F1CF1_15 Chemistry of Pharmaceutical Excipients

Faculty of Pharmacy
Spring 2020
Extent and Intensity
1/1/0. 2 credit(s). Type of Completion: zk (examination).
Teacher(s)
doc. PharmDr. Oldřich Farsa, Ph.D. (lecturer)
doc. PharmDr. Oldřich Farsa, Ph.D. (seminar tutor)
Guaranteed by
doc. PharmDr. Oldřich Farsa, Ph.D.
Department of Chemical Drugs – Departments – Faculty of Pharmacy
Prerequisites
The discipline is prinarilly intended for students of the 3rd year od study. Despite of it, all who have successfully passed exams in general and inorganic and organic chemistry can pass through this discipline without major problems.
Course Enrolment Limitations
The course is also offered to the students of the fields other than those the course is directly associated with.
fields of study / plans the course is directly associated with
Course objectives
Pharmaceutical excipients are inorganic or organic compounds, which are necessary
for formulation of medicinal preparations suitable for direct aplication to a
patient, although, they are not holders of any pharmacological activity. In the study
program of pharmacy in the Czech Republic, such substances are the matter of interest
predominantly from the point of view of their use in application forms, and from
the point of view of physico-chemical properties related to it. Pharmaceutics, in the
middle Europe often called pharmaceutical technology or galenic pharmacy, is the
discipline which deals with them applying such approaches. Medicinal chemistry had
been marginally interested in structures, syntheses and partially structure-activity relationships
of some selected classes of excipients like preservatives, colorants and
sweeteners and appropriate chapters in older textbooks of medicinal chemistry had
been also devoted to them but increasing number of chemical drugs crowded out
stepwisely these topics. Indeed, neither any of these above mentioned nor other discipline
offers a comprehensive view to chemical structures, synthetic ways and typical
analytical procedures of these compounds. It is in contradiction to the fact that most
of modern pharmacopeias have for excipients the same requierements on purity as
for active ingredients. Chemistry of pharmaceutical excipients could be a discipline
capable to fill out this blank and build a bridge between pharmaceutics on one side and medicinal chemistry together with pharmaceutical analysis on another one. It will also
have a small overlap with margins of pharmacognosy in fields of natural sweeteners,
dyes and antioxidants.
Syllabus
  • The topics of 6 two hours lectures are as follows:
    1. Circumscription of the concept of pharmaceutical excipients. Their fundamental
    division from the points of view of their usage and structure. Compounds
    at the border between drugs and excipients.
    2. Compounds enhancing disintegration of tablets. Stabilizers of physico-chemical
    properties of dispersion systems: viscosity-increasing, emulsifying and suspending
    agents. Oligo- and polysacharides and their semisynthetic derivatives.
    (Starch, alkylated starches, cellulose, cellulose ethers and esters,
    cyclodextrines). Specific methods of their pharmacopeial analysis including
    applications of NMR spectroscopy. (Determination of substitution grade of
    hydroxypropylbetadex, i.e. hydroxypropyl- alpha-cyclodextrine according to European
    and Czech pharmacopeias.
    3. Stabilizers of chemical composition of medicinal preparations: antioxidants
    (inorganic and organic compounds suitable for either hydrophilic or hydrophobic media), antimicrobial and antifungal preservatives (organic compounds
    containing heavy metals in their molecules, phenolic compounds including a
    homologic series of parabens (nipagins), carboxylic acids, quarternary ammonium
    salts, aldehydes and their precursors). Dependence of activity of
    preservatives on pH. Structure-activity relationships including selected QSAR regression models, syntheses of principal compounds.
    4. Selected compounds controling bioavailability of drugs. Transdermal, buccal
    and gastro-intestinal penetration enhancers. (Percutaneous permeation
    accelerants, which have been beeing most widely studied, are accentuated.)
    Overview of basic structural groups, proposed and particularly evidenced
    mechanisms of their actions, special demands of enhancers used in topical
    application forms, methods of determination and quantitative expression of
    their activity.
    5. Compounds triming taste and flavour of medicinal preparations.
    Sweeteners of natural origin: carbohydrates, alcoholic sugars, glycosides useful
    as sweeteners. Alternate sweeteners: basic structural types, their toxicity,
    syntheses of some principal compounds. Quantitative expression of sweetening ability, its relationship to structure. Volatile compounds of both natural and
    synthetic origin suitable as odour regulating agents.
    6. Colour corrigentia ? pharmaceutical dyes and colouring agents. Specific methods of analysis of colour substances. Quantitative description of a colour in
    CIE L*a*b* system and similar systems according to USP Chapter 1061,
    "Color ? instrumental measurement."3) Overview of approved dyes of both
    natural and synthetic origin, their toxicity, lipohilicity and spectral properties
    (absorption extremes). Structure-colour relationships of anthocyanines.
    The topics of two 4-hours sections of laboratory are as follows:
    1. Synthesis of an antimicrobial preservative ? paraben with longer and/or branched
    alkyl chain. (Alternative: synthesis of an artificial sweetener ? sacharine.)
    2. Analysis of pharmaceutical colorants. Quantitative description of a colour in
    CIE L*a*b* system and evaluation of purity and
    homogenity of colour substances (for better exploitation of time, the work on
    both topics overlaps).
Literature
    required literature
  • Rowe R. et al. Handbook of pharmaceutical excipients. London, 2005. info
    recommended literature
  • Hrabálek A., Doležal P., Šklubalová Z., Farsa O., Krebs A. Akceleranty transdermální penetrace. Chem. listy 93, 107-119 (1999). URL info
  • Šubert J., Čižmárik J. Využití instrumentálního měření barevnosti ve vývoji a v kontrole jakosti léčiv. Chem. listy 101, 55-59 (2007). URL info
  • Farsa, O. PHARMACEUTICAL EXCIPIENTS FROM THE POINT OF VIEW OF A MEDICINAL CHEMIST. Khimyia/Chemistry 18, 165-171 (2009). Sofia, 2009. URL info
  • Auterhoff H., Knabe H. J., Höltje H. D. Lehrbuch der Pharmazeutischen Chemie. Stuttgart, 1999. info
  • Melichar B. et al. Chemická léčiva. Praha, 1987. info
Teaching methods (in Czech)
Přednášení
Laborování
Assessment methods (in Czech)
Známkou
Písemná zkouška
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
Attendance in all practical classes, passing of syntheses products on, processing of all topics of practical classes in the form of laboratory reports ("protocols"), knowledge of the contents of lectures.
The course is also listed under the following terms Spring 2021, Spring 2023, Spring 2024, Spring 2025.
  • Enrolment Statistics (Spring 2020, recent)
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