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  • Clinical Pharmacy Programe

    Practical Medicinal Chemistry

    PC609

    Third Level

    2015 2016

    Prepared by

    Staff Members of Medicinal Chemistry Department

  • Clinical Pharmacy Practical Handouts (PC 609) 2015/2016

    Medicinal Chemistry 1

    Subject index

    Subject page

    Intended Learning Outcomes of courses (ILO's) 3

    Part 1: Drawing standards of chemical structures 4

    Part 2: Physicochemical properties of drug action 34

    Acid/base properties 34

    Predicting degree of ionization of drug molecule 38

    Hydrophilic/lipophilic properties 42

    The hydrophobicity constant 46

    Case study 50

    Part 3: Case study "Antifungal Drugs" 58

    Part 4: Titrimetric determination of pharmaceutical preparations 62

    Penicillins: Benzylpenicillin 62

    Cephalosporins: Cephalexin 64

    Sulfonamides 66

    Determination of ZnSO4/Sulfacetamide sodium 68

    Assay of zinc undecenoate 71

    Propylparaben 73

    Betadine 75

    Isoniazide (INH) 77

    Busulphan 97

    Problems 81

    Evaluation sheet 84

  • Clinical Pharmacy Practical Handouts (PC 609) 2015/2016

    Medicinal Chemistry 2

    Evaluation of the Practical pharmaceutical chemistry

    PC609

    The 25 Marks of practical course will be distributed as following:

    The total degree of practical course 25 Marks

    ChemBioDraw exam 8 Marks

    Physicochemical exam 5 Marks

    Assay exam 5 Marks

    Quiz on assay 3 Marks

    Behavior and attendance 3 Marks

  • Clinical Pharmacy Practical Handouts (PC 609) 2015/2016

    Medicinal Chemistry 3

    Intended Learning Outcomes of courses (ILO's)

    Upon completion of the course the student should be able to:

    1. Draw chemical structures in two and three dimension using ChemDraw

    program.

    2. Draw diagrams and sketches of different equipment and glassware used in

    chemical reactions using ChemDraw program.

    3. Explore in detail some further useful application of ChemDraw program.

    4. Understand the relationship between the chemical and physical properties of

    related compound and their medicinal use and pharmacological activity.

    5. Handle laboratory chemicals in a correct and safe way to obtain optimum

    results without harmful effects.

    6. Perform titrimetric techniques for determination of some pharmaceutical

    compounds, handling data in term of graphical presentation.

    7. Be familiar with the analysis of drugs and the laboratory techniques used for

    that.

    8. Analyze pharmaceutical dosage forms and determine their active constituents

    by different analytical methods.

    9. Identifying the drug impunities and different related substances and giving

    possible explanation of their existence.

  • Clinical Pharmacy Practical Handouts (PC 609) 2015/2016

    Medicinal Chemistry 4

    PART 1

    Drawing Standards of Chemical Structures Overview

    The information required to begin using Chem Draw includes how to do the following:

    Start Chem Draw.

    Create, open, and save documents.

    Identify the parts of the Chem Draw interface.

    Drawing the different chemical structures and showing the chemical properties,

    stereochemistry, fragmentation pattern, 1H-NMR, ..etc..

    Drawing the synthesis, degradation and metabolic pathways of the drugs.

    Interpretation of the mode of actions of drugs and drug receptor interaction in

    diagram form.

    Basics drawing using Chem Draw

    Starting Chem Draw

    You can start the Chem Draw application in the following ways:

    From the desktop, double-click the Chem Draw icon, or:

    From the Start menu, choose Chem Draw, where a new document is created.

    The Work Area:

    The work area appears whenever you launch Chem Draw. By default, the work area

    displays commonly used toolbars, the main menu, and document status bar. The

    work area appears below:

  • Clinical Pharmacy Practical Handouts (PC 609) 2015/2016

    Medicinal Chemistry 5

    Optional Toolbars

    ChemDraw provides a number of optional toolbars and information windows to

    facilitate production of ChemDraw documents. These toolbars are accessed from the View

    menu. They are divided into three basic groups:

    Standard Toolbars and Show Windows

    Tool Palettes

    Templates

    Showing and Hiding Toolbars

    To show or hide a toolbar:

    From the View menu, select a toolbar.

    A check mark appears next to the item when the toolbar is displayed.

  • Clinical Pharmacy Practical Handouts (PC 609) 2015/2016

    Medicinal Chemistry 6

    Docking and Undocking Toolbars

    The standard toolbars, can be docked or undocked. Docked toolbars can attach to any edge

    of the ChemDraw window. Undocked toolbars can float anywhere in the ChemDraw screen.

    To dock a toolbar:

    Drag the toolbar to the edge of the ChemDraw screen where you want it to dock.

    Double-click the toolbar background. This wil dock the toolbar in the default

    position.

    To undock a toolbar:

    Drag the toolbar into the position you want.

    The Main Toolbar

    Most common tools are on the main toolbar. These include all tools necessary to draw

    and edit structures, reactions, and shapes. Go to View>Show Main Toolbar.

    The main toolbar has other toolbars extending from it. You can tear off these smaller

    tool bars and place them anywhere on your screen. To tear off a toolbar:

    1. Click the arrow on the lower right of a tool in the main toolbar.

    2. While holding the mouse button down, point to the title bar, and release the button.

  • Clinical Pharmacy Practical Handouts (PC 609) 2015/2016

    Medicinal Chemistry 7

    Opening Documents

    To open a document, do one of the following:

    Go to File>Open. In the Open dialog box, select the name and location of the file and

    click Open.

    In the File menu, choose the document from the list at the bottom.

    Saving Documents

    Go to File>Save; Choose a folder in which to store the file.

    Type a file name in the Save As text box.

    Select a file format then Click Save.

    Selecting Objects

    Use the Lasso or the Marquee tool to select any object. You use the Lasso for freehand

    selection and the Marquee to select rectangular regions. When you select a structure or

    object, the selection is displayed with a light blue frame around it with three types of

    selection handles:-

    A) Drag this handle to rotate the object.

    B) Drag any corner to resize.

    C) Drag any side handle to distort.

  • Clinical Pharmacy Practical Handouts (PC 609) 2015/2016

    Medicinal Chemistry 8

    The Lasso Tool

    Use the Lasso tool to make freehand selection of irregular areas. To select objects using

    the Lasso tool:

    1. Select the Lasso tool.

    2. Press the mouse button while the pointer is not over any object.

    3. Drag around part of a structure or other object.

    The Marquee Tool

    Use the Marquee tool to select objects and structures within a rectangular area.

    1. Select the Marquee tool.

    2. Click and drag diagonally over the structures or other object.

    As you drag, a rectangle appears that defines the selection area. Bonds and other objects

    are selected only if they are entirely within the rectangle.

    Selecting entire structures

    To select an entire chemical structure, double-click a bond or atom in the structure

    using a selection tool.

    Character Map

    The floating Character Map window displays the 256 characters in any font. The

    default font is Symbol. Use it to add symbols or styled fonts to labels. The character map is

    active only when a text box is open for editing.

    With a text box open, mouse over the character map to view a larger version of the

    characters in the top right corner of the window.

    Click any character in the table to enter that character in the text box.

  • Clinical Pharmacy Practical Handouts (PC 609) 2015/2016

    Medicinal Chemistry 9

    Bonds

    The Main toolbar and Multiple Bonds toolbar offer numerous options for drawing

    bonds.

    To draw the first bond of your structure, select the solid bond tool in the Main toolbar

    and click in the document window.

    To draw another bond, point to an atom where a grey box appears then click.

    You can draw a bond in any direction. Using a bond tool, click and drag from an

    existing atom or an empty area in the document window.

  • Clinical Pharmacy Practical Handouts (PC 609) 2015/2016

    Medicinal Chemistry 10

    There are several ways to draw a double bond:

    Draw a bond using the Double bond tool.

    Draw a single bond over an existing single bond.

    Using any bond or

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