FAFB2_15 Medicinal Chemistry II

Faculty of Pharmacy
Autumn 2023
Extent and Intensity
3/5/0. 11 credit(s). Type of Completion: zk (examination).
Teacher(s)
prof. RNDr. Jozef Csöllei, CSc. (lecturer)
doc. PharmDr. Oldřich Farsa, Ph.D. (lecturer)
PharmDr. Tomáš Goněc, Ph.D. (lecturer)
prof. RNDr. Jozef Csöllei, CSc. (seminar tutor)
doc. PharmDr. Oldřich Farsa, Ph.D. (seminar tutor)
Mgr. Aleš Kroutil, Ph.D. (lecturer)
Guaranteed by
doc. PharmDr. Oldřich Farsa, Ph.D.
Department of Chemical Drugs – Departments – Faculty of Pharmacy
Timetable
Mon 8:00–10:30 44-037
  • Timetable of Seminar Groups:
FAFB2_15/01: each even Thursday 11:15–19:35 44-246, O. Farsa
Prerequisites (in Czech)
FAKULTA(FaF) || OBOR(MUSFaF)
Course Enrolment Limitations
The course is only offered to the students of the study fields the course is directly associated with.
fields of study / plans the course is directly associated with
Course objectives
Medicinal Chemistry (MC) is a discipline dealing mainly with relationships between chemical structure and therapeutic activity of medicines which are mostly organic but also inorganic molecules. That is why it observes the impact of physico-chemical properties, space arrangement and further structure features on the activity of a drug. It concerns in detail with mechanisms of drug intearactions with target structures such as receptors´ or enzyme active sites. As a scientific discipline, MC participates importantly in the drug design and development process. As a specific discipline of the pharmacetical study, MC is one of five stem subjects in which students do the state final exam. Here, MC can be divided into general and special parts. General MC presents general aspects of structure-activity relationships, both qulitative and quantitative, as well as common principles of derivation and proposal of structures of new medicines (analogy, homology, isomerism, isosterism...). Systematic MC deals then with the particular therapeutic groups of drugs respecting the system used in pharmacology. Here, it brings a comprehensive overwiev of fundamental structural types and tries to grasp main structure-activity relationships within each group. It also reports syntheses and methabolic pathways of some representatives of these groups. Simply said, MC builds some type of bridge between fundamental chemical disciplines, represented mainly by organic chemistry, and pharmacology.
Learning outcomes
Every student will, after passing the subject, be capable to characterize the main groups of drugs; their main common structural characteristics if they exist; structure-activity relationships (SAR) inside narrower structural groups; their acido-basic and lipo-hydrophilic properties based on the structure; their general mechanisms of activity; particular examples of drugs in use or development from every structural group together with the exact structure or at least with main structure features in more complex molecules.
Syllabus
  • Medicinal Chemistry II (FAFB2)
    (English Master study programme)
    3rd year of study
    Syllabi identical with topics of particular lectures:
    Lecture No. Topic (Name of the lecturer)

    1. Antibacterial chemotherapeutics: sulfonamides, quinolones, nitrofurans, tetracyclines. (Farsa)
    2. Antibacterial chemotherapeutics continued: beta-lactam antibiotics: penicillins and cephalosporins, (poly)peptide antibiotics, aminoglycoside antibiotics, macrolide antibiotics, antibiotics of various other structures. (Farsa)
    3. Tuberculostatics, leprostatics. Antiviral agents, liver protectants. (Farsa)
    4. Disinfectants, antiseptics, antiparasitics: antiprotozoal and vermicidal agents, insecticides. (Farsa)
    5. Diuretics, cholagogues, cholelitholytics, laxatives, anti-diarrhoeics. (Farsa)
    6. Antineoplastic agents. (Kroutil)
    7. Drugs that control blood clotting. Antihyperlipidemics. (Goněc)
    8. Cardiotonic drugs, coronary vascular dilators. Drugs improving heart perfusion. (Goněc)
    9. Anti-arrhythmics, drugs for the treatment of erectile dysfunction. (Goněc).
    10. Anti-hypertensive drugs. (Goněc)
    11. Insulin and its analogs, synthetic anti-diabetics. Hormones derived from the single amino acid, thyreostatics, peptide hormones. (Farsa)
    12. Drugs affecting gastrointestinal tract: acids, antacids, anti-ulcerative agents: antisecretory agents, histamine H2-receptor antagonists, H+/K+-ATPase inhibitors, gastric cytoprotectants, drugs fighting Helicobacter pylori (Goněc)
    13. Steroid hormones, anabolic agents. Biologic therapeutic agents (biologics: therapeutic monoclonal antibodies, soluble receptor molecules, therapeutic enzymes, antisense oligonucleotides, etc.) (Farsa)

    doc. PharmDr. Oldřich Farsa, Ph.D.

    Syllabi of practical courses
    1. A short reminder of the principles of work safety and fire prevention. Organization instructions. Sulfacetamide: synthesis, identity by 1H-NMR, purity by TLC. An alternative: calcium dobesilate: synthesis, identity and purity confirmation by UV-VIS spectrophotometry.
    2. Lidocaine: synthesis, identity and purity confirmation by melting point, IR spectroscopy and TLC.
    3. Acetylsalicylic acid: synthesis, identity and purity confirmation by melting point and TLC, purity by HPLC.
    4. Phenytoine: synthesis, identity and purity confirmation by 1H and 13C-NMR spectroscopy. ) Alternative: Methylthiouracil: synthesis, TLC.)
    5. Parabens (methyl-, ethyl-, propyl-, isopropyl- or isobutylparaben): synthesis, identity and purity confirmation by melting point and 1H-NMR spectroscopy.
    6. Determination of the acid dissociation constant of phenytoine (or nitrofurantoin) by means of UV-VIS spectrophotometry. Final test.
    7. An eventual substitute course and/or a repeated final test.
    Continuous checking of study: attendance, observing of protocols at the end of every lesson, tests are possible and can occur at any time during the semester without any preliminary warning.
    Credit requirements: 100% attendance, handing-over of reports and prepared compounds including their characterization data (melting points, chromatograms, NMR and/or IR spectra excerpts), at least 60% success in tests.
    Teachers: doc. PharmDr. Oldřich Farsa, Ph.D., PharmDr. Tomáš Goněc, Ph.D.
    Laboratory assistant: Anna Sedláčková

    doc. PharmDr. Oldřich Farsa, Ph.D.
Literature
    recommended literature
  • J. J. Li: Medicinal Chemistry for Practitioners. John Wiley & Sons Inc, 2021, ISBN 9781119607304, available for free at https://z-lib.org/
  • V. Alagarsamy: Textbook of medicinal chemistry. / Volume I. Elsevier, 2010, ISBN 978-81-312-2189-1, available for free at https://z-lib.org/ ; including general chapters
  • V. Alagarsamy: Textbook of medicinal chemistry. / Volume II. Elsevier, 2012, ISBN: 978-81-312-2190-7, available for free at https://z-lib.org/
  • Fischer János, Ganelin C. Robin. Analogue-based Drug Discovery. Weinheim, 2006. ISBN 3-527-31257-9. URL info
  • Fischer János, Ganelin C. Robin. Analogue-based Drug Discovery II. Wiley and Sons, Weinheim, 2010. ISBN 978-3-527-32549-8. Available for free from https://z-lib.org
  • Fischer János, Ganelin C. Robin, Rotella David P.. Analogue-based Drug Discovery III. Wiley and Sons, Weinheim, 2013. ISBN 978-3-527-33073-7. Available for free from https://z-lib.org
  • Wermuth Camille Georges. The practice of Medicinal Chemistry. Third Edition. Amsterdam, 2008. info
  • Kar Ashutosh. Medicinal Chemistry. Third edition. Tunbridge Wells, UK, 2006. info
  • Ng Rick. Drugs: From Discovery to Approval. Second Edition. 2009. ISBN 978-0-470403587. URL info
  • Vardanyan R. S., Hruby V. J. Synthesis of Essential Drugs. Amsterdam, 2006. ISBN 978-0-444-52166-8. URL info
  • Sneader, W. Drug Discovery - A History. 2005. ISBN 9780470015520. URL info
Teaching methods
Lectures
Laboratory work
Assessment methods
A grade
A written exam
Language of instruction
English
Further comments (probably available only in Czech)
Study Materials
The course can also be completed outside the examination period.
Teacher's information
Requirements for the credit: 100% attendance in practical classes, handover of both products and complete laboratory reports including required identification of products (chromatograms, spectra). Minimum 60% success in tests.
Requirements for the exam: knowledge of structures and structure-activity relationships in required range, knowledge of general topics and mainly understanding to the given matter.
The course is also listed under the following terms Autumn 2020, Autumn 2021, Autumn 2022, Autumn 2024.
  • Enrolment Statistics (Autumn 2023, recent)
  • Permalink: https://is.muni.cz/course/pharm/autumn2023/FAFB2_15