AUTACOIDS Flashcards
dictates receptor activity profile in opioid analgesics
substituent of N
receptor activity when N substituent of an opioid analgesic is methyl or aralkyl
mu receptor agonist
receptor activity when N substituent of an opioid analgesic is a dimethylallyl or cyclobutylmethyl
mu/kapa receptor agonist
receptor activity when N substituent of an opioid analgesic is a cyclopropylmethyl or allyl
pure antagonist
essential for aspartic acid anchoring of opioid drug
N cation
effect of replacing H at C14 of opioid drug with beta-OH (oxy derivatives)
increase activity 2-3 times over H
what happens when the C7 and C8 of an opioid drug gets saturated
increase activity
in opioids, replacing 6 alpha-OH in 7,8-dihydro system with alpha 6-keto (hydro derivatives)
6x increased activity
dihydrofuran oxygen (removal of O in furan) in an opioid analgesic pharmacophore
increased polarity only
removal of furan ring (ring E) in opioid analgesic pharmacophore
more lipophilic = better at targeting of CNS receptors = increased activity
purpose of 3-phenol ring in opioid analgesics
essential for agonist/antagonist activity
what structure is targeted by prodrug design in an opioid analgesic
ether/ester form at the OH of 3-phenol ring structure
purpose of aromatic phenyl ring
agonist/antagonist activity
opioids with rings A,B,C,D,E
phenanthrene-type
opioids with rings A,B,C,B
morphinan-type
opioids with rings, A,B,D
benzomorphan-type
opioids with rings A,D
phenylpiperidine-type
diacetyl morphine
heroin
derivative of morphine with saturated C6-C7 bond and 6-keto
hydromorphone (hydro derivative)
derivative of morphine with saturated C6-C7 bond, 6-keto and OH substitution at C14
oxymorphone (oxy derivative)
has OCH substitution at the the 3-phenol
codeine
codeine with saturated C6-C7 and 6-keto
hydrocodone (hydro derivative)
codeine with saturated C6-C7, 6-keto and OH at C14
oxycodone (oxy derivative)
opioids which are known to cause cardiotoxicity with prolonged use
codeine and oxycodone
common ADR among opioid analgesics and worsened by alcohol intake
fatal respiratory depression
phenanthrene-type of opioid which does not produce dependence-promoting euphoria
buprenorphine
receptor activity of buprenorphine
partial mu agonist
receptor activity of nalbuphene
kappa agonist, mu antagonist
phenanthrene-type opioid which is mainly used for post-operative/obstetrical anesthesia
nalbuphene
morphinan-type opioid which is a mu agonist and is 4-8x more potent than morphine
levorphanol
morphinan-type opioid which is both a mu antagonist and kappa agonist; 5x more potent that morphine
butorphanol
benzomorphan-type opioid which is both a kappa agonist and mu antagonist; .25x more potent than morphine
pentazocine
phenylpiperidine-type opioids which are 80x more potent than morphine and are used for cancer pain
fentanyl
receptor activity of fentanyl
mu agonist
phenyl-piperidine which is 0.1x more potent than morphine and may cause hypotension and neurotoxicity
meperidine
meperidine metabolite in which a methyl substituent from the original structure is removed; formed in the liver
normeperidine
