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Propoxyphene

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Propoxyphene
DPropoxyphene.png
General
Systematic name 4-(dimethylamino)-3-methyl-
1,2-diphenylbutan-2-yl propanoate
Other names

Darvon
Propoxyphene Hydrochloride
D-Propoxyphene
Dextropropoxyphene
Dextropropoxyphene-M
Dextroproxifeno

Molecular formula C22H29NO2
SMILES CCC(=O)OC(CC1=CC=CC=C1)
(C(C)CN(C)C)C1=CC=CC=C1
Molar mass Molar mass::339.319829 g/mol
Appearance white powder
CAS number 469-62-5
Properties
Solubility in water >1 g/100 ml water (22°C)
Melting point Melting point::75°C
Boiling point Boiling point::444°C
Hazards
MSDS Material Safety Data Sheet
Main hazards Possible teratogen.
Toxic by ingestion, inhalation
and through skin contact. May
cause heritable genetic damage.
Skin, eye and respiratory irritant.
Flash point 130.6°C
R/S statement R: R23 R24 R25 R36 R37 R38
S: S39 S51
Related compounds
Related compounds Propoxyphene Napsylate
Propoxyphene Compound 65
Except where noted otherwise, data are given for
materials in their standard state (at 25 °C, 100 kPa)
Disclaimer and references

Propoxyphene (Darvon) is an analgesic (pain killer) that has been used in the medical field for many years. It was first introduced as an alternative that was stronger than over-the-counter drugs but not as potent as substances such as morphine. Propoxyphene works by inhibiting neurotransmitters connected to OP3 receptors, thereby dulling physical pain. After being used as a prescription drug for a number of years, it was revealed that propoxyphene caused heart failure to its users. In November of 2010, the drug was recalled across the U.S. and banned from the public market. [1]

Properties

Propoxyphene is an uncommon compound used only in medicine. In addition, it was banned in the United States in 2010, making information concerning its properties especially difficult to obtain. The compound is a specific carbon, hydrogen, nitrogen, and oxygen mixture. When combined, these elements form a white powder, called propoxyphene. Propoxyphene works by inhibiting an exchange between proteins essential to the performance of OP3 receptors. This handicap reduces the effectiveness of neurotransmitters, reducing a person’s ability to feel pain. This qualifies propoxyphene as a potential pain killer, comparable to heavy doses of aspirin. However, because of its potency, it is also frequently used for personal pleasure or suicide. Because of its potency and potential for illegal use, propoxyphene was created to have a very low solubility in water, making it difficult for irresponsible drug users to administer. [2]

Uses

Propoxyphene is used in the production of painkillers used to treat moderate pain in humans and animals. Propoxyphene itself is an analgesic, meaning that its purpose is to reduce pain without affecting a person’s consciousness, in addition to being an antitussive (cough suppressant). The most common sedative containing propoxyphene is called Darvon. When used in painkillers, it is often combined with other medications such as aspirin and acetaminophen (Tylenol) to make Darvon with A.S.A. (with aspirin), Darvocet (with acetaminophen), and Darvon Compound (with aspirin and caffeine). Propoxyphene is usually amalgamated with other drugs because, while it is effective alone, it has been proven to be even more useful when combined.[3]

Pain medications containing propoxyphene are generally used during surgical procedures. For patients who are allergic to painkillers such as codeine, as it has about the same strength, it is often used as an alternative. It is also utilized in drug abuse rehabilitation. As it is powerful, but not quite as strong as other opiates, it is used to wean patients off the stronger drugs. The drug itself, in small doses, is not very effective in this field by way of substituting for mental cravings, but it does help alleviate withdrawal effects, such as muscle cramps.[4]

Because of its somewhat significant strength, it is usually only available by prescription; but is sometimes sold separately under its generic name. Nausea is a common side effect with painkillers containing propoxyphene; but rest, as well as medication to ease nausea, will often suffice to elevate serious issues. Though not a potent as morphine, propoxyphene is still a very substantial drug and a person should not exceed their daily prescription dose. Each drug also has an individual maximum daily dose amount: i.e. propoxyphene napsylate; 600 mg a day. [5]

Some foods, such as grapefruits, have been known to interfere with the effectiveness of propoxyphene. Other drugs, including non-narcotic pain relievers can be very harmful when taken in combination with propoxyphene painkillers. To avoid upset and potential harm, a person taking such painkillers should be aware of such products that could have negative effects when combines with the drugs and conscientiously avoid them. Propoxyphene can also be harmful to a person who has breathing disorders, such as asthma, COPD, or sleep apnea; liver or kidney disease; head or brain tumors; stomach or intestinal disorders; suicidal thoughts or behaviors; mental illness; a history of drug or alcohol addiction. Any of these health issues in combination with propoxyphene pain killers can result in repercussions such as breathing dysfunction and addiction. [6][5]

Recall

Pink Darvon pills.

Darvon, the pure propoxyphene pain sedative, was first approved by the FDA in 1957. Since then, approximately six hundred million for medications containing the drug have been prescribed. There have been many conspiracies throughout the years concerning the threat of propoxyphene-based drugs. Initially, people were concerned by the overwhelming numbers of deaths caused by the drugs. Many were considered suicides, but some were considered accidental deaths as they occurred within the margins of prescribed doses. It is to be expected that, as with any such drug on the market, there will be people who abuse the privilege; and, in the end, people are bound to get hurt when the warning labels are not being taken seriously. The FDA recognized this and, regardless of the number of deaths from substances containing propoxyphene, they kept the drugs on the market.[1]

It was not until a number of medical reports connecting propoxyphene and heart failure began surfacing that the FDA decided to reassess their endorsement. Upon further research, the FDA discovered the extent of the negative effects that the drugs were having on heart health. Propoxyphene had been altering the rhythms of users’ heart beats, putting them at serious risk. Many reports of heart arrhythmia connected to propoxyphene began surfacing, in addition to a number of deaths. Based on this newfound information, on November 19, 2010, the FDA concluded that the harmful effects that the drugs were having on patients outweighed any benefit that they could have, and they decided to recall the drug. [7]

All prescription drugs composed of pure propoxyphene or propoxyphene compounds were immediately withdrawn and efforts began to gradually wean patients who were taking the drugs onto better alternatives. Despite the FDA’s seemingly drastic measures to remove this harmful drug from the medicine cabinets of Americans, there are still a great number of brand name and generic manufacturers providing various forms of propoxyphene.[8]

References

  1. 1.0 1.1 Propoxyphene U.S. National Library of Medicine, December 1, 2010.
  2. Propoxyphene: Brands, Medical Use, Clinical Data Druglib.com, last accessed: February 17, 2011.
  3. Darvon, Darvocet and Other Prescription Painkillers Jim Parker, March 2010.
  4. Darvon What is Darvon? Karl Harrison, last accessed: February 17, 2011.
  5. 5.0 5.1 Propoxyphene N-Acetaminophen Oral WebMD, last accessed: February 15, 2011.
  6. Darvocet Information Drugs.com, last accessed: February 15, 2011.
  7. FDA Recall - Propoxyphene (Darvon and Darvocet) Taken Off the Market Shawn Watson, November 22, 2010.
  8. Propoxyphene Recall Rottenstein Law Group, last accessed: February 17, 2011.