Anxiety & Bipolar Med Chem Flashcards by Cory Montez

Assign a rank to each of the Benzodiazepine half-lives:

1: 14 hours
2: 2 hours
3: 36 hours
5: 20 hours

1: 14 hours (intermediate)
2: 2 hours (Short)
3: 36 hours (Long)
5: 20 hours (Intermediate)

Short: <10 hr

Intermediate:10-24 hr

Long: >24 hr

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The medication Chlordiazepoxide exhibits good absorption when given ___ but will exhibit slow and erratic absorption when given ___.

A Intrathecal, IM

B. Orally, IM

C. IM, Orally

D. SubQ, IM

B. Oral, IM

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(Short answer) According to the picture provided, why is it that Benzodiazepines such as Chlordiazepoxide are long-acting?

The medication Chlordiazepoxide is metabolized to other active metabolites that have thier own half-lives. Because of this the parent drug and its active metabolites will continue to work at the BZD binding sites on GABA-A receptors and increase their affinity for GABA-A.

The accumulation of parent drug and active metabolites is the main reason for the adverse side effects and sedation as well

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Chlordiazepoxide HCl is the first Class __ Anxiolytic

A. A

B. B.

A. Class A.

The rest from there are derivatives are chlordiazepoxide

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According to the picture what type of reaction is happening between Chlordiazepoxide and Demoxepam?

A. N-Demethylation and Hydroxylation

B. N-Demethylation and Deamination

C. N-Methylation and Amination

D. N-Methylation and Hydroxylation

B. N-Demethylation and Deamination

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According to the picture what type of reaction is occuring between Nordazepam and Oxazepam?

A. Deamination

B. Methylation

C. Reduction

D. Hydroxylation

D. Hydroxylation

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Which of the following metabolites of Diazepam is sold as a separate medication? (select all)

A. Orange

B. Green

C. Red

B. Green

C. Red

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(Short Answer) Based on the structure of Oxazepam, why is it short acting in comparison to other BZDs?

The OH group that is present in the drug molecule enables it to go through rapid metabolism via glucuronidation (UGTS). Since it is succeptible to this form of metabolism it is not as long-acting as other BZDs

It also makes it a safer medication since it doesn’t have cumulative effects that other BZDs have. This is because they produce other active metabolites such as Nordazepam and even Oxazepam itself.

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The medication Clorazepate Dipotassium (Tranxene) is considered a prodrug for what reason?

A. Immediately undergoes carboxylation to form active metabolite Nordazepam

B. Immediately undergoes decarboxylation to form active metabolite Nordazepam

C. Immediately undergoes Hydroxylation to form active metabolite Nordazepam

D. Immediately undergoes dehydroxylation to form active metabolite Nordazepam

B. Immediately undergoes decarboxylation to form active metabolite Nordazepam

The reason the medication is considered a prodrug is because as soon as it enters the body it is immediately converted to the active metabolite Nordazepam (DMD). Because of this the overall pharmacological effects of the medication reside within the active metabolite Nordazepam instead of the parent molecule Clorazepate Dipotassium.

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Based on the picture provided what do you predict will be the active metabolite?

A. Citalopram

B. Diazepam

C. Chlordiazepoxide HCl

D. Oxazepam

D. Oxazepam

As you can see from other medications, Oxazepam is typically the result of the metabolism of Nordazepam (DMD). Oxazepam will then undergo glucuronidation when it is metabolized.

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In the metabolism of Clonazepam, what type of reaction is occuring?

A. Nitro-methylation

B. Nitro-Oxidation

C. Nitro-Reduction

D. Nitrogenation

C. Nitro-Reduction

Undergoes Nitro-reduction to an amine

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In the BZD Clonazepam (Klonopin), the amine functional group can be metabolized by ___ and the OH group can undergo__.

A. Reduction, Hydroxylation

B. Hydroxylation, Reduction

C. N-Acetylation, Hydroxylation

D. N-Acetylation, O-Glucuronidation

D. N-Acetylation, O-Glucuronidation

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Clonazepam (Klonopin) is known as an ___ analog.

A. Acetyl Benzodiazepine

B. Nitro Benzodiazepine

C. Acyl Benzodiazepine

D. Amino Benzodiazepine

B. Nitro Benzodiazepine

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Which of the following medications forms Oxazepam as an active metabolite? (Select All)

A. Clorzazepite Dipotassium

B. Lorazepam

C. Chlordiazepoxide

D. Diazepam

A. Chlorzazepite

C. Chlordiazepoxide

D. Diazepam

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Which enzyme is responsible for the metabolism of Oxazepam?

A. CYP2D6

B. CYP3A4

C. SULT

D. UGTS

D. UGTS

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Which of the following are possible advantages of using Oxazepam (Serax)? (Select All)

A. Long-Acting medication

B. Short-Acting medication

C. Less cumulative effects

D. Produces longer-acting metabolites for prolonged duration

E. Fewer side effects due to non-cumulative effects.

B. Short-Acting medication

C. Less cumulative effects

E. Fewer side effects due to non-cumulative effects.

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Lorazepam (Ativan) is a synthetic derivative of:

A. Chlordiazepoxide

B. Oxazepam

C. Diazepam

D. Clonazepam

B. Oxazepam

Based on the structure of Lorazepam (Ativan) which of the following enzymes would you predict to be involved in its metabolism?

A. CYP2D6

B. CYP3A4

C. UGTS

D. SULT

E. NAT

C. UGTS

Lorazepam is a derivative of Oxazepam and also has an exposed OH group that will lead to metabolism via UGTS (glucuronidation)

In the medication Alprazolam (Xanax), the newly-added red group is known as a ___ ring and classifies the medication as a class ___ Benzodiazepine.

A. Pyrazine, B

B. Pyrimidine, B

C. Triazole, A

D. Triazole, B

D. Triazole, B

Tri-3

Azole-nitrogen

Three-membered Nitrogen Ring= TriAzole Ring.

What type of reaction is occuring in the metabolism of Alprazolam (Xanax)?

A. Alpha-Reduction

B. Beta-Hydroxylation

C. Alpha-Hydroxylation

D. Beta-Reduction

C. Alpha-Hydroxylation

Based on the initial metabolism of Alprazolam (Xanax) what type of metabolism to you expect to occur next?

A. Reduction

B. Hydroxylation

C. Glucuronidation

D. Acetylation

C. Glucuronidation (UGTS)

The exposed OH group will be succeptible to glucuronidation like other medications are such as Oxazepam and Lorazepam

Short DOA due to rapid metabolism resulting from glucuronidation.

The medication Flumazenil is known as a(n) ___ Benzodiazepinone.

A. Tetrazole

B. Imidazole

C. Pentazole

D. Hexazole

B. Imidazole

Flumazenil is known as an ultra-short acting benzodiazepine due to rapid ___ of the ___ group.

A. Hydrolysis, Ester

B. Reduction, Ester

C. Hydrolysis, Carboxylic acid

D. Reduction, Carboxylic acid

A. Hydrolysis, Ester

(Short Answer) Why is Flumazenil used in BZD toxicity?

Flumazenil is an ultra-short acting benzodiazepine that has a much higher affnitiy for the benzodiazepine binding site on GABA receptors and as a result it competes with other benzodiazepines that are causing the toxicity. In a way it displaces the longer-acting benzodiazepine that was overdosed on. Also the medication flumazenil does not promote the activity of GABA like other benzodiazepines do.

Regarding the SAR of Benzodiazepines, which of the following statements is true about **Ring A?** (Select All) A. Must be a Phenyl ring B. Can be a Heteroaromatic or Phenyl ring C. Substitutions on C6,C8 and C9 will decrease activity D. Electron withdrawing groups at C7 are not required for activity E. Ring A is required for π-π stacking (Ring Stacking)

B. Can be a Heteroaromatic or Phenyl ring C. Substitutions on C6,C8 and C9 will decrease activity E. Ring A is required for π-π stacking (Ring Stacking) Heteroaromatic means all the members of the ring system can be carbons or other atoms such as Nitrogen

Regarding the SAR of Benzodiazepines, which of the following statements is true about **Ring B**? (Select All) A. C2 ketone is optimal for activity B. Alkyl groups at C3 decrease activity of medication C. Phenyl group attached (red ring) is required for activity D. C2 Ketone is not needed for activity E. Phenyl group attached (red ring) is not required for activity

A. C2 ketone is optimal for activity B. Alkyl groups at C3 decrease activity of medication E. Phenyl group attached (red ring) is not required for activity

Regarding the SAR of Benzodiazepines, which of the following statments about **Ring C** is FALSE? A. Electron withdrawing groups at position 2 and 6 increase activity. B. C4 substitution will increase activity C. Ring C is not required for benzodiazepine activity D. Substitution at C4 will decrease activity

B. C4 substitution will increase activity

Buspirone (Buspar) contains a unique functional group circled in blue known as a(n) A. Tetrazole B. Imidazole C. Nitrobenzne D. Azapirone

D. Azapirone

Buspirone is a ___ agonist at the ___ receptors. A. Full, 5-HT1_A B. Full, GABA C. Partial, Benzodiazepine D. Partial, GABA E. Partial, 5-HT1_A

E. Partial, 5-HT1A

Which of the following statements regarding Buspirone (Buspar) is true? A. Comes with limited sedation side effects due to slight GABA activation B. Binds to GABA receptors instead of 5-HT1 receptors so the effects sedative effects are limited C. It is a benzodiazepine with only partial agonist activity at 5-HT1 receptors and thus comes with little sedative side effects. D. It does not bind to GABA receptors and is only a partial agonist at 5-HT1 receptors and this makes it non-sedating.

D. It does not bind to GABA receptors and is only a partial agonist at 5-HT1 receptors and this makes it non-sedating. Remember that GABA receptor activation can lead to sedating effects but since this medication contains no GABA receptor activity it will not lead to sedating effects that Benzodiazepines typically lead to.

Which of the following statements is true regarding the metabolites of Burspirone? (Select All) A. Metabolism through CYP3A4 produces a metabolite that is less active than the parent drug. B. The type of reaction occuring using CYP3A4 in Buspirone is known as an N-Dealkylation. C. The metabolite on the left undergoes a reduction reaction in order to be produced. D. The metabolite on the left undergoes a hydroxylation reaction in order to be produced.

A. Metabolism through CYP3A4 produces a metabolite that is less active than the parent drug. B. The type of reaction occuring using CYP3A4 in Buspirone is known as an N-Dealkylation. D. The metabolite on the left undergoes a hydroxylation reaction in order to be produced.

T/F Benzodiazepines are preferred over SSRIs in treatment of anxiety disorders due to lacking addictive properties that SSRIs can typically carry

F This statement is actually reversed. SSRIs lack the addictive properties that most benzodiazepines have and as a result are more preferred in treatment of anxiety disorders.

T/F Lithium is a cation that **competes** with Na, K, Ca and Mg ions at their **receptor** sites

T. This is a sentence taken from a slide that he wants us to know Lithium also passes through **Na** channels and can block **K** channels at **_higher concentrations._**

The elmination half-life of Lithium in: **Elderly** is \_\_. **Adults** is \_\_. **Adolescents** is \_\_. A. 39h, 18h, 24h B. 18h, 24h, 39h C. 39h, 24h, 18h D. 24h, 39h, 18h

C. 39h, 24h, 18h Just remember that the older you get the longer the medication stays in the body.

Which of these medications will **always** _decrease_ lithium levels? A. Thiazides B. NSAIDs C. Potassium-sparing diuretics D. Loop Diuretics E. Ca Channel Blockers

C. Potassium Sparing Diuretics

Which of these medications will **always** _increase_ Lithium levels?(Select All) A. Thiazides B. NSAIDs C. ACE-Inhibitors D. Loop Diuretics E. Ca Channel Blockers

A. Thiazides B. NSAIDs C. ACE-Inhibitors Thiazides- decrease sodium levels so the body will try to reabsorb more sodium but instead lithium may get absorbed in its place. NSAIDs- decreases vasodilatory prostaglandins at the kidney and causes more lithium to be retained in the body rather than excreted through filtration ACE-I- Can possibly cause AKI and decrease filtration of lithium from the body (check with profesor for clarification)

Which of these medications may **either** **increase or decrease** lithium levels? A. Thiazides B. NSAIDs C. Loop Diuretics D. ACE-Inhibitors E. Ca-Channel Blockers

C. Loop diuretics E. Ca-Channel blockers

Regarding the metaboism of Valproic Acid (Depakote), what pH is the medication comopletely **ionized** at to form an **active valproate ion** metabolite? (pka 4.7) A. pH of 3 B. pH of 5 C. Physiologic pH (7.4) D. pH of 4

C. Physiologic pH (7.4)

Based on the structure of Valproic Acid (Depakote), what functional group makes it **highly protein bound?** A. Amine functionality B. Two propyl functionalities (lipohilic) C. Carboxylic acid functionality D. Ketone functionality

C. Carboxylic functionality

What is the **limitation** of using Valproic Acid (Depakote) in pharmacological treatment? (select all) A. Nephrotoxic at any dose B. Dose-dependent hepatotoxicity C. Neurotoxic at any dose D. Dose-dependent tetratogenicity

B. Dose-dependent hepatotoxicity D. Dose-dependent tetratogenicity