University of the
West of England
MODULE SPECIFICATION
Code: USSJ8A-20-2 Title: MEDICINAL CHEMISTRY Version:
Level: UWE credit rating: ECTS credit rating:
Owning Faculty: Health and Life Sciences Field:
Faculty Committee approval: Q&S Committee (School of Life Sciences) Date: June 2010
Approved for Delivery by: N/A
Valid from: October 2010 Discontinued from:
Pre-requisites:
Co-requisites:
Entry Requirements:
N/A
Excluded Combinations:
Learning Outcomes:
The student will be able to:
• apply chemical knowledge to rationalise drug design, structural modification and synthesis;
• carry out experimental techniques commonly used in preparing drug intermediates;
• illustrate how physicochemical properties of drugs can be measured and used to study structure-activity relationships;
• explain the action and related synthetic approaches to selected examples of antimicrobial and anti-cancer agents, cholinergic and anticholinergic drugs, anti-depressants and antihypertensive agents.
Syllabus Outline:
Principles of Drug Design, Synthesis and Development.
Origins of natural and synthetic drug leads. Types of drug target and physicochemical origins of drug-target interactions. Synthetic methods for optimising binding interactions.
The use of X-ray crystallography and spectroscopy in drug identification, conformational analysis and computer modelling of drug-target interactions.
Solid phase synthesis and combinatorial chemistry.
The importance of chirality to drug activity, and methods of controlling stereochemistry during synthesis.
Strategies for chemical modification in drug development - structure-activity relationships (SARs). Identifying the pharmacophore. Ring expansion/contraction, rigidification, bioisosteres. Quantitative assessment of structure-activity relationships (QSAR).
Chemical strategies for altering drug solubility/stability - relevance to drug delivery and formulation.
Types of prodrugs, sleeping drugs, orphan drugs.
Case studies.
To illustrate the major classes of drugs, their origins, chemical development and action, the chemistry of some of the following topics will be discussed:
Types of drug interaction with DNA - alkylating and intercalating agents, bleomycin;
Some examples of SARs - development of ibuprofen and naproxen from aspirin, benzocaine and novacain anaesthetics from cocaine, morphinans and methadone from morphine;
Structure and activity of the antibacterial sulphonamides, penicillins and cephalosporins;
Drugs acting on the peripheral nervous system - some cholinergic and anticholinergic drugs;
Antiulcer treatment - QSAR in the development of cimetidine;
An antihypertensive agent - development of a lead (from snake venom to captopril);
Structure and activity of some anti-depressants - Prozac and Amitriptyline;
Teaching and Learning Methods:
The module will be presented as lectures, tutorials, workshop sessions and practical classes.
Reading Strategy:
All students will be encouraged to make full use of the print and electronic resources available to them through membership of the University. These include a range of electronic journals and a wide variety of resources available through web sites and information gateways. The University Library’s web pages provide access to subject relevant resources and services, and to the library catalogue. Many resources can be accessed remotely. Students will be presented with opportunities within the curriculum to develop their information retrieval and evaluation skills in order to identify such resources effectively.
Any essential reading will be indicated clearly, along with the method for accessing it, e.g. students may be expected to purchase a set text, be given or sold a print study pack or be referred to texts that are available electronically, etc. This guidance will be available either in the module handbook, via the module information on Blackboard or through any other vehicle deemed appropriate by the module/programme leaders.
If further reading is expected, this will be indicated clearly. If specific texts are listed, a clear indication will be given regarding how to access them and, if appropriate, students will be given guidance on how to identify relevant sources for themselves, e.g. through use of bibliographical databases.
Indicative Reading List:
• Patrick, G L, An Introduction to Medicinal Chemistry, Oxford University Press, 4th edition (2009)
• Thomas, G, Medicinal Chemistry – an introduction, Wiley (2000)
• Volhardt P, Schore N., Organic Chemistry - structure and function, Freeman Palgrave Macmillan, 6th edition (2009)
• Moynihan H, Crean A, The Physicochemical Basis of Pharmaceuticals, Oxford University Press (2009)
Additional useful texts can be accessed at shelf marks 615.1 and 541.22.
Assessment:
Weighting between components A and B (standard modules only) A: 50% B: 50%
FIRST ATTEMPT
First Assessment Opportunity
Component A (controlled) Element Wt (Ratio)
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Component B Element Wt (Ratio)
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Second Assessment Opportunity (Resit) further attendance at taught classes
Component A (controlled) Element Wt (Ratio)
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Component B Element Wt (Ratio)
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EXCEPTIONAL SECOND ATTEMPT Attendance at taught classes .
Specification confirmed by …………………………………………………Date ……………………………
(Associate Dean/Programme Director)