1)CC(=N)O)O

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
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.

Originator

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

Approval Year

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
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
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
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
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 Aug 5
An efficient asymmetric synthesis of (S)-atenolol: using hydrolytic kinetic resolution.
2005 Feb 1
Insights into cyclodextrin interactions during sample stacking using capillary isotachophoresis with on-line microcoil NMR detection.
2005 Sep
Development of safer molecules through chirality.
2006 Oct
The future lies in chiral purity: a perspective.
2007 Apr
Infrared spectroscopy of racemic and enantiomeric forms of atenolol.
2007 Aug
Enantioanalysis of bisoprolol in human plasma with a macrocyclic antibiotic HPLC chiral column using fluorescence detection and solid phase extraction.
2007 Feb
Direct enantiomeric resolution of betaxolol with application to analysis of pharmaceutical products.
2007 Feb 6
Pharmacokinetic-pharmacodynamic modelling of S(-)-atenolol in rats: reduction of isoprenaline-induced tachycardia as a continuous pharmacodynamic endpoint.
2007 Jun
Mechanism-based pharmacodynamic modeling of S(-)-atenolol: estimation of in vivo affinity for the beta1-adrenoceptor with an agonist-antagonist interaction model.
2008 Mar
Clinical pharmacology.
2008 Oct
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 Oct
A comparative study of nebivolol and (S) atenolol on blood pressure and heart rate on essential hypertensive patients.
2010 Dec
3-[4-(2-Amino-2-oxoeth-yl)phen-oxy]-2-hy-droxy-N-isopropyl-propanaminium 1,1'-binaphthyl-2,2'-diyl phosphate.
2010 Dec 11
Spectrophotometric method for simultaneous estimation of atenolol in combination with losartan potassium and hydrochlorothiazide in bulk and tablet formulation.
2010 Oct
Patents

Sample Use Guides

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
Name Type Language
ATENOLOL, (-)-
Common Name English
4-((2S)-2-HYDROXY-3-((1-METHYLETHYL)AMINO)PROPOXY)BENZENEACETAMIDE
Systematic 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
(-)-ATENOLOL
Common Name English
(S)-ATENOLOL
Common Name English
ESATENOLOL
INN   JAN   MART.   WHO-DD  
INN  
Official Name English
2-(P-((2S)-2-HYDROXY-3-(ISOPROPYLAMINO)PROPOXY)PHENYL)ACETAMIDE
Common Name English
ESATENOLOL [JAN]
Common Name English
ESATENOLOL [WHO-DD]
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
Classification Tree Code System Code
WHO-VATC QC07AB11
Created by admin on Sat Jun 26 08:19:43 UTC 2021 , Edited by admin on Sat Jun 26 08:19:43 UTC 2021
WHO-ATC C07AB11
Created by admin on Sat Jun 26 08:19:43 UTC 2021 , Edited by admin on Sat Jun 26 08:19:43 UTC 2021
NCI_THESAURUS C29576
Created by admin on Sat Jun 26 08:19:43 UTC 2021 , Edited by admin on Sat Jun 26 08:19:43 UTC 2021
Code System Code Type Description
PUBCHEM
175540
Created by admin on Sat Jun 26 08:19:43 UTC 2021 , Edited by admin on Sat Jun 26 08:19:43 UTC 2021
PRIMARY
EPA CompTox
93379-54-5
Created by admin on Sat Jun 26 08:19:43 UTC 2021 , Edited by admin on Sat Jun 26 08:19:43 UTC 2021
PRIMARY
CAS
93379-54-5
Created by admin on Sat Jun 26 08:19:43 UTC 2021 , Edited by admin on Sat Jun 26 08:19:43 UTC 2021
PRIMARY
INN
7337
Created by admin on Sat Jun 26 08:19:43 UTC 2021 , Edited by admin on Sat Jun 26 08:19:43 UTC 2021
PRIMARY
FDA UNII
DPF757BOSR
Created by admin on Sat Jun 26 08:19:43 UTC 2021 , Edited by admin on Sat Jun 26 08:19:43 UTC 2021
PRIMARY
DRUG CENTRAL
4702
Created by admin on Sat Jun 26 08:19:43 UTC 2021 , Edited by admin on Sat Jun 26 08:19:43 UTC 2021
PRIMARY
EVMPD
SUB06608MIG
Created by admin on Sat Jun 26 08:19:43 UTC 2021 , Edited by admin on Sat Jun 26 08:19:43 UTC 2021
PRIMARY
ChEMBL
CHEMBL343633
Created by admin on Sat Jun 26 08:19:43 UTC 2021 , Edited by admin on Sat Jun 26 08:19:43 UTC 2021
PRIMARY
DRUG BANK
DB13443
Created by admin on Sat Jun 26 08:19:43 UTC 2021 , Edited by admin on Sat Jun 26 08:19:43 UTC 2021
PRIMARY
NCI_THESAURUS
C81661
Created by admin on Sat Jun 26 08:19:43 UTC 2021 , Edited by admin on Sat Jun 26 08:19:43 UTC 2021
PRIMARY