AUTACOIDS

Question 1

dictates receptor activity profile in opioid analgesics

Answer 1

substituent of N

Question 2

receptor activity when N substituent of an opioid analgesic is methyl or aralkyl

Answer 2

mu receptor agonist

Question 3

receptor activity when N substituent of an opioid analgesic is a dimethylallyl or cyclobutylmethyl

Answer 3

mu/kapa receptor agonist

Question 4

receptor activity when N substituent of an opioid analgesic is a cyclopropylmethyl or allyl

Answer 4

pure antagonist

Question 5

essential for aspartic acid anchoring of opioid drug

Answer 5

N cation

Question 6

effect of replacing H at C14 of opioid drug with beta-OH (oxy derivatives)

Answer 6

increase activity 2-3 times over H

Question 7

what happens when the C7 and C8 of an opioid drug gets saturated

Answer 7

increase activity

Question 8

in opioids, replacing 6 alpha-OH in 7,8-dihydro system with alpha 6-keto (hydro derivatives)

Answer 8

6x increased activity

Question 9

dihydrofuran oxygen (removal of O in furan) in an opioid analgesic pharmacophore

Answer 9

increased polarity only

Question 10

removal of furan ring (ring E) in opioid analgesic pharmacophore

Answer 10

more lipophilic = better at targeting of CNS receptors = increased activity

Question 11

purpose of 3-phenol ring in opioid analgesics

Answer 11

essential for agonist/antagonist activity

Question 12

what structure is targeted by prodrug design in an opioid analgesic

Answer 12

ether/ester form at the OH of 3-phenol ring structure

Question 13

purpose of aromatic phenyl ring

Answer 13

agonist/antagonist activity

Question 14

opioids with rings A,B,C,D,E

Answer 14

phenanthrene-type

Question 15

opioids with rings A,B,C,B

Answer 15

morphinan-type

Question 16

opioids with rings, A,B,D

Answer 16

benzomorphan-type

Question 17

opioids with rings A,D

Answer 17

phenylpiperidine-type

Question 18

diacetyl morphine

Answer 18

heroin

Question 19

derivative of morphine with saturated C6-C7 bond and 6-keto

Answer 19

hydromorphone (hydro derivative)

Question 20

derivative of morphine with saturated C6-C7 bond, 6-keto and OH substitution at C14

Answer 20

oxymorphone (oxy derivative)

Question 21

has OCH substitution at the the 3-phenol

Answer 21

codeine

Question 22

codeine with saturated C6-C7 and 6-keto

Answer 22

hydrocodone (hydro derivative)

Question 23

codeine with saturated C6-C7, 6-keto and OH at C14

Answer 23

oxycodone (oxy derivative)

Question 24

opioids which are known to cause cardiotoxicity with prolonged use

Answer 24

codeine and oxycodone

Question 25

common ADR among opioid analgesics and worsened by alcohol intake

Answer 25

fatal respiratory depression

Question 26

phenanthrene-type of opioid which does not produce dependence-promoting euphoria

Answer 26

buprenorphine

Question 27

receptor activity of buprenorphine

Answer 27

partial mu agonist

Question 28

receptor activity of nalbuphene

Answer 28

kappa agonist, mu antagonist

Question 29

phenanthrene-type opioid which is mainly used for post-operative/obstetrical anesthesia

Answer 29

nalbuphene

Question 30

morphinan-type opioid which is a mu agonist and is 4-8x more potent than morphine

Answer 30

levorphanol

Question 31

morphinan-type opioid which is both a mu antagonist and kappa agonist; 5x more potent that morphine

Answer 31

butorphanol

Question 32

benzomorphan-type opioid which is both a kappa agonist and mu antagonist; .25x more potent than morphine

Answer 32

pentazocine

Question 33

phenylpiperidine-type opioids which are 80x more potent than morphine and are used for cancer pain

Answer 33

fentanyl

Question 34

receptor activity of fentanyl

Answer 34

mu agonist

Question 35

phenyl-piperidine which is 0.1x more potent than morphine and may cause hypotension and neurotoxicity

Answer 35

meperidine

Question 36

meperidine metabolite in which a methyl substituent from the original structure is removed; formed in the liver

Answer 36

normeperidine