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IDT Fall > Anesthetics + Analgesics Medchem > Flashcards

Anesthetics + Analgesics Medchem Flashcards

1
Q

For LAs, a tertiary amine and benzoate ester are important for?

A

anesthetic properties

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2
Q

why does procaine have a short duration?

A

ester hydrolysis

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3
Q

what is the name of the metabolite of procaine?

A

PABA

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4
Q

what are the 3 general structural features for LAs?

A
  1. lipophilic portion (usually aromatic ring)
  2. intermediate chain
  3. Hydrophilic portion (usually a tertiary amine
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5
Q

for amino ester LAs, what does an electron-donating group in ortho or para position do?

A

increase anesthetic potency

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6
Q

what is the name of the metabolite of tetracaine?

A

PABA

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7
Q

what is the name of the metabolite of chloroprocaine?

A

PABA-like metabolite

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8
Q

why does chloroprocaine have a shorter duration than procaine?

A

the Cl makes it more susceptible to hydrolysis

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9
Q

Cocaine, procaine, tetracaine, and chloroprocaine are what classification of LAs?

A

Esters

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10
Q

why were amino amide LAs developed? (benefits compared to esters like procaine)

A

they have faster, more intense, and longer acting local anesthesia

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11
Q

what is the difference in metabolism that makes amino amides have longer duration?

A

slower rate of amide hydrolysis

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12
Q

route of metabolism for lidocaine?

A

1A2

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13
Q

what is one issue with bupivacaine?

A

some cardiotoxicity

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14
Q

why is ropivacaine used as single S-enantiomer?

A

R-enantiomer has cardiotoxicity

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15
Q

what are the modifications to morphine that decrease activity?

A

-remove the position 3 hydroxy group
-replace the 3-OH with a 3-OMe
-CH3CO- ester at position 3
-remove N-methyl (becomes a secondary amine)

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16
Q

what are the modifications to morphine that increase activity?

A

-remove the position 6 hydroxy group
-reduce the 7-8 double bond
-add a 14 beta hydroxy group
-CH3CO- ester at position 6

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17
Q

major route of metabolism of morphine?

A

Glucuronidation

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18
Q

what active metabolite of morphine may contribute to analgesic effects?

A

M6G

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19
Q

what are the minor routes of metabolism of morphine?

A

N-demethyl
Sulfonation

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20
Q

what routes of metabolism does codeine undergo?

A

3A4 and 2D6

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21
Q

what route of metab turns codeine into morphine?

A

2D6

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22
Q

what metabolizes hydromorphone/oxymorphone??

A

glucuronidation

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23
Q

what is the only difference b/w hydromorphone and hydrocodone?same difference b/w oxymorphone and oxycodone?
how does this effect acitivty?

A

morphones have an OH at bottom of structure, codones have an OCH3 at bottom of structure
OCH3 of codones means they will have decreased activity in comparison

24
Q

what route of metab is hydrocodone/oxycodone?
what do they metabolize into?

A

2D6
hydromorphone/oxymorphone

25
Q

what is route of metab of levorphanol?

A

glucuronidation

26
Q

what 2 routes of metab does meperidine undergo?

A

ester hydrolysis and n-demethylation

27
Q

what is the toxic metabolite of meperidine?

A

Normeperidine

28
Q

tramadol is used as a racemate of?

A

R,R and S,S

29
Q

route of metab of tramadol?

A

2D6

30
Q

why is remifentanil very short acting?

A

rapid ester hydrolysis

31
Q

why does Naloxegol not pass the BBB?

A

its a substrate for p-glycoprotein and PEG tail reduces diffusion

32
Q

what drug class is naloxegol?

A

opioid antagonist

33
Q

what drug class is naldemedine?

A

opioid antagonist

34
Q

what drug class is samidorphan?

A

opioid antagonist

35
Q

what drug class is alvimopan?

A

opioid antagonist

36
Q

why does alvimopan have limited CNS access?

A

it is a zwitterionic character (both + and - charges in same molecule)

37
Q

what drug class is butorphanol?

A

opioid partial agonist

38
Q

what drug class is nalbuphine?

A

opioid partial agonist

39
Q

what drug class is pentazocine?

A

opioid partial agonist

40
Q

what drug class is buprenorphine?

A

opioid partial agonist

41
Q

what drug class is diphenoxylate?

A

antidiarrheal

42
Q

why does diphenoxylate have limited CNS access?

A

it is a zwitterionic character

43
Q

why does loperamide have limited CNS access?

A

it’s a good substrate for -glycoprotein in BBB

44
Q

what is the name of the opioid agonist in kratom?

A

mitragynine

45
Q

what is the only drug with 1A2 metabolism?

A

lidocaine

46
Q

what are the only 2 drugs with both 3A4 and 2D6 metabolism?

A

codeine and oliceridine

47
Q

which drugs undergo glucuronidation? (Oh No Oh No The Hairy Lady Monster)

A

Oxymorphone
Naloxone
Oliceridine
Naltrexone
Tapentadol
Hydromorphone
Levorphanol
Morphine

48
Q

what drugs have only 2D6 metabolism? (H.O.T)

A

Hydrocodone
Oxycodone
Tramadol

49
Q

what drugs have only 3A4 metabolism? (No Bacon For Susan’s Niece)

A

Naloxegol
Buprenorphine
Fentanyl
Sufentanil
Naldemedine

50
Q

what are the 2 drugs that are NMDA antagonists?

A

Levorphanol
Methadone

51
Q

structurally, codeine and morphine are identical except for one difference. what is the difference and how does it affect activity?

A

Codeine has an OCH3 at bottom of structure which decreases activity

52
Q

structurally, hydromorphone and morphine are identical except for one difference which is?

A

Hydromorphone has a double bond O instead of OH at the top right

53
Q

what is the only difference b/w hydromorphone and oxymorphone? same difference b/w hydrocodone and oxycodone?
how does this effect activity?

A

oxymorphone and oxycodone have an OH group at top of structure instead of an H. This increases activity

54
Q

Structurally, how does levorphanol differ from morphine?

A

does not have hydroxy group at top right and no O group on the right side

55
Q

what is the structural key difference b/w fentanyl and sufentanil?
is sufentanil more or less potent?

A

the 6-membered ring on left side is replaced by a 5-membered ring with sulfur in it
more potent

IDT Fall (29 decks)

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