FaF:F1CF1_15 Chemistry of Pharmaceutical Ex - Course Information

F1CF1_15 Chemistry of Pharmaceutical Excipients

Extent and Intensity

1/1/0. 3 credit(s). Type of Completion: zk (examination).
In-person direct teaching

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.
The capacity limit for the course is 24 student(s).
Current registration and enrolment status: enrolled: 0/24, only registered: 0/24, only registered with preference (fields directly associated with the programme): 0/24

fields of study / plans the course is directly associated with

• Pharmacy (programme FaF, M-FARM)
• Multidisciplinary studies at Faculty of Pharmacy (programme CST, KOS)

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.

Learning outcomes

A student will capable after passing the subject:
-to know main groups of pharmaceutical excipients from the point of view of both function and chemical structure
-to know structures and important propreties of several main representatives of each group
-to distinguish between excipients with a quatifiable activity and without it
-to know and describe quantities which are possible to use for such a activity quantification
-to know and express syntheses and mechanisms of activity of selected excipients

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

Lectures
Practical class(es) devoted to a particular group of excipients, or a seminar devoted to a QSAR or similar calculations. Particular dates and times of practical classes will be specified during the semester.

Assessment methods

With a mark
A written quiz.

Language of instruction

Czech

Further comments (probably available only in Czech)

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.

• Enrolment Statistics (Spring 2025, recent)
  
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