Assays and methods of analysis of the Pharmacopoeias and lab of drug identification

A.Y. 2019/2020
12
Max ECTS
128
Overall hours
SSD
CHIM/08
Language
Italian
Learning objectives
The main objective of the teaching (U.D. Assays and Analytical Methodologies of Pharmacopoeias) is to furnish the basic and specific information in the field of quality control of drugs and of their formulations. In detail, the teachers will provide a wide account of the chemical and instrumental methodologies used for the structural characterization and the quantitative analysis of drugs and excipients encoded in the European Pharmacopoiea (EP), for determination of their impurities, and for the stability studies. In addition, the knowledge necessary for the isolation and purification of the analyte of interest from complex matrices (sample preparation) is provided. Finally, the teaching highlights the analytical principles required for the quality control of herbal drugs and their derivatives (extracts and essential oils) according to EP, and for the chemical/instrumental characterization of their active principles.
The U.D. Laboratory of Drugs Identification (individual and obligatory experimental training) provides students with the ability to identify unknown substances encoded in EP through the application of chemical and instrumental methodologies. These skills are essential to pass the practical tests of the State Examination for the qualification to the profession of Pharmacist.
Expected learning outcomes
1.Knowledge of the main physico-chemical properties of drugs based on their chemical structure
2.Theoretical and applied knowledge of UV-VIS and IR spectroscopic techniques
3.Identification of drugs registered in the European Pharmacopoeia on the basis of chemical and instrumental methodologies
4.Ability to analyze and solve problems related to the resolution of mixtures (pharmaceutical forms) and the chemical and instrumental identification of active ingredients and excipients
Course syllabus and organization

Linea AL

Responsible
Lesson period
year
Course syllabus
PROGRAM OF THE MODULE: ASSAYS AND ANALYTICAL METHODOLOGIES OF PHARMACOPOEIAS
1) Chemical Analysis of drugs in EP
- Principles of pharmaceutical analysis
- Differentiation between organic, organometallic and inorganic substances
- Solubility
- Elemental analysis
- Chemical reactivity and functional group analysis: alkenes and alkynes, aromatic compounds, conjugated systems, alcohols, ethers, phenols, carbonyl compounds, carboxylic acids, esters, amides, amines, nitro compounds, sulfonic acids and sulfonyl compounds.
- Identification assays for amino acids and proteins, alkaloids, local anaesthetics, antibiotics, barbiturates, carbohydrates and glycosyl derivatives, steroids, sulfonamides, vitamins.
- Identification assays applied to specific drugs.
- Identification of active principles in complex matrices
- Quality control of plant drugs and their derivatives (phytoextracts)
- Assays and purity criteria for essential oils
- Determination of the alcohol content in hydroalcoholic phytoextracts

2) Instrumental analysis: principles and application to drug identification/quantitation
- Solvent extraction, partition coefficient
- Determination of the physical constants: melting point, density, refractometry and refractive index, polarimetry and determination of the specific rotation
- Cromatographic methods: Liquid-solid and liquid-liquid chromatography. Thin layer chromatography (TLC); gaschromatography (GC); high performance liquid chomatography (HPLC);
- Exclusion, affinity and ion exchange chromatography.
- Sample preparation: application of extraction and chromatographic methods
- Electrophoretic methods
- Spectroscopic methods: UV/Visible, fluorescence and infrared spectroscopy
- Guidelines for the choice and application of the more appropriate technique to solve different analytical problems.


PROGRAM OF THE MODULE: LABORATORY OF DRUGS IDENTIFICATION
- General scheme of analysis of drugs and pharmaceutical excipients listed in EP
- Combustion assay for differentiating organic, metallo-organic and inorganic compounds
- Identification of organic compounds
a) Elemental analysis (identification of nitrogen, sulfur, halogens, phosphorus); solubility according to EP; tests for identification of functional groups.
b) Qualitative assays for identification of classes of compounds: sugars, sulphonamides, alkaloids, aminoacids
c) Determination of melting point
- Identification of inorganic compounds
a) Solubility
b) Analysis of water-soluble and acid-soluble inorganic compounds (pH measurement, tests for identification of cations according to the periodic system and of anions)
c) Analysis of water- and acid-insoluble compounds
- Identification of metallo-organic compounds: analysis of the inorganic and organic portions according to the methods and criteria above reported.
- Identification of unknown inorganic, metallo-organic and inorganic compounds.
Prerequisites for admission
Attendance at the courses of the previous years, with particular reference to all chemical courses (analytical chemistry, inorganic chemistry, organic chemistry, pharmaceutical chemistry, analysis of inorganic substances of pharmaceutical use and laboratory of qualitative analysis, principles of quantitative pharmaceutical analysis and laboratory of quantitative analysis).
Teaching methods
MODULE: ASSAYS AND ANALYTICAL METHODOLOGIES OF PHARMACOPOEIAS
The teaching method is formally traditional, as it is based on slide projection in class (slides can be downloaded by the Ariel Platform). In addition, several analytical exercises are solved in class to provide the students the ability to pass the final exam and to better understand the theoretical aspects.

MODULE: LABORATORY OF DRUGS IDENTIFICATION
This module consists in two sections. In details, the first one involves lectures dealing lab procedures to be adopted in order to identify compounds described in the European Pharmacopoeia. These lectures are followed by experimental training on known substances, in order to get familiar with the procedures. The second section is dedicated to experimental training on unknown compounds that students are asked to identify.
Bibliography
1. R. Cozzi, P. Protti, T. Ruaro, Analisi Chimica Strumentale. II Edizione. Zanichelli Ed., Bologna (2001).
2. Materials provided by the teacher (available on Ariel platform).
3. Farmacopea Europea
4. V. Cavrini, V. Andrisano. Principi di Analisi Farmaceutica. III edizione. Società Editrice Esculapio srl., Bologna (2013).
5. F. Savelli, O. Bruno, Analisi Chimico Farmaceutica. Ed. Piccin (2005)
6. A. Carta, M.G. Mamolo, F. Novelli, S. Piras. Analisi Farmaceutica Qualitativa. EdiSES srl, Napoli (2011).
Information about the course, teaching materials and notices to students can be found on the Ariel platform of Unimi at the following address https://mcarinismaf.ariel.ctu.unimi.it/v5/home/Default.aspx
Assessement methods and criteria
The Laboratory unit does not provide for an examination test, but a frequency recognition, which is granted only if the student has correctly performed at least 75% of the unknown analyses. The examination, for which there are no ongoing tests, consists of a written test, divided into 2 or 3 questions (one of which is divided into 4 or 3 subquestions respectively). The test requires the answer to questions both of application type (with contents and difficulties similar to those faced in classroom exercises and for which the solution is allowed to consult tables) and of theoretical type. Students are required to answer within a maximum time of two hours. Each question/sub-question is assigned a score based on the complexity of the answer, the sum of which constitutes the final grade expressed in 30/30.
Unità didattica: Laboratorio di identificazione dei farmaci
CHIM/08 - PHARMACEUTICAL CHEMISTRY - University credits: 4
Single bench laboratory practical: 64 hours
Professor: Carini Marina
Shifts:
Turno 1
Professor: Carini Marina
Unità didattica: Saggi e metodologie analitiche delle farmacopee
CHIM/08 - PHARMACEUTICAL CHEMISTRY - University credits: 8
Lessons: 64 hours
Professor: Carini Marina

Linea MZ

Responsible
Lesson period
year
Course syllabus
Assays and Analytical Methodologies of Pharmacopoeias program:
1) Chemical Analysis of drugs in EP
- Principles of pharmaceutical analysis
- Differentiation between organic, organometallic and inorganic substances
- Solubility
- Elemental analysis
- Chemical reactivity and functional group analysis: alkenes and alkynes, aromatic compounds, conjugated systems, alcohols, ethers, phenols, carbonyl compounds, carboxylic acids, esters, amides, amines, nitro compounds, sulfonic acids and sulfonyl compounds.
- Identification assays for amino acids and proteins, alkaloids, local anaesthetics, antibiotics, barbiturates, carbohydrates and glycosyl derivatives, steroids, sulfonamides, vitamins.
- Identification assays applied to specific drugs.
- Identification of active principles in complex matrices
- Quality control of plant drugs and their derivatives (phytoextracts)
- Assays and purity criteria for essential oils
- Determination of the alcohol content in hydro-alcoholic phytoextracts

2) Instrumental analysis: principles and application to drug identification/quantitation
- Solvent extraction, partition coefficient
- Determination of the physical constants: melting point, density, refractometry and refractive index, polarimetry and determination of the specific rotation
- Chromatographic methods: Liquid-solid and liquid-liquid chromatography. Thin layer chromatography (TLC); gas-chromatography (GC); high performance liquid chromatography (HPLC);
- Exclusion, affinity and ion exchange chromatography.
- Sample preparation: application of extraction and chromatographic methods
- Electrophoretic methods
- Spectroscopic methods: UV/Visible, fluorescence and infrared spectroscopy
- Guidelines for the choice and application of the more appropriate technique to solve different analytical problems.


Laboratory of Drugs Identification program:
General scheme of analysis of drugs and pharmaceutical excipients listed in EP
- Combustion assay for differentiating organic, metal-organic and inorganic compounds
- Identification of organic compounds
a) Elemental analysis (identification of nitrogen, sulfur, halogens, phosphorus); solubility according to EP; tests for identification of functional groups.
b) Qualitative assays for identification of classes of compounds: sugars, sulphonamides, alkaloids, aminoacids
c) Determination of melting point

- Identification of inorganic compounds
a) Solubility
b) Analysis of water-soluble and acid-soluble inorganic compounds (pH measurement, tests for identification of cations according to the periodic system and of anions)
c) Analysis of water- and acid-insoluble compounds
- Identification of metal-organic compounds: analysis of the inorganic and organic portions according to the methods and criteria above reported.
- Identification of unknown inorganic, metal-organic and inorganic compounds.
Prerequisites for admission
Attendance at the courses of the previous years, with particular reference to all chemical courses (analytical chemistry, inorganic chemistry, organic chemistry, pharmaceutical chemistry, analysis of inorganic substances of pharmaceutical use and laboratory of qualitative analysis, principles of quantitative pharmaceutical analysis and laboratory of quantitative analysis).
Teaching methods
The course includes two teaching units:
Assays and Analytical Methodologies of Pharmacopoeias, based on lectures, and Laboratory of Drugs Identification, based on 16 individual and obligatory experimental training.

Assays and Analytical Methodologies of Pharmacopoeias: the teaching method is formally traditional, as it is based on slide projection in class (slide can be downloaded from Ariel platform). In addition, several analytical exercises are solved in class to provide students the ability to pass the final exam and to better understand the theoretical aspects.

Laboratory of Drugs Identification: this module consists in two sections. In details, the first one involves lectures about lab procedures to be adopted in order to identify compounds described in the European Pharmacopoeia; these lectures are followed by experimental training on known substances, in order to get familiar with the procedures. The second section is dedicated to experimental training on unknown compounds which students are asked to identify.
Bibliography
1. R. Cozzi, P. Protti, T. Ruaro, Analisi Chimica Strumentale. II Edizione. Zanichelli Ed., Bologna (2001).
2. Appunti del corso e materiale bibliografico fornito dal docente.
3. Farmacopea Europea
4. V. Cavrini, V. Andrisano. Principi di Analisi Farmaceutica. III edizione. Società Editrice Esculapio srl., Bologna (2013).
5. F. Savelli, O. Bruno, Analisi Chimico Farmaceutica. Ed. Piccin (2005)
6. A. Carta, M.G. Mamolo, F. Novelli, S. Piras. Analisi Farmaceutica Qualitativa. EdiSES srl, Napoli (2011).

Information about the course, teaching materials and notices to students can be found on Ariel platform in Unimi website at the following address https://moriolismafliflmz.ariel.ctu.unimi.it/v5/home/Default.aspx
Assessement methods and criteria
Assays and Analytical Methodologies of Pharmacopoeias:
written test divided into 2 or 3 questions (one of which is divided into 4 or 3 sub-questions respectively). The test requires the answer to questions both of application type (with contents and difficulties similar to those faced in classroom exercises and for which the solution is allowed to consult tables) and of theoretical type. Students are required to answer within a maximum time of two hours. Each question/sub-question is assigned a score based on its complexity, the sum of which constitutes the final grade expressed in 30/30.

Laboratory of Drugs Identification:
the lab unit does not provide for an examination test, but a frequency recognition, which is granted only if the student has correctly performed at least 75% of the unknown analyses.
Unità didattica: Laboratorio di identificazione dei farmaci
CHIM/08 - PHARMACEUTICAL CHEMISTRY - University credits: 4
Single bench laboratory practical: 64 hours
Professor: Orioli Marica
Shifts:
Turno 2
Professor: Orioli Marica
Unità didattica: Saggi e metodologie analitiche delle farmacopee
CHIM/08 - PHARMACEUTICAL CHEMISTRY - University credits: 8
Lessons: 64 hours
Professor: Orioli Marica