CHIMICA FARMACEUTICA E TOSSICOLOGICA I
Academic Year 2026/2027 - Teacher: AGOSTINO MARRAZZOExpected Learning Outcomes
At the end of the course students will be able to illustrate the basic concepts of general medicinal and toxicological chemistry concerning drug action, molecular targets and drug-target interactions, the effects of stereochemistry on drug activity, and the main qualitative and quantitative receptor theories underlying drug-receptor interactions; consider the basic aspects of pharmacokinetics and the chemical and physicochemical properties influencing it; apply selected principles of drug design and discovery; understand the mechanisms of action of enzyme inhibitors based on the chemical characteristics of the molecules involved and analyze structure-activity relationships; critically analyze medicinal chemistry texts and scientific papers.
2. Applying Knowledge and Understanding
Students will know the fundamental molecular mechanisms of action and structure-activity relationships of antibacterial, anti-infective and antineoplastic drugs and apply fundamental principles and practical strategies for designing new active compounds.
3. Making Judgements
Critically analyze therapeutic approaches, evaluate alternative strategies and compare advantages and limitations.
4. Communication Skills
Clearly and comprehensively present concepts and methodologies learned during the course using appropriate medicinal chemistry and toxicological terminology.
5. Learning Skills
Independently retrieve scientific information from specialized literature sources, update knowledge, deepen methodologies and integrate biological, pharmacological, chemical and pharmaceutical technology knowledge.
Course Structure
The course will be conducted through lectures (9 CFU; 63 hours).
According to the RDA, Art. 12 – University Educational Credits (CFU), the standard workload of 25 hours of total student effort corresponding to one credit may comprise: a) 7 hours dedicated to lectures or equivalent activities, with the remainder devoted to individual study; b) between 12 and 15 hours dedicated to classroom exercises or equivalent supervised activities, with the remainder devoted to study and personal review.
Should the course be delivered in a hybrid or remote format, necessary adjustments to the above arrangements may be introduced to ensure compliance with the planned curriculum outlined in this syllabus.
Required Prerequisites
Chimica Organica I (propedeutica).
Attendance of Lessons
Absences are permitted for no more than 30% of the total teaching hours, calculated across all forms of instruction.
Attendance is mandatory, as stipulated by the academic regulations of the Degree Course in CTF. Absences are permitted for no more than 30% of the total teaching hours, calculated across all forms of instruction (Academic Regulations | Degree Course in Pharmacy).
Detailed Course Content
Unit 1: Introduction, definition and classification of drugs. Tasks of pharmaceutical research. Sources of pharmaceutical agents. Drug design. Lead generation methods. Stages of drug development. CADD methodologies. Drug development and registration. Preclinical studies including chemical, analytical, pharmaceutical, pharmacodynamic, pharmacokinetic and toxicological evaluation, carcinogenicity and mutagenicity studies. Clinical trials, regulations, Good Clinical Practice, Ethics Committees, phases. Structure-activity relationships. Patents. Me-too, generic and off-label drugs. Therapeutic innovation. Scale-up. Orphan medicines. Stability and drug combinations.
Unit 2: Stages of drug action. Pharmaceutical phase and routes of administration. Pharmacokinetic phase: absorption, partition coefficient and logP, transport, distribution, metabolism, phase I and phase II biotransformations, enzyme inhibition and induction, elimination and excretion. Prodrugs, double prodrugs, mutual prodrugs and soft drugs. Pharmacodynamic phase: drug-biological system interactions, binding types and mechanisms, graded and quantal dose-response curves, antagonism and classifications.
Unit 3: Auxophoric groups and pharmacophores. Stereochemistry and biological activity. Configurational and conformational isomerism. Stereoselectivity and stereospecificity. Eudismic index. Molecular modifications, classical and non-classical isosterism and bioisosterism. Nonproprietary names, INN nomenclature, pharmacovigilance and ATC classification.
MODULE B – SYSTEMATIC PART (4.5 ECTS)
Unit 4: Anti-infective drugs. History, bacterial growth curves, mechanisms and selectivity of action, antibiotic resistance. Antibacterial chemotherapeutic agents. Sulfonamides, nitrofurans, nitroimidazoles, quinolones and fluoroquinolones, oxazolidinones and Linezolid with classification, synthesis, mechanisms of action and structure-activity relationships.
Unit 5: Antimycobacterial chemotherapeutic agents and antibiotics. Antitubercular and antileprosy therapy. Dapsone, acedapsone, p-aminosalicylic acid, isoniazid, pyrazinamide, ethambutol, cycloserine, rifamycins and streptomycin.
Unit 6: Antibacterial antibiotics inhibiting cell wall biosynthesis. Beta-lactams, penicillins, production, degradation, SAR, benzathine benzylpenicillin, oxacillin, cloxacillin, flucloxacillin, ampicillin, amoxicillin, bacampicillin, carbenicillin, sulbenicillin, suncillin, piperacillin, azlocillin, mezlocillin and combinations with clavulanic acid and sulbactam.
Unit 7: Cephalosporins from first to fourth generation, carbapenems, monobactams, aztreonam and related SAR and synthesis.
Unit 8: Protein synthesis inhibitors. Tetracyclines, glycylcyclines, tigecycline, amphenicols, chloramphenicol and thiamphenicol.
Unit 9: Macrolides, ketolides, lincosamides, aminoglycosides, rifamycins, polypeptides and lipopeptides.
Unit 10: Antifungal drugs. Griseofulvin, nystatin, amphotericin B, imidazoles (clotrimazole, miconazole, econazole, isoconazole, ketoconazole) and triazoles (terconazole, fluconazole).
Unit 11: Antiviral drugs. Aminoadamantanes, nucleoside antimetabolites, acyclovir derivatives, oseltamivir, zanamivir. New therapeutic approaches for HIV infection: CCR5 antagonists, fusion inhibitors, NRTIs, NNRTIs, integrase inhibitors and protease inhibitors. Drugs for HCV infection: NS3/4A protease inhibitors, NS5A phosphoprotein inhibitors, NS5B polymerase inhibitors and therapeutic combinations.
Unit 12: Antineoplastic drugs. Tumor classification, carcinogenesis and therapies. Alkylating agents, platinum compounds, intercalating agents, antimetabolites, Vinca alkaloids, bleomycin, immunostimulants, hormonal inhibitors. New approaches: kinase inhibitors, histone deacetylase inhibitors and farnesyl transferase inhibitors.
Textbook Information
1. The most appropriate texts for studying the topics covered will be indicated during the lecture.
2. Teaching materials provided by the lecturer: https://studium.unict.it/dokeos/2027/
3. G. Costantino, G. Sbardella – *Chimica Farmaceutica* – 1st ed. (2024) – EdiSES.
4. *Foye’s Principi di Chimica Farmaceutica* – 6th Italian ed. (2014) – Piccin.
5. Graham L. Patrick – *Chimica Farmaceutica* – 3rd ed. (2015) – EdiSES.
6. Wilson & Gisvold – *Chimica Farmaceutica* – 1st ed. (2014) – Casa Editrice Ambrosiana.
7. Gasco A., Gualtieri F. – *Chimica Farmaceutica* – 1st ed. (2015) – Casa Editrice Ambrosiana.
8. G. Greco – *Farmacocinetica e Farmacodinamica su basi chimico-fisiche* – (2007) – Loghìa.
9. G. Greco – *Farmaci antibatterici* – (2009) – Loghìa.
Recommended reading:
- *Burger’s Medicinal Chemistry and Drug Discovery*, Vol. I – Ed. M.E. Wolff – J. Wiley & Sons.
Course Planning
| Subjects | Text References | |
|---|---|---|
| 1 | MODULE A - GENERAL PART (see course content - general part) | Teaching materials provided by the lecturer: http://studium.unict.it/dokeos/2027/ |
| 2 | MODULE B - SYSTEMATIC PART (see course content - systematic part) | Teaching materials provided by the lecturer: http://studium.unict.it/dokeos/2027/ |
| 3 | There are no mandatory minimum topics required to pass the exam; basic knowledge of the topics in the syllabus is assessed. | The teacher provides the material necessary for studying the topics covered in class via the STUDIUM platform. |
Learning Assessment
Learning Assessment Procedures
Learning outcomes will be assessed via an oral examination aimed at verifying:
• possession of fundamental theoretical knowledge regarding the medicinal chemistry aspects covered (Descriptor 1);
• the ability to apply the theoretical and methodological principles taught during the course (Descriptor 2);
• the aptitude for critically analyzing experimental results (Descriptor 3);
• the ability to synthesize and discuss concepts, methodologies, and applications in medicinal chemistry using appropriate scientific terminology and correct technical language, with particular reference to biotechnological drugs (Descriptor 4);
• the ability to independently integrate the knowledge acquired during the course and to link biological, biochemical, pharmacological, and medicinal chemistry aspects (Descriptor 5).
Generally, the oral exam consists of 3 questions covering different parts of the syllabus (one per module) and lasts approximately 40–60 minutes.
The assessment may also be conducted remotely, should conditions require it.
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ASSESSMENT CRITERIA
The final exam will be evaluated based on the following aspects:
Knowledge and Understanding
• accuracy of theoretical knowledge regarding pharmaceutical biotechnology, recombinant DNA technology, and the development processes for biotechnological drugs;
• completeness of information provided on the biological mechanisms and biotechnological methodologies covered in the course;
• ability to identify and describe the biological, biochemical, and medicinal chemistry principles underlying the production and characterization of therapeutic biomolecules.
Application Skills
• ability to apply theoretical knowledge to the interpretation of experimental methods used in laboratory activities;
• ability to interpret data derived from experiments involving bacterial transformation, gene expression, and the production and purification of recombinant proteins; • ability to solve problems related to the design, production, and characterization of biopharmaceutical drugs.
Making Judgments
• ability to critically analyze the experimental results obtained;
• identification of potential critical issues or limitations in the biotechnological processes studied;
• evaluation of the effectiveness of experimental and production strategies adopted for obtaining therapeutic proteins.
Communication Skills
• correct use of scientific terminology specific to pharmaceutical biotechnology;
• clarity and coherence in presenting biotechnological concepts, methodologies, and applications;
• ability to coherently integrate biological, biochemical, pharmacological, and medicinal-chemical aspects.
Learning Skills
• ability to integrate knowledge from different parts of the syllabus and from prerequisite disciplines;
• appropriate use of specialized bibliographic sources and relevant scientific documentation;
• ability to independently keep up to date with new technologies and the latest developments in the field of pharmaceutical biotechnology and biopharmaceutical drugs.
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GRADING CRITERIA
Grades are awarded on a scale of 30, according to the following scheme:
Fail: the student lacks the minimum required knowledge of the course's main content and demonstrates poor command of technical language.
Grade 18-21: the student possesses essential knowledge of the topics with limited capacity for critical integration and uses simple yet substantially correct scientific language.
Grade 22-25: the student demonstrates fair knowledge of the topics with an adequate ability to make connections and use appropriate technical language.
Grade 26-28: the student demonstrates good command of the content and correctly applies the knowledge acquired, using appropriate technical language. Grade 29–30 with honors: the student possesses in-depth knowledge of the topics, a high level of critical ability, independent judgment, and full command of specialized terminology.
Examples of frequently asked questions and / or exercises
• Preclinical studies.
• Clinical studies.
• Antibiotics: beta-lactams.
• Antifungals.