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Encyclopedia > Dextropropoxyphene
Chemical structure of Dextropropoxyphene
Dextropropoxyphene
Systematic (IUPAC) name
[(2R,3R)-4-dimethylamino- 3-methyl-1,2-diphenyl-butan-2-yl] propanoate
Identifiers
CAS number 469-62-5
ATC code N02AC04
PubChem 10100
Chemical data
Formula C22H29NO2
Mol. weight 339.471
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

? Image File history File links Dextropropoxyphene. ... 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 . ... A chemical formula (also called molecular formula) is a concise way of expressing information about the atoms that constitute a particular chemical compound. ... The molecular mass of a substance (less accurately 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 medication that reaches the systemic circulation, one of the principal pharmacokinetic properties of drugs. ... Drug metabolism is the metabolism of drugs, their biochemical modification or degradation, usually through specialized enzymatic systems. ... The elimination half-life of a drug (or any xenobiotic agent) refers to the timecourse necessary for the quantity of the xenobiotic agent in the body (or plasma concentration) to be reduced to half of its original level through various elimination processes. ... 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

Prescription Only (S4)(AU) Schedule IV (in dosage form) The regulation of therapeutic goods, that is drugs and therapeutic devices, varies by jurisdiction. ... The Standard for the Uniform Scheduling of Drugs and Poisons, abbreviated SUSDP, is a document used in the regulation of drugs and poisons in Australia. ... Anthem: Advance Australia Fair Royal anthem: God Save the Queen Capital Canberra Largest city Sydney Official languages English (de facto 1) Government Constitutional monarchy (federal)  - Queen Elizabeth II  - Governor-General Michael Jeffery  - Prime Minister John Howard Independence from the UK   - Constitution 1 January 1901   - Statute of Westminster 11 December 1931... The Controlled Substances Act (CSA) was enacted into law by the Congress of the United States as Title II of the Comprehensive Drug Abuse Prevention and Control Act of 1970. ...

Routes  ?

Dextropropoxyphene is an analgesic in the opioid category. It is used to treat mild to moderate pain and as an antitussive. It can be used to ease pain before, during and after an operation. It is often combined with acetaminophen in the preparation co-proxamol (Darvocet in the US and CAPADEX in AUS). 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. ... An analgesic (colloquially known as a painkiller) is any member of the diverse group of drugs used to relieve pain (achieve analgesia). ... An opioid is a chemical substance that has a morphine-like action in the body. ... A cough medicine is a drug used to treat coughing and related conditions. ... Acetaminophen (USAN) or paracetamol (INN), is a popular analgesic and antipyretic drug that is used for the relief of fever, headaches, and other minor aches and pains. ... Dextropropoxyphene is an analgesic in the opioid category. ... Manufactured and distributed by Eli Lilly and Company, Darvocet is a brand name for mild narcotic analgesic drug which combines Acetaminophen and Propoxy or Propoxyphene, prescribed for the relief of mild to moderate pain, with or without fever. ... CAPADEX is prescription only medication consisting of Dextropropoxyphene Hydrochloride (32. ...


It is an optical isomer of Levopropoxyphene. The racemic mixture is called Propoxyphene. Optical isomerism is a form of isomerism (specifically stereoisomerism) whereby the different 2 isomers are the same in every way except being non-superimposable mirror images* of each other. ... The structure of Levopropoxyphene Levopropoxyphene is an antitussive. ... In chemistry, a racemate is a mixture of equal amounts of left- and right-handed stereoisomers of a chiral molecules. ...


Some preparations that contain dextropropoxyphene include: Distalgesic and Doloxene.

Contents

Indications

Analgesia

Dextropropoxyphene, like codeine, is a "weak" opioid. Codeine is more commonly used, however some individuals (approximately 10-20% of the Caucasian population) are unable to metabolize it, due to poor functioning of the enzyme CYP2D6. It is in these people that dextropropoxyphene is particularly useful, as its metabolism does not require CYP2D6. Codeine (INN) or methylmorphine is an opiate used for its analgesic, antitussive and antidiarrheal properties. ... It has been suggested that Caucasoid race be merged into this article or section. ... Cytochrome P450 2D6 (abbreviated CYP2D6, EC 1. ...


Opioid withdrawal

In pure form, dextropropoxyphene is commonly used to ease the withdrawal symptoms in people addicted to opioids. Being very weak in comparison to the opioids that are commonly abused, dextropropoxyphene can only act as a "partial" substitute. It does not have much effect on mental cravings; however it can be effective in alleviating physical withdrawal effects, such as muscle cramps. Withdrawal refers to the characteristic signs and symptoms that appear when a drug that causes a physical dependency is regularly used for a long time and then suddenly discontinued or decreased in dosage. ...


Dextropropoxyphene is subject to some controversy: while many physicians prescribe it for a wide range of mildly to moderately painful symptoms as well as for treatment of diarrhoea, many others refuse to prescribe it, citing its highly addictive nature and limited effectiveness. The Doctor by Samuel Luke Fildes This article is about the term physician, one type of doctor; for other uses of the word doctor see Doctor. ... Diarrhoea is the correct way to spell the word Diarrhoea. ...


The therapeutic index of dextroproxyphene is relatively small. In the UK, dextropropoxyphene and co-proxamol are now discouraged from general use; and, since 2004, preparations containing only dextropropoxyphene have been discontinued. This has been a somewhat controversial decision, since it has caused abusers to switch to the combined product and risk acetaminophen toxicity. Australia declined to follow suit and opted to allow pure dextropropoxyphene to remain available by prescription. The therapeutic index of a medication is a comparison of the amount that causes the therapeutic effect to the amount that causes toxic effects. ...


In the United States, dextropropoxyphene HCl is available as a prescription formulation with acetaminophen in ratio anywhere from 30mg / 600mg to 60mg / 325mg, respectively. These are usually named "Darvocet." On the other hand, "Darvon" is a pure Propoxyphene preparation available in the U.S. that does not contain acetaminophen. In Australia, dextropropoxyphene is available on prescription, both as a combined product (32.5mg dextropropoxyphene per 325mg acetaminophen) known as either "Di-gesic", "Capadex", or "Paradex," and in pure form (100mg capsules) known as "Doloxene". Acetaminophen (USAN) or paracetamol (INN), is a popular analgesic and antipyretic drug that is used for the relief of fever, headaches, and other minor aches and pains. ...


Adverse effects

Darvocet overdose is commonly broken into two categories: liver toxicity (from acetaminophen poisoning) and dextropropoxyphene overdose. Many users experience toxic effects from the acetaminophen in pursuit of the endlessly-increasing dose required to achieve euphoria. They suffer acute liver toxicity, which causes severe stomach pain, nausea, and vomiting (all of which are increased by light or stimulation of the sense of sight). The liver is an organ in some animals, including vertebrates (and therefore humans). ... Look up euphoria in Wiktionary, the free dictionary. ... For other uses, see Nausea (disambiguation). ... Vomiting (also throwing up or emesis) is the forceful expulsion of the contents of ones stomach through the mouth and sometimes the nose. ...


Dextropropoxyphene also has several other non-opioid side-effects.


Both propoxyphene and its metabolite norpropoxyphene, have local anesthetic effects at concentrations about 10 times those necessary for opioid effects. In this respect, norpropoxyphene is more potent than propoxyphene, and they are both more potent than lidocaine.[1] Anesthesia (AE), also anaesthesia (BE), is the process of blocking the perception of pain and other sensations. ... Lidocaine (INN) (IPA: ) or lignocaine (former BAN) (IPA: ) is a common local anesthetic and antiarrhythmic drug. ...


Both propoxyphene and norpropoxyphene also have direct cardiac effects which include decreased heart rate, decreased contractility, and decreased electrical conductivity (ie, increased PR, AH, HV, and QRS intervals). Norpropoxyphene is several times more potent than propoxyphene in this activity. These effects appear to be due to their local anesthetic activity and are not reversed by naloxone.[1][2][3] The infant/neonatal rate of heartbeat is around 130-150 bpm, the toddlers about 100–130 bpm, the older childs about 90–110 bpm, and the adolescents about 80–100 bpm. ... Contractility is one of the factors which affect myocardial performance. ... Electrical conductivity is a measure of a materials ability to conduct an electric current. ... Naloxone is a drug used to counter the effects of opioid overdose, for example heroin and morphine overdose. ...


Both propoxyphene and norpropoxyphene are potent blockers of cardiac membrane sodium channels and are more potent than lidocaine, quinidine, and procainamide in this respect.[4] Sodium channels are integral membrane proteins that exist in a cells plasma membrane and regulate the flow of sodium (Na+) ions into it. ... Lidocaine (INN) (IPA: ) or lignocaine (former BAN) (IPA: ) is a common local anesthetic and antiarrhythmic drug. ... Quinidine is a pharmaceutical agent that acts as a class I antiarrhythmic agent in the heart. ... Procainamide (trade name Pronestyl®) is a pharmaceutical antiarrhythmic agent used for the medical treatment of cardiac arrhythmias, classified by the Vaughan Williams classification system as class Ia. ...


They (propoxyphene and nor-propoxyphene) appear to have the characteristics of a Vaughn Williams Class IC antiarrhythmic.


Darvon, a dextropropxyphene made by Eli Lilly, which had been on the market for 25 years, came under heavy fire in 1978 by consumer groups that said it was associated with suicide. Darvon was never withdrawn from the market, but Lilly has waged a sweeping, and largely successful, campaign among doctors, pharmacists and Darvon users to defend the drug as safe when it is used in proper doses and not mixed with alcohol. One of the worlds largest corporations, Eli Lilly and Company (NYSE: LLY) is a global pharmaceutical company with headquarters in Indianapolis,Indiana, USA. A Fortune 500 corporation, the company had revenues of $12. ... Suicide (from Latin sui caedere, to kill oneself) is the willful act of killing oneself. ...


Toxicologic Mechanism

A) Excessive opioid receptor stimulation is responsible for the CNS depression, respiratory depression, miosis, and gastrointestional effects seen in propoxyphene poisoning. It may also account for mood/thought altering effects. Clinical depression is a state of sadness, melancholia or despair that has advanced to the point of being disruptive to an individuals social functioning and/or activities of daily living. ... In medicine, hypoventilation exists when ventilation is inadequate to perform gas exchange. ... Miosis should not be confused with meiosis, the cellular division process involved in sexual reproduction. ... Mood may refer to: chese Grammatical mood Emotional mood This is a disambiguation page, a list of pages that otherwise might share the same title. ... Personification of thought (Greek Εννοια) in Celsus Library in Ephesos, Turkey Thought or thinking is a mental process which allows beings to model the world, and so to deal with it effectively according to their goals, plans, ends and desires. ...


B) Local anesthetic activity appears to be responsible for the arrhythmias and cardiovascular depression seen in propoxyphene poisoning.[3] Widening of the QRS complex appears to be a result of a quinidine-like effect of propoxyphene, and sodium bicarbonate therapy appears to have a positive direct effect on the QRS dysrhythmia.[5] A cardiac arrhythmia, also called cardiac dysrhythmia, is a disturbance in the regular rhythm of the heartbeat. ... Sodium bicarbonate is the chemical compound with the formula NaHCO3. ...


C) Seizures may result from either opioid or local anesthetic effects.[1] This article is about the medical term, epileptic seizure, as distinct from psychogenic non-epileptic seizure. ...


D) Pulmonary edema may result from direct pulmonary toxicity, neurogenic/anoxic effects, or cardiovascular depression.[3] Pulmonary edema is swelling and/or fluid accumulation in the lungs. ... The nervous system of an animal coordinates the activity of the muscles, monitors the organs, constructs and processes input from the senses, and initiates actions. ... Hypoxia is a pathological condition in which the body as a whole (generalised hypoxia) or region of the body (tissue hypoxia) is deprived of adequate oxygen supply. ...


Recreational use

Those who take dextropropoxyphene for recreational purposes tend to take anywhere from 240 to 420 milligrams of dextropropoxyphene and, if it is not extracted, the acetaminophen that is present in the preparation. Some adverse effects of recreational dextropropoxyphene use are: a persistent dry mouth, decreased appetite, urinary retention and constipation that may lead to diverticulitis. Xerostomia is the medical term for a dry mouth due to a lack of saliva. ... Anorexia (deriving from the Greek όρεξη (orexe) = appetite) is the decreased sensation of appetite. ... Urinary retention also known as ischuria is a lack of ability to urinate. ... Constipation or irregularity, is a condition of the digestive system where a person (or animal) experiences hard feces that are difficult to eliminate; it may be extremely painful, and in severe cases (fecal impaction) lead to symptoms of bowel obstruction. ... Diverticulitis is a common disease of the bowel, in particular the large intestine. ...


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External links

  • Links to external chemical sources

References

  1. ^ a b c Nickander et al., 1984
  2. ^ Bredgaard, Sorensen et al., 1984
  3. ^ a b c Strom et al., 1985b
  4. ^ Holland & Steinberg, 1979
  5. ^ Stork et al., 1995

  Results from FactBites:
 
Dextropropoxyphene - Wikipedia, the free encyclopedia (389 words)
Dextropropoxyphene is an analgesic in the opioid category.
It is used to treat mild to moderate pain and as an antitussive.
In pure form, dextropropoxyphene is commonly used to ease the withdrawal symptoms in people addiced to opioids.
Data Sheet (2048 words)
Dextropropoxyphene is metabolised in the liver to yield nordextropropoxyphene.
Dextropropoxyphene is not recommended for use in children, because documented clinical experience has been insufficient to establish safety and a suitable dosage regimen in the paediatric age group.
The abuse liability of dextropropoxyphene is qualitatively similar to that of codeine although quantitatively less, and dextropropoxyphene should be prescribed with the same degree of caution appropriate to the use of codeine.
  More results at FactBites »


 
 

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