Pharmaceutical Chemistry

30:715:307 (2 credits)
Fall 2018
Time: M, W 6:05-7:00 pm, PH-130
Course Description: The mission of the Pharmaceutical Chemistry course is to introduce
students to the structure, properties, and analysis of pharmaceutical agents and metabolites as well
as some fundamental techniques used for near patient testing and pharmacokinetic analysis. Topics
include basic concepts in medicinal chemistry as well as methods of pharmaceutical and
biomedical analysis: 1) the drug discovery and development process, 2) review of organic
functional groups found in drug molecules, 3) drug-target interactions, 4) physicochemical
properties related to drug action such as acid-base properties, equilibrium, and stereochemistry, 5)
Chemistry of OTC inorganic drugs, 6) Effect of chemical structure on the metabolism of drug
molecules, 7) Fundamentals of neurochemistry, and 8) Chromatographic (especially HPLC and
LC-MS) analysis of pharmaceutical agents, metabolites, and clinical samples.
Course Objectives: Students completing the Pharmaceutical Chemistry course will be expected
to demonstrate the following abilities based outcomes (ABOs)
1. Develop and demonstrate depth and breadth of knowledge in biomedical, pharmaceutical,
social/administrative/behavioral, and clinical sciences. (1.1.1)
2. Integrate knowledge from foundational sciences to explain how specific drugs or drug
classes work and evaluate their potential value in individuals and populations. (1.1.2)
3. Apply knowledge in foundational sciences to solve therapeutic problems. (1.1.3)
Course Instructors: Longqin Hu, Ph.D. (Coordinator)
Professor of Medicinal Chemistry
Email: longhu@pharmacy.rutgers.edu
Allen N. Jones, Ph.D.
Adjunct Professor, Medicinal Chemistry
Email: allen.jones@rutgers.edu
Michael Totleben, Ph.D.
Adjunct Professor, Medicinal Chemistry
Email: mt973@pharmacy.rutgers.edu
Course Material: Textbook, Study Guide, and Class Lectures
https://sakai.rutgers.edu/

Required Textbook: Organic Chemistry Concepts and Applications for Medicinal

Chemistry, Joseph E. Rice, Academic Press, 2014, Softcover;
ISBN 9780128007396 or eBook; ISBN 9780128008324.
Reference Books: David G. Watson. Pharmaceutical Analysis, A Textbook for
Pharmacy Students and Pharmaceutical Chemists, 3rd Edition,
2012, Elsevier.
Examinations: Three exams (two mid-terms and one comprehensive final)
and around 10 in-class quizzes. The final is optional for students
w/ average 70 after the second mid-term exam.
Grading: Exam 1 25%
Exam 2 25%
Quizzes 15%
Final Examination (cumulative) 35%
Total 100%
Pharmaceutical Chemistry 30:715:307 Fall 2018

Pharmaceutical Chemistry

Fall 2018

Tentative Course Outline:

Week Lecture Topics covered

Course Introduction and Importance of Pharmaceutical Chemistry in

Understanding Drug Action and Clinical Test Results (Hu): Drug
discovery and development process, Sequence of events after drug
1 Lecture 1
administration, List of physico-chemical properties related to drug
action, Clinical Chemistry and the importance of fundamental chemistry
concepts and analytical techniques

Lecture 2
Review of Organic Functional Groups and Acid-Base Concepts
2
(Totleben): Chemical bonding
Lecture 3

Lecture 4 Drug-Target Interactions (Hu): Structural Effects on Biological Action,

Role and types of chemical bonding interactions between drug and target,
3
Binding of neurotransmitters to their receptors, Thalidomide: Lessons as
Lecture 5
related to chirality of drugs

Lecture 6
4
Review of Organic Functional Groups and Acid-Base Concepts
Lecture 7
(Totleben): Functional groups, Electron donating and withdrawing
groups; Acids and bases, Henderson-Hasselbach equation; Estimating
Lecture 8
pKa and pKb; Heterocycles
5
Lecture 9

Lecture 10 Review of Stereochemistry and Physico-Chemical Properties Related to

6 Drug Action (Totleben): Stereoisomers, Stereochemistry of unsaturated
Lecture 11 compounds, Enantiomers, Diastereomers, Partition coefficients

Chemistry of Over-the-Counter (OTC) Inorganic Drugs (Hu): Structures,

chemical properties and mechanisms of action of antacids (Tums®, Pepto-
Lecture 12
Bismol, Milk of Magnesia), inorganic germicides, imaging agents, and platinum
7 anticancer agents

Lecture 13 Fundamentals of Neurochemistry (Hu): Structures, chemical properties,

metabolism, and actions of select neurochemicals including acetylcholine,
epinephrine, norepinephrine, dopamine, serotonin, glutamate, GABA, and nitric
Lecture 14 oxide) and of nicotine
8
Exam 1 Midterm Exam 1 (cover lectures 1-13)
Pharmaceutical Chemistry 30:715:307 Fall 2018

Lecture 15 Fundamentals of Neurochemistry (Hu): (Cont’d)

9
Lecture 16 Chemical Aspects of Drug Metabolism (Hu): Introduction, Effects of
chemical structure on Phase I oxidative, reductive, and hydrolytic reactions,
Effects of chemical structure on phase II conjugative reactions (COMT and
Lecture 17 PNMT-catalyzed methylation, acetylation, sulfation, glucuronidation, amino
10 acid conjugation, mercapturic acid formation), Sites of metabolism, Metabolic
Lecture 18 pathways of selected common drugs, Metabolites identified for a new anticancer
drug, Imatinib

Lecture 19
11 Introduction to Analytical Separations (Jones): Basic separation techniques
in chemistry laboratories and in clinical drug monitoring, Extraction, Effect of
Lecture 20
pH, Available formats and types of chromatographic techniques, Efficiency of
separation, van Deemter equation
Lecture 21
12
Thanksgiving Recess

Lecture 22
13 Chromatographic Analysis of Pharmaceutical Agents, Metabolites, and
Lecture 23 Clinical Samples (Jones): HPLC components, Separation process in
comparison with GC, Classification based on retention mechanisms, Normal vs
Lecture 24 reversed phases, Isocratic vs gradient elution, Criteria of good separation,
Applications of HPLC in quantitative analysis of pharmaceutical agents and
14 metabolites, Hyphenated techniques in clinical drug monitoring, LC-MS in the
Lecture 25 metabolism and disposition studies of drugs – metabolite patterns in patients
urine, plasma
Lecture 26
15
Exam 2 Midterm Exam 2 (covering lectures 14-26)

Finals
16 Comprehensive Final Exam (optional for students w/ 70%)
Week

Required Textbook: Organic Chemistry Concepts and Applications for Medicinal Chemistry,
Joseph E. Rice, Academic Press, 2014, Softcover; ISBN 9780128007396 or
eBook; ISBN 9780128008324.
Reference Book: David G. Watson. Pharmaceutical Analysis, A Textbook for Pharmacy
Students and Pharmaceutical Chemists, 3rd Edition, 2012, Elsevier.
https://sakai.rutgers.edu/