CHEM 390 : Medicinal Chemistry


2020 Semester One (1203) (15 POINTS)

Course Prescription

Nature of cellular targets for drug action – lipids, proteins, enzymes, DNA. Principles of molecular recognition. Enzymes and receptors as targets for drug action. DNA as a target for drug action. An overview of approaches to drug discovery and development. Structure-activity relationships, stereochemistry and drug action, prodrugs, drug solubilisation and delivery, drug metabolism and antibiotic resistance. Laboratories focus on the synthesis, computer modelling and biological testing of drugs.

Course Overview

The concepts, principles and applications of medicinal chemistry will be examined and include: the drug discovery and development process, molecular recognition and structure-activity relationships in biological systems, drug-DNA interactions, enzymes as therapeutic targets, mechanisms of ligand-receptor interactions, combinatorial approaches to discovery of novel chemotherapeutic agents and drug metabolism and drug resistance.

Course Requirements

Prerequisite: CHEM 110 and a minimum of 165 points passed

Capabilities Developed in this Course

Capability 1: Disciplinary Knowledge and Practice
Capability 2: Critical Thinking
Capability 3: Solution Seeking
Capability 4: Communication and Engagement
Capability 6: Social and Environmental Responsibilities
Graduate Profile: Bachelor of Science

Learning Outcomes

By the end of this course, students will be able to:
  1. Describe how antimicrobial peptides function understand the basic principles of peptide synthesis and be able to write the structure of a Peptide from constituent amino acids. (Capability 1, 2 and 3)
  2. Apply he principles of molecular recognition and intermolecular bonding interactions, to the development of enzyme inhibitors and receptor agonists and antagonists as drugs. (Capability 1, 2 and 3)
  3. Describe the mechanism of action and structure-activity-relationship of classic molecules like Penicillin, Morphine, Cisplatin, antigene and antisense oligonucleotides etc. (Capability 1, 2, 3, 4 and 6)
  4. Apply the "profit: need : threat" rationale for the drug discovery process using examples, describe How Lipinski’s 'rule of five' to determine 'drug-like molecules’ and Explain why halogens are often incorporated into pharmaceuticals, using examples. (Capability 1, 2 and 3)
  5. Apply he principles of combinatorial chemistry solid-phase organic synthesis (SPOS) in the drug discovery process to generating new drug leads. (Capability 1, 2 and 3)
  6. Apply the principles and ideas are behind QSAR studies, explain the concept of prodrugs, explain the importance of the molecular shape and flexibility (stereochemistry principles) and how the physicochemical properties of the drugs are important and can be incorporated in drug design. (Capability 1, 2, 3 and 4)
  7. Evaluate the influence of tissue pH, drug pKa and logP to the ability of the drug to cross membranes and enter cells as well as use the Henderson-Hasselbalch equation to determine the percentage of drug ionisation (known pKa) in tissue at a particular pH and understand the effect that pH has on solubility and hence therapeutic effectiveness (Capability 1, 2, 3 and 4)
  8. Describe the structural features of surfactants and liposomes that make them useful as drug delivery agents in order to overcome issues of drug solubility and metabolic stability and to improve drug targeting. (Capability 1, 2 and 3)
  9. Identify and explain metabolic reactions into phase I and II, relate these to the functional group or structure may undergo and predict the resultant metabolite; identify the types of enzymes and co-enzymes needed for the metabolic reaction and describe some examples where knowledge of the metabolic fate of a lead compound has been used to design a more effective drug. (Capability 1, 2 and 3)
  10. Describe he general mechanisms utilised by bacteria in drug resistance and give an example of an antibiotic that succumbs to each mechanism (Capability 1, 2, 3, 4 and 6)


Assessment Type Percentage Classification
Laboratories 30% Individual Coursework
Test 20% Individual Test
Final Exam 50% Individual Examination
Assessment Type Learning Outcome Addressed
1 2 3 4 5 6 7 8 9 10
Final Exam
 Students must pass both the theory (test and exam) and the laboratory to gain an overall pass for the course.

Key Topics

(12 lectures): Cellular target for drug action: Introduction, Lipids as target for drug action, Protein structure, Principles of molecular recognition, Enzymes as targets for drug action, Receptors as targets for drug action. DNA structure and function and DNA as a target for drug action.
(5 lectures): An overview of approaches to drug discovery and development (including combinatorial approaches).
(8 lectures): Structure-activity relationships and computer-aided methods, Stereochemistry/chirality and drug action, prodrugs.
(9 lectures): Drug absorption and metabolism. Drug resistance.

Learning Resources

Electronic copy of lecture notes, lecture recordings, laboratory manual and lab report books and examples of previous test and exam papers with model answers

Special Requirements

Must complete practical work
Must pass theory (test and exam together) and practical work (laboratories) separately to pass the course.

Workload Expectations

This course is a standard [15] point course and students are expected to spend 10 hours per week involved in each 15 point course that they are enrolled in.

For this course, you can expect [30] hours of lectures, a [6] hour tutorial, [60] hours of reading and thinking about the content and [40] hours of work on assignments and/or test preparation.

Digital Resources

Course materials are made available in a learning and collaboration tool called Canvas which also includes reading lists and lecture recordings (where available).

Please remember that the recording of any class on a personal device requires the permission of the instructor.


The content and delivery of content in this course are protected by copyright. Material belonging to others may have been used in this course and copied by and solely for the educational purposes of the University under license.

You may copy the course content for the purposes of private study or research, but you may not upload onto any third party site, make a further copy or sell, alter or further reproduce or distribute any part of the course content to another person.

Academic Integrity

The University of Auckland will not tolerate cheating, or assisting others to cheat, and views cheating in coursework as a serious academic offence. The work that a student submits for grading must be the student's own work, reflecting their learning. Where work from other sources is used, it must be properly acknowledged and referenced. This requirement also applies to sources on the internet. A student's assessed work may be reviewed against online source material using computerised detection mechanisms.

Inclusive Learning

All students are asked to discuss any impairment related requirements privately, face to face and/or in written form with the course coordinator, lecturer or tutor.

Student Disability Services also provides support for students with a wide range of impairments, both visible and invisible, to succeed and excel at the University. For more information and contact details, please visit the Student Disability Services’ website at

Special Circumstances

If your ability to complete assessed coursework is affected by illness or other personal circumstances outside of your control, contact a member of teaching staff as soon as possible before the assessment is due.

If your personal circumstances significantly affect your performance, or preparation, for an exam or eligible written test, refer to the University’s aegrotat or compassionate consideration page:

This should be done as soon as possible and no later than seven days after the affected test or exam date.

Student Feedback

During the course Class Representatives in each class can take feedback to the staff responsible for the course and staff-student consultative committees.

At the end of the course students will be invited to give feedback on the course and teaching through a tool called SET or Qualtrics. The lecturers and course co-ordinators will consider all feedback.

Your feedback helps to improve the course and its delivery for all students.

Student Charter and Responsibilities

The Student Charter assumes and acknowledges that students are active participants in the learning process and that they have responsibilities to the institution and the international community of scholars. The University expects that students will act at all times in a way that demonstrates respect for the rights of other students and staff so that the learning environment is both safe and productive. For further information visit Student Charter (


Elements of this outline may be subject to change. The latest information about the course will be available for enrolled students in Canvas.

In this course you may be asked to submit your coursework assessments digitally. The University reserves the right to conduct scheduled tests and examinations for this course online or through the use of computers or other electronic devices. Where tests or examinations are conducted online remote invigilation arrangements may be used. The final decision on the completion mode for a test or examination, and remote invigilation arrangements where applicable, will be advised to students at least 10 days prior to the scheduled date of the assessment, or in the case of an examination when the examination timetable is published.

Published on 11/01/2020 02:51 p.m.