Related Experiment Video
Updated: Jun 12, 2026
05:28
A Semi-Quantitative Drug Affinity Responsive Target Stability (DARTS) assay for studying Rapamycin/mTOR interaction
Published on: August 27, 2019
Tautomerism in drug discovery
Alan R Katritzky1, C Dennis Hall, Bahaa El-Dien M El-Gendy
1Center for Heterocyclic Compounds, Department of Chemistry, University of Florida, Gainesville, FL 32611-7200, USA. katritzky@chem.ufl.edu
Journal of Computer-Aided Molecular Design
|May 22, 2010
Summary
Tautomerism significantly impacts drug structure and biological interactions. Understanding these structural changes, influenced by pH, solvent, and temperature, is crucial for drug design.
Area of Science:
- Medicinal Chemistry
- Physical Chemistry
- Biochemistry
Background:
- Tautomerism is a key phenomenon influencing molecular structure.
- Drug efficacy is directly related to precise molecular interactions with biological targets.
- Understanding tautomeric shifts is essential for predicting drug behavior.
Purpose of the Study:
- To discuss the influence of tautomerism on drug structure.
- To explore the thermodynamic and kinetic aspects of tautomerism in drugs.
- To survey tautomerism types in current drugs and influencing factors.
Main Methods:
- Thermodynamic analysis of tautomeric equilibria.
- Kinetic studies of tautomeric interconversions.
- Survey of drug structures exhibiting tautomerism.
Main Results:
- Tautomerism affects drug conformation and biological activity.
- pH, solvent polarity, and temperature are critical factors modulating tautomeric forms.
- Various tautomeric types are prevalent in commonly used pharmaceuticals.
Conclusions:
- Tautomerism is a critical determinant of drug structure-activity relationships.
- Controlling tautomeric states through environmental factors can optimize drug performance.
- Further investigation into tautomerism is vital for rational drug development.
Related Concept Videos
01:26Drug Discovery: Overview
Drug discovery is a multifaceted process involving extensive screening, testing, and optimization of lead compounds to identify potential new drugs for therapeutic use. It combines several approaches, including screening large numbers of natural products, chemical modification of known active molecules, identification of new drug targets, and rational design based on biological mechanisms and drug-receptor structure. These approaches are carried out in both academic research laboratories and...
01:11Pharmacogenetics of Drug Targets: β₂-Adrenergic Receptors, Apo E, Thymidylate Synthase
Genetic polymorphisms in drug targets have emerged as critical determinants of interindividual variability in drug response and toxicity. Pharmacogenomic investigations increasingly focus on identifying these variations to personalize and optimize therapeutic interventions. A drug target may be a receptor, enzyme, or signaling protein involved in pharmacologic responses or disease-related pathways. While early pharmacogenetic studies focused primarily on drug metabolism, current research...
01:28Structure-Activity Relationships and Drug Design
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 its...
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 its...
01:14Keto–Enol Tautomerism: Mechanism
The keto and enol forms are known as tautomers and they constantly interconvert (or tautomerize) between the two forms under acid or base catalyzed conditions. Both the reactions involve the same steps—protonation and deprotonation— although in the reverse order.
01:27Pharmacogenetics of Phase II Enzymes: N-acetyltransferase, Thiopurine S-methyltransferase, UDP-glucuronosyltransferase
Phase II biotransformation reactions are essential for detoxifying and eliminating xenobiotics, including many pharmaceutical compounds. These reactions typically involve conjugation, the covalent attachment of polar endogenous groups such as glucuronic acid, sulfate, methyl, or acetyl moieties to functional groups introduced during Phase I metabolism. The resulting conjugates are more water-soluble, enabling efficient renal or biliary excretion.The major classes of Phase II enzymes include...
01:29Pharmacogenomics: Identification of New Drug Targets
Advances in genomics have profoundly influenced drug discovery by increasing both the speed and accuracy of pharmaceutical development. Pharmacogenomics, which examines how genetic variation influences drug response, facilitates the identification of novel therapeutic targets and enables patient stratification for personalized treatment. These strategies contribute to improved drug efficacy, minimized adverse effects, and more efficient clinical trial design.Mapping genetic differences...