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
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
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
Sources: http://adisinsight.springer.com/drugs/800006004 | https://www.google.com/patents/WO1991007175A1
Curator's Comment: originally atenolol was discovered by ICI http://www.world-medicinehistory.com/2014/08/discovery-of-atenolol.html
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL213 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | ADBETA Approved UseThis 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. |
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Primary | ADBETA Approved UseThis 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. |
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Primary | ADBETA Approved UseThis 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
Title | Date | PubMed |
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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 |
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Binding of (-)-[3H]-CGP12177 at two sites in recombinant human beta 1-adrenoceptors and interaction with beta-blockers. | 2004 May |
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An efficient asymmetric synthesis of (S)-atenolol: using hydrolytic kinetic resolution. | 2005 Feb 1 |
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Development of safer molecules through chirality. | 2006 Oct |
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Enantioanalysis of bisoprolol in human plasma with a macrocyclic antibiotic HPLC chiral column using fluorescence detection and solid phase extraction. | 2007 Feb |
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Direct enantiomeric resolution of betaxolol with application to analysis of pharmaceutical products. | 2007 Feb 6 |
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Clinical pharmacology. | 2008 Oct |
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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 |
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NCI_THESAURUS |
C29576
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ACTIVE MOIETY