firestine intro/ med chem

are charged or uncharged molecules absorbed

uncharged

configurational vs conformational isomers

conform= single bond rotation

config= double bond (e/z) OR have a chiral center

Enantiomers vs. Diastereomers

-enantiomers are non-superimposable mirror images of each other

-diastereomers have 2+ chiral centers and are NOT mirror images

a lower Kd means ________ affinity

greater

van der Waals

attraction btwn hydrocarbon chains

3 point attachment rule

3 points of contact are needed to select btwn 2 enantiomers and determine stereospecificity

racemates

a mixture composed of equal amounts of R and S enantiomers

racemic switch

A drug that is already sold as a racemate is patented and sold as a single enantiomer (the eutomer)

bioisosteres

classical and nonclassical; adding functional group to change a drug property while keeping effect

describe aromatic and benzylic oxidations

OH added to para position/ least substituted spot

omega oxidations

OH added to longest aliphatic chain

describe 3/2/1 amine dealkylation

OH replaces H on the C of one of the R groups, becomes carbonyl, breaks off

3amine-> 2 amine + ket/ald

2amine-> 1 amine + ket/ald

1amine-> NH3 + ket/ald

primary amine N-oxidation

if R group on primary amine does not have H, OH can be added without carbonyl breaking off

ether o-dealkylation

OH added to R group attached to O, breaks off

ROR-> ROH and O=C

does N-dealkylation only happen at amines or other groups like imides/amides

ONLY AT AMINES

t/f: hydrolysis can happen at any carbonyl

true

t/f: reduction only happens at aldehydes and ketones

true

reduction

aldehyde/ketones gaining H, become alcohol

ester hydrolysis

ester reacts with H2O to produce a carboxylic acid and an alcohol

(this can happen to any carbonyl!)

amide hydrolysis

Amide + Water --> Carboxylic Acid + Amine

which hydrolysis is faster: esters or amides

esters is faster

phase 2 metabolism

CONJUGATION. Acetylation, Glucuronidation, sulfation. Add groups to increase excretion

glucuronidation

MOST COMMON PATHWAY

adds gluc to phenols, COOH, and nitrogens

sulfation

MOSTLY WITH PHENOLS; common in children

adds SO3- to phenol

which amino acids are used in phase 2 metabolism

glycine and glutamine; added to COOH (makes new amide bond)

glutathione phase 2

glutathione (nucleophile) added to electrophilic groups

1) good leaving group

2) e- withdrawing group

acetylation mainly happens at

primary aromatic or aliphatic amines