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Pharmacology 2 > B-16. Semisynthetic and synthetic opiates > Flashcards

B-16. Semisynthetic and synthetic opiates Flashcards

1
Q

Semi-synthetic opiates

A

all are phenanthrenes

  1. Strong μ agonists:
    a. Heroin - diacetylmorphine
    b. Oxycodone
  2. Weak-Intermediate μ agonists:
    a. Dihydrocodeine
  3. Mixed agonist / antagonists:
    a. Nalbuphine
    b. Buprenorphine
  4. Antagonists:
    a. Naloxone
    b. Naltrexone
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2
Q

Synthetic opiates

A
  1. Strong μ agonists: all are phenylpiperidines (exc. methadone)
    a. Meperidine
    b. Fentanyl; Al- / Su- / Remifentanil … (Fentanyl family consists of “Al, Sue and Remy”).
    c. Methadone
  2. Weak-Intermediate μ agonists:
    a. Dextromethorphan
    b. Diphenoxylate
    c. Loperamide
    d. Tramadol
    e. Tapentadol
  3. Mixed agonist / antagonists:
    a. Butorphanol
    b. Pentazocine
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3
Q

Heroin

A

a phenanthrene. diacetylmorphine. metabolized to morphine via tissue esterases.

Highly lipophilic → enters brain suddenly in high concentration.
Strong euphoric effect.
long-lasting (2 hour DOA).
no medical use - a drug of abuse

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4
Q

Oxycodone

A

phenanthrene derivative; similar to morphine, better oral absorption.

Indications:

  1. cancer-related pain and cough.
  2. other moderate-severe pain.

Often combined with atg naloxone (oral → high first-pass effect; only works in GI to prevent constipation)

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5
Q

Dihydrocodeine

A

stronger than codeine, weaker than morphine.

Indications: used as analgesic, antitussive (esp. in pleuritis).

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6
Q

Buprenorphine (MOA, kinetics, indications)

A

MOA: acts as a partial μ agonist and κ antagonist … (all “bu” drugs are partial μ agonists)

Kinetics: long DOA
sublingual admin to avoid first-pass metab; transdermal patch for chronic tx

Indications:

  1. Breakthrough pain - sublingual
  2. Chronic pain - transdermal
  3. Opiate addiction - as “bridge” therapy; slow receptor dissociation → milder withdrawal symptoms
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7
Q

Nalbuphine (MOA, SE, indications)

A

MOA: acts as a κ agonist and partial μ agonist … (all “bu” drugs are partial μ agonists)
κ receptor not involved in respiratory depression → respiratory dep. effects max out before lethality
Less euphoria → less dependence

Side Effects:

  1. Dysphoria - κ agonist effect
  2. Sedation
  3. Sweating

Indications:

  1. Pain - moderate to severe
  2. Surgery - in combo with other anesthetics + for pre- and post-op pain
  3. Obstetric - analgesia during labor/delivery
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8
Q

Naltrexone

A

semisynthetic μ atg; given orally; 10 hr DOA; used for treating opiate addiction.

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9
Q

Naloxone

A

semisynthetic μ atg; 1-2 hour DOA; parenteral; used for opiate overdose (short DOA → repeat doses).

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10
Q

Methadone

A

a diphenylheptane.

Good oral availability; accumulates in tissues → slow elimination → easier to discontinue due to weaker withdrawal sx.
Used for tx of opiate addiction

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11
Q

Phenylpiperidines (list)

A
  1. Meperidine (Pethidine)
  2. Fentanyl
  3. Diphenoxylate
  4. Loperamide
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12
Q

Meperidine (Pethidine) - trade name Demerol (indications, SE)

A

similar to morphine but with less urinary retention, uterine relaxation, and sedation
no constipation or antitussive effect; no meiosis → OD harder to detect.

Indications:

  1. Obstetrics - previously the #1 opioid analgesic for L&D; less now due to toxic metabolite + sfx.
  2. Diverticulitis - preferred analgesic due to effect of ↓ GI luminal pressure.

Side Effects:

  1. Antimuscarinic effects - dry mouth, visual disturbances, tachycardia, no meiosis
  2. With MAOI → serotonin syndrome
  3. metabolite norpethidine can cause seizures
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13
Q

Fentanyl (kinetics, indications, analogs)

A

100x analgesic effect of morphine; strongest clinical opioid.

Severe respiratory depression effect!

Kinetics: DOA only 30-60 mins → IV, transdermal patch, sublingual pill.

Indications:

  1. Neuroleptanalgesia - given IV in combo with antipsychotic (droperidol)
  2. Surgical analgesia - IV
  3. Chronic Cancer Pain - transdermal patch
  4. “Breakthrough” pain - any acute increase in pain in cancer pts; as sublingual pill

Analogs -
Sufentanil + Alfentanil - shorter DOAs; Remifentanil - shortest DOA (1-10 mins)
* Remember Sue, Al and Remy as the members of the Fentanyl family; longest name = shortest DOA

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14
Q

Diphenoxylate

A

antidiarrheal; low BBB entry; combo w/ atropine (trade name Reasec) for watery diarrhea.

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15
Q

Loperamide

A

antidiarrheal; not absorbed from GI tract

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16
Q

Morphinans (list)

A
  1. Dextromethorphan

2. Butorphanol

17
Q

Dextromethorphan (MOA, indications, SE)

A

MOA: SERT/NET inhibitor; sigma-1 agonist, μ agonist
* also NMDA-R non-competitive atg; nAChR negative allosteric modulator; 5-HT/H1/α-2/M ligand

Indications: cough suppression

Side Effects: many, but not listed in slides… see Wiki

18
Q

Butorphanol (MOA, indications)

A

MOA: μ and κ partial agonist …
(all “bu” drugs are partial μ agonists).

Indications:

  1. migraine as an intranasal spray.
  2. moderate pain - parenteral admin
19
Q

Benzomorphans: Pentazocine

A

MOA: κ agonist and μ antagonist.

indications: pain (but has a “ceiling effect” → above certain doses no additional effect is achieved).

20
Q

Other opiates (list)

A
  1. Tramadol

2. Tapentadol

21
Q

Tramadol (MOA, indications, SE)

A

MOA: weak μ agonist; weak NE reuptake inhibitor; enhances 5HT release
less respiratory depression; low abuse potential

Indications:
Mild-Moderate Pain - when NSAIDs not sufficient

SE:
nausea/vomiting, dizziness, sweating
Seizures - with high doses
Serotonin syndrome - w/ MAOI, TCA, SSRI co-admin

22
Q

Tapentadol (MOA, indications)

A

MOA: acts as a μ agonist and NET inhibitor → similar effect to tramadol

Indications:
Diabetic Neuropathy - NET inhibition is helpful in neuropathic pain conditions
Other musculoskeletal pain

23
Q

Opiate Addiction Treatment

A
  1. Methadone - good for oral admin; withdrawal is slower/less severe.
  2. Naltrexone - pt first goes through withdrawal, then takes naltrexone as an antagonist
    • 2 theories:
      a. give original drug of abuse with naltrexone → disconnect drug of abuse from desired effect
      b. give naltrexone alone → if pt relapses, drug of abuse does not have effect
  3. Buprenorphine - bridge therapy; replace original drug with partial agonist to decrease craving, withdrawal without strong euphoria
    * slow elimination → eventual withdrawal is easier; less euphoria / resp depression than methadone
  4. UROD - ultra-rapid opioid detoxification → anesthetize patient + administer antagonist
  5. Other drugs:
    a. Clonidine - sedative, antihypertensive
    • releases β endorphin → diminished withdrawal symptoms
      b. β Blockers - less tremor, anxiety, htn
      c. BZDs - to ↓ anxiety

Pharmacology 2 (13 decks)

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