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Related Concept Videos

SN2 Reaction: Stereochemistry02:23

SN2 Reaction: Stereochemistry

10.9K
In an SN2 reaction, the nucleophilic attack on the substrate and departure of the leaving group occurs simultaneously through a transition state. As the nucleophile approaches the substrate from the back-side, the configuration of the substrate carbon changes from tetrahedral to trigonal bipyramidal and then back to tetrahedral, leading to an inversion in the configuration of the product.
If the substrate is an achiral molecule at the α-carbon, the inversion of configuration is not...
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Stereoisomers02:32

Stereoisomers

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On the basis of mirror symmetry, stereoisomers of an organic molecule can be further classified into diastereomers and enantiomers. Diastereomers are stereoisomers that are not mirror images of each other. Substituted alkenes, such as the cis and trans isomers of 2-butene, are diastereomers, as these molecules exhibit different spatial orientations of their constituent atoms, are not mirror images of each other, and do not interconvert. Here, the interconversion is suppressed due to...
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Principles of Drug Action01:24

Principles of Drug Action

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Drugs are chemical substances that modify biological responses by interacting with macromolecular targets such as receptors, ion channels, transporters, and enzymes. Pharmacodynamics describes the course of action of drugs leading to the physiological effect at a specific site in the body.
Drugs can be agonists or antagonists. Like the endogenous ligands, agonists always bind and activate the target to produce a cellular response. Agonist binding induces a conformational change which in turn...
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Structure-Activity Relationships and Drug Design01:28

Structure-Activity Relationships and Drug Design

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Drug design is a dynamic field that involves discovering and developing new medications based on specific biological targets. This process heavily relies on structure-activity relationships (SAR) and quantitative structure-activity relationships (QSAR) to guide the design and optimization of efficient drugs.
SAR studies the intricate relationship between a drug's chemical structure and biological activity. It focuses on understanding how modifications to a drug's structure can influence...
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Factors Affecting Dissolution: Drug Permeability, Stability and Stereochemistry01:20

Factors Affecting Dissolution: Drug Permeability, Stability and Stereochemistry

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Orally administered drugs primarily enter the systemic circulation via passive diffusion through the intestinal membranes. The drug's absorption is influenced by drug stability in the gastrointestinal GI tract, membrane permeability, the surface area available for absorption, luminal drug concentration, and residence time in the lumen. Drug permeability can be enhanced by adjusting the lipophilicity, polarity, or molecular size of the drug, promoting its passive transport across intestinal...
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Radical Halogenation: Stereochemistry01:33

Radical Halogenation: Stereochemistry

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Stereochemistry is the study of the different spatial arrangements of atoms in a given molecule. The stereochemistry of radical halogenations can be understood from three different situations:
Halogenation to form a new chiral center:
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Related Experiment Video

Updated: Nov 19, 2025

Diagonal Method to Measure Synergy Among Any Number of Drugs
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Stereochemistry in Drug Action.

Jonathan McConathy1, Michael J. Owens

  • 1Laboratory of Neuropsychopharmacology, Department of Psychiatry & Behavioral Sciences, Emory University School of Medicine, Atlanta, Ga.

Primary Care Companion to the Journal of Clinical Psychiatry
|May 25, 2004
PubMed
Summary

Stereochemistry is crucial for drug action, especially in psychiatric medications. Understanding single-enantiomer drugs offers improved selectivity, therapeutic index, and pharmacokinetics compared to enantiomer mixtures.

Area of Science:

  • Pharmacology
  • Medicinal Chemistry
  • Clinical Pharmacy

Background:

  • Many psychiatric drugs are administered as enantiomer mixtures.
  • Stereochemistry significantly impacts drug efficacy and safety.
  • Clinicians need to understand stereochemistry for informed prescribing.

Purpose of the Study:

  • To review stereochemistry nomenclature and enantiomer differences.
  • To highlight the clinical benefits of single-enantiomer drugs.
  • To guide physicians in choosing optimal pharmacotherapy.

Main Methods:

  • Review of stereochemistry nomenclature.
  • Analysis of biological and pharmacologic differences between enantiomers.
  • Case studies of single-enantiomer selective serotonin reuptake inhibitors (SSRIs).

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Main Results:

  • Single-enantiomer drugs can offer enhanced target selectivity and improved therapeutic indices.
  • Pharmacokinetic profiles may differ significantly between enantiomers.
  • Clinical examples demonstrate advantages of single-enantiomer SSRIs like fluoxetine and citalopram.

Conclusions:

  • Familiarity with stereochemistry is essential for modern pharmacotherapy.
  • Single-enantiomer drugs provide potential advantages over racemic mixtures.
  • Informed decisions on drug formulations optimize patient outcomes.