Hydromorphone

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Chemical structure of Hydromorphone
Hydromorphone
Systematic (IUPAC) name
4,5 alpha-epoxy-3-hydroxy-17-methyl morphinan-6-one
Identifiers
CAS number 466-99-9
ATC code N02AA03
PubChem 5284570
DrugBank APRD01021
Chemical data
Formula C17H19NO3 
Mol. mass 285.338 g/mol
Pharmacokinetic data
Bioavailability 30–35%
Protein binding 20%
Metabolism Hepatic
Half life 2–3 hours[1]
Excretion Renal
Therapeutic considerations
Pregnancy cat.

C
Legal status

Class A (UK),
DEA Schedule II (USA)
Dependence Liability High
Routes oral, intramuscular, intravenous, rectal

Hydromorphone is a drug developed in Germany in the 1920s and introduced to the mass market beginning in 1926. It is used to relieve moderate to severe pain and severe, painful dry coughing. Hydromorphone is known by the trade names Hydal, Sophidone, Hydrostat, and most famously, "Dilaudid®", though an extended-release version called Palladone® SR was available for a short time in the United States before being voluntarily withdrawn from the market after an FDA advisory released in July 2005 warned of a high overdose potential when taken with alcohol; it is still available in the United Kingdom as of March 2007. Another extended-release version called Hydromorph Contin®, manufactured as controlled release capsules, continues to be produced and distributed in Canada by Purdue Pharma Inc. in Pickering, Ontario.

Hydromorphone is becoming more popular in the treatment of chronic pain in many countries, and it is used as a substitute for heroin and morphine where these two drugs are not marketed on account of hydromorphone's superior solubility and speed of onset and less troublesome side effect and dependence liability profile as compared to morphine and heroin. Many chronic pain patients find that hydromorphone has a spectrum of actions which suit them just as well as morphine, and better than synthetics like methadone or levorphanol in alleviating suffering, as contrasted with simple pain of equal objective intensity.

Contents

[edit] Available Forms

  1. Tablets
    • 1 mg (Dilaudid 1mg available in Canada)
    • 2 mg
    • 3 mg
    • 4 mg
    • 8 mg
  2. Capsules (Palladone)
    • 1.3 mg
    • 2.6 mg
  3. Modified Release capsules (Palladone SR)
    • 2 mg
    • 4 mg
    • 8 mg
    • 16 mg
    • 24 mg
    • 30 mg
    • 32 mg
  4. Controlled Release capsules (Hydromorph Contin)
    • 3 mg
    • 6 mg
    • 12 mg
    • 18 mg
    • 24 mg
    • 30 mg
  5. Suppository
    • 3 mg
  6. Powder for injection
    • 250 mg (hydromorphone HCl)
  7. Oral liquid (HCl)
    • 1 mg/mL (480 mL)
  8. Injection (HCl)
    • 1 mg/mL (1 mL)
    • 2 mg/mL (1 mL, 20 mL)
    • 4 mg/mL (1 mL)
    • Dilaudid-HP®
      • 10mg/ml (1 mL, 5mL, 50mL)

[edit] Details

Hydromorphone, a semi-synthetic μ-opioid agonist, is a hydrogenated ketone of morphine and shares the pharmacologic properties typical of opioid analgesics. Hydromorphone and related opioids produce their major effects on the central nervous system and gastrointestinal tract. These include analgesia, drowsiness, mental clouding, changes in mood, euphoria or dysphoria, respiratory depression, cough suppression, decreased gastrointestinal motility, nausea, vomiting, increased cerebrospinal fluid pressure, increased biliary pressure, pinpoint constriction of the pupils, increased parasympathetic activity and transient hyperglycemia.

CNS depressants, such as other opioids, anesthetics, sedatives, hypnotics, barbiturates, phenothiazines, chloral hydrate and glutethimide may enhance the depressant effects of hydromorphone. MAO inhibitors (including procarbazine), first-generation antihistamines (brompheniramine, promethazine, diphenhydramine, chlorpheniramine), beta-blockers and alcohol may also enhance the depressant effect of hydromorphone. When combined therapy is contemplated, the dose of one or both agents should be reduced.

[edit] Pharmacokinetics

Patients with kidney problems must exercise caution when dosing hydromorphone. In those with renal impairment, the half-life of hydromorphone can increase to as much as 40 hours. This could cause an excess buildup of the drug in the body, and result in fatality. The typical half-life of intravenous hydromorphone is 2.3 hours. Peak plasma levels usually occur between 30 and 60 minutes after dosing.[2]

[edit] Side effects

Adverse effects of hydromorphone are similar to those of other opioid analgesics, and represent an extension of pharmacological effects of the drug class. The major hazards of hydromorphone include respiratory and CNS depression. To a lesser degree, circulatory depression, respiratory arrest, shock and cardiac arrest have occurred. The most frequently observed adverse effects are sedation, nausea, vomiting, constipation, lightheadedness, dizziness and sweating.

[edit] Chemistry

Commercially, hydromorphone is made from morphine either by direct re-arrangement or reduction to dihydromorphine followed by oxidation with potassium tert butoxide. The 6 ketone group can be replaced with a methylene group via the wittig reaction to produce 6 methylene desomorphine which is 80x stronger than morphine.

[edit] References

[edit] Notes

  1. ^ Vallner JJ, Stewart JT, Kotzan JA, Kirsten EB, Honigberg IL. "Pharmacokinetics and bioavailability of hydromorphone following intravenous and oral administration to human subjects." Journal of Clinical Pharmacology. 1981 Apr;21(4):152-6. PMID 6165742 Fulltext
  2. ^ That's Poppycock - Hydromorphone

[edit] External links

v • d • e
Analgesics (N02A, N02B)
Opioids Bezitramide, Buprenorphine, Butorphanol, Dextromoramide, Dextropropoxyphene, Diamorphine, Dihydrocodeine, Fentanyl, Hydromorphone, Ketobemidone, Methadone, Morphine, Nalbufine, Nicomorphine, Opium, Oxycodone, Papaveretum, Pethidine, Piritramide, Tramadol (see also longer list)
Salicylic acid and derivatives Aspirin (Acetylsalicylic Acid), Diflunisal, Ethenzamide -- See also: NSAIDs
Pyrazolones Aminophenazone, Metamizole, Phenazone
Anilides Paracetamol (acetaminophen), Phenacetin
Others Ziconotide, Tetrahydrocannabinol, Ibuprofen, Ketoprofen, Mefenamic Acid, Naproxen, Diclofenac, Flurbiprofen, Diflunisal, Fenoprofen, Indomethacin, Ketorolac, Meclofenamate, Meloxicam, Piroxicam, Tolmetin
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