pchem exam 2

In theory, the diol I can be enzymatically oxidized to the aldehyde Il (see scheme below).

Which of the following statements about I are valid? (there may be more than one that apply)

I and II only

Which of the following is/are correct about the molecule shown below?

I. it is involved in local immune response

II. it is involved in the regulation of physiological function in the gut

III. all of its receptors are GPCRs

I, II, and III

Which of the following enzymes can be involved in the metabolic reaction shown below? - OXIDATIVE DEAMINATION

I. alcohol dehydrogenase

II. CYP450

III. MAO

II and III only

Which of the following is/are correct about the molecule shown below?

I. It can cross the blood brain barrier

Il. It is a substrate of COMT

IIl. It is charge neutral under physiological pH

I, II, and III

Which of the following is/are correct about the molecule shown below?

I. it is highly water soluble

II. it is charge neutral under physiological pH

III. there is no reuptake mechanism for its elimination from the synapse

I and II only

a molecule that is a 50:50 mix on enantiomers is

racemic

The drug below is know to undergo metabolically aromatic hydroxylation reaction.

Where is the hydroxyl group most likely to go for the aromatic hydroxylation?

A

Below are benzene and phenol.

The logP for benzene is 2.13 and the logP for phenol is 1.46

Calculate the πOH Value

-0.67

True or False:

Phase 2 conjugation reactions always lead to increase in water solubility.

False

Which of the following compounds can undergo direct glucuronidation?

A, B, C, E

Which of the following receptors can the molecule shown below bind to and activate?

I. AMPA receptor

Il. Kainate receptor

III. NMDA receptor

I, II, and III

What is the intermediate in O-dealkylation?

hemiacetal

Which of the following is/are correct about the molecule shown below?

I. It is the neurotransmitter serotonin

Il. It is eliminated from the synapse through reuptake

IlI. It has a net positive charge under physiological pH

I, II, and III

Which of the following functional groups/compounds can be acetylated metabolically?

amino acids, aromatic amines, hydrazaine, sulfonamides

NOT TERTIARY AMINES

Which of the following compounds/drugs can be a direct substrate of glutathione S-transferase?

A, B, C, D

which of the following functional groups can be reduced metabolically?

aldehyde, aromatic nitro, azo, ketone

complete the sentence to make it true: the lower the πx value,

the lower the lipophilicity

True or False:

An aldehyde is more likely to be oxidized metabolically than reduced.

True

What is the cosubstrate in metabolic acetylation reactions?

CH3CO-SCoA

For Idose, use the glyceraldehyde rule to determine if the configuration of Idose is D or L

D

For 1,2-cyclohexane diol, determine if the configuration is cis or trans

trans

True or False:

All cholinergic receptors are ligand-gated ion channels.

False

Which of the following is/are correct about the nerve gas Soman?

I. it inhibits choline acetyltransferase

II. it inihibits the hydrolysis of acetylcholine

III. it increases the amount of acetylcholine in the synaptic cleft

II and III only

The drug below is used only as a local anesthetic because

I. It is too lipophilic to be absorbed from the injection site

II. It has no other pharmacological activity at sites other than the injection site

III. It is quickly hydrolyzed by esterases once it is absorbed from the injection site

III only

For Mevinphos, determine which isomer is E and which is Z

I = E; II = Z

If the logP value of phenol is 1.46 and the πNO2 is -0.28, determine the logP value for 2,4,6-trinitrophenol

0.62

Mavamectin is in Phase III clinical trials for treatment of cardiomyopathy.

Assign the configuration to the chiral center.

S

Permethrin can be used as an insecticide and as a drug to treat scabies and lice.

Assign stereochemistry to centers 1 and 2, respectively

R,S

What is the cosubstrate in metabolic sulfation reactions?

PAPS

Which of the following is/are correct about the molecule shown below?

I. It is synthesized in the synaptic cleft

II. it is highly water soluble due to the quaternary ammonium cation

III. it can produce excitatory actions

II and III only

True or False:

Hydrolysis of esters is a common phase 1 oxidative metabolic reaction.

false

The combination of Levodopa and carbiDOPA can be used to treat Parkinson's Disease because

I. Parkinson's Disease is related to the deficiency of Levodopa in the brain

Il. carbiDOPA is an inhibitor of the peripheral decarboxylase

III. carbiDOPA helps to extend the plasma half-life of Levodopa

II and III only

Select All That Apply:

lleperidone is an antipsychotic agent indicated for schizophrenia.

Which of the following metabolic reactions can happen to iloperidone directly?

N-Dealkylation

O-Dealkylation

Reductive reaction

What is the intermediate in N-dealkylation?

carbinolamine

Select All That Apply:

Diphenhydramine (Benadry®) is an antihistamine mainly used to treat allergies.

Which of the following metabolic reactions can happen to diphenhydramine directly?

aromatic hydroxylation

deamination

N-dealkylation

O-dealkylation

Below are 4 conformers of 2-methyl pentane.

Which conformer has the lowest energy?

I

True or False:

All metabotropic glutamate receptors are GPCRs.

True

What is the intermediate in S-dealkylation?

thiohemiacetal

The scheme below shows an equilibrium between two cyclohexane conformations.

Which conformer will have the lowest energy?

I

Which of the following is/are correct about the molecule shown below?

I. It is a neurotransmitter present only in the central nervous system

II. It is negatively charged at physiological pH

III. It is eliminated in the synapse through the action of catechol O-methyl transferase (COMT) as one of the mechanisms

III only

Which of the following enzymes can be involved in the metabolic reaction shown below? - N-OXIDE formation

I. aldehyde oxidase

II. CYP450

III. Flavin-containing monooxygenase (FMO)

II and III only

Select All That Apply:

What are the enzymes involved in mercapturic acid formation?

Acetylase

Cysteinyl-glycinase

Glutamyl transferase

Glutathione S-transferase

The concentration of a drug in the lipid phase divided by the concentration

of a drug in the aqueous phase is known as what?

the partition coefficient

True or False:

Drug Metabolism always leads to inactivation of a drug.

False

Flumazenil is a benzodiazepine receptor antagonist used to treat benzodiazepine overdose.

It has a short half-life of 7 - 15 min after iv administration.

What is/are the most likely reason(s) that its half-life is so short?

I. quick elimination through glucuronidation

II. quick metabolism through aromatic hydroxylation on the left benzene ring

III. quick hydrolysis of the ester bond by serum esterases

III only

Which of the following is/are correct about the molecule shown below?

I. It is the neurotransmitter dopamine

II. All of its receptors are GPCRs

III. It has a net positive charge under physiologica pH

I, II, and III

select All That Apply:

Which of the following metabolic reactions can happen to the drug below?

N-dealkylation

Deamination

Hydrolysis of the amide bond

True or False:

Drug metabolism can happen in the kidneys.

True

Which of the following compounds can be a substrate of UDP-glucuronyl transferase?

Alcohols

Amines

R-SH (sulfhydryl)

Carboxylic acids

Phenols

Terfenadine (Seldane®), a second generation antihistamine, was converted in vivo extensively to fexofenadine. Fexofenadine was later developed as a third generation antihistamine - Allegra®.

What is/are involved in the metabolic conversion from terfenadine to fexofenadine?

I. aliphatic hydroxylation

II. oxidation of alcohol to aldehyde

III. oxidation of aldehyde to carboxylic acid

I, II, and III