Anesthetics + Analgesics Medchem

Question 1

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

Answer 1

anesthetic properties

Question 2

why does procaine have a short duration?

Answer 2

ester hydrolysis

Question 3

what is the name of the metabolite of procaine?

Answer 3

PABA

Question 4

what are the 3 general structural features for LAs?

Answer 4

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

Question 5

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

Answer 5

increase anesthetic potency

Question 6

what is the name of the metabolite of tetracaine?

Answer 6

PABA

Question 7

what is the name of the metabolite of chloroprocaine?

Answer 7

PABA-like metabolite

Question 8

why does chloroprocaine have a shorter duration than procaine?

Answer 8

the Cl makes it more susceptible to hydrolysis

Question 9

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

Answer 9

Esters

Question 10

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

Answer 10

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

Question 11

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

Answer 11

slower rate of amide hydrolysis

Question 12

route of metabolism for lidocaine?

Answer 12

1A2

Question 13

what is one issue with bupivacaine?

Answer 13

some cardiotoxicity

Question 14

why is ropivacaine used as single S-enantiomer?

Answer 14

R-enantiomer has cardiotoxicity

Question 15

what are the modifications to morphine that decrease activity?

Answer 15

-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)

Question 16

what are the modifications to morphine that increase activity?

Answer 16

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

Question 17

major route of metabolism of morphine?

Answer 17

Glucuronidation

Question 18

what active metabolite of morphine may contribute to analgesic effects?

Answer 18

M6G

Question 19

what are the minor routes of metabolism of morphine?

Answer 19

N-demethyl
Sulfonation

Question 20

what routes of metabolism does codeine undergo?

Answer 20

3A4 and 2D6

Question 21

what route of metab turns codeine into morphine?

Answer 21

2D6

Question 22

what metabolizes hydromorphone/oxymorphone??

Answer 22

glucuronidation

Question 23

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

Answer 23

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

Question 24

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

Answer 24

2D6
hydromorphone/oxymorphone

Question 25

what is route of metab of levorphanol?

Answer 25

glucuronidation

Question 26

what 2 routes of metab does meperidine undergo?

Answer 26

ester hydrolysis and n-demethylation

Question 27

what is the toxic metabolite of meperidine?

Answer 27

Normeperidine

Question 28

tramadol is used as a racemate of?

Answer 28

R,R and S,S

Question 29

route of metab of tramadol?

Answer 29

2D6

Question 30

why is remifentanil very short acting?

Answer 30

rapid ester hydrolysis

Question 31

why does Naloxegol not pass the BBB?

Answer 31

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

Question 32

what drug class is naloxegol?

Answer 32

opioid antagonist

Question 33

what drug class is naldemedine?

Answer 33

opioid antagonist

Question 34

what drug class is samidorphan?

Answer 34

opioid antagonist

Question 35

what drug class is alvimopan?

Answer 35

opioid antagonist

Question 36

why does alvimopan have limited CNS access?

Answer 36

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

Question 37

what drug class is butorphanol?

Answer 37

opioid partial agonist

Question 38

what drug class is nalbuphine?

Answer 38

opioid partial agonist

Question 39

what drug class is pentazocine?

Answer 39

opioid partial agonist

Question 40

what drug class is buprenorphine?

Answer 40

opioid partial agonist

Question 41

what drug class is diphenoxylate?

Answer 41

antidiarrheal

Question 42

why does diphenoxylate have limited CNS access?

Answer 42

it is a zwitterionic character

Question 43

why does loperamide have limited CNS access?

Answer 43

it's a good substrate for -glycoprotein in BBB

Question 44

what is the name of the opioid agonist in kratom?

Answer 44

mitragynine

Question 45

what is the only drug with 1A2 metabolism?

Answer 45

lidocaine

Question 46

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

Answer 46

codeine and oliceridine

Question 47

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

Answer 47

Oxymorphone Naloxone Oliceridine Naltrexone Tapentadol Hydromorphone Levorphanol Morphine

Question 48

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

Answer 48

Hydrocodone Oxycodone Tramadol

Question 49

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

Answer 49

Naloxegol Buprenorphine Fentanyl Sufentanil Naldemedine

Question 50

what are the 2 drugs that are NMDA antagonists?

Answer 50

Levorphanol Methadone

Question 51

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

Answer 51

Codeine has an OCH3 at bottom of structure which decreases activity

Question 52

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

Answer 52

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

Question 53

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

Answer 53

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

Question 54

Structurally, how does levorphanol differ from morphine?

Answer 54

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

Question 55

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

Answer 55

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