Multicyclic Opioids 2

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kyleannkelsey
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269346
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Multicyclic Opioids 2
Updated:
2014-04-05 21:13:09
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Multicyclic Opioids
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Multicyclic Opioids 2
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Multicyclic Opioids 2
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  1. What structure indicates that this is a potent mu agonist?
    • N-CH3

  2. What structure indicates that this is a potent mu agonist?
    • N-CH3

  3.  How do these drugs differ from their parent morphine and codeine structures?
    • Presence of the 7,8- dihydro structure and the C6-keto group

  4.  What is the benefit of the reduced 7-8 double bond in these opioids?
    • Increased molecular flexibility
    • C ring can achieve a chair conformation rather than higher energy pseudo-boat conformation
    • Allows Keto to accept an H from ASN
    • High affinity bonding results
    • 8-10x potency over their parent structures
  5. How does analgesic potency of Hydrocodone compare to morphine?
    Half as active as morphine
  6. How does analgesic potency of Hydrocodone compare to codeine?
    8-10x more potent than Codeine
  7. Is Hydrocodone abused?
    Yes, 2nd most abused prescription in the US
  8. What is the most abused prescription medication in the US?
    Oxycodone

  9. What is this drug?
    Hydrocodone
  10. What Zohydro?
    ER hydrocodone that contains no aspirin or acetaminophen or abuse-deterring opioid antagonist
  11. What is this drug?
    Hydromorphone

  12. What is this drug?
    Oxycodone

  13. What is this drug?
    Oxymorphone

  14. How does the distribution to the CNS of these drugs compare to Morphine?
    • Reduced due to the 14 Beta – OH (H in morphine)

  15. What effect does this group have on these drugs?
    • Decreases Lop P
    • Decreases CNS distribution
    • Allows for a favorable H-bond with TYR on the mu receptor
    • Properly orients the N-substituent for better mu receptor binding
    • Creates low antitussive activity

  16. How does the potency of these drugs compare to these?
    Oxycodone and Oxymorphone (top) have 2-3 times the analgetic activity of hydromorphone and hydrocodone (bottom) RESPECTIVELY

  17. How does the potency of these drugs compare to these?
    Oxymorphone and Oxycodone (top) 10-12 times the potency of morphine and codeine (bottom) RESPECTIVELY

  18. How does Oxycodone’s potency compare to morphine’s?
    Equipotent
  19. The sustained release formulation of oxycodone comes in what formulation inteneded to reduce risk of abuse?
    Incorporates the drug in a non-crushable viscous liquid capsule to maintain even blood levels whether the drug is consumed with water or alcohol
  20. How does the risk of sedation and respiratory depression with oxymorphone compare to other drugs?
    Relatively high due to the exceptionally high mu agonism
  21. Oxymorphone should not be use in what patient population?
    • Opioid naive patients
    • Compromised respiration
    • Pain is not significant or not expected to persist
    • Predisposed to CV event
  22. Oxycodone and Oxymorphone have an increase risk of fatal CV event or death by all causes under what conditions?
    • Fatal CV event = 6 months of use
    • Death by all causes = 30 days of use
  23. Can you give Oxycodone orally?
    Yes, stable enough against pre-hepatic and first pass metabolism
  24. Can you give Oxymorphone orally?
    Not recommended, extensively metabolized in the gut and by first pass to C3-glucuronide and sulfate
  25. What drugs are is Oxycodone available in combination with?
    Aspirin and acetaminophen

  26. What is this drug?
    Nalbuphine

  27. What receptor will this drug act on?
    • Kappa agonist
    • Mu antagonist
    • (Nalbuphine)

  28. What feature indicates that this is a Kappa agonist?
    • N-cyclobutylmethyl
    • (Nalbuphine)

  29. What effect will this drug be used for?
    • Analgetic
    • (Nalbuphine)

  30. What structure indicates that this drug will have mu antagonism?
    • Cyclobutane ring will fit into the mu antagonist site (though not well)
    • (Nalbuphine)

  31. Would you expect this drug to percipiate withdrawal if swapped for a mu agonist?
    • Yes, because it has potent Kappa agonism and mu antagonism
    • Due to the N-cyclobutylmethyl
    • (Nalbuphine)

  32. How does this drug’s analgesic activity compare to Morphine?
    • 0.5- 1 times that of morphine
    • (Nalbuphine)

  33. What structure(s) enhances potency of the agonist and antagonist actions of this drug over morphine?
    • 14 Beta-OH

  34. Would you expect a women or man to get a better response from this drug, why?
    • Women due to the Kappa agonism
    • (Nalbuphine)

  35. How does the negative effects profile of this drug compare to a mu agonism?
    • less respiratory depression, constipation, euphoria, and potential for addiction
    • Same as mu agonist: decreases oxygen demand in the myocardium after infarct
    • (Nalbuphine)

  36. Would you expect Kappa related dysphoria with this drug?
    • No, not common like with other Kappa agonists
    • (Nalbuphine)

  37. Which of these drugs is the least likely to cause Dysphoria and this is the safest?
    • Nalbuphine
    • (A = Nalbuphine, B= butorphanol, C= pentazocine)

  38. What type of Oral bioavailability does this drug have and why?
    Low oral bioavailability due to extensive first pass metabolism

  39. What are the major metabolites of this drug?
    • Nornalbuphine, 6-ketonalbuphine and nalbuphine-3-glucuronide (not shown)

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