F1CL1_15 Basics of Chemical Drugs

Faculty of Pharmacy
Autumn 2021
Extent and Intensity
2/1/0. 4 credit(s). Type of Completion: zk (examination).
Teacher(s)
prof. RNDr. Jozef Csöllei, CSc. (lecturer)
Mgr. Petr Mokrý, Ph.D. (lecturer)
Mgr. Petr Mokrý, Ph.D. (seminar tutor)
Guaranteed by
Mgr. Petr Mokrý, Ph.D.
Department of Chemical Drugs – Departments – Faculty of Pharmacy
Supplier department: Department of Chemical Drugs – Departments – Faculty of Pharmacy
Timetable
Tue 10:40–12:20 44-056
  • Timetable of Seminar Groups:
F1CL1_15/02: each odd Tuesday 16:25–18:05 45-224
F1CL1_15/03: each even Tuesday 14:30–16:10 45-224
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.

The capacity limit for the course is 120 student(s).
Current registration and enrolment status: enrolled: 21/120, only registered: 0/120
fields of study / plans the course is directly associated with
Course objectives
The course Basics of chemical drugs will enable students to combine their knowledge of Organic chemistry with the basic principles of Medicinal chemistry. The aim is to provide students with general knowledge about the chemical structure of drugs and the effect of structural modifications on the biological effect.
The lectures focus on nomenclature principles of synthetic drugs, structural factors influencing the biological activity of drugs and modification of their structure using the principles of isomerism, homology and analogy. The separate part is represented by the lectures about selected active fragments and heterocyclic structures occurring in several pharmacological groups.
The seminar part offers the overview of synthetic reactions leading to the formation of selected compounds, used as drugs or as their intermediates.
Learning outcomes
After completing the course, a student will be able to:
- describe the basic principles of drug structure modification;
- predict how changes in physicochemical properties, spatial arrangement or other structural factors will affect drug activity;
- describe basic methods of biologically active substances preparation ;
- design partial synthetic steps for the preparation of simple organic compounds.
Syllabus
  • Lectures:
  • 1. Definition and characterization of the subject, nomenclature of organic compounds, nomenclature principles of chemical drugs.
  • 2. Structural factors influencing the biological activity of drugs – hydrocarbon component and nitrogen-containing functional groups.
  • 3. Structural factors influencing the biological activity of drugs – oxygen-containing functional groups and organic sulfur compounds.
  • 4. Structural modifications of drugs – alkyl and alkylene homology.
  • 5. Structural modifications of drugs – analogy – hydrogenation and dehydrogenation, alkyl and radical analogy.
  • 6. Structural modifications of drugs – analogy – isostery, analogy of functional groups, cyclic and ring analogy, models and doubling of molecules.
  • 7. Structural modifications of drugs – chain isomerism, positional and geometric isomers.
  • 8. Structural modifications of drugs – stereoisomerism, optical isomers.
  • 9. Structural modifications of drugs – temporary changes in the drug properties.
  • 10. Phenylalkylamine structure in several pharmacological groups.
  • 11. Aromatic-aliphatic structural fragment in several pharmacological groups.
  • 12. Derivatives of 4-aminobenzenesulfonic acid, beta-lactams and polycyclic aromatic compounds as the drug structure basis.
  • 13. Five- and six-membered heterocycles with one or more heteroatoms as the drug structure basis.
  • Seminars:
  • 1.-2. Carbon-carbon bond forming reactions - Friedel-Crafts reactions, alkylation of active hydrogen compounds, Gattermann reaction, Grignard reaction, Wurtz-Fittig reaction, halogenalkylation (chloromethylation), Kolbe-Schmitt reaction. Synthesis: adrenaline, chlorprothixene, barbital, thiopental, fenipentol, fluconazole, amphetamine, mesalazine
  • 3. Carbon-hydrogen bond forming reactions - reduction of multiple bonds carbon-carbon, dehalogenation, dehydroxylation, deamination, decarboxylation, desulfonylation. Synthesis: terazosin, adiphenine, valproic acid, propofol
  • 4. Carbon-halogen bond forming reactions - substitution reactions (halogenation of alkanes, cycloalkanes and aromatic compounds, substitution of halogen and hydroxy derivatives), addition reaction of carbon-carbon multiple bonds. Synthesis: chloroxine, diphenhydramine, cinchocaine, atropine
  • 5. Carbon-oxygen bond forming reactions - preparation of alcohols, phenols, ethers, carbonyl compounds, carboxylic acids, esters and lactones. Synthesis: gentisic acid, bisacodyl, sodium picosulfate, metoprolol, isoflurane, isoniazid, diclofenac, warfarin
  • 6. Carbon-nitrogen bond forming reactions - preparation of amines, nitro and azo compounds, amides, lactams and hydrazides. Synthesis: trimecaine, chlorambucil, metoprolol, benzocaine, paracetamol, piracetam, isoniazid
Literature
    recommended literature
  • J. SVOBODA. Organická syntéza. Praha: Vysoká škola chemicko-technologická v Pra, 2017. ISBN 978-80-7080-990-7. info
  • F. HAMPL, S. RÁDL, J. PALEČEK. Farmakochemie. 3. vydání. Praha: Vysoká škola chemicko-technologická v Pra, 2015. ISBN 978-80-7080-875-7. info
  • J. MCMURRY. Organická chemie. Brno: Vysoké učení technické v Brně, nakladatels, 2015. ISBN 978-80-214-4769-1. info
  • L. BENEŠ, O. FARSA. Farmaceutická chemie (Farmakochemie): Úvod do studia chemických léčiv. Brno: Veterinární a farmaceutická univerzita Brn, 2005. ISBN 80-730-5516-3. info
  • M. DOLEŽAL. Technologie syntetických léčiv. Praha: Karolinum, 1999. ISBN 80-7184-984-7. info
Teaching methods
lectures – explanation
seminars – explanation and practice (examples solving)
Assessment methods
- 100% attendance at seminars required
- credit test (at least 60 % of the points)
- written exam
Language of instruction
Czech
Further Comments
Study Materials
The course can also be completed outside the examination period.
The course is also listed under the following terms Autumn 2020, Autumn 2022, Autumn 2023, Autumn 2024.
  • Enrolment Statistics (Autumn 2021, recent)
  • Permalink: https://is.muni.cz/course/pharm/autumn2021/F1CL1_15