AND ANSWERS LATEST 2025
phase 1 reactions - Answermetabolic oxidations at carbon; these generally occur at the activated sites of
the carbon
displacable hydrogen - AnswerWhat does carbon need to have in order to undergo metabolism? (Phase
1 Reactions)
organic oxidations - AnswerThese reactions in Phase 1 usually involve:
Gain of an oxygen
Loss of a hydrogen
Loss of an alkyl group (dealklyation)
Loss of a heteroatom (N, S)
locations of oxidative reactions - Answer(Phase 1 Reactions) sites for these include:
para and benzylic positions, double bonds, allylic positions, the ends of alkyl chains, the next-to-last
carbons of alkyl chains
chlorpromazine - Answeranti-psychotic that CYP450 hydroxylates; example of aromatic hydroxylation,
will be hydroxylated on its most electron-rich and least hindered carbon
dioxin - Answeragent orange compound that has a high logP (hydrophobic), not easily hydroxylated by
CYP450 so it stays in the body and accumulates in the body tissue. Metabolism blocked so it'll stay with
you forever and kill you slowly. Used to devastating effect in the Vietnam War.
,phenytoin - Answeranti-seizure medication that is a pro-chiral molecule, only one of its two aromatic
rings on the chiral center will be oxidized by CYP450. The (S) phenytoin is the most commonly occurring
metabolite, not (R).
carbamazepine - Answeranti-epileptic drug that is an example of CYP450 oxidation of non-aromatic
double bonds; this is how this drug gets metabolized, one of its double bonds gets turned into a single
bond via an EPOXIDE, then the epoxide bursts open and Hs are added so there are two OH groups where
the double bond used to be.
benzylic carbon oxidation - Answeranother reaction that CYP450 does; the benzylic position of a drug
gets hydroxylated to OH, then to aldehyde, then to carboxylic acid. (Phase 2 Reaction)
allylic carbon oxidation - Answeranother reaction that CYP450 does; the allylic position has a OH group
added.
Example: hexobarbital
diazepam - Answerexample of a drug that CYP450 oxidizes in the position right next to the drug's
carbonyl group. One of the first benzodiazepines
aliphatic chain oxidation - Answerreaction by CYP450 where a carbon at the end of the chain gets
oxidized into a carboxylic acid
Example: valproic acid (seizure drug)
heteroatom oxidation - AnswerCYP450 reactions where an O is added to a heteroatom (usually N or S)
Example: thioperoxide (SOH) formation
N-dealkylation - AnswerCYP450 reaction where the alkyl chain is cleaved from the N, producing two
products: amine group, and alkyl chain.
S-dealkylation - AnswerCYP450 reaction where the alkyl chain is cleaved from the S, producing two
products: thiol group, and alkyl chain.
Example: 6-Methylthiopurine anticancer drug
, O-dealkylation - AnswerCYP450 reaction where the alkyl chain is cleaved from the O, producing two
products: OH group, and alkyl chain. This is good for making drug metabolites more polar.
Example: encalnide
iron - Answerthe CYP450 dealkylation mechanism involves oxidation and reduction of this atom:
flavin monooxygenase (FMO) - Answergroup of enzymes (5 total) that catalyze N and S oxidations.
Enzymes 1-3 are involved in drug metabolism
ester hydrolysis - Answerreaction where an ester is broken down into carboxylate and alcohol
amide hydrolysis - Answerreaction where an amide is broken down into free amine and carboxylic acid.
true - AnswerTrue or false: in general, esters are much more readily hydrolyzed than amides
trichloroethanol - Answerchloral hydrate (an aldehyde) gets metabolically reduced to ______________
because aldehydes are highly reactive and can lead to toxic effects if in the body too long
reduced - Answeraldehydes get __________ when metabolized.
NADPH dependent reductase - Answerreductions of aldehydes and ketones are catalyzed by the enzyme
__________
amines - Answernitro groups (-NO2) are reduced to _______
example: chloramphenicol to arylamine
mechanism cycle of CYP450 - Answerthe process used to oxidize a drug with a CYP450 enzyme; it often
replaces a H with an OH group
Step 1 of CYP450 mechanism - Answerthe drug molecule binds to the hydrophobic active site on the
CYP450 enzyme (active site is near the heme ion).
A water molecule is displaced.