1. No category

Pharmaceutical Chemistry
30:715:306 (3 credits)
Spring 2015
Time: T, Th 5:00-6:20 pm
Place: ARC 103
Course Description: The mission of the Pharmaceutical Chemistry course is to introduce
students to the structure, properties, and analysis (both qualitative and quantitative) of
pharmaceutical agents and metabolites as well as the fundamental techniques used for near
patient testing in clinical laboratories. Topics include some of the basic concepts in medicinal
chemistry as well as methods of pharmaceutical and biomedical analysis such as 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, 8) Chromatographic analysis of pharmaceutical agents, metabolites, and clinical
samples, 9) Methods for identification of pharmaceutical agents and metabolites, and 10)
Spectral techniques used in quantitative analysis of clinical samples.
Course Instructors:
Longqin Hu, Ph.D. (Coordinator)
Professor of Medicinal Chemistry
Joseph E. Rice, Ph.D.
Associate Professor of Medicinal Chemistry
Xumu Zhang, Ph.D.
Professor II of Medicinal Chemistry and Chemistry
Course Material:
Textbook, Study Guide, and Class Lectures
Website:
http://medchem.rutgers.edu/pharmchem/pharm_chm.html
https://sakai.rutgers.edu/
Requried Textbook:
Organic Chemistry Concepts and Applications for Medicinal
Chemistry, Joseph E. Rice, Academic Press, 2014, Softcover;
ISBN 9780128007396 or eBook; ISBN 9780128008324.
Ref. Textbook:
David G. Watson. Pharmaceutical Analysis, A Textbook for
Pharmacy Students and Pharmaceutical Chemists, 2nd Edition,
2005, Elsevier.
Reference Book:
Lawrence A. Kaplan and Amadeo J. Pesce. Clinical Chemistry:
Theory, Analysis, Correlation, 5th Edition, 2007, St. Louis, MO:
Mosby.
Examinations:
Four exams (three mid-term and one comprehensive final)
and around 10 in-class quizzes. The final is optional for students
w/ average 70 after the third mid-term exam.
Grading:
Mid-Term Exam 1
Mid-Term Exam 2
Mid-Term Exam 3
Quizzes
Final Examination (cumulative)
20%
20%
20%
10%
30%
Total
100%
Pharmaceutical Chemistry
30:715:306
Spring 2015
Pharmaceutical Chemistry
Spring 2015
Tentative Course Outline:
Week Lecture
1
Lecture 1
Lecture 2
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
administration, List of physico-chemical properties related to drug
action, Clinical Chemistry and the importance of fundamental chemistry
concepts and analytical techniques
Drug-Target Interactions (Hu): Structural Effects on Biological Action,
Role and types of chemical bonding interactions between drug and target,
Binding of neurotransmitters to their receptors, Thalidomide: Lessons as
related to chirality of drugs
2
3
4
5
6
7
8
Lecture 3
Lecture 4
Lecture 5
Lecture 6
Lecture 7
Lecture 8
Review of Organic Functional Groups and Acid-Base Concepts (Rice):
Chemical bonding, Functional groups, Electron donating and
withdrawing groups; Acids and bases
Acid-Base Concepts (Rice): Henderson-Hasselbach equation; Estimating
pKa and pKb; Heterocycles
Review of Stereochemistry and Physico-Chemical Properties Related to
Drug Action (Rice): Stereoisomers, Stereochemistry of unsaturated
compounds, Enantiomers, Diastereomers, Partition coefficients
Lecture 9
Methods for Identification of Pharmaceutical Agents and Metabolites
(Zhang): UV for conjugative systems, IR for organic functional groups,
NMR for relative positions of C and H, and MS for molecular weights
and fragmentation patterns
Exam 1
Midterm Exam 1 (cover lectures 1-8)
Lecture 10
Methods for Identification of Pharmaceutical Agents and Metabolites
(Zhang) (Cont’d)
Lecture 11
Lecture 12
Lecture 13
Lecture 14
Lecture 15
Methods for Identification of Pharmaceutical Agents and Metabolites
(Zhang) (Cont’d)
Spectral Techniques Used in Quantitative Analysis of Clinical Samples
(Zhang): Light and matter, Absorption spectroscopy, Beer-Lambert law,
Principles of atomic absorption and emission spectrophotometry,
Principles of molecular emission – fluorometry, time-delayed
fluorescence, and chemiluminescence, fluorescence polarization
Pharmaceutical Chemistry
Week Lecture
9
Spring 2015
Topics covered
No Lectures Spring Break
Lecture 16
10
Exam 2
11
30:715:306
Lecture 17
Lecture 18
Chemistry of Over-the-Counter (OTC) Inorganic Drugs (Hu): Structures,
chemical properties and mechanisms of action of antacids (Tums®, PeptoBismol, Milk of Magnesia), inorganic germicides, imaging agents, and platinum
anticancer agents
Midterm Exam 2 (covering lectures 9-16)
Fundamentals of Neurochemistry (Hu): Structures, chemical properties,
metabolism, and actions of select neurochemicals including acetylcholine,
epinephrine, norepinephrine, dopamine, serotonin, glutamate, GABA, and nitric
oxide) and of nicotine
Chemical Aspects of Drug Metabolism (Hu): Introduction, Effects of
12
Lecture 19
Lecture 20
chemical structure on Phase I oxidative, reductive, and hydrolytic reactions,
Effects of chemical structure on phase II conjugative reactions (COMT and
PNMT-catalyzed methylation, acetylation, sulfation, glucuronidation, amino
acid conjugation, mercapturic acid formation), Sites of metabolism, Metabolic
pathways of selected common drugs, Metabolites identified for a new
anticancer drug, Imatinib
Introduction to Analytical Separations (Hu): Basic separation techniques in
13
Lecture 21
Lecture 22
chemistry laboratories and in clinical drug monitoring, Extraction, Effect of pH,
Available formats and types of chromatographic techniques, Efficiency of
separation, van Deemter equation
Chromatographic Analysis of Pharmaceutical Agents, Metabolites, and
Clinical Samples (Hu): Gas chromatographic separation, Types of columns
and stationary phases, carrier gases, injection modes, and detectors, Examples
of GC analysis (peppermint oil and a decongestion syrup), Effect of
derivatization, Quantitative analysis of methyltestosterone tablet
14
15
Lecture 23
Lecture 24
Chromatographic Analysis of Pharmaceutical Agents, Metabolites, and
Clinical Samples (Hu): HPLC components, Separation process in comparison
with GC, Classification based on retention mechanisms, Normal vs reversed
phases, Isocratic vs gradient elution, Criteria of good separation, Applications
of HPLC in quantitative analysis of pharmaceutical agents and metabolites
Lectures 25
Chromatographic Analysis of Pharmaceutical Agents, Metabolites, and
Clinical Samples (Hu): Hyphenated techniques in clinical drug monitoring,
Exam 3
Midterm Exam 3 (covering lectures 17-25)
LC-MS in the metabolism and disposition studies of drugs – metabolite patterns
in patients urine, plasma
16
Final Exam Comprehensive Final Exam
Requried Textbook: Organic Chemistry Concepts and Applications for Medicinal Chemistry,
Joseph E. Rice, Academic Press, 2014, Softcover; ISBN 9780128007396 or
eBook; ISBN 9780128008324.
Ref. Textbook: David G. Watson. Pharmaceutical Analysis, A Textbook for Pharmacy
Students and Pharmaceutical Chemists, 2nd Edition, 2005, Elsevier.
Website:
http://medchem.rutgers.edu/pharmchem/pharm_chm.html
https://sakai.rutgers.edu/
Pharmaceutical Chemistry
Course Schedule
TTh 5:00-6:20 PM ARC-103
30:715:306
Week Day Date
Lecture Topic
Week Day Date
Lecture Topic
Spring 2015
Week Day Date
Lecture Topic
1
T
20-Jan L1 - Intro/Drug Discovery & Development (Hu)
6
Th
26-Feb L11 - Methods for Identification (Zhang)
Sa
4-Apr
1
W
21-Jan
6
F
27-Feb
Su
5-Apr
1
Th
22-Jan L2 - Drug Target Interactions (Hu)
Sa
28-Feb
12
M
6-Apr
1
F
23-Jan
Su
1-Mar
12
T
7-Apr L19- Chemical Aspects of Metabolism (Hu)
Sa
24-Jan
7
M
2-Mar
12
W
8-Apr
Su
25-Jan
7
T
3-Mar L12 - Methods for Identification (Zhang)
12
Th
M
26-Jan
7
W
4-Mar
12
F
10-Apr
2
T
27-Jan L3 - Rev Org Functional Groups (Rice)
7
Th
5-Mar L13 - Spectral Techniques (Zhang)
Sa
11-Apr
2
W
28-Jan
7
F
6-Mar
Su
12-Apr
2
Th
29-Jan L4 - Acid-Base Concepts (Rice)
Sa
7-Mar
13
M
13-Apr
2
F
30-Jan
Su
8-Mar
13
T
14-Apr L21 - Introduction to Separations (Hu)
Sa
31-Jan
8
M
9-Mar
13
W
15-Apr
Su
1-Feb
8
T
10-Mar L14 - Spectral Techniques (Zhang)
13
Th
16-Apr L22 - Introduction to Separations (Hu)
3
M
2-Feb
8
W
11-Mar
13
F
17-Apr
3
T
3-Feb L5 - Henderson-Hasselbach, pKa (Rice)
8
Th
12-Mar L15 - Spectral Techniques (Zhang)
Sa
18-Apr
3
W
4-Feb
8
F
13-Mar
Su
19-Apr
3
Th
5-Feb L6 - pKa, pKb, Heterocycles (Rice)
Sa
14-Mar
14
M
20-Apr
3
F
6-Feb
Su
15-Mar
14
T
21-Apr L23 - Chromatographic Analysis: GC (Hu))
Sa
7-Feb
9
M
16-Mar Spring Break
14
W
22-Apr
Su
8-Feb
9
T
17-Mar Spring Break
14
Th
23-Apr L24 - Chromatographic Analysis: HPLC (Hu)
4
M
9-Feb
9
W
18-Mar Spring Break
14
F
24-Apr
4
T
10-Feb L7 - Stereochemistry (Rice)
9
Th
19-Mar Spring Break
Sa
25-Apr
4
W
11-Feb
9
F
20-Mar Spring Break
Su
26-Apr
4
Th
12-Feb L8 - Partition coefficients (Rice)
Sa
21-Mar
15
M
27-Apr
4
F
13-Feb
Su
22-Mar
15
T
28-Apr L25 - Chromatographic Analysis: HPLC (Hu)
Sa
14-Feb
10
M
23-Mar
15
W
29-Apr
Su
15-Feb
10
T
24-Mar L16 - OTC Inorganic Drugs (Hu)
15
Th
30-Apr EXAM 3 (5:00 PM) ARC103
5
M
16-Feb
10
W
25-Mar
15
F
1-May
5
T
17-Feb L9 - Methods for Identification (Zhang)
10
Th
26-Mar EXAM 2 (5:00 PM) ARC103
Sa
2-May
5
W
18-Feb
10
F
27-Mar
Su
3-May
5
Th
19-Feb EXAM 1 (5:00 PM) ARC103
Sa
28-Mar
16
M
4-May Last Day of Classes
5
F
20-Feb
Su
29-Mar
16
T
5-May Reading Day
Sa
21-Feb
11
M
30-Mar
16
W
6-May Reading Day
31-Mar L17 - Fundamentals of Neurochemistry (Hu)
2
Su
22-Feb
11
T
6
M
23-Feb
11
W
1-Apr
6
6
T
W
24-Feb L10 - Methods for Identification (Zhang)
25-Feb
11
11
Th
F
2-Apr L18 - Fundamentals of Neurochemistry (Hu)
3-Apr
9-Apr L20 - Chemical Aspects of Metabolism (Hu)
TBA
CUMULATIVE FINAL
(optional for students w/ 70%)
Pharmaceutical Chemistry
30:715:306
Spring 2015
Pharmaceutical Chemistry 306
Course Policies
Quizzes and Examinations
There will be about ten in-class quizzes, three “hour” exams and one cumulative final
examination. Quizzes are worth 10% combined, each hour exam is worth 20%, and the final
exam is worth 30% of total course score. The cumulative final exam is optional for students
with 70% average after the third “hour” exam. There will be no lecture on the three
scheduled hour exam days. To be excused from a quiz, an hour exam or the final exam you must
produce a legal or medical excuse that has been approved by the Dean Office. As it is not our
policy to permit make-ups on quizzes and hour exams, your quiz average will be used for any
excused quiz and the final exam will be required more heavily weighted for an excused absence
in any hour exam. NO MAKE-UPS ON HOUR EXAMS OR QUIZZES! If you are excused
from the final exam, your course grade will be an “incomplete” or T-grade. You will have until
the end of the following semester to make-up for the final exam. Due to the extended period of
time that the student has available to study for the make-up final, the make-up final exam is more
rigorous and may include an oral examination component. You must bring a photo ID (either a
valid Rutgers Student ID card or a valid driver’s license that bears your photo) when you take
any examination. You will be required to sign all exams and quizzes. In addition, you must
check-in all book bags, notebooks, coats, and hats at the entrance to the lecture hall when you
enter to take an exam. You will only need No. 2 pencils and a simple calculator for all exams.
Graphing calculators, smart phones or any instrument with an alphanumeric keypad are
NOT permitted! Cell phones must be turned off during an exam.
Submitting Exams and Quizzes for Regrade
7-DAY GRACE PERIOD – for the hour exams and quizzes, you have seven days from the date
of return/posting of the graded exam/quiz to submit same for regrade, you must attach a letter
specifying which questions need to be reviewed and why. Submit the exam or quiz with the
letter to the lecture instructor. The instructor reserves the right to regrade the entire exam/quiz.
Academic Misconduct
University’s policy on academic integrity will be strictly followed. If a student is found to be
cheating during an exam or quiz, a grade of “F” will be given for the exam or quiz in question.
Pharmaceutical Chemistry
30:715:306
Spring 2015
RUTGERS UNIVERSITY POLICY ON ACADEMIC INTEGRITY
FOR
UNDERGRADUATE AND GRADUATE STUDENTS
A.
B.
CHEATING – Cheating is the use of inappropriate and unacknowledged materials,
information or study aids in any academic exercise (exam, quiz, etc.). The use of books,
notes, programmable calculators and conversation with others is restricted or forbidden
during exams and quizzes. Their use in these cases constitutes cheating.
FACILITATING ACADEMIC DISHONESTY – Students who knowingly or negligently
allow their work to be used by other students or who otherwise aid others in academic
dishonesty are violating academic integrity. Such students are guilty of intellectual
dishonesty as the student who receives the material even though they may not themselves
benefit academically from that dishonesty.
LEVEL THREE VIOLATIONS
1.
2.
3.
4.
5.
6.
Copying on hourly exams or the final exam.
Acting to facilitate copying during an exam.
Using prohibited materials (i.e. books, notes) during an examination.
Collaborating before an exam to develop methods of exchanging information and
implementation thereof.
Altering examinations for the purposes of re-grading.
Acquiring or distributing an examination from unauthorized sources prior to the
examination.
The minimum sanction for Level III offenses is one semester suspension from the University.
The instructor has the option of assigning a failing grade (a zero!) for the exam/quiz in question.
LEVEL FOUR VIOLATIONS
1.
2.
Repeat LEVEL III offenses.
Having a substitute take an examination or taking an examination for someone else.
Level IV violations carry a penalty of permanent expulsion from the University.