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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
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
Binding of (-)-[3H]-CGP12177 at two sites in recombinant human beta 1-adrenoceptors and interaction with beta-blockers.
2004 May
An efficient asymmetric synthesis of (S)-atenolol: using hydrolytic kinetic resolution.
2005 Feb 1
Development of safer molecules through chirality.
2006 Oct
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
Clinical pharmacology.
2008 Oct
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
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
In Vitro Use Guide
Unknown
Name Type Language
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
(-)-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 Fri Dec 15 16:13:49 UTC 2023 , Edited by admin on Fri Dec 15 16:13:49 UTC 2023
WHO-ATC C07AB11
Created by admin on Fri Dec 15 16:13:48 UTC 2023 , Edited by admin on Fri Dec 15 16:13:48 UTC 2023
NCI_THESAURUS C29576
Created by admin on Fri Dec 15 16:13:49 UTC 2023 , Edited by admin on Fri Dec 15 16:13:49 UTC 2023
Code System Code Type Description
CHEBI
31556
Created by admin on Fri Dec 15 16:13:48 UTC 2023 , Edited by admin on Fri Dec 15 16:13:48 UTC 2023
PRIMARY
PUBCHEM
175540
Created by admin on Fri Dec 15 16:13:49 UTC 2023 , Edited by admin on Fri Dec 15 16:13:49 UTC 2023
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EPA CompTox
DTXSID10239405
Created by admin on Fri Dec 15 16:13:49 UTC 2023 , Edited by admin on Fri Dec 15 16:13:49 UTC 2023
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CAS
93379-54-5
Created by admin on Fri Dec 15 16:13:48 UTC 2023 , Edited by admin on Fri Dec 15 16:13:48 UTC 2023
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SMS_ID
100000084564
Created by admin on Fri Dec 15 16:13:49 UTC 2023 , Edited by admin on Fri Dec 15 16:13:49 UTC 2023
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INN
7337
Created by admin on Fri Dec 15 16:13:49 UTC 2023 , Edited by admin on Fri Dec 15 16:13:49 UTC 2023
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FDA UNII
DPF757BOSR
Created by admin on Fri Dec 15 16:13:49 UTC 2023 , Edited by admin on Fri Dec 15 16:13:49 UTC 2023
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DRUG CENTRAL
4702
Created by admin on Fri Dec 15 16:13:49 UTC 2023 , Edited by admin on Fri Dec 15 16:13:49 UTC 2023
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EVMPD
SUB06608MIG
Created by admin on Fri Dec 15 16:13:48 UTC 2023 , Edited by admin on Fri Dec 15 16:13:48 UTC 2023
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ChEMBL
CHEMBL343633
Created by admin on Fri Dec 15 16:13:49 UTC 2023 , Edited by admin on Fri Dec 15 16:13:49 UTC 2023
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DRUG BANK
DB13443
Created by admin on Fri Dec 15 16:13:49 UTC 2023 , Edited by admin on Fri Dec 15 16:13:49 UTC 2023
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NCI_THESAURUS
C81661
Created by admin on Fri Dec 15 16:13:49 UTC 2023 , Edited by admin on Fri Dec 15 16:13:49 UTC 2023
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