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PHRM 501 > Medchem > Flashcards

Medchem Flashcards

1
Q

Strong bases have

A

high solubility

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2
Q

Weak bases have

A

low solubility

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3
Q

H-Bond donors

A

Hydrogens that are attached to N or o

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4
Q

H-Bond acceptors

A

O and N

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5
Q

In an amide

A

N cannot accept H-bonds

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6
Q

An increase in one pH unit, means

A

an 10-fold increase in [H+]

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7
Q

Log P >0

A

more drug in octanol

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8
Q

Log P<0

A

more drug in water

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9
Q

ClogP

A

estimates the logP of molecules

- calculated value

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10
Q

Groups w negative values have

A

increased water solubility and decreased membrane permeability

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11
Q

Groups w positive values (logP or ClogP)

A

decreased water solubility and increased membrane permeability

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12
Q

Pro-drugs

A

A pro‐drug is an INACTIVE drug that is transformed by the body into an ACTIVE drug. Usually this is used to solve a solubility or permeability issue with the
active drug

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13
Q

Isomers

A

Two compounds are isomers if they have the same molecular formula but different chemical structures

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14
Q

STRUCTURAL ISOMERS

A

Same molecular formula, but different bond

connectivity

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15
Q

GEOMETRIC ISOMERS

A

Same bond connectivity, but different arrangement about a fixed bond

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16
Q

STEREO‐ISOMERS

A

Different chirality

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17
Q

CONFORMATIONAL ISOMERS

A

Same bond connectivity, arrangement, and
chirality – but different temporal conformations.
(generally these rapidly interconvert)

18
Q

R-steriochemistry

A

clockwise

starting Carbon molcule from the dashed wedge then go to colored in wedge

19
Q

S-steriochemistry

A

counterclockwise

starting from the dashed wedge then go to colored in wedge

20
Q

Enantiomers

A

have identical physical properties

- if ALL of the stereocenters are switched

21
Q

Diastereomers

A 
have similar (but different) physical properties
-if SOME (but not all) of the stereocenters are
switched
22
Q

Note that a chiral center with a strait line

or squiggly line indicates

A

a mixture of stereo‐isomers

23
Q

(+) compounds are

A

chiral molecules that rotate light clockwise

24
Q

(‐) compounds are

A

chiral molecules that rotate light counterclockwise

25
Q

(+/‐) compounds are

A

chiral molecules that are racemic

26
Q

Epimerization

A

The process of converting one stereochemical center into another.

27
Q

Small molecule drugs have

A 
< 1000 Da
Synthesis
Pill (oral)
t1/2-Hours 
High membrane permeability
Bio target is intracellular
28
Q

Large molecule drugs have

A 
> 20000 Da
Cellular expresiion
taken through IV
t1/2- days/weeks
Low membrane perm
Bio target- extracellular
29
Q

Pharmacophore

A

The key structural components that drive binding to the biological target
-A “map” of the “core” interactions
that hold a drug in the binding site

30
Q

Amines and carboxylic acids can be inserted for

two purposes

A

1) To form an ionic interaction with the biological target

2) To increase the solubility of the drug

31
Q

How do enzymes work?

A

1) By increasing the “effective concentration” of reactants

2) By stabilizing the “transition state” of the intermediate

32
Q

Enzymes decrease

A

activation energy

33
Q

Antimetabolites

A

designed to “look” like an essential biological molecule – but cannot be processed by a normal metabolic pathway

34
Q

Irreversible inhibitors (suicide inhibitors)

A

bind covalently to the active site of the enzyme

  1. Inhibitor binds
  2. Formation of covalent adduct
  3. inactivated enzyme
  • enzyme is usually permanently inactivated
35
Q

Competitive inhibitors sterically

A

block the active site of the enzyme

-closing the lid of the hopper

36
Q

Potent inhibitor

A

a molecule that mimics intermediate

37
Q

Noncompetitive inhibitors

A 
Binding to allosteric site can activate or inhibit 
enzyme activity (but usually inhibits...
38
Q

Proteases

A

cleaves an amide

39
Q

Esterases

A

cleaves an ester

40
Q

Kinases

A

adds a phosphate (from ATP) to Ser, Thr, or Tyr

41
Q

Phosphatase

A

removes a phosphate from Ser, Thr, or Tyr

PHRM 501 (21 decks)

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