pharmaceutical chemistry Flashcards
focuses on quality aspects of medicines and aims to ensure fitness for the purpose of medicinal products
pharmaceutical chemistry
the study of drugs, and involves drug development; usually done in a laboratory setting
pharmaceutical chemistry
involves cures and remedies for disease, analytical techniques, pharmacology, metabolism, quality assurance, and drug chemistry
pharmaceutical chemistry
same atoms but linked together differently
constitutional isomers
constitutional isomers are also known as
geometrical isomers
isomers in which the atoms have different connectivity
constitutional isomers
isomers with different carbon atom arrangements and different hydrogen atom arrangements
skeletal isomers
isomers that differ in the location of the functional group
positional isomers
isomers that contain different functional groups
functional group isomers
this is positioning the different functional groups in their sites of action
stereochemistry
3 main groups of stereoisomers
- optical isomer
- geometric isomers
- conformational isomers
contain at least one asymmetric, or chiral, carbon atom
optical isomers
carbons that have four non-identical substituents around it
chiral
TRUE OR FALSE
each asymmetric carbon atom can exist in one of two non-superimposable isomeric forms
true
optical isomers that are mirror images of one another
enantiomers
have identical physical and chemical properties except that one rotates the plane of polarized light
enantiomers
clockwise direction
dextrorotatory (d/+)
counterclockwise
levorotatory (l/-)
equal mixture of d and l enantiomers
racemic mixture
TRUE OR FALSE
racemic mixtures are considered optically active
false
they are optically inactive
used to designate the handedness of glyceraldehyde enantiomers
D and L system
(( Fischer Projection Formulas ))
TRUE OR FALSE
enantiomers are optically active
true
chiral compound that rotates light towards the right
dextrorotatory
chiral compound that rotates light towards left
levorotatory
TRUE OR FALSE
there is no correlation between D, L, and +, -
true
in D and L you need to look at the _____
structure
+ and - are determined by using a ____
polarimeter
enantiomers can have large differences in:
- potency
- receptor fit
- biological activity
- transport
- metabolism
result when the drug molecule has an asymmetric interaction
neither mirror images nor superimposable
diastereomers
drugs must have at least two chiral centers in order to exist in diastereomers
diastereomers
TRUE OR FALSE
diastereomers have some stereochemical centers that are identical and some that are opposite
true
TRUE OR FALSE
diastereomers
possess different physicochemical properties and, thus, differ in properties, such as solubility, volatility, and melting points
a special type of diastereomers because all epimers are also diastereomers
epimers
compounds that are structurally identical in all respects except for the stereochemistry of one chiral center
epimers
the process of ____ (in which the stereochemistry of one chiral center is inverted) is important in drug degradation and inactivation
epimerization
occurs due to restricted rotation of double bonds based on the longest chain (not mirror images and have different physicochemical properties and pharmacologic activity)
geometric isomer
based on a set of priority rules about the relative position of the two higher-priority groups
based on cahn ingold prelog rules
E and Z nomenclature
alkene on the same side
Z
German: zusammen = together
alkene on opposite sides
E
German: entgegen = opposite
“boat” and “chair” forms
conformational isomers
non-superimposable orientations of a molecule which result from the rotation of atoms about single bonds
conformational isomers
provide a more exact representation of the three-dimensional conformation of sugars in nature
conformational isomers
functional groups that are interchangeable with minimal impact on the activity of a molecule
based on the size of functional group
isosteres
isosteric replacement of functional groups can:
- increase potency
- decrease side effects
- separate biologic activities
- increase the duration of action by altering metabolism
containing groups that are spatially and electronically equivalent and, thus, interchangeable without significantly altering the molecules’ physicochemical properties
bioisosteres
3 types of isosteres
- interchangable univalent groups
- interchangable divalent groups
- interchangable ring groups
groups are interchangeable based on similar charge and hydrogen bonding (and not the size)
bioisosteres
give example of an bioisosteres
procainamide
this has a longer duration of action than procaine because of the isosteric replacement of the ester oxygen with a nitrogen atom
procainamide
TRUE OR FALSE
procainamide is an amide
true
TRUE OR FALSE
procaine is an ether
false
it is an ester
TRUE OR FALSE
isosteric analogs may act antagonistically to the parent molecule
true
TRUE OR FALSE
alloxanthine is an isostere of xanthine
true
substrates where a drug interacts with
- receptor
- transport protein
- metabolizing enzyme
- molecules
have the same molecular formula but differs in molecular structure
constitutional isomers
aka structural isomers
same molecular formula but differs in the molecular arrangement
stereoisomers
aka spatial isomers
similar substituents found in opposite/different sides
“trans-“
geometric isomer
two identical substituents found in the same side
“cis-“
geometric isomer
where does E and Z nomenclature based of?
cahn ingold prelog rules
what is alloxanthine?
- inhibitor of xanthine oxidase
- isostere of xanthine
