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	Oral: 30–35%, Intranasal: 52–58%[1]
Protein binding	20%
Metabolism	Hepatic
Half life	2–3 hours[2]
Excretion	Renal
Therapeutic considerations
Pregnancy cat.	C Image File history File links Hydromorphone. ... IUPAC nomenclature is a system of naming chemical compounds and of describing the science of chemistry in general. ... CAS registry numbers are unique numerical identifiers for chemical compounds, polymers, biological sequences, mixtures and alloys. ... The Anatomical Therapeutic Chemical Classification System is used for the classification of drugs. ... A section of the Anatomical Therapeutic Chemical Classification System. ... PubChem is a database of chemical molecules. ... The DrugBank database available at the University of Alberta is a unique bioinformatics and cheminformatics resource that combines detailed drug (i. ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... General Name, Symbol, Number carbon, C, 6 Chemical series nonmetals Group, Period, Block 14, 2, p Appearance black (graphite) colorless (diamond) Standard atomic weight 12. ... General Name, Symbol, Number hydrogen, H, 1 Chemical series nonmetals Group, Period, Block 1, 1, s Appearance colorless Atomic mass 1. ... General Name, Symbol, Number nitrogen, N, 7 Chemical series nonmetals Group, Period, Block 15, 2, p Appearance colorless gas Standard atomic weight 14. ... General Name, Symbol, Number oxygen, O, 8 Chemical series nonmetals, chalcogens Group, Period, Block 16, 2, p Appearance colorless (gas) very pale blue (liquid) Standard atomic weight 15. ... The molecular mass (abbreviated MM) of a substance, formerly also called molecular weight and abbreviated as MW, is the mass of one molecule of that substance, relative to the unified atomic mass unit u (equal to 1/12 the mass of one atom of carbon-12). ... In pharmacology, bioavailability is used to describe the fraction of an administered dose of unchanged drug that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... seadonkey rules =P ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... It has been suggested that Effective half-life be merged into this article or section. ... Excretion is the process of eliminating waste products of metabolism and other materials that are of no use. ... The pregnancy category of a pharmaceutical agent is an assessment of the risk of fetal injury due to the pharmaceutical, if it is used as directed by the mother during pregnancy. ...
Legal status	Class A (UK), DEA Schedule II (USA) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... The Misuse of Drugs Act 1971 is an Act of Parliament, by which the United Kingdom aims to control the possession and supply of numerous drugs and drug-like substances, as listed under the Act, and to enable international co-operation against illegal drug trafficking. ... The Controlled Substances Act (CSA), Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970, is the legal foundation of the United States governments fight against the abuse of drugs and other substances. ...
Dependence Liability	High
Routes	oral, intramuscular, intravenous, intranasal, 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. In pharmacology and toxicology, a route of administration is the path by which a drug, fluid, poison or other substance is brought into contact with the body 1. ... Oral medication A medication is any drug taken to cure or reduce the symptoms of an illness or ongoing medical condition. ... Hurting redirects here. ...

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. Heroin ((INN) Diacetylmorphine , (BAN) diamorphine) is a semi-synthetic opioid. ... This article does not adequately cite its references or sources. ...

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)

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. To meet Wikipedias quality standards, this article may require cleanup. ... Agonists An agonist is a substance that binds to a receptor and triggers a response in the cell. ... Hydrogenation is a class of chemical reactions in which the net result is an addition of hydrogen. ... Ketone group A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a chemical compound that contains this functional group. ... This article does not adequately cite its references or sources. ... An opioid is any agent that binds to opioid receptors found principally in the central nervous system and gastrointestinal tract. ... An opioid is a chemical substance that has a morphine-like action in the body. ... A diagram showing the CNS: 1. ... The gastrointestinal tract (GI tract), also called the digestive tract, alimentary canal, or gut, is the system of organs within multicellular animals that takes in food, digests it to extract energy and nutrients, and expels the remaining waste. ... For other uses of painkiller, see painkiller (disambiguation) An analgesic (colloquially known as painkiller) is any member of the diverse group of drugs used to relieve pain. ... Look up euphoria in Wiktionary, the free dictionary. ... Look up dysphoria in Wiktionary, the free dictionary. ... Anatomy and Physiology of the A.N.S. In contrast to the voluntary nervous system, the involuntary or autonomic nervous system is responsible for homeostasis, maintaining a relatively constant internal environment by controlling such involuntary functions as digestion, respiration, and metabolism, and by modulating blood pressure. ... Hyperglycemia or High Blood Sugar is a condition in which an excessive amount of glucose circulates in the blood plasma. ...

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. Anesthesia (AE), also anaesthesia (BE), is the process of blocking the perception of pain and other sensations. ... A sedative is a substance which depresses the central nervous system (CNS), resulting in calmness, relaxation, reduction of anxiety, sleepiness, slowed breathing, slurred speech, staggering gait, poor judgment, and slow, uncertain reflexes. ... Hypnotic drugs are a class of drugs that induce sleep, used in the treatment of severe insomnia. ... Barbiturates are drugs that act as central nervous system (CNS) depressants, and by virtue of this they produce a wide spectrum of effects, from mild sedation to anesthesia. ... Phenothiazines are the largest of the 5 main classes of antipsychotic drugs. ... Chloral hydrate, also known as trichloroacetaldehyde monohydrate, 2,2,2-trichloro-1,1-ethanediol, and under the tradenames Aquachloral, Novo-Chlorhydrate, Somnos, Noctec, and Somnote, is a sedative and hypnotic drug as well as a chemical reagent and precursor. ... Glutethimide is a hypnotic sedative that was introduced in 1954 as a safe alternative to barbiturates to treat insomnia. ... Monoamine oxidase inhibitors (MAOIs) are a class of antidepressant drugs prescribed for the treatment of depression. ... Procarbazine (Matulane® (US), Natulan (Canada)) is an antineoplastic chemotherapy drug for the treatment of Hodgkins lymphoma and certain brain cancers (such as Glioblastoma multiforme). ... An antihistamine is a drug which serves to reduce or eliminate effects mediated by histamine, an endogenous chemical mediator released during allergic reactions, through action at the histamine receptor. ... Categories: Stub | Antihistamines ... Promethazine is a first-generation H1 receptor antagonist antihistamine and antiemetic medication. ... Diphenhydramine hydrochloride (trade name Benadryl, as produced by Pfizer, or Dimedrol outside the U.S.) is an over-the-counter (OTC) antihistamine and sedative. ... Chlorphenamine (INN) or chlorpheniramine (USAN, former BAN), commonly marketed as its salt chlorphenamine maleate (CPM), is first-generation antihistamine used in the prevention of the symptoms of allergic conditions such as rhinitis and urticaria. ... Beta blockers (sometimes written as β-blockers) are a class of drugs used for various indications, but particularly for the management of cardiac arrhythmias and cardioprotection after myocardial infarction. ... is a awesome drink  !!!!!!!!!! Functional group of an alcohol molecule. ...

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.^[3] Peak plasma levels usually occur between 30 and 60 minutes after oral dosing.^[4]

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.

Chemistry

Commercially, hydromorphone is made from morphine either by direct re-arrangement (made by reflux heating of alcoholic or acidic aqueous solution of morphine in the presence of platinum or palladium catalyst), or reduction to dihydromorphine (usually via catalytic hydrogenation), followed by oxidation with benzophenone in presence of potassium tert butoxide or aluminium tert butoxide (Oppenauer oxidation). 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.^{[citation needed]} This article does not adequately cite its references or sources. ... Illustration of a redox reaction Redox (shorthand for oxidation/reduction reaction) describes all chemical reactions in which atoms have their oxidation number (oxidation state) changed. ... Dihydromorphine is a semi-synthetic opioid invented in Germany in the first years of the twentieth century. ... The most fundamental reactions in chemistry are the redox processes. ... Benzophenone, also known as diphenylmethanone, phenyl ketone, diphenyl ketone, or benzoylbenzene. ... Oppenauer oxidation, named after Rupert Viktor Oppenauer [1], is a gentle method for oxidising secondary alcohols to ketones. ... Ketone group A ketone is either the functional group characterized by a carbonyl group linked to two other carbon atoms or a chemical compound that contains this functional group. ... In chemistry, methylene is a divalent functional group CH2 derived formally from methane. ... The Wittig reaction is a chemical reaction of an aldehyde or ketone with a phosphonium ylide to give an alkene and triphenylphosphine oxide. ...

References

• Hydromorphone Consumer Drug Information Drugs.com.

• Article Discussing Withdrawal of Extended-Release Hyrdromorphone from the U.S. Market

• Pain Care and Patient Information about Opioid Analgesics

Notes

1. ^ Coda BA, Rudy AC, Archer SM, Wermeling DP. "Pharmacokinetics and Bioavailability of Single-Dose Intranasal Hydromorphone Hydrochloride in Healthy Volunteers." Anesthesia Analgesia. 2003 Jul;97(1):117-23. PMID 12818953 Fulltext
2. ^ 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
3. ^ That's Poppycock - Hydromorphone
4. ^ Dilaudid Clinical Pharmacology

External links

• Links to external chemical sources