CHIMICA FARMACEUTICA E DEI PRODOTTI NATURALI

1. Knowledge and Understanding

The student will be able to describe and explain the fundamental concepts that characterize Medicinal Chemistry.

2. Applying Knowledge and Understanding

The student will acquire the skills necessary to understand the strategies used for the discovery and design of new active ingredients, the steps required for their development into drugs, and their development into medicines. Furthermore, the student will have knowledge and understanding of the stages of action of drugs and natural substances, from administration to elimination, and the properties that influence the drug/natural substance-biophase interaction. The student will have knowledge of selected classes of drugs and natural substances and will understand how they interact with neurotransmitter receptors, intracellular receptors, enzymes, and ion channels, exploring their mechanisms of action, chemical-pharmaceutical and toxicological properties, and structure-activity relationships (SARs).

3. Making judgments

Students develop critical thinking skills in evaluating the properties of a drug or natural substance in relation to their chemical structure.

4. Communication skills

Students acquire the ability to communicate and convey what they have learned during the course using appropriate scientific language and to comment on the techniques used for drug design, synthesis, and development.

5. Learning skills

Students will develop the ability to independently locate literature and update their skills, including through the consultation of specialized databases, in the context of issues related to drug design, molecular mechanism of action, drug/natural substance-receptor interactions, toxicity, metabolism, and structure-activity relationships of the drug classes examined, particularly those of natural origin.

The course will be taught primarily through lectures, with the aid of PowerPoint presentations and online videos (DE Teaching Method). During lectures, students will be required to actively participate in discussions on the topics covered, through exercises and problem-based learning (DI Interactive Teaching Method). During the course, some classroom exercises will also be offered, structured in the same way as the exam.

According to the RDA, art. 12 - University Educational Credits (CFU), the standard 25-hour total student workload, corresponding to one credit, may include: a) 7 hours dedicated to lectures or equivalent teaching activities and the remainder to individual study; b) at least 12 hours and no more than 15 hours dedicated to classroom exercises or equivalent supervised activities (workshops) and the remainder to personal study and revision.

If teaching is taught in blended or distance learning mode, any necessary changes to what was previously stated may be introduced in order to comply with the planned program reported in the syllabus.

Prerequisites as per the study plan. A proper understanding of the topics covered in the course requires prior knowledge of General Chemistry (important), Organic Chemistry (essential), and Anatomy and Physiology (useful).

Attendance is mandatory in accordance with the teaching regulations of the Degree Course in SFA, as reported at the link: http://www.dsf.unict.it/corsi/l-29_sfa/regolamento-didattico

The course consists of 42 hours of lectures (6 credits) and 12 hours of classroom exercises (1 credit).

Attendance, as per the teaching regulations, is mandatory for at least 70% of the course lessons, assessed in all their forms.

If the course is taught in a blended or distance learning format, any necessary changes to the previously stated curriculum may be made in order to comply with the planned program and the syllabus.

GENERAL PART

Definition and objectives of Medicinal Chemistry, history and evolution. Drug discovery from natural products. Definition of a drug. Different methods for classifying drugs. ATC classification of drugs. Nomenclature of drugs. Phases of action of drugs and natural substances: pharmaceutics, pharmacokinetics, pharmacodynamics. Pharmacokinetics: absorption, distribution, metabolism (phase I and phase II), and elimination of a drug and a natural substance. Pharmacodynamics: Targets of drugs and natural substances. Drug (natural substance)-molecular target interaction: description of the different chemical bonds involved in the interaction. Receptors: G protein-coupled receptors, receptors with intrinsic enzymatic activity, ligand-gated and voltage-gated ion channels. Enzymes and enzyme inhibition, competitive and noncompetitive inhibitors. Nucleic acids. Lipids. Carbohydrates. Drug discovery, design, and development. Optimizing target interaction. Optimizing target access. Prodrugs and softdrugs. The introduction of drugs to the market.

SYSTEMATIC PART

Examples of drugs derived from natural substances (the following examples will be integrated into the lectures).

OPIOID ANALGESICS. Introduction. Morphine: structure and properties, structure-activity relationships. Opioid receptors, development of morphine analogues, agonists, antagonists.

ANTICANCER DRUGS. General information on neoplastic diseases and therapeutic approaches, classification of anticancer drugs. Plant-based anticancer drugs.

According to the RDA, art. 12 - University Educational Credits (CFU), the standard 25-hour workload of the student, corresponding to one credit, may include: a) 7 hours dedicated to lectures or equivalent teaching activities and the remaining hours to individual study; b) at least 12 hours and no more than 15 hours dedicated to classroom exercises or equivalent assisted activities (laboratories) and the remainder to personal study and reworking.

1. G.L. Patrick, Medicinal Chemistry, 3rd Italian Edition, EdiSES, Naples, 2015

2. T.L. Lemke et al., Foye's Essentials, Principles of Medicinal Chemistry, 1st Italian Edition, Piccin, Padua, 2017.

3. R.B. Silverman, M.W. Holladay., Handbook of Medicinal Chemistry, Design, Mechanism of Action, and Metabolism of Drugs. Edra

4. G. Costantino, G. Sbardella, Medicinal Chemistry, Edises University, 2024

5. Lecture Notes and Slides

The instructor provides the necessary materials for studying the topics covered, both in the classroom (or using the MS Teams platform) and through the STUDIUM platform.

The assessment consists of a written test (90 minutes) comprising multiple-choice and open-ended questions. Multiple-choice questions will be awarded a fixed score for a positive answer, zero for a negative or null answer. Open-ended questions will be awarded a variable score based on the level of detail given.

The test is designed to assess

• the level of knowledge of the basic concepts of Medicinal Chemistry (Descriptor 1);

• the fundamental aspects regarding the design, molecular mechanisms of action, and SARs of the classes of drugs and natural substances covered during the course (Descriptor 2);

• the critical ability to evaluate the properties of a drug or natural substance in relation to its chemical structure (Descriptor 3);

• the ability to communicate and convey what has been learned during the course through correct and appropriate scientific language (Descriptor 4);

• the ability to independently integrate the information learned during the course (Descriptor 5).

Assessment Criteria

The final exam will be assessed based on indicators weighted equally and consistently with those described in the expected learning outcomes (Dublin Descriptors).

Therefore, the final grade takes into account various factors listed below.

Quality of knowledge, skills, and competencies possessed and/or demonstrated:

a) appropriateness, correctness, and congruence of knowledge

b) appropriateness, correctness, and congruence of skills

c) appropriateness, correctness, and congruence of skills

Method of presentation:

a) Expressive ability

b) Appropriate use of subject-specific language;

c) Logical ability and consistency in connecting content;

d) Ability to connect different topics by identifying common ground and establishing a coherent overall design, i.e., by focusing on the structure, organization, and logical connections of the presentation;

e) Ability to synthesize, including through the use of subject-specific symbolism and the graphical expression of notions and concepts, such as formulas, diagrams, and equations.

Relational skills:

a) Willingness to exchange and interact with the instructor during the interview.

Personal qualities:

a) Critical thinking;

b) Self-assessment skills;

c) Problem-solving skills;

d) Decision-making skills.

Based on the above, the assessment may be:

Not sufficient or very insufficient (Exam failed, grade from 10 to 17):

The student does not possess the minimum required knowledge of the main content of the course. The ability to use specific language is very limited or nonexistent, and the student is unable to independently apply the acquired knowledge.

Sufficient (Grade 18-20):

The student demonstrates little knowledge acquired, a superficial level, and many gaps; Has a modest ability to integrate and critically analyze the situations presented and presents the arguments sufficiently clearly, although their command of language is poorly developed.

Fair (Grade 21-23):

The student has a fair grasp of knowledge and few gaps, but little depth; expressive skills are more than sufficient to sustain a coherent dialogue; acceptable mastery of scientific language; logical skills and consistency in connecting moderately complex arguments; more than adequate ability to summarize and acceptable graphic expression.

Good (Grade 24-26)

The student demonstrates a fairly broad knowledge base, moderate depth, with small gaps; satisfactory expressive skills and significant mastery of scientific language; clearly discernible dialogue skills and critical thinking; good ability to summarize and more than acceptable graphic expression.

Distinguished (Grade 27-29):

The student demonstrates a very broad knowledge base, well-rounded, with only minor gaps; notable expressive skills and a high command of scientific language; Presents topics clearly using appropriate language, with excellent summary and graphical expression skills.

Excellent (30 - 30 cum laude):

The student has a broad and in-depth knowledge base, excellent expressive skills, and a high command of scientific language; excellent communication skills, a strong aptitude for making connections between different topics; excellent summary skills, and excellent graphical expression skills. Cum laude is awarded to candidates who are significantly above average and demonstrate excellence in all aspects considered.

Assessment may also be conducted online, if circumstances warrant.

Information for students with disabilities and/or learning disabilities (LDs):

To ensure equal opportunities and in compliance with applicable laws, interested students may request a personal interview to plan any compensatory and/or dispensatory measures, based on their educational objectives and specific needs.

Students may also contact the CInAP (Center for Active and Participatory Integration - Services for Disabilities and/or Learning Disabilities) contact person in our Department, Professor Santina Chiechio.

Exam Dates

Exam dates are published on the Degree Program website: https://www.dsf.unict.it/it/corsi/l-29_sfa/calendario-esami

 

1.    If a substance dissolves in oil but not in water, it will likely be

• polar

• nonpolar

• ionic

• buffered

• dissociated

2.    An agonist is a substance capable of

• irreversibly blocking an allosteric site

• Binding to a receptor without activating it

• Producing a response without binding to a receptor

• Irreversibly blocking a receptor

• Binding to a receptor and activating it

3.    Phase I enzymes catalyze reactions of

• oxidation-reduction and hydrolysis

• conjugation with glucuronic acid

• phosphorylations

• conjugation with the tripeptide glutathione

• alkylation