(S)-(-)-Atenolol - CAS 93379-54-5
Category: Inhibitor
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Molecular Formula:
C14H22N2O3
Molecular Weight:
266.34
COA:
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Targets:
Adrenergic Receptor
Description:
(S)-(-)-Atenolol is the active enantiomer of (RS)-atenolol, which is a cardioselective β-adrenergic blocker. It has antihypertensive, antianginal, antiarrhythmic (class II) effects.
Purity:
≥97% by HPLC
Synonyms:
(S)-Atenolol; 4-[(2S)-2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide; (-)-Atenolol; Esatenolol; (S)-(-)-4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide; (−)-4-[2-Hydroxy-3-[(1-methylethyl)amino]propoxy]benzeneacetamide
MSDS:
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InChIKey:
METKIMKYRPQLGS-LBPRGKRZSA-N
InChI:
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
Canonical SMILES:
CC(C)NCC(COC1=CC=C(C=C1)CC(=O)N)O
1.Enantioanalysis of bisoprolol in human plasma with a macrocyclic antibiotic HPLC chiral column using fluorescence detection and solid phase extraction.
Hefnawy MM;Sultan MA;Al-Shehri MM Chem Pharm Bull (Tokyo). 2007 Feb;55(2):227-30.
A sensitive, enantioselective, high-performance liquid chromatographic (HPLC) method was developed and validated to determine S-(-)- and R-(+)-bisoprolol in human plasma. Baseline resolution was achieved using the teicoplanin macrocyclic antibiotic chiral stationary phase (CSP) known as Chirobiotic T with a polar ionic mobile phase (PIM) consisting of methanol-glacial acetic acid-triethylamine (100 : 0.02 : 0.025, v/v/v) at a flow rate of 1.5 ml/min and fluorescence detection set at 275 nm for excitation and 305 nm for emission. All analyses with S-(-)-atenolol as the internal standard were conducted at ambient temperature. The assay involved the use of a solid-phase extraction procedure for human plasma samples prior to HPLC analysis. The C18 cartridge gave good recovery rates for both enantiomers without any interference. The method was validated over the range of 20-200 ng/ml for each enantiomer concentration. Recovery rates for S-(-)- and R-(+)-bisoprolol enantiomers were in the range of 95-102%. The method proved to be precise (within-run precision expressed as % RSD ranged from 1.0-6.2% and between-run precision ranged from 0.9-6.7%) and accurate (within-run accuracies expressed as percentage error ranged from 0.
2.Enantioselective analysis of (R)- and (S)-atenolol in urine samples by a high-performance liquid chromatography column-switching setup.
Lamprecht G;Kraushofer T;Stoschitzky K;Lindner W J Chromatogr B Biomed Sci Appl. 2000 Apr 14;740(2):219-26.
An HPLC column-switching method for the enantioselective determination of (R,S)-atenolol in human urine was developed and validated. Diluted urine samples were injected onto a LiChrospher ADS restricted access column and atenolol was separated from most of the matrix components using 0.01 M Tris buffer. The atenolol peak was sharpened by a step gradient of 30% acetonitrile and the atenolol-containing fraction was switched onto an enantioselective column. Separation of the atenolol enantiomers was carried out on a Chirobiotic T (Teicoplanin) column using acetonitrile-methanol-acetic acid-triethylamine (55:45:0.3:0.2, v/v/v/v) as eluent. Detection of the effluent was performed by fluorescence measurement. Several experiments were carried out to suppress the high blank reading, which was efficiently achieved using Tris buffer in the first dimension. For the enantioselective analysis of (R)- and (S)-atenolol in plasma under the same conditions the sample capacity of the ADS column is considerably lower.
3.The relationship of electrocardiographic left ventricular hypertrophy to decreased serum potassium.
Okin PM;Kjeldsen SE;Lindholm LH;Dahlöf B;Devereux RB Blood Press. 2012 Jun;21(3):146-52. doi: 10.3109/08037051.2011.649537. Epub 2012 Jan 16.
BACKGROUND: ;Low serum potassium (K) is associated with increased blood pressure, impaired cardiac function and renal dysfunction. Although lower serum K is associated with cardiac hypertrophy in animal models, the relationship of low serum K to the presence and severity of electrocardiographic left ventricular hypertrophy (LVH) is unclear.;METHODS: ;Baseline and yearly Cornell product LVH levels were examined in relation to low serum K (serum K ≤ 3.90 mEq/l, the lowest quartile of baseline K levels) in 8586 patients with baseline K levels. Patients were randomized to losartan-vs atenolol-based treatment and additional hydrochlorothiazide (HCTZ) therapy as needed.;RESULTS: ;After adjusting for age, sex, race, prior antihypertensive treatment, losartan vs atenolol therapy, HCTZ use, baseline diastolic and systolic pressure, body mass index, serum creatinine and urine albumin/creatinine ratio, baseline serum K ≤ 3.90 was associated with significantly higher mean baseline Cornell product LVH (2898 vs 2801 mm•ms, p = 0.001) and a 24% higher risk of Cornell product LVH > 2440 mm•ms at baseline (OR 1.24, 95% CI 1.11-1.38, p < 0.001). After also adjusting for baseline Cornell product and changes in diastolic and systolic pressure between baseline and each year of measurement, in-treatment serum K ≤ 3.
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CAS 93379-54-5 (S)-(-)-Atenolol

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