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Related Concept Videos

Stereoisomerism02:52

Stereoisomerism

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Isomerism in Complexes
Isomers are different chemical species that have the same chemical formula.
Transition metal complexes often exist as geometric isomers, in which the same atoms are connected through the same types of bonds but with differences in their orientation in space. Coordination complexes with two different ligands in the cis and trans positions from a ligand of interest form isomers. For example, the octahedral [Co(NH3)4Cl2]+ ion has two isomers (Figure 1) In the cis...
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Changes in polymorphic forms can significantly influence the bioavailability of poorly soluble drugs. Although the FDA defines pharmaceutical equivalence based on having the same active ingredient, dosage form, and route of administration, it does not automatically disqualify products with different polymorphic forms. This means two products with different polymorphs can still be deemed pharmaceutically equivalent. However, polymorphic differences can affect properties like wettability,...
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Properties of Enantiomers and Optical Activity02:24

Properties of Enantiomers and Optical Activity

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It is essential to understand the difference between chiral and achiral interactions and the implications thereof in optical activity and their applications. Just as our feet, which are chiral, interact uniquely with chiral objects, such as a pair of shoes, but identically with achiral socks, enantiomers of a molecule exhibit different properties only when they interact with other chiral media. An example of a significant implication from this facet is the phenomenon known as optical activity,...
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Stereoisomerism of Cyclic Compounds02:33

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In this lesson, we delve into the role of ring conformation and its stability, which determines the spatial arrangement and, consequently, the molecular symmetry and stereoisomerism of cyclic compounds. 1,2-Dimethylcyclohexane is used as a case study to evaluate the possible number of stereoisomers. Here, given the multiple (n = 2) chiral centers, there are 2n = 4 possible configurations that lack a plane of symmetry, as the ring skeleton exists in a non-planar chair conformation. In addition,...
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Pharmaceutical Alternatives: Stability-Related Therapeutic Nonequivalence01:22

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Generic intravenous (IV) drugs are considered bioequivalent to their branded counterparts due to their 100% bioavailability upon administration. However, variations in stability among different drug products can significantly influence their therapeutic performance, even if they are pharmaceutically equivalent.Cefuroxime, a prophylactic antimicrobial, is often used as a single-dose IV injection for patients undergoing coronary artery bypass grafting surgery. A 3 g dose typically provides...
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Adrenergic Agonists: Chemistry and Structure-Activity Relationship01:16

Adrenergic Agonists: Chemistry and Structure-Activity Relationship

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Adrenergic agonists' structure-activity relationship (SAR) determines their selectivity and efficacy. These agonists comprise a phenylethylamine moiety with an aromatic ring and an ethylamine side chain.
Aromatic ring substitutions: Substituting the aromatic ring with –OH groups at positions 3 and 4 yields catecholamines (e.g., epinephrine), which have a high affinity for adrenoceptors. Hydrogen bonding between –OH groups and receptors enhances adrenergic activity.
Separation of...
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Beta2-Agonist Doping Control and Optical Isomer Challenges.

Glenn A Jacobson1, J Paul Fawcett2

  • 1School of Medicine, University of Tasmania, Private Bag 26, Hobart, TAS, 7001, Australia. glenn.jacobson@utas.edu.au.

Sports Medicine (Auckland, N.Z.)
|May 12, 2016
PubMed
Summary
This summary is machine-generated.

The World Anti-Doping Agency (WADA) permits inhaled beta2-agonists, but enantiopure versions of salbutamol and formoterol may enable doping. Routine enantioselective analysis is crucial for detecting performance-enhancing drug use in athletes.

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Area of Science:

  • Sports Science
  • Pharmacology
  • Anti-Doping

Background:

  • Beta2-agonists like salbutamol, formoterol, and salmeterol are approved for asthma treatment but may enhance athletic performance.
  • These drugs are typically racemic mixtures, but enantiopure versions are now available.

Purpose of the Study:

  • To address the implications of enantiopure beta2-agonists in sports doping.
  • To recommend changes in anti-doping strategies for beta2-agonists.

Main Methods:

  • Review of current World Anti-Doping Agency (WADA) regulations regarding beta2-agonists.
  • Analysis of the pharmacological differences between racemic and enantiopure beta2-agonists.
  • Discussion of the impact of chiral switches on urine thresholds and doping detection.

Main Results:

  • Enantiopure salbutamol and formoterol effectively double urine thresholds, facilitating doping.
  • Current doping control methods may not adequately detect the misuse of enantiopure beta2-agonists.
  • Salmeterol lacks a urinary threshold, posing a doping risk.

Conclusions:

  • Enantioselective assays for beta2-agonists should be implemented routinely in doping control.
  • WADA should establish a urinary threshold for salmeterol to prevent doping.