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 
                 1     Lecture 1    discovery and development process, Sequence of events after drug 
                                    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, 
                 3                  Role and types of chemical bonding interactions between drug and target, 
                       Lecture 5    Binding of neurotransmitters to their receptors, Thalidomide: Lessons as 
                                    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 
                       Lecture 8    groups; Acids and bases, Henderson-Hasselbach equation; Estimating 
                                    pK and pK ; Heterocycles 
                 5                     a       b
                       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, 
                                                                                           ®
                       Lecture 12   chemical properties and mechanisms of action of antacids (Tums , Pepto-
                 7                  Bismol, Milk of Magnesia), inorganic germicides, imaging agents, and platinum 
                                    anticancer agents 
                       Lecture 13   Fundamentals  of  Neurochemistry  (Hu):  Structures,  chemical  properties, 
                                    metabolism,  and  actions  of  select  neurochemicals  including  acetylcholine, 
                       Lecture 14   epinephrine, norepinephrine, dopamine, serotonin, glutamate, GABA, and nitric 
                 8                  oxide) and of nicotine 
                       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                      Chemical  Aspects  of  Drug  Metabolism  (Hu):  Introduction,  Effects  of 
                            Lecture 16      chemical structure on Phase I oxidative, reductive, and hydrolytic reactions, 
                            Lecture 17      Effects  of  chemical  structure  on  phase  II  conjugative  reactions (COMT and 
                                            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      Introduction to Analytical Separations (Jones): Basic separation techniques 
                     11                     in chemistry laboratories and in clinical drug monitoring, Extraction, Effect of 
                            Lecture 20      pH, Available formats and types of chromatographic techniques, Efficiency of 
                            Lecture 21      separation, van Deemter equation 
                     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, 
                     14                     Applications of HPLC in quantitative analysis of pharmaceutical agents and 
                            Lecture 25      metabolites, Hyphenated techniques in clinical drug monitoring, LC-MS in the 
                                            metabolism and disposition studies of drugs – metabolite patterns in patients 
                                            urine, plasma 
                            Lecture 26 
                     15 
                            Exam 2          Midterm Exam 2 (covering lectures 14-26) 
                     16     Finals          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/