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OUR LADY OF FATIMA UNIVERSITY UNIT OUTCOMES

College of Pharmacy
At the end of this module, the students are expected to:
1. Identify what is Pharmaceutical Chemistry
PHARMACEUTICAL AND 2. Relate the physicochemical properties of the functional
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MEDICINAL ORGANIC groups in drug design
3. Identify the stereochemistry of organic medicinal and
CHEMISTRY relate this to drug design
PMOC 311 4. Apply principles of organic medicinal chemistry and
pharmaceutical chemistry in the synthesis and
characterization of organic medicinal
Pharmaceutical Chemistry
WEEK 2

UNIT OUTLINE REQUIRED READINGS and VIDEOS

1. Define Pharmaceutical Chemistry Please read the following article thru the given link.
2. Define stereochemistry • https://courses.lumenlearning.com/boundless-
chemistry/chapter/functional-group-names-properties-and-reactions/
3. Identify three main groups of stereochemistry
4. Identify chiral and achiral carbon • Please watch the following videos thru the given link.
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5. Define Bioisosteres molecules • https://www.khanacademy.org/science/organic-

chemistry/stereochemistry-topic/chirality-r-s-system/v/introduction-to-
chirality?modal=1
• https://www.khanacademy.org/science/organic-
chemistry/stereochemistry-topic/diastereomers-meso-
compounds/v/stereoisomers-enantiomers-diastereomers-constitutional-
isomers-and-meso-compounds?modal=1

• NOTE: This has been assigned to you by your instructor during the
previous meeting.

CHECKLIST

 Read course outcomes

 Read course guide prior to class attendance
 Proactively participate in discussions
Pharmaceutical Chemistry
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 Watch videos related to the topic

 Participate in discussion board (Canvas)
 Answer and submit course unit tasks
PMOC 311

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Pharmaceutical Chemistry
• focused on quality aspects of
medicines and aims to assure
fitness for the purpose of
medicinal products.
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• the study of drugs, and it
involves drug development. Stereochemistry
• Pharmaceutical chemistry work
is usually done in a lab setting.
• Involves cures and remedies for
disease, analytical techniques,
pharmacology, metabolism,
quality assurance, and drug
chemistry.

Constitutional isomers

•Same atoms but linked together differently

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Stereochemistry
Positioning the different functional groups in their •Optical isomers contain at least one
sites of action asymmetric, or chiral, carbon atom
• Chiral - carbons that have four non-identical substituents
Three main groups: around it
• optical isomer
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• ENANTIOMER – D and L forms •Each asymmetric carbon atom can exist in

• DIASTEREOMER - ex Epimers one of two non-superimposable isomeric
• geometric isomers forms
• Cis and Trans
• conformational isomers
• Boat and Chair

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Enantiomers
Chiral or non chiral
• optical isomers that are mirror images of one another
• have identical physical and chemical properties except that
one rotates the plane of polarized light
• clockwise direction (dextrorotatory, designated
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d or +)
• counterclockwise direction (levorotatory,
designated l or -)
• racemic mixture
• equal mixture of d and l enantiomers
• optically inactive

Chiral or non chiral Chiral or non chiral

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ENANTIOMERS
Chiral or non chiral
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Enantiomers can have large differences in potency, receptor fit,

biologic activity, transport and metabolism. These differences
result when the drug molecule has an asymmetric interaction
with a receptor, a transport protein, or a metabolizing enzyme.
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DIASTEREOMERS Epimers

• neither mirror images nor • special type of diastereomers because all epimers are also diastereomers
superimposable • compounds that are structurally identical in all respects except for the
• drug must have at least two chiral stereochermistry about one chiral center. The process of epimerization
centers in order to exist in (in which the stereochemistry of one chiral center is inverted) is
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diastereomers important in drug degradation and inactivation

• Unlike enantiomers, in which all
stereochemical centers are opposite,
diastereomers have some
stereochemical centers that are
identical and some that are opposite
• possess different physicochemical
properties and, thus, differ in
properties, such as solubility,
volatility, and melting points.

doxorubicin epirubicin

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GEOMETRIC ISOMER GEOMETRIC ISOMER

Occurs due to restricted rotation of double bond

based on the longest chain
not mirror images and have different physicochemical
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propeties and pharmacologic activity.

E and Z nomenclature

• cis Z and trans E

H H
Z
• based on a set of priority rules
• relative position of the two higher
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priority groups
• (Z)-alkene on the same side
(German; zusammen = together) L L
• (E)-alkene on opposite sides
(German; entgegen = opposite)

cis but -2-ene

z but -2-ene

H L

E
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L H

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Conformational isomers Bioisosteres molecules

• boat and "chair" forms
• non-superimposable orientations of a molecule •containing groups that are spatially and
which result from the rotation of atoms about
single bonds electronically equivalent and, thus,
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• provide a more exact representation of the interchangeable without significantly
three-dimensional conformation of sugars in altering the molecules’ physicochemical
nature properties.

Biosteres
 Procainamide
•Isosteric replacement of functional groups:
•can increase potency an amide, has a longer duration of action than
•decrease side effects procaine, an ester, because of the isosteric
replacement of the ester oxygen with a
•separate biologic activities
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nitrogen atom
•increase the duration of action by altering
metabolism.

•isosteric analog may act antagonistically to the

parent molecule.
•Alloxanthine is an inhibitor of xanthine
oxidase. It is also an isostere of xanthine, the
normal substrate for the enzyme
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End of Discussion

xanthine alloxanthine

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ASSIGNMENT

• Reminder: Prepare for Online Quiz.

• Assignment 2 :
• Physicochemical Properties of functional groups
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(see canvas for the assignment)

• Note: Submit this thru CANVAS