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Biomedical Lab III > Lab 1 > Flashcards

Lab 1 Flashcards

1
Q

define drugs

A

synthetic or biological compounds used in the treatment or prevention of disease

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2
Q

How do most drugs produce physiological changes?

A

by binding to biological receptors

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3
Q

the knowledge of ________ is used to predict the physiochemical properties and potential biological effects of drugs

A

MOLECULAR STRUCTURE

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4
Q

name some physiochemical properties that are the basis for pharmacological and pharmaceutical evaluation

A

crystalline structure
solubility
melting/boiling point
polarity
lipophilicity
pka
steric effects
partition coefficient

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5
Q

give 2 words to describe the word “pharmacological”

A

pharmacodynamic and pharmacokinetic

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6
Q

pharmacodynamics studies what?

A

the effects of drugs ON THE BODY (mechanism of action, therapeutic and adverse effects”

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7
Q

pharmacokinetics studies what?

A

the effect of the BODY on the drug (ADME)

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8
Q

PHYSIOCHEMICAL, PHARMACODYNAMIC, AND PHARMACOKINETIC EFFECTS ARE INFLUENCED BY ____________

A

drug concentration

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9
Q

define “molecular constitution”

A

describes the IDENTITY and CONNECTIVITY of the atoms in a molecular entity

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10
Q

does “molecular constitution” take into account double and triple bonds? what about spatial arrangement?

A

takes into account single/double/triple bonds but NOT spatial arrangement

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11
Q

what is a “molecular entity”

A

any chemically or isotopically distinct atom/molecule/ion/pair/radical ion, etc which can be distinguished as a SEPARATELY DISTINGUISHABLE ENTITY

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12
Q

true or false

REGARDLESS of the administration route, drugs MUST be in solution in order to be permeable and thus absorbed

A

true

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13
Q

when comparing molecules of similar polarity, ____(large or small) molecules are generally less soluble in water than the alternative

A

LARGE molecules are LESS soluble in water

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14
Q

true or false

drug permeability is not limited by molecular size

A

false

compounds with molecule size greater than 100nm and molecular weight greater than 1000g/mol do NOT DIFFUSE READILY through the cell membrane, and transport mechanisms may be inept for this size

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15
Q

what imparts specific properties to a drug?

A

its functional group

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16
Q

define polarity

A

the difference in electronegativity within a molecular bond

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17
Q

true or false

polarity plays a key role in molecular interactions

A

true

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18
Q

molecules containing ___ and ___ are polar

ionic compounds such as ___, ____, and ____ are polar and are electrolytes

_____ and ____ are nonpolar (hydrophobic/lipophilic)

A
  1. oxygen and nitrogen
  2. salts, acids, and bases
  3. unsubstituted aromatic rings and aliphatic chains
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19
Q

functional groups can modify ______ properties such as……

A

physiochemical properties such as taste, solubility, and stability

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20
Q

what is the SOLUBLE SALT of acyclovir

A

acyclovir phosphate

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21
Q

what is the INSOLUBLE salt of chloramphenicol?
what is it formulated as?

A

chloramphenicol palmitate
formulated as a tasteless suspension

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22
Q

____, _____, and _____ are ____ groups and are very susceptible to hydrolysis

A

amides, esters, and lactams are NEUTRAL groups and are very sensitive to hydrolysis

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23
Q

can the proximity (distance) of each functional group to each other alter the properties of each group, and the overall properties of the drug?

A

yes

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24
Q

define chirality

A

the geometric property of a rigid object of being NON-SUPERPOSABLE on its mirror image

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25
Q

achiral definition

A

an object that IS superposable on its mirror image

26
Q

define chirality centre

A

an atom holding a set of ligands in a spatial arrangement that is non-superposable on its mirror image

27
Q

define an isomer

A

one of several chemical species (or molecular entities) that have the SAME stoichiometric molecular formula, but different constitutional/stereochemical formulae and HENCE DIFFERENT PHYSICAL AND/OR CHEMICAL PROPERTIES

28
Q

do isomers have the same physical and chemical properties?

A

no – not necessarily.
isomers have the same stoichiometric formulae BUT different constitutional or stereochemical formulae

29
Q

further classify isomers

A

2 types of isomers: constitutional or stereoisomers

30
Q

differentiate between constitutional isomers and stereoisomers

A

constitutional isomers have the same molecular formula, but different connectivity (sequence of the atoms) and they differ in their physicochemical properties

stereoisomers have the same chemical formula and same order of attachment, but the groups differ in their spatial arrangement (3D)

stereoisomers can be divided into conformational and configurational

31
Q

differentiate between configurational and conformational isomers

A

both are stereoisomers (same molecular formula, same order of connectivity, but different spatial arrangement)

With conformational isomers, they can be interconverted by rotations about single bonds

configurational isomers CANNOT be interconverted by rotations about single bonds, either due to restricted rotation (ie: cis-trans) or not (optical: enantiomers and diastereomers).
configurational isomers MAY SHARE SOME PHYSICOCHEMICAL PROPERTIES BUT DIFFER IN SPECIFICITY TO RECEPTOR BINDING AND ENZYME SUBSTRATE

32
Q

2 molecules have the same molecular formula, same connectivity, cannot be interconverted about single bonds (due to restricted rotation)

classify these 2 molecules

A

cis-trans isomers (geometric)

33
Q

2 molecules have the same molecular formula, same connectivity, and can be interconverted by rotation about single bonds

classify these 2 structures

A

conformational isomers

34
Q

2 molecules have the same molecular formula, but the atoms are NOT connected in the same order (not the same connectivity)

classify these 2 structures

A

constitutional isomers — either functional, positional, or skeletal

35
Q

2 molecules have the same molecular formula, same connectivity, CANNOT be interconverted by rotation about single bonds (NOT due to restricted rotation)

classify these 2 molecules

A

optical isomers – either enantiomers (non-superimposable mirror images) or diastereomers (non-superimposable non mirror images)

36
Q

define cis- trans- isomers

A

2 molecules that have the same molecular formula, same order of atoms (connectivity) but CANNOT be interconverted due to restricted rotation about a carbon bond (either double bond or in a ring)

37
Q

a sample is said to possess optical activity if….

A

the sample of material is able to rotate the plane of polarization of a beam of transmitted plane-polarized light

38
Q

optical rotation is the classic distinguishing characteristic of systems containing unequal amounts of ______(what kind of moelcules)

A

ENANTIOMERS

39
Q

true or false

enantiomers are stereoisomers

A

true

40
Q

an enantiomer causing rotation in a clockwise direction (when viewed in the direction facing ____) is said to be ______ and its chemical name or formula is designated with what prefix?

A

FACING THE ONCOMING LIGHT BEAM, dextrorotatory, (+) prefix

41
Q

an enantiomer causing rotation in a counter clockwise direction is ____ and has ___ prefix

A

laevorotory, (-)

42
Q

what are optical isomers?
how are they able to rotate plane-polarized light?

A

same molecular formula, same connectivity (stereoisomers) that are not able to be interconverted (NOT due to restricted rotation).
basically they are either enantiomers or diastereomers

they are able to rotate plane polarized light due to their CHIRAL CENTERS

43
Q

what is a chiral center

A

an asymmetric atom (generally carbon) with 4 different chemical groups

44
Q

how can you calculate the maximum number of stereoisomers possible of optical isomers?

A

2^n, where n is the number of CHIRAL CARBONS present in the molecule

45
Q

true or false

enantiomers are NOT IDENTICAL in their physical properties

A

FALSE – they are identical in all physical properties EXCEPT that they rotate the plane of polarized light in an equal, but opposite direction

46
Q

enantiomers have the SAME CHEMICAL PROPERTIES except when…..

A

another chiral molecule is involved

47
Q

the degree of rotation of enantiomers is dependent on what?

A

the concentration of the solution

48
Q

what is a racemic mixture?

A

an equimolar mixture of a pair of enantiomers.

49
Q

do racemic mixtures exhibit optical activity?

A

NO

50
Q

How is the chemical name or formula of a racemic mixture distinguished from those of the enantiomers it contains?

A

by the prefix (k) or rac- or racem-
OR the symbols R and S

51
Q

to be diastereoisomers, at least one chiral carbon must ____ and at least one chiral carbon must be _____

A

at least one must be the same (R,R) and at least one must be different (R,S)

52
Q

what can you say about the physical and chemical properties of enantiomers and diastereomers

A

enantiomers have the SAME physical properties, except for the fact that they rotate the plane of polarized light in an equal but opposite direction. They have the same chemical properties EXCEPT when another chiral molecule is involved

diastereomers have DIFFERENT PHYSICAL PROPERTIES and have some differences in chemical behavior towards both achiral and chiral reagants

53
Q

what are epimers?

A

stereoisomers (same molecular formula, same connectivity) that contain more than one chiral carbon and differ in configuration at JUST ONE STEREOCENTER

54
Q

what are meso compounds?

A

stereoisomers with the internal plane of molecular symmetry

55
Q

EACH HALF of a meso compound is….

A

a non superimposable mirror image

56
Q

true or false

meso compounds are optically inactive

A

TRUE
the individual chiral centers in a meso compound are optically active and rotate the plane of polarized light in equal and opposite directions.

HOWEVER, this cancels the optical activity of the molecule as a whole, and thus meso compounds are optically INACTIVE

57
Q

the Fischer-Rosanoff convention is no longer used.

D is equivalent to the current ___ while L is equivalent to the current ___

A

D —> R
L –> S

58
Q

____ provides the sequence rules used to assign R and S configuration to stereocenters

A

the Cahn-Ingold Prelog System

59
Q

give the steps of assigning R and S configurations, according to the Cahn-Ingold Prelog System

A
  1. Identify chiral carbon
  2. Assign a priority to each chiral atom based on the molecular (atomic) number. The higher the molecular number, the higher the priority
  3. in case of a tie, use the next atoms along the chain
  4. if clockwise, R. if counterclockwise, S
  5. The lowest priority group should always be directed AWAY FROM YOU. if it is directed towards, the assigned configuration reverses
60
Q

give the formula for retention factor

A

Rf = distance moved by compound/distance moved by solvent front

61
Q
A

Biomedical Lab III (10 decks)

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