Significance of the eudismic ratio and enantiomeric purity of the albuterol distomer

Jalba, Mihai S.

doi:10.1016/j.jaci.2004.05.062

Cited by 3 publications

(2 citation statements)

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“…When drug-receptor interactions are considered it is postulated that "the lower the effective dose of a drug, the greater the difference in the pharmacological effect of the optical isomers" [2]. The ratio of the more active enantiomer (eutomer) compared to the less active enantiomer (distomer) is defined as the eudismic ratio, and the higher the eudismic ratio, the higher the effectiveness of the drug [3].…”

Section: Introductionmentioning

confidence: 99%

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Chemo-Enzymatic Synthesis of Synthons as Precursors for Enantiopure Clenbuterol and other β2- Agonists

Blindheim¹,

Hansen²,

Evjen³

et al. 2018

Preprint

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(R)-1-(4-Amino-3,5-dichlorophenyl)-2-bromoethan-1-ol has been synthesised in 93% enantiomeric excess (ee) by asymmetric reduction of the corresponding ketone catalysed by a ketoreductase and NADPH as the co-factor in DMSO. (S)-N-(2,6-Dichloro-4-(1-hydroxyethyl)phenyl)acetamide has been synthesised in >98% ee by the same system. Both synthons are potential precursors for clenbuterol enantiomers. Clenbuterol is a β2-agonist used in veterinary treatment of asthma in several countries. The drug is listed on the World Anti-doping Agency’s Prohibited list due to its effect on increased protein synthesis in the body. However, racemic clenbuterol has recently been shown to reduce the risk of Parkinson’s disease. In order to reveal which one (or both) of the enantiomers that cause this effect, the pure enantiomers need to be studied separately. Our biocatalytic approach in order to obtain enantiopure clenbuterol should be applicable to industrial scale.

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Section: Introductionmentioning

confidence: 99%

“…JHH = 7.7 Hz), 3.62-3.60 (dd, 1H, CH-Br,3 JHH = 4.4 Hz, 2 JHH = 10.5 Hz), 3.56-3.53 (dd, 1H, CH-Br, 3 JHH = 7.7 Hz, 2 JHH = 10.5 Hz), 2.13 (s, 3H, CO-CH3). 13 C NMR (600 MHz, CD3OD): δ 170.2, 138.2, 137.6, 126.4, 119.6, 73.1, 37.8, 22.4.…”

mentioning

confidence: 99%

Chemo-Enzymatic Synthesis of Synthons as Precursors for Enantiopure Clenbuterol and other β2- Agonists

Blindheim¹,

Hansen²,

Evjen³

et al. 2018

Preprint

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Ameredes¹,

Panettieri²

2006

Journal of Allergy and Clinical Immunology

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CorrespondenceEffect of genotype on responses to enantiomers and the significance of the eudismic analysis in asthma researchTo the Editor:I read with interest the article by Ameredes and Calhoun 1 on advances in asthma research. Unfortunately, the authors did not take into account the haplotypes of the donors and did not present the results of the eudismic analysis.In asthma, the response to b-agonists acting at b 2adrenergic receptors (b 2 ARs) displays extensive interindividual variation, in part because of genetic variation in the b 2 AR genotypes. b 2 -Adrenergic polymorphisms might have influenced the treatment effect in this study mainly for 2 reasons:

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Three Generations of Ongoing Controversies Concerning the Use of Short Acting Beta-Agonist Therapy in Asthma: A Review

Jalba¹

2008

Journal of Asthma

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An increase in asthma mortality in 1960s noted by British authors stirred a debate about the use of beta-adrenergic therapy that has persisted in the medical literature. The cause appears to be isoproterenol and fenoterol overuse. A second debate evolved around the possible deleterious, pro-inflammatory effects, of the albuterol distomer. Most clinical studies showed improved bronchodilatation, but limited benefits from using levalbuterol. Recently, genotyping has uncovered a single nucleotide polymorphism at codon 16 that appears to affect the long term response to both regular and as needed use of albuterol, calling for a new genotype based therapeutic approach in asthma.

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Significance of the eudismic ratio and enantiomeric purity of the albuterol distomer

Cited by 3 publications

References 2 publications

Chemo-Enzymatic Synthesis of Synthons as Precursors for Enantiopure Clenbuterol and other β2- Agonists

Chemo-Enzymatic Synthesis of Synthons as Precursors for Enantiopure Clenbuterol and other β2- Agonists

Reply

Three Generations of Ongoing Controversies Concerning the Use of Short Acting Beta-Agonist Therapy in Asthma: A Review

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Significance of the eudismic ratio and enantiomeric purity of the albuterol distomer

Cited by 3 publications

References 2 publications

Chemo-Enzymatic Synthesis of Synthons as Precursors for Enantiopure Clenbuterol and other &beta;2- Agonists

Chemo-Enzymatic Synthesis of Synthons as Precursors for Enantiopure Clenbuterol and other &beta;2- Agonists

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Three Generations of Ongoing Controversies Concerning the Use of Short Acting Beta-Agonist Therapy in Asthma: A Review

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Chemo-Enzymatic Synthesis of Synthons as Precursors for Enantiopure Clenbuterol and other β2- Agonists

Chemo-Enzymatic Synthesis of Synthons as Precursors for Enantiopure Clenbuterol and other β2- Agonists