Proteau Antagonist Notes Flashcards
what feature of the phenol ring is important for antagonists where they cannot hydrogen bond?
the groups on the ring should be at the meta and para positions
Propranolol is used as a ____
racemate
the _ enantiomer of Propranolol is the active one
S
Propranolol was the first _____ _ antagonist
general beta
what structural differences between pronethalol and propranolol were implemented to no longer cause tumors with use of propranolol?
added an oxymethalene bridge
moved side chain from C2 to C1 of naphalene ring
what makes propranolol fairly lipophilic?
the naphalene ring
the ability for a beta-targeting structure to H bond likely contributes to what property of the drug?
gives it partial agonistic properties
T/F an N-t-butyl group gives a drug specificity to B2 selectivity
False, does not specify B2 selectivity
which enantiomer of Sotalol is active?
the R enantiomer
why does Sotalol not have H bonding?
the methane sulfonamide group is bulky enough to prevent H bonding
what makes Sotalol a full antagonist?
the methane sulfonamide group
T/F sotalol is used as a racemate
true
T/F sotalol is lipophilic
true
what is the contributing structural factor for labetalols B antagonism?
the carboxamide group
what likely contributes to Labetalol’s B2 partial agonism?
the para hydroxy group
what agonistic/antagonistic activity do the four stereoisomers of labetalol have?
R,R-isomer => B1 antagonist, B2 partial agonist
R,S-isomer => inactive
S,R-isomer => a1 antagonist activity
S,S-isomer => a1 antagonist activity
Carvedilol is given has a racemate, which enantiomer has B antagonist action? (R or S)
S-enantiomer
Both enantiomers of Carvedilol have what antagonist/agonistic function?
both contribute to a1 antagonism
Labetalol and Carvedilol have overall greater _ antagonism than _ antagonism
B
a1
what are the three standard features of B1 antagonists that make them identifiable?
- all are 4’ (para) substituted aryloxypropanolamines which lack a 3’ (meta) substituent; a small 2’ (ortho) group is possible
- The 4’ para group is variable
- they typically have an N-isopropyl group (never t-butyl)
what is the major enzyme that metabolizes Metoprolol?
CYP2D6
Metoprolol has which two metabolites?
are they active to CYP2D6?
a-hydroxy or O-demethyl metabolite
both inactive to 2D6
T/F the SRRR isomer of nebivolol is 1000-fold more potent than the RSSS enantiomer
True
d-Nebivolol is considered?
dextrorotatory