F1FB2_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)
doc. PharmDr. Oldřich Farsa, Ph.D. (seminar tutor)
PharmDr. Tomáš Goněc, Ph.D. (seminar tutor)
Mgr. Petr Mokrý, Ph.D. (seminar tutor)
RNDr. Eva Havránková, Ph.D. (seminar tutor)
Mgr. Veronika Murgašová (seminar tutor)
PharmDr. Magdaléna Onuščáková (seminar tutor)
PharmDr. Jan Otevřel, Ph.D. (seminar tutor)
Guaranteed by
doc. PharmDr. Oldřich Farsa, Ph.D.
Department of Chemical Drugs – Departments – Faculty of Pharmacy
Supplier department: Department of Chemical Drugs – Departments – Faculty of Pharmacy
Timetable
Wed 7:50–9:20 44-056, Wed 11:30–12:30 44-056
  • Timetable of Seminar Groups:
F1FB2_15/01: each odd Monday 12:00–20:20 44-246, except Mon 18. 12., except Mon 1. 1., P. Mokrý, M. Onuščáková
F1FB2_15/02: each even Monday 12:00–20:20 44-246, P. Mokrý, M. Onuščáková
F1FB2_15/03: each odd Tuesday 7:50–16:10 44-246, except Tue 19. 12., except Tue 2. 1., O. Farsa, V. Murgašová
F1FB2_15/04: each even Tuesday 7:50–16:10 44-246, E. Havránková, J. Otevřel
F1FB2_15/05: each odd Friday 7:50–16:10 44-246, E. Havránková, V. Murgašová
Prerequisites
F1FB1_15 Medicinal Chemistry I
Passing Medicinal Chemistry I finished with the credit.
Course Enrolment Limitations
The course is only offered to the students of the study fields the course is directly associated with.

The capacity limit for the course is 160 student(s).
Current registration and enrolment status: enrolled: 120/160, only registered: 0/160
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 physicochemical properties, space arrangement, and further structure features on the activity of a drug. It concerns in detail with mechanisms of drug interactions 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 pharmaceutical 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 qualitative 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 overview of fundamental structural types and tries to grasp the main structure-activity relationships within each group. It also reports the syntheses and metabolic 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 - autumn semester of the 3rd year of study
    Syllabi identical with topics of particular lectures:
    Lecture No. Topic Name of the lecturer)
    1.Antibacterial chemotherapeutics: sulphonamides, 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. (Farsa)
    4.Antiviral agents, liver protectants. (Farsa)
    5.Disinfectants, antiseptics, antiparasitics: antiprotozoal and vermicide agents, insecticides. (Farsa)
    6.Diuretics, cholagogues, cholelitholytics, laxatives, antidiarrheals. (Farsa)
    7.Drugs that control blood clotting. Antihyperlipidemics. (Csöllei)
    8.Cardiotonics, coronary vascular dilators. Drugs improving heart perfusion. (Csöllei)
    9.Anti-arrhytmics, antihypertensive agents, drugs for the treatment of erectile dysfunction. (Csöllei).
    10.Drugs affecting respiratory tract: acids, antacids, anti ulcerative agents: antisecretory agents, histamine H2-receptors antagonists, H+/K+-ATPase inhibitors, gastric cytoprotectants, drugs fighting Helicobacter pylori. (Csöllei)
    11.Antineoplastics. (Farsa)
    12.Insulin and its analogs, synthetic antidiabetics. Hormones derived from one amino acid, thyreostatics, peptide hormones, steroid hormones, anabolic agents.
    13.Biologic therapeutic agents (biologics: therapeutic monoclonal antibodies, therapeutic enzymes, antisense oligonucleotides, etc.) (Farsa)
    Syllabi of practical courses
    1.A short recommendation of principles of work safety and fire prevention. Sulfacetamide: synthesis, identity, confirmation by 1H-NMR.
    2.Lidocaine: synthesis, identity and purity confirmation by melting point, NMR or IR spectroscopy and TLC.
    3.Parabens (methyl-, ethyl-, propyl-, isopropyl- or isobutylparaben): synthesis, identity and purity confirmation by melting point and 1H-NMR spectroscopy.
    4.Acetylsalicylic acid: synthesis, identity, and purity confirmation by melting point and TLC, purity by HPLC.
    5.Phenytoin: synthesis, identity, and purity confirmation by melting point and/or NMR spectroscopy. Alternative: Methylthiouracil: synthesis, TLC.
    6.Determination of the acid dissociation constant of nitrofurantoin or phenytoin 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 reports, and entering tests are possible.
    Requirements to allow to do the exam: 100% attendance, handing-over of reports, and prepared compounds including their characterization data (melting points, chromatograms, spectra interpretaions), at least 60% success in tests.

Literature
    recommended literature
  • J. Hartl, K. Palát: Farmaceutická chemie I (obecná). Karolinum, Praha, 2016, ISBN 9788024620336, dostupné z e-shopu https://www.cupress.cuni.cz
  • Beneš, L., Farsa, O. Farmaceutická chemie. (Farmakochemie). Úvod do studia chemických léčiv. VFU Brno, 2005. ISBN 80-7305-516-3. info
  • J. J. Li: Medicinal Chemistry for Practitioners. John Wiley & Sons Inc, 2021, ISBN 9781119607304, dostupné zdarma přes https://z-lib.org/
  • DOLEŽAL, Martin. Farmaceutická chemie : léčiv působících na kardiovaskulární, trávicí a vylučovací systém. První vydání. Praha: Univerzita Karlova, vydavatelství Karolinum, 2022, 317 stran. ISBN 9788024651026. info
  • Hartl J. a kol. Farmaceutická chemie IV (dezinf., antisept., antimykotika, antiprotozoika, chemoterapeutika antibakteriální, antivirotika, chemoterapeutika nádorového bujení). info
  • DOLEŽAL, Martin. Farmaceutická chemie léčiv působících na centrální nervový systém. Vydání 1. Praha: Karolinum, 2013, 188 stran. ISBN 9788024623825. info
  • V. Alagarsamy: Textbook of medicinal chemistry. / Volume I. Elsevier, 2010, ISBN 978-81-312-2189-1, dostupné zdarma přes https://z-lib.org/ ; též obecné kapitoly
  • V. Alagarsamy: Textbook of medicinal chemistry. / Volume II. Elsevier, 2012, ISBN: 978-81-312-2190-7, dostupné zdarma přes https://z-lib.org/
  • Borovanský A., Csöllei J. Farmaceutická chemie (Farmakochemie). IV. Léčiva s účinkem na kardiovaskulární systém, VFU Brno 2001. info
  • Borovanský A., Csöllei J. Farmaceutická chemie.(Farmakochemie) V. Léčiva s účinkem na respirační, gastrointestinální a vylučovací trakt. info
  • Beneš L. Biofarmaceutika (Bioléčiva) Chem. listy 101, 18 - 24 (2007). URL info
Teaching methods
Lectures, practical lessons.
Assessment methods
Successfull passing of practical lessons based on full attandance, goving of products, reports and a success in final test; oral exam from the topics of lectures.
Language of instruction
Czech
Further comments (probably available only in Czech)
Study Materials
The course can also be completed outside the examination period.
Teacher's information
Requirements on the successful passing of the practical lessons (= a condition of doing exam): 100% attendance, giving of complete reports including prepared compounds together with their characteristic (chromatography, spectra), at least 60% success in tests.
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/F1FB2_15