Learning objectives
The course provides an introduction to Medicinal Chemistry and is integrated with the Medicinal Chemistry courses delivered in the following years.
The course provides knowledge and understanding of the basic chemical and toxicological concepts related to drugs and drug action, to be applied to the study of the classes of drugs presented in the systematic part of the course. The knowledge and methodology acquired during the course allow the student to analyze, describe and discuss, with proper language, the most relevant aspects of drug structure and action.
Besides the general aspects of drug activity, the student will learn the most important drugs belonging to the therapeutic classes treated in detail, with consideration for their name, molecular formula and related chemical and physicochemical properties, mechanism of action, therapeutic application, metabolic fate and toxicity.
At the end of the course the student is expected to:
1. Understand how structural, chemical and physicochemical properties of a drug affect the biological activity, pharmacokinetic behavior, adverse reactions and interaction with other drugs.
For the classes of drugs treated during the course: know names of drugs, simple formulas, origin and application. Understand (recognize, explain and discuss) complex formulas, structure-activity relationships, chemical, physicochemical, toxicological and metabolic properties of drugs (Knowledge and understanding).
2. For drugs specifically treated and their structural analogs: go from formula to name and vice versa. Infer chemical and physicochemical properties of drugs from their molecular structure and discuss how these properties can affect biological activity, including metabolism and toxicity (Applying knowledge and understanding).
3. Draw consequences on the use of drugs based on their structural, chemical and physicochemical properties. Answer to questions, suggestions and criticisms during the examination, and formulate opinions on the topics treated in the course (Making judgements).
4. Report with proper language, to specialists and non-specialists, knowledge and concepts related to the classes of drugs treated during the course (Communication skills).
5. Learn to infer general rules/concepts from examples. Learn to search and critically evaluate sources of information and literature (Learning skills).
Prerequisites
Basic notions of general and organic chemistry, physiology, microbiology and biochemistry. Chemical equilibrium, equilibria in solution, in particular acid/base equilibria and redox reactions. Knowledge of functional groups of organic chemistry and their properties, in particular reactivity and acid/base profile. Nomenclature of heterocycles. Knowledge of structure and function of proteins, sugars, lipids and nucleic acids. Basic concepts of cell and organ physiology. Basic notions on bacteria, fungi, protozoa and viruses.
Course unit content
The first lessons introduce general concepts on drugs, such as names/nomenclature and origin of drugs. Structural, chemical and physicochemical properties affecting the different aspects of drug action are also described. Relevant mechanisms of action are exemplified, as well as basic concepts and applications of structure-activity relationships. Drug absorption, distribution, metabolism and excretion, with particular attention to metabolic reactions, are treated in the general part of the course. Prodrug strategies will also be described and discussed, with examples of prodrug activation mechanisms.
The second part of the course deals with the most relevant classes of antibacterial, antiprotozoal, antifungal, antiparasitic, antiviral and anticancer drugs. For each class, the chemical formulas of the most important drugs are described and commented, and information on the mechanism of action, therapeutic application, structure-activity relationships, chemical and physicochemical properties, metabolic reactions and toxicity is provided.
Full programme
Names and classification of drugs
Origin of drugs
Chemical and physicochemical properties influencing drug action
Moments of drug action: the pharmaceutical, pharmacodynamic and pharmacokinetic phases.
Membrane crossing and protein binding
Drug metabolism and elimination
Drug toxicity and drug resistance, in particular antibiotic resistance.
Drug targets: membranes, receptors, enzymes, nucleic acids.
Mechanisms of drug action
Prodrugs
Isosteres and bioisosteres
Structure-activity relationships
Antibacterial agents: sulfa-drugs, beta-lactams, quinolones, aminoglycosides, tetracyclines, macrolides, oxazolidinones; antimicrobial peptides, glyco- and lipopeptides. Antimycobacterial and leprostatic agents.
Antiprotozoal drugs: nitro-heterocyclic drugs, antimalarial drugs; other antiprotozoal agents.
Antifungal drugs: azoles, allylamines, polyenic drugs, other antifungal agents.
Insecticides: pyrethrum and derivatives
Antiviral drugs: anti-herpetic, anti-HIV, anti-flu, drugs for hepatitis B and C; other antiviral agents.
Anticancer drugs: alkylating agents, intercalating agents, antimetabolites, antimitotics, DNA-polymerase and topoisomerase inhibitors, tyrosine kinase inhibitors; other anticancer agents.
Bibliography
Alberto Gasco, Fulvio Gualtieri, Carlo Melchiorre: Chimica Farmaceutica, seconda edizione; Casa Editrice Ambrosiana, Milano.
Thomas L. Lemke, David A. Williams, Victoria F. Roche, S. William Zito: Foye’s Principi di Chimica Farmaceutica, sesta edizione italiana; Piccin, Padova.
G. L. Patrick: Chimica Farmaceutica, terza edizione; Edises Napoli.
Slides commented during the lessons will be available to students at the Elly website before the beginning of the course.
Teaching methods
Teacher-led lessons (72 hours corresponding to 9 CFU) with slides used to describe and discuss the topics of each lesson. Chemical structures and mechanisms will be also illustrated on the blackboard. The student is expected to study and understand the content of the lessons using the textbook and the material provided through the ELLY platform (copy of slides). The teacher is available to explain and discuss the course contents at the end of the lesson, during lesson breaks or by appointment (e-mail request).
Assessment methods and criteria
The oral examination will be preceded by a written questionnaire (5 open questions) about the most relevant concepts/knowledge presented during the course. The questionnaire will take about 15 minutes. If the answers will be evaluated sufficient (usually 3 correct answers), the student will pass to the oral examination. With questions related to all the topics treated during the course, the level of knowledge and comprehension achieved by the student will be evaluated. The ability of the student to apply the acquired knowledge and understanding will be also assessed through connections among topics.
Other information
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2030 agenda goals for sustainable development
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