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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
Low-molecular-weight chiral cation exchangers: novel chiral stationary phases and their application for enantioseparation of chiral bases by nonaqueous capillary electrochromatography.
2002 Feb
Binding of (-)-[3H]-CGP12177 at two sites in recombinant human beta 1-adrenoceptors and interaction with beta-blockers.
2004 May
Insights into cyclodextrin interactions during sample stacking using capillary isotachophoresis with on-line microcoil NMR detection.
2005 Sep
Mechanism-based pharmacodynamic modeling of S(-)-atenolol: estimation of in vivo affinity for the beta1-adrenoceptor with an agonist-antagonist interaction model.
2008 Mar
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
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WHO-ATC C07AB11
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NCI_THESAURUS C29576
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
Code System Code Type Description
CHEBI
31556
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PUBCHEM
175540
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EPA CompTox
DTXSID10239405
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CAS
93379-54-5
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SMS_ID
100000084564
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INN
7337
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FDA UNII
DPF757BOSR
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DRUG CENTRAL
4702
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EVMPD
SUB06608MIG
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ChEMBL
CHEMBL343633
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DRUG BANK
DB13443
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
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NCI_THESAURUS
C81661
Created by admin on Fri Dec 15 16:13:49 GMT 2023 , Edited by admin on Fri Dec 15 16:13:49 GMT 2023
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