Analgesic Med Chem Flashcards by Cory Montez

Morphine is a prototypical drug that is __ selective ___.

A. nAChR, Agonist

B. nAChR, Antagonist

C. Mu, Agonist

D. Mu, Antagonist

C. Mu, Agonist

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Which of the following statements is true regarding Morphine? (Select All)

A. Consists of a 4 ring structure (Ring A-D)

B. Levo (-)- morphine is the active form of morphine

C. Derived from poppy seed

D. Can be made now using Total Synthesis

E. Can only be obtained by extracting it from poppy seed

B. Levo (-)- morphine is the active form of morphine

C. Derived from poppy seed

D. Can be made now using Total Synthesis

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Morphine belongs to the ___ class of compounds based on its core structure.

A. Tribenzylazole

B. Triphenylbenzyl

C. Phenanthrene

D. Tetraphenylthreonine

C. Phenanthrene

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The structure of morphine contains the rings ____ while Phenanthrene contains the rings ___.

A. ABCDE, ACE

B. ABCD, ABCDE

C. ABC, ABCDE

D. ABCDE, ABC

D. ABCDE, ABC

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What type of reaction metabolism is occuring in the pathway of CYP3A4?

A. N-Methylation

B. N-Demethylation

C. Benzyl-Demethylation

D. O-Demethylation

B. N-Demethylation

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The two hydroxyl groups on carbons 3 and 6 are vulnerable to __ and __ metabolism.

A. Hydroxylation, O-Glucuronidation

B. N-Sulfation, N-Glucuronidation

C. O-Sulfation, O-Glucuronidation

D. Hydroxylation, O-Sulfation

C. O-Sulfation, O-Glucuronidation

OH groups are succeptible to both sulfation and glucuronidation

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Sulfation on carbons 3 or 6 will lead to ___ metabolites of Morphine.

A. Active

B. Inactive

B. Inactive

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Glucuronidation on carbon 3 of morphine wil lead to a(n)___ metabolite and glucuronidaiton on carbon 6 wil lead to a(n)__ metabolite

A. Active, Inactive

B. Inactive, Inactive

C. Active, Active

D. Inactive, Active

D. Inactive, Active

Remember that when glucuronidation occurs at the 3rd carbon it is inactive but when the metabolite has a glucuronidated 6th carbon it is active. Not only is the metabolite active it is actually MORE active than the parent drug morphine

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Which of the following statements is true when comparing the structure of Morphine to Hydrocodone? (Select All)

A. The added methoxy group on carbon 3 of Hydrocodone gives it greater analgesic effects than morphine

B. Both medications are classified as Phenanthrenes

C. The added methoxy group on carbon 3 of Hydrocordone gives it greater antitussive activity and low analgesic activity.

D. The analgesic effect of codeine is superior to morphine while the antitussive effects of morphine are more pronounced than Hydrocodone.

B. Both medications are classified as Phenanthrenes

C. The added methoxy group on carbon 3 of Hydrocordone gives it greater antitussive activity and low analgesic activity.

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Adding the methoxy group onto hydrocodone makes it ___ lipophilic and it ___ its analgesic potency.

A. Less, Decreases

B. More, Decreases

C. Less, Increases

D. More, Increases

A. More, Decreases

Decreases analgesic effect but the methoxy group adds antitussive effect instead.

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Oxycodone is a derivative of Hydrocodone. The additional 14-B Hydroxy group ___ Oxycodones affinity for the Mu receptor and ___ its analgesia effect.

A. Increases, Decreases

B. Decreases, Increases

C. Increases, Increases

D. Decreases, Decreases

C. Increases, Increases

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According to the SAR of Phenanthrene medications, the amine at the top must be a(n)___ amine.

A. Primary

B. Secondary

C. Tertiary

D. Quaternary

C. Tertiary

It will always have two carbons bound to it from the ring. The additional methyl or alkyl group on the nitrogen in the R1 position will change the medications activity.

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Which of the following is true regarding the SAR of the R1 group on the amine of Phenantrene medications? (Select All)

A. CH3 (methyl) groups will make the drug an agonist

B. Alkyl chains or Alkene chains will make the drug an antagonist.

C. Adding a chloro group on the R1 will increase hydrophiliicty

D. Adding a fluoro group on the R1 will increase hydrophilicity

A. CH3 (methyl) groups will make the drug an agonist

B. Alkyl chains or Alkene chains will make the drug an antagonist.

The green groups shown in the picture are examples of the alkyl and alkene chains that will make the drug an antagonist

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The R2 group on Carbon 3 needs to be an ___ group in order to have Mu (µ) and Kappa activity.

A. H

B. OH

C. F

D. Cl

B. OH

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The R3 group on Carbon 14 be which of the following (Select All)

A. H

B. Cl

C. OH

D. F

A. H

C. OH

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The R4 group on Carbon 6 can have a ___ but not having this group can ___ lipophilicity and activity.

A. H, Increase

B. OH, Increase

C. OH, Decrease

D. F, Decrease

B. OH, Increase

Phenanthrene contains __ chiral carbons and the formation of the __ isomer is the more active isomer at Mu (µ) receptors.

A. 3, Levo-(-)-

B. 5, R-(+)-

C. 5, Levo-(-)-

D. 3, R-(+)-

C. 5, Levo-(-)-

The levo isomer has the most activity at Mu receptors.

Buprenorphine (Buprenex) is considerd a ___ class opiate and is ___ potent than morphine.

A. Phenanthrene, More

B. Orapavine, Less

C. Phentrhene, Less

D. Orapavine, More

D. Orapavine, More

The boxed structure in Buprenorphine is mean to ___ lipophilicity and __ potency.

A. Increase, Decrease

B. Increase, Increase

C. Decrease, Increase

D. Decrease, Decrease

B. Increase, Increase

Why is Buprenorphine (Buprenex) known as a Psudoirreversible Mu agonist?

A. Permanently binds to the Mu receptor and agonizes it

B. Binds to the Mu receptor and quickly dissociates from the receptor

C. Binds to the Mu receptor and slowly dissociates from the receptor

D. Binds to the Kappa receptor and irreversibly binds to it and agonizes receptor.

C. Binds to the Mu receptor and slowly dissociates from the receptor

T/F

When a patient is taking Buprenorphine they do not need to enroll in an Office Based Opiod Treatment Program (OBOT)

He may want us to know this.

The medication Levorphanol Tartrate is classified as a(n) ___ opiate.

A. Orapavine

B. Morphinan

C. Phenanthrene

D. Decanoate

C. Phenanthrene

What is true regarding the metabolite of buprenorphine?

A. Completely inactive

B. Acts as an allosteric modulator

C. 40x less active than the parent drug

D. Acts only as an agonist

C. 40x less active than the parent drug

Also notice it has a alkyl chain on the nitrogen. Because of this it exhibits partial Mu/delta agonist activity AND Kappa-Antagonist activity.

Morphian medications such as Levorphanol lack the __ ring in in thier structures.

A. A

B. B

C. C

D. D

E. E

E. E ring

Levorphanol Tartrate is ___ potent than morphine and has __ flexibility and affinity for mu receptors due since it lacks the ether bridge. A. More, More B. Less, Less C. More, Less D. Less, More

A. More, More

What is occuring in the extensive first pass metabolism of Butorphanol Tartrate? A. Methylation B. Phenyl Hydroxylation C. Hydroxylation D. Methyl Hydroxylation

C. Hydroxylation

What is the opiod classification of Butorphanol Tartrate based on its structure? A. Phenanthrene B. Oripavine C. Decanoate D. Morphinan

D. Morphinan It has the ABCD rings but missing the E ring. Also note that it contains an alkyl chain at the end of the amine group so it will have **antagonist properties.** In this case it is mu antagonist properties

Benzomorphans such as Pentazocine lack which of the following rings? (Select All) A. A ring B. B ring C. C ring D. D ring E. E ring

C. C-Ring E. E-Ring

Pentazocrine is available in both a Cis and Trans conformation (Based on the purple methyls). Which of the following statements is true regarding the conformations? (Select All) A. Cis-Methyl conformation lacks addictive properties B. Trans-Methyl conformation lacks addictive properties C. Trans-methyl conformation contains addictive properties D. Cis-methyl conformation contains addictive properties

A. Cis-Methyl conformation lacks addictive properties C. Trans-methyl conformation contains addictive properties

Merperidine HCl is classified as a \_\_\_opiate based on its core structure. A. Benzomorphan B. Phenylpiperidine C. Orapavine D. Phenanthrene

B. Phenylpiperdine

Meperidine produces an active metabolite that is generated by CYP3A4 and 2B6 in the brain. This metabolite is **Normeperidine** and is linked to CNS excitation. What do you expect to see if CYP3A4 and 2B6 undergo enzymatic induction? (Select All) A. Decreased CNS excitation and more inactive ester-hydrolyzed metabolite B. Increased CNS excitation and toxicity C. Higher risk of Grand Mal seizures D. Higher risk of CNS depression and respiratory depression from cascading effects.

B. Increased CNS excitation and toxicity C. Higher risk of Grand Mal seizures

Medications such as Fentanyl and Remifentanyl are classified as ___ medications due to their core structures. A. Benzomorphan B. Phenylpiperidine C. Phenanthrene D. Analidopiperidines

D. Analidopiperidines Anali=Aniline. An analine is a phenyl group that is connected to an amine group. Piperidine= One nitrogen and no double bonds in a 6 membered ring system.

T/F Remifentanyl is known as a "Soft Drug" due to the fact that it was designed to under go a **predictable** type of metabolism and has a **Rapid Offset**.

True He stressed on these two points for the medication so we may have to know it. **Rapid offset** means that it is quickly inactivated by hydrolyzing its esters to COOH groups and **does not rely on hepatic enzymes.**