CHIMICA FARMACEUTICA E TOSSICOLOGICA 1

Upon completion of the course, students are expected to possess knowledge and skills in accordance with the five Dublin Descriptors:

1.   Knowledge and understanding: Describe the fundamental concepts related to drugs, rational drug design, pharmacological targets, pharmacokinetics, and pharmacodynamics, as well as the main drug classes covered in the course. Assessment method: Questions in the written exam.

2.   Applying knowledge and understanding: Apply medicinal chemistry principles to interpret structure-activity relationships (SAR), mechanisms of action, and the ADME profiles of drugs and case studies discussed during the course. Assessment method: Questions in the written exam.

3.   Making judgements: Analyze, compare, and critically evaluate the relationships between drug structure, properties, targets, and activity, justifying conclusions based on the acquired knowledge. Assessment method: Evaluation and discussion of critical assignments.

 

4.   Communication skills: Present and discuss the structural characteristics, mechanisms of action, and structure-activity relationships of drugs using appropriate technical terminology. Assessment method: Terminological accuracy and descriptive clarity during interactive teaching sessions and guided case study discussions.

5.   Learning skills: Independently research and expand upon medicinal chemistry topics using reference textbooks and course materials. The overall learning outcomes will be assessed through a written exam and an oral interview, in accordance with the procedures outlined in the Assessment Methods section.

Delivery method: Face-to-face/traditional teaching. The course will be delivered through face-to-face classroom lectures divided into two modules:

Module I (4 CFU): The instructor will deliver 28 hours of face-to-face lectures during the first semester.

Module II (5 CFU): The instructor will deliver 35 hours of face-to-face lectures during the first and second semesters.

Should the course be delivered in a blended or distance learning format, necessary variations to the above may be introduced in order to ensure compliance with the planned program outlined in this Syllabus.

As stated in the University Teaching Regulations (RDA), Art. 12 - University Educational Credits (CFU), the standard workload of 25 hours of total student effort corresponding to one credit may include:

a) 7 hours dedicated to face-to-face lectures or equivalent educational activities, with the remaining hours devoted to independent study;

b) at least 12 and no more than 15 hours dedicated to classroom practical exercises or equivalent guided activities (laboratories), with the remaining hours devoted to personal study and revision.

Information for students with disabilities and/or SLD (Specific Learning Disabilities)

To guarantee equal opportunities and in compliance with current regulations, interested students may request a personal interview to plan any compensatory and/or dispensatory measures based on the educational objectives and specific needs. Students can contact Prof. Santina Chiechio (santina.chiechio@unict.it) in her capacity as the CInAP (Center for Active and Participatory Inclusion - Services for Disabilities and/or SLD, https://www.cinap.unict.it/content/referenti) reference professor for the Department of Drug and Health Sciences.

To successfully complete this course, fundamental knowledge of General and Inorganic Chemistry, Bioinorganic Chemistry, Pharmaceutical Biology, Microbiology, Organic Chemistry I and II, and Biochemistry is essential. Additionally, a basic understanding of Pharmacology is indispensable for undertaking the course material. This background knowledge forms the primary academic foundation required to understand drugs as chemical structures in relation to their pharmacodynamic, pharmacokinetic, and toxicological properties.

Attendance is mandatory, as established by the Academic Regulations of the Degree Program. Absences are permitted for no more than 30% of the total course hours, taking into account all forms of teaching delivery (https://www.dsf.unict.it/it/corsi/lm-13_ctf/regolamento-didattico).

Contribution to the 2030 Agenda goals: The course promotes an informed understanding of the use of medicines, drug research and development, as well as safety and toxicology aspects, in alignment with the educational objectives of the course.

 

The course consists of face-to-face classroom lectures. The course syllabus (9 CFU) is divided as follows:

Module 1 (4 CFU): General Part

General introduction to the course: What a drug is, historical background, general process of drug action.

Drug discovery and design: Overview of statistical data on the use of human medicines in Italy. Rational drug design, computer-assisted methods, molecular modeling. Phases of: hit finding, hit-to-lead, lead finding, lead optimization, structure-activity relationship (SAR) studies, modulation/modification of functional groups, modification of structural properties. Pharmacophore identification.

Structural properties and development: Structural properties of drugs. Isosterism and bioisosterism. Development phases of a new drug: preclinical phase – chemical and chemical-analytical optimization, formulation (galenic), pharmacokinetics, pharmacodynamics, toxicology, carcinogenicity, and mutagenicity studies. Clinical phase studies. Introduction to personalized medicine.

Drug properties: Physico-chemical properties in drug action. Different types of drug classification.

Phases of the drug action process: Pharmaceutical phase, pharmacokinetic phase (ADME), pharmacodynamic phase.

Pharmaceutical phase: Routes of drug administration, hepatic first-pass effect.

Pharmacokinetic phase (ADME): Drug absorption: different types of transport – active, passive, transcytosis. Distribution, factors influencing distribution, apparent volume of distribution, drug-protein binding. Metabolism: Phase I and Phase II reactions. Drug elimination and toxicity. Genetic factors influencing ADME. Prodrugs.

Pharmacodynamic phase: Drug targets: definition, types of binding, examples, and role in therapeutic action. Drug targets: proteins, enzymes, nucleic acids, other targets. Drug-target interaction. Definition of agonist and antagonist, dose-response curves, different types of dose-response curves. Haptophoric groups, pharmacophoric groups. Drug properties influencing receptor interaction: physico-chemical, stereochemical, and structural properties.

Drug classifications and regulations: Drug nomenclature. Patents. "Me-too" drugs. Off-label drugs. Orphan drugs. Therapeutic innovation and innovative drugs.

 

Module 2 (5 CFU): Systematic Part

Antibiotics: General concepts, historical background, classification, SARs, mechanism(s) of action.

Synthetic Antibacterials: General concepts, historical background, classification, SARs, mechanism(s) of action.

Antimycobacterials: General concepts, historical background, classification, SARs, mechanism(s) of action.

Antifungals: General concepts, historical background, classification, SARs, mechanism(s) of action.

Antimalarials: General concepts, historical background, classification, SARs, mechanism(s) of action.

Antivirals: General concepts, historical background, classification, SARs, mechanism(s) of action.

Antineoplastics: General concepts, historical background, classification, SARs, mechanism(s) of action.

1. G. L. Patrick, G. Costantino, Chimica Farmaceutica, Edises (2015).
2. A. Gasco, F. Gualtieri, C. Melchiorre, Chimica Farmaceutica, 2nd edition, CEA, Rozzano, Milan (2020).
3. V. F. Roche, D. A. Williams, Foye's Principi di Chimica Farmaceutica [Foye's Principles of Medicinal Chemistry], 7th ed., Piccin (2021).
4. Additional teaching material: lecture notes and slides provided during classes.

 

The assessment of learning for this course is unified and consists of two written exams designed to verify the expected learning outcomes in both modules. The first written exam includes questions and/or exercises related to the course contents, with particular focus on pharmacokinetics, pharmacodynamics, drug design, physico-chemical properties, structure-activity relationships, target interactions, as well as the structures and syntheses of the drugs covered in the syllabus. Both written exams serve to delve deeper into these contents, evaluating, in particular, the relevance and accuracy of the answers, the ability to connect different themes within the syllabus, reasoning skills, and the use of appropriate technical language. To take the exam, students must have successfully passed Organic Chemistry I.

Exam dates are published on the Pharmacy Degree Program website: https://www.dsf.unict.it/it/corsi/lm-13/calendario-esami

Evaluation Criteria

In accordance with the Dublin Descriptors, the exam evaluation considers the quality of knowledge, skills, and competencies demonstrated. It assesses the ability to analyze, integrate, and connect contents; the ability to apply knowledge to the structures, mechanisms of action, and structure-activity relationships of drug classes; mastery of technical language; clarity and logical flow of the presentation; as well as synthesis and problem-solving skills.

The final grade is expressed on a 30-point scale according to the following criteria:

Fail: The student lacks the minimum required knowledge of the core course contents. The ability to use specific terminology is highly inadequate, and the student is unable to independently apply the acquired knowledge.

18-21: Minimum knowledge of the contents, modest ability to integrate and critically analyze the presented scenarios, sufficiently clear written presentation but underdeveloped mastery of language.

22-25: Fair knowledge of the main topics, with integration and critical analysis skills that are not always consistent, and a fair mastery of language.

26-28: Good knowledge, ability to integrate and critically analyze topics in a logical manner, sufficient autonomy in problem-solving, and appropriate use of language.

29-30 cum laude: In-depth knowledge, prompt and accurate ability to integrate and critically analyze information, full autonomy in solving complex problems, and excellent communication skills with an outstanding mastery of language.

Learning assessments may also be conducted online, should conditions require it

MODULE A: Questions will focus on the pharmaceutical, pharmacokinetic, pharmacodynamic, and drug design aspects of the individual drugs or drug classes covered during lectures. These discussions may be based on an original medicinal chemistry research article analyzed and explained in class. In such instances, the article will be provided to students for reference during the exam.

 

MODULE B: Questions will require discussing the physico-chemical properties and structure-activity relationships of a drug class, as well as their interactions with specific targets and the respective mechanisms of action for the drug classes included in the syllabus. One or more questions will involve drawing the chemical structure of specific drugs, identifying a provided chemical structure, and detailing the chemical synthesis of at least two drugs explained in class.