Morphine Derivatives

Morphine (Roxanol®, MS Contin®)

Diacetylmorphine (Heroin)

Codeine (Paveral®)

Hydromorphone (Dilaudid®)

Oxymorphone HCl (Numorphan®)

Hydrocodone (Lortab®, Vicodin®)

Oxycodone HCl (Oxycontin®, Percodan®, Tylox®)

Dihydrocodeine (Paracodin®)

Apomorphine HCl (Apokyn®)

Morphine

Roxanol®, MS Contin®

Strong Opioid Agonist

Metabolism: O-demethylation, Conjugation (3-OH)

SE: Addiction, constipation, nausea, vomiting, respiratory depression, miosis, histamine release, CV effects at high doses

Has antitussive as well as analgesic properties in moderate to severe pain

Notes: GI absorption is slow and erratic, has significant first pass metabolism, excreted renally

DI: MAOIs, sedative hypnotics, TCAs, Antipsychotics

DOA: 3-6 hours

Morphine Derivative (Phenanthrenes)

Diacetylmorphine

Heroin

Strong Opioid Agonist

Not used as an analgesic in the US due to high rates of addiction

Produced by acetylation of morphine which produces a 3-fold increase in potency

Crosses BBB quickly to produce a more exaggerated euphoria

Converted to morphine through

6-monoacetylmorphine but lasts about 1/2 as long

Morphine Derivatives (Phenanthrenes)

Codeine

Paveral®

Moderate Opioid Agonist

Less potent analgesic than morphine, lower abuse potential, higher oral efficacy, less euphoria

Good antitussive activity but has been replaced with Dextromethorphan

Used in combination with Aspirin or Tylenol

Morphine Derivatives (Phenanthrenes)

Hydromorphone

Dilaudid®

Strong Opioid Agonist

Structurally similar to morphine but 4-8x stronger

Normally given 1-2 mg, DOA: 3-4 hours

Used for relief of moderate to severe pain and painful dry coughing

One of the most used opioids in the relief of pain for the terminally ill because of its minimal side effects and high potency

Also available as a rectal suppository when oral and parenteral routes are undesirable

Morphine Derivatives (Phenanthrenes) 

Oxymorphone

Numorphan®

Strong Opioid Agonist

10x more potent than morphine

Available as IV, IM, SubQ, Rectal

Morphine Derivative (Phenanthrenes)

Hydrocodone

Lortab®, Vicodin®

Moderate Opioid Agonist

Used in combination with Ibuprofen or Tylenol 

Morphine Derivatives (Phenanthrenes)

Oxycodone HCl

Oxycontin®, Percodan®, Tylox®, Roxicodone®

Moderate Opioid Agonist

Used in combination with Aspirin and Tylenol

Semisynthetic derived from Thebaine, Equipotent to Morphine

Used for relief of moderate to moderately severe pain

Morphine Derivative (Phenanthrenes)

Dihydrocodeine

Paracodin®

Moderate Opioid Agonist

Has a faster onset than Morphine

Used in combination with Aspirin and Tylenol

Morphine Derivative (Phenanthrenes)

Apomorphine HCl

Apokyn®

Used as an antiemetic and as an orphan drug in Parkinsonism

Formed from dehydration of Morphine

Administered SubQ

Morphine Derivative (Phenanthrenes)

Mixed Agonists/Antagonists

 Nalbuphine HCl (Nubain®)

Butorphanol tartrate (Stadol®)

Buprenorphine HCl (Buprenex®)

Dezocine (Delgan®)

Pentazocine (Talwin®)

Nalbuphine HCl

 Nubain®

Mu antagonist/ Kappa agonist (This is correct, Cooperwood has it opposite)

Metabolism: Conjugation of 3-OH in feces

Drug of choice in pregnancy, causes less respiratory depression than morphine but harder to control

Mixed Agonist/Antagonist (Phenanthrenes)

Butorphanol tartrate

Stadol®

Analgesic is equivalent to Buprenorphine and Nalbuphine

Kappa agonist

Only opioid currently available in the US as a nasal formulation

Associated with race horse doping

Side effects are cardiovascular associated

Mixed Agonist/Antagonist (Morphinans)

Buprenorphine HCl

Buprenex®

Partial agonist at Mu receptor

It can antogonize Morphine, more potent than morphine

Metabolized in the liver and excreted in the bile and urine

Binds tightly to Mu receptors therefore it has a long DOA

SE: Respiratory depression, decreased blood pressure, nausea, dizziness

Mixed Agonist/Antagonist (Phenanthrenes)

Dezocine 

Dalgan®

 High affinity for Mu receptor, less for Kappa receptor

Similar to morphine

Structurally related to Pentazocine

Mixed Agonist/Antagonist (Benzomorphan)

Pentazocine 

Talwin®

Kappa Agonist, weal Mu and Delta Antagonist, Binds to Sigma receptor causing dysphoria

Causes less euphoria than Morphine

At higher doses it causes respiratory depression, decreased GI motility, increased blood pressure, hallucinations, nightmares, tachycardia, dizziness

CI in angina patients

Tolerance and dependance can develop on repeated use

Mixed Agonist/Antagonist (Benzomorphan)

Demerol Related Compounds

Meperidine HCl (Demerol®)

Fentanyl citrate (Sublimaze®)

Sufentanil citrate (Sufenta®)

Alfentanil HCl (Alfenta®)

Remifentanil HCl (Ultiva®)

Methadone HCl (Dolophine®)

Propoxyphene (Darvon®, Dolene®, Doxaphene®)

Diphenoxylate HCl (Lomotil®)

Ethoheptazine citrate (Zactane®)

 Meperidine HCl

Demerol®

Strong Opioid Agonist

Synthetically produced from Morphine

Produces less urinary retention than Morphine

Orally well absorbed but usually give IM, DOA: 2-4 hours

Metabolism: N-demethylation

Posesses significant anticholinergic side effects

Demerol Related Compounds (Phenylpiperidines)

Fentanyl citrate

Sublimaze®

Strong Opioid Agonist

100x more potent than Morphine, more potent than Demerol

Rapid onset and short DOA

DOA: 15-30 minutes

Also available as: Oral transmucosal lozenges, fentanyl lollipops (Actiq®), Buccal tablets (Fentora™), Transdermal patches (Duragesic®), Injectable formulations

Sufentanil citrate

Sufenta®

Strong Opioid Agonist

5-7x more potent than Fentanyl

 Faster onset and shorter duration than Fentanyl

Demerol Related Compounds (Phenylpiperidines)

Alfentanil HCl

Alfenta®

Strong Opioid Agonists

Less potent than Fentanyl

Demerol Related Compounds (Phenylpiperidines)

Remifentanil HCl

Ultiva®

Rapidly metabolized in the tissues by cholinesterases resulting in a short half life

More potent than Alfenta

Demerol Related Compounds (Phenylpiperidines)

Methadone HCl

Dolophine®

Strong Opioid Agonist

Equipotent to Morphine, Mostly affects Mu receptors

Used in controlled withdrawl of addicts from Morphine and Heroin

It causes milder withdrawl syndrome, which develops more slowly than seen from Morphine

Has a dependence liability

Demerol Related Compounds (Phenylheptylamines)

Propoxyphene

Darvon®, Dolene®, Doxaphene®

Moderate Opioid Agonist

Equal to codeine in potency

Derivative of methadone, used in combination with Aspirin and Tylenol, can be used in addiction

Well absorbed orally, peak plasma levels in an hour, metabolized by the liver

SE: Nausea, anorexia, constipation

Toxicity: Respiratory depression, convulsions, hallucinations, confusion

Demerol Related Compounds (Phenylheptylamines)

Diphenoxylate HCl

Lomotil®

Moderate Opioid Agonist

No analgesic properties

Used as an antidiarrheal

Demerol Related Compounds (Phenylpiperidines)

Ethoheptazine citrate

Zactane®

Used in combination with Aspirin for moderate pain

No addiction potential

Toxic at high doses

Demerol Related Compounds

Miscellaneous Opioids/Narcotics

Tramadol HCl (Ultram®)

Opium extract (Paregoric®)

Levorphanol (Levodromoran®)

Anileridine (Leritine®)

Tramadol HCl

Ultram®

Moderate Opioid Agonist

Has affinity for Mu receptor, Moderately inhibits serotonin reuptake and weakly inhibits norepinephrine reuptake

Metabolized to O-desmethyltramadol

SE: Seizures, red, blistering, peeling skin rash, shallow breathing, weak pulse, dizziness, drowsiness, weakness

Used in combination with Tylenol

No addiction potential so it is not scheduled

Miscellaneous Opioids (Phenanthrenes)

Opium Extract

Paregoric®

Used for diarrhea

Miscellaneous Opioids

Levorphanol

Levodromoran®

Miscellaneous Opioids (Morphians)

Anileridine

Leritine®

Miscellaneous Opioids

Narcotic Antagonists

Naloxone HCl (Narcan®)

Naltrexone (Trexan®, Re Via®)

Nalmefene HCl (Revex®)

Naloxone HCl

Narcan®

Competative antagonist at the opioid receptors

Drug of choice in narcotic opioid overdose

Has no agonist effects and shows no withdrawal effect after long-term use

Use is limited due to short duration of action

(≈ 4 hours)

Narcotic Antagonist

Naltrexone

Trexan®, Re Via®

 An analog of  naloxone with a cyclopropylmethyl substituent

Preferred drug for treating former opiate addicts because it is long-acting

Given only 3 x weekly to block the high from narcotic analgesic such as heroin

Narcotic Antagonist

Nalmefene HCl

Revex®

 6-methylene analog of ReVia

Pure antagonist

Used for opioid overdose

Longer acting than Narcan

Narcotic Antagonist

Medications for Neuropathic Pain

Carbamazepine (Tegretol®)

Amitriptyline (Elavil®)

Gabapentin (Neurontin®)

Pregabalin (Lyrica®)

Carbamazepine

Tegretol®

Inhibits sodium channels

"If you inhibit sodium channels you stop the pain from occuring"

Neuropathic Pain (Anticonvulsant)

Amitriptyline

Elavil®

Inhibits the reuptake of NE and serotonin

Neuropathic Pain (TCAs)

 Gabapentin

Neurontin®

Works on calcium to stop pain

Neuropathic Pain (Anticonvulsant)

Pregabalin

Lyrica®

Inhibits the voltage-gated calcium channels to stop pain

Neuropathic Pain (Anticonvulsant)