Stereoconfiguration of antiallergic and immunologic drugs

Bielory, Leonard; Leonov, Andrey

doi:10.1016/s1081-1206(10)60396-1

Cited by 15 publications

(7 citation statements)

References 46 publications

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“…Pyranenamine has two chiral centres. SS-isomer was found to have a much more potent inhibitor effect on the allergic response when compared with the RR-isomer 164 . Fexofenadine contains one asymmetric carbon and is distributed as a racemate.…”

Section: Antihistaminesmentioning

confidence: 94%

“…SS-isomer, similarly to salbutamol, may be antagonistic to RR-formoterol. In the case of terbutaline, R(+)-isomer has higher activity in β-adrenergic receptor antagonist action 164 . Formoterol is eliminated mainly through glucuronidation, which is stereoselective and favours SSisomer 161 .…”

Section: Pharmacodynamics and Pharmacokineticsmentioning

confidence: 97%

“…In the case of terbutaline, R(+)-isomer has higher activity in b-adrenergic receptor antagonist action. 164 Formoterol is eliminated mainly through glucuronidation, which is stereoselective and favours SS-isomer. 161 Bambuterol is a prodrug of terbutaline.…”

Section: Pharmacodynamicsmentioning

confidence: 99%

“…SS-Isomer was found to have a much more potent inhibitor effect on the allergic response when compared with the RR-isomer. 164 Fexofenadine contains one asymmetric carbon and is distributed as a racemate. Its enantiomers have equal potencies but different pharmacokinetics e.g.…”

Section: Antihistamines Antihistamines Block Histamine H1mentioning

confidence: 99%

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Pharmacologically active compounds in the environment and their chirality

2010

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Pharmacologically active compounds including both legally used pharmaceuticals and illicit drugs are potent environmental contaminants. Extensive research has been undertaken over the recent years to understand their environmental fate and toxicity. The one very important phenomenon that has been overlooked by environmental researchers studying the fate of pharmacologically active compounds in the environment is their chirality. Chiral drugs can exist in the form of enantiomers, which have similar physicochemical properties but differ in their biological properties such as distribution, metabolism and excretion, as these processes (due to stereospecific interactions of enantiomers with biological systems) usually favour one enantiomer over the other. Additionally, due to different pharmacological activity, enantiomers of chiral drugs can differ in toxicity. Furthermore, degradation of chiral drugs during wastewater treatment and in the environment can be stereoselective and can lead to chiral products of varied toxicity. The distribution of different enantiomers of the same chiral drug in the aquatic environment and biota can also be stereoselective. Biological processes can lead to stereoselective enrichment or depletion of the enantiomeric composition of chiral drugs. As a result the very same drug might reveal different activity and toxicity and this will depend on its origin and exposure to several factors governing its fate in the environment. In this critical review a discussion of the importance of chirality of pharmacologically active compounds in the environmental context is undertaken and suggestions for directions in further research are made. Several groups of chiral drugs of major environmental relevance are discussed and their pharmacological action and disposition in the body is also outlined as it is a key factor in developing a full understanding of their environmental occurrence, fate and toxicity. This review will be of interest to environmental scientists, especially those interested in issues associated with environmental contamination with pharmacologically active compounds and chiral pollutants. As the review will outline current state of knowledge on chiral drugs, it will be of value to anyone interested in the phenomenon of chirality, chiral drugs, their stereoselective disposition in the body and environmental fate (212 references).

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Section: Antihistaminesmentioning

confidence: 94%

Section: Pharmacodynamics and Pharmacokineticsmentioning

confidence: 97%

Section: Pharmacodynamicsmentioning

confidence: 99%

Section: Antihistamines Antihistamines Block Histamine H1mentioning

confidence: 99%

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Pharmacologically active compounds in the environment and their chirality

2010

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“…Chirality is a ubiquitous feature in living systems. Today, it is widely recognized that many biologically interesting compounds, such as drugs, agrochemicals, food additives, and fragrances, are chiral and their physiological properties usually rely on their chirality due to the extremely high chiral discrimination ability of enzymes and receptors. − Particularly, the different pharmacological effects between enantiomers are ultimately an important concern in the pharmaceutical field in which only one enantiomer of a chiral drug often exhibits the desirable therapeutic activity, while the other shows an antagonistic function, side effects, or even toxic effects. − …”

Section: Introductionmentioning

confidence: 99%