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Opioids

Majd Fawaz Medicinal Chemistry 1 All Inglés 65 fichas

Opioids

Fichas del conjunto (65)

  1. 1Define - Analgesics - Narcotics - Opium - Opioid - Opiate- Analgesics: Agents that reduce pain + No loss of consciousness
    - Narcotics: Agents that reduce pain + Loss of consciousness
    - Opium: Crude extract of 20 alkaliods from Papavera Somniferum
    - Opioid: Substances with morphine like effects
    - Opiate: Natural Opioids
  2. 2Name the first 4 amino acids in endogeneous opioid peptide- TYR-GLY-GLY-PHE
    - They bind to the receptor
  3. 3—- (-) Morphine
    - Good analgesic agonist
    - pH=7 ==> Acid form (N+)
    - Must be protected or phenol will oxidize into inactive quinone    - (-) Morphine - Good analgesic agonist - pH=7 ==> Acid form (N+) - Must be protected or phenol will oxidize into inactive quinone
  4. 4—- Benzoquinone
    - Inactive metabolite of Morphine    - Benzoquinone - Inactive metabolite of Morphine
  5. 5—- 3-Deoxymorphine
    - 10% potency of morphine
    - Better lipophilicity
    - Better bioavailability    - 3-Deoxymorphine - 10% potency of morphine - Better lipophilicity - Better bioavailability
  6. 6—- Codeine
    - Weak u agonist (15% morphine)
    - Potent antitussive activity (for cough)
    - Undergoes partial (10%) O-demethylation --> morphine (still addictive)
    - Higher lipophilicity
    - Higher bioavailability    - Codeine - Weak u agonist (15% morphine) - Potent antitussive activity (for cough) - Undergoes partial (10%) O-demethylation --> morp...
  7. 7—- Ethylmorphine
    - 10% morphine    - Ethylmorphine - 10% morphine
  8. 8—- 3-Monoacetylmorphine (3-MAM)
    - Metabolite of Heroin    - 3-Monoacetylmorphine (3-MAM) - Metabolite of Heroin
  9. 9—- Diacetylmorphine (Heroin)
    - Weak u agonist
    - More lipophilic --> Better CNS Distribution --> More potent than Morphine --> More popular for abuse
    - Hydrolizes to give 6-MAM, 3-MAM, Morphine    - Diacetylmorphine (Heroin) - Weak u agonist - More lipophilic --> Better CNS Distribution --> More potent than Morphine --> Mor...
  10. 10—- 6-Deoxymorphine
    - More lipophilic --> More potent
    - x10 Morphine    - 6-Deoxymorphine - More lipophilic --> More potent - x10 Morphine
  11. 11—- 6-Methoxymorphine
    - x5 Morphine    - 6-Methoxymorphine - x5 Morphine
  12. 12—- 6-Ethoxymorphine
    - x2.5 Morphine    - 6-Ethoxymorphine - x2.5 Morphine
  13. 13—- 6-MAM
    - Potent u agonist
    - Active metabolite of Heroin (>potent)
    - x4.2 Morphine    - 6-MAM - Potent u agonist - Active metabolite of Heroin (>potent) - x4.2 Morphine
  14. 14—- Morphone
    - 66% Morphine    - Morphone - 66% Morphine
  15. 15—- Dihydromorphine
    - x1.2 Morphine    - Dihydromorphine - x1.2 Morphine
  16. 16—- Hydromorphone
    - x5-6 Morphine    - Hydromorphone - x5-6 Morphine
  17. 17—- Oxymorphone
    - x10 Morphine
    - More analgesic activity
    - Less antitussive activity    - Oxymorphone - x10 Morphine - More analgesic activity - Less antitussive activity
  18. 18—- Dihydrocodeine
    - x1.15 Codeine
    - 30% of Morphine    - Dihydrocodeine - x1.15 Codeine - 30% of Morphine
  19. 19—- Hydrocodone
    - x5 Codeine
    - 70% of Morphine    - Hydrocodone - x5 Codeine - 70% of Morphine
  20. 20—- Oxycodone
    - Equipotent to Morphine
    - x7 Codeine
    - Better bioavailability than Morphine
    - Less antitussive activity than Codeine    - Oxycodone - Equipotent to Morphine - x7 Codeine - Better bioavailability than Morphine - Less antitussive activity than Codeine
  21. 21—- Normorphine
    - Less BBB penetration (Less active)
    - Metabolite of Morphine and Codeine    - Normorphine - Less BBB penetration (Less active) - Metabolite of Morphine and Codeine
  22. 22—- N-phenethylnormorphine
    - Very potent agonist activity (exception)    - N-phenethylnormorphine - Very potent agonist activity (exception)
  23. 23—- Nalbuphine
    - Mixed agonist/antagonist    - Nalbuphine - Mixed agonist/antagonist
  24. 24—- Naloxone
    - Pure nonselective antagonist
    - Not orally active (First Pass Gluco)
    - Short Half life    - Naloxone - Pure nonselective antagonist - Not orally active (First Pass Gluco) - Short Half life
  25. 25—- Naltrexone
    - Pure nonselective antagonist
    - Given orally
    - Gives active metabolite (B-Naltrexol)    - Naltrexone - Pure nonselective antagonist - Given orally - Gives active metabolite (B-Naltrexol)
  26. 26—- 6B-Naltrexol
    - Active metabolite of Naltrexone    - 6B-Naltrexol - Active metabolite of Naltrexone
  27. 27—- Norcodeine
    - Inactive metabolite of Codeine    - Norcodeine - Inactive metabolite of Codeine
  28. 28—- Morphine-6-glucuronide
    - Active metabolite of Morphine    - Morphine-6-glucuronide - Active metabolite of Morphine
  29. 29—- Morphine-3-glucuronide
    - Inactive metabolite of Morephine    - Morphine-3-glucuronide - Inactive metabolite of Morephine
  30. 30- Name the 2 opioids - Name the CYP + Process - Elaborate on the CYP- CYP 2D6 polymorphisim (Fast or Slow)- Name the 2 opioids - Name the CYP + Process - Elaborate on the CYP- Name the 2 opioids - Name the CYP + Process - Elaborate on the CYP
  31. 31—- (-) Levorphanol
    - Strong u agonist
    - x10 Morphine
    - Chemical Class: Morphinane    - (-) Levorphanol - Strong u agonist - x10 Morphine - Chemical Class: Morphinane
  32. 32—- Butorphanol
    - Mixed Agonist/Antagonist
    - Chemical Class: Morphinane    - Butorphanol - Mixed Agonist/Antagonist - Chemical Class: Morphinane
  33. 33—- (+) Dextromethorphan (3-Methoxydextrophan)
    - Chemical Class: Morphinane
    - Lacks analgesia
    - Has antitussive activity    - (+) Dextromethorphan (3-Methoxydextrophan) - Chemical Class: Morphinane - Lacks analgesia - Has antitussive activity
  34. 34—- Metazocine
    - Potent u agonist (>Morphine)
    - Chemical Class: Benzomorphane    - Metazocine - Potent u agonist (>Morphine) - Chemical Class: Benzomorphane
  35. 35—- Cyclazocine
    - Mixed Agonist/Antagonist
    - Chemical Class: Benzomorphane    - Cyclazocine - Mixed Agonist/Antagonist - Chemical Class: Benzomorphane
  36. 36—- Phenazocine
    - Pure potent u agonist (> x10 Morphine)
    - Chemical Class: Benzomorphane    - Phenazocine - Pure potent u agonist (> x10 Morphine) - Chemical Class: Benzomorphane
  37. 37—- Pentazocine
    - Mixed Agonist/Antagonist
    - Chemical Class: Benzomorphane    - Pentazocine - Mixed Agonist/Antagonist - Chemical Class: Benzomorphane
  38. 38—- Pentazocine + Naloxone
    - Potent analgesic (oral)
    - If given IV (abuse), Naloxone will antagonize Pentazocine --> Withdrawl Symptoms --> Discourage abuse
    Note: Naloxone has no effect orally at 0.5 mg    - Pentazocine + Naloxone - Potent analgesic (oral) - If given IV (abuse), Naloxone will antagonize Pentazocine --> Withdrawl Symptoms ...
  39. 39—- Meperidine (Demerol)
    - 25% Morphine (analgesic)
    - Chemical Class: Phenylpiperidine
    - Short DOA (ester hydrolysis)
    - Achiral (No isomers)    - Meperidine (Demerol) - 25% Morphine (analgesic) - Chemical Class: Phenylpiperidine - Short DOA (ester hydrolysis) - Achiral (No isomers)
  40. 40—- Meperidinic acid
    - Inactive metabolite of Meperidine    - Meperidinic acid - Inactive metabolite of Meperidine
  41. 41—- Normeperidine
    - Less active metabolite of Meperidine
    - Longer half life
    - Neurotoxicity (Seizures)    - Normeperidine - Less active metabolite of Meperidine - Longer half life - Neurotoxicity (Seizures)
  42. 42—- MPPP ( N-Methyl Phenyl-4-Propionoxy Piperidine)
    - Reverse Ester:
    * Long DOA
    * Good leaving group
    - Decomposes into MPTP --> MPP+    - MPPP ( N-Methyl Phenyl-4-Propionoxy Piperidine) - Reverse Ester: * Long DOA * Good leaving group - Decomposes into MPTP --> MPP+
  43. 43—- MPTP (1-Methyl-4-Phenyl-1,2,3,6-TetrahydroPyridine)
    - Metabolite of MPPP    - MPTP (1-Methyl-4-Phenyl-1,2,3,6-TetrahydroPyridine) - Metabolite of MPPP
  44. 44—- MPP+ (1-methyl-4-phenylpyridinium)
    - Metabolite of MPTP by MAO-B
    - DA neuron damage --> Parkinsonism    - MPP+ (1-methyl-4-phenylpyridinium) - Metabolite of MPTP by MAO-B - DA neuron damage --> Parkinsonism
  45. 45—- Fentanyl
    - Potent u agonist (x80)
    - Chemical Class: Anilidopiperidines
    - Very Lipophilic --> Fast penetration of BBB + High affinity u (Noncovalent bonds)    - Fentanyl - Potent u agonist (x80) - Chemical Class: Anilidopiperidines - Very Lipophilic --> Fast penetration of BBB + High affinity...
  46. 46—- Sufentanyl
    - Potent u agonist (x800)
    - Chemical Class: Anilidopiperidines
    - Very lipophilic --> Fast penetration of BBB + High affinity u (Noncovalent bonds)
    - So potent --> Used as anesthetic    - Sufentanyl - Potent u agonist (x800) - Chemical Class: Anilidopiperidines - Very lipophilic --> Fast penetration of BBB + High affin...
  47. 47—- Alfentanyl
    - Potent narcotic analgesic (x20)
    - Tetrazolinone makes it less lipophilic --> less potent than the rest    - Alfentanyl - Potent narcotic analgesic (x20) - Tetrazolinone makes it less lipophilic --> less potent than the rest
  48. 48—- Methadone
    - u agonist (=morphine)
    - Chemical Class: Diphenylheptane
    - Same pharmacology and toxicology of Morphine except:
    * Given orally
    * Longer DOA
    - Used on recovering addicts:
    * Cross tolerance (Heroin)
    * No needles (No HIV risk)
    * Long DOA
    * Not addictive
    - Used on terminally ill patients    - Methadone - u agonist (=morphine) - Chemical Class: Diphenylheptane - Same pharmacology and toxicology of Morphine except: * Given oral...
  49. 49—- Methadol
    - Active metabolite of Methadone    - Methadol - Active metabolite of Methadone
  50. 50—- Normethadol
    - Active metabolite of Methadone/Methadol    - Normethadol - Active metabolite of Methadone/Methadol
  51. 51—- Normethadone
    - Active metabolite of Methadone    - Normethadone - Active metabolite of Methadone
  52. 52—- Dinormethadone
    - Active metabolite of Methadone/Normethadone    - Dinormethadone - Active metabolite of Methadone/Normethadone
  53. 53—- Dinormethadol
    - Active metabolite of Methadone/Methadol/Normethadol/Normethadone/Dinormethadone    - Dinormethadol - Active metabolite of Methadone/Methadol/Normethadol/Normethadone/Dinormethadone
  54. 54—
  55. 55—- (+) Propoxyphene
    - 10% Morphine
    - Chemical Class: Diphenyl propionate
    - Less abuse potential than Codeine
    - Withdrawn from the market
    * Used for suicide
    * Causes arrhythmias    - (+) Propoxyphene - 10% Morphine - Chemical Class: Diphenyl propionate - Less abuse potential than Codeine - Withdrawn from the market *...
  56. 56—- Diphenoxylate
    - Opioid agonist (min. analgesia)
    - Chemical Class: Meperidine/Methadone hybrid
    - Used for diarrhea (Slowing Intestinal Contractions)
    - Rapid metabolism into Difenoxin (zwitterion) --> Limit CNS Penetration --> Limit abuse
    - Addiction in high doses --> Lomotil (Diphenoxylate+Atropine)    - Diphenoxylate - Opioid agonist (min. analgesia) - Chemical Class: Meperidine/Methadone hybrid - Used for diarrhea (Slowing Intestinal C...
  57. 57—- Difenoxin
    - x5 more active    - Difenoxin - x5 more active
  58. 58—- Loperamide
    - Opioid agonist + No analgesia (No BBB)
    - Chemical Class: Meperidine/Methadone hybrid
    - Orally active
    - High lipophilicity
    - Nonhydrolyzable amide analogue of Meperidine
    - No central activity:
    * Efflux protein P-gp
    * First Pass Metabolism
    * Low dissolution
    - Low abuse potential    - Loperamide - Opioid agonist + No analgesia (No BBB) - Chemical Class: Meperidine/Methadone hybrid - Orally active - High lipophilicity ...
  59. 59—- Etorphine
    - Extremey potent analgesic
    - Chemical Class: Oripavine
    - Sever resperatory depression
    - Used on large animals (elephants)    - Etorphine - Extremey potent analgesic - Chemical Class: Oripavine - Sever resperatory depression - Used on large animals (elephants)
  60. 60—- Buprenorphine
    - Partial u agonist
    - Chemical Class: Oripavine
    - x25-50 morphine
    - Sligh longer DOA
    - Moderate abuse potential (maintenance therapy)    - Buprenorphine - Partial u agonist - Chemical Class: Oripavine - x25-50 morphine - Sligh longer DOA - Moderate abuse potential (maintena...
  61. 61—- Tramadol (Tramal)
    - Weak u agonist (100-fold less)
    - Orally active
    - Opioid + Nonopioid analgesia --> Naloxone can't fully reverse effect
    - O-demthylated metabolite is responsible for opioid activity
    - Less resperatory depression than Morphine    - Tramadol (Tramal) - Weak u agonist (100-fold less) - Orally active - Opioid + Nonopioid analgesia --> Naloxone can't fully reverse e...
  62. 62—- Dezocine
    - Mixed agonist/antagonist (Unknown Receptor)
    - Equipotent to Morphine
    - Only primary amine opioid    - Dezocine - Mixed agonist/antagonist (Unknown Receptor) - Equipotent to Morphine - Only primary amine opioid
  63. 63Define: -Tolerance -Dependence- Tolerance: Decreased response to a drug with repeated use. Develops with most but not eye and GI opioids (Drug Present)
    - Dependence: Withdrawl signs that develope cocurrently with Tolerance. (Drug Absent)
  64. 64Withdrawl SymptomsFlu Like Symptoms (Severity inc. 2-3 days)
    - Sneezing
    - Lacrimation
    - Weakness
    - Depression
    - Muscle cramps, Nausea, Vomting, Diarrhea
    - Agitation, Poor sleep
    - dysphoria
    - Increased HR, BP
  65. 65Side Effects- Euphoria
    - CNS Depression
    - Nausea+Vomiting
    - Resperatory Depression
    - Urinary Retention
    - Diaphorisis+Flushing
    - Miosis
    - Constipation
    - Itching

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Lebanese American University - Medicinal Chemistry 1
Creado por
Majd Fawaz
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