Everything about Phenacetin totally explained
Phenacetin, introduced in
1887, was used principally as an
analgesic, and was one of the first synthetic fever reducers to go on the market. It is also known historically, to be the first analgesic without anti-inflammatory properties. Typical doses of 300mg to 500mg a day result in an
analgesic effect. Its analgesic effects are due to its actions on the sensory tracts of the spinal cord. In addition, phenacetin has a depressant action of the heart, where it acts as a negative
inotrope. It is an
antipyretic, acting on the brain to decrease the temperature set point. It is also used to treat
rheumatoid arthritis (subacute type),
intercostal neuralgia, and some forms of
ataxia.
Preparation
The first synthesis was reported in 1878 by Harmon Northrop Morse.
Phenacetin may be synthesized as an example of the
Williamson ether synthesis:
ethyl iodide,
Paracetamol, and anhydrous
potassium carbonate are refluxed in
methyl ethyl ketone to give the crude product, which is recrystallized from water.
Uses
Phenacetin was widely used until the third quarter of the twentieth century, often in the form of an
"APC" (
aspirin, phenacetin,
caffeine) tablet, but was then largely replaced by non-carcinogenic drugs. Some branded phenacetin-based preparations continued to be sold, but with the phenacetin replaced by safer alternatives. A popular brand of phenacetin was
Roche's
Saridon, which was reformulated in
1983 to contain
propyphenazone,
paracetamol and
caffeine.
Coricidin was also reformulated without Phenacetin. Paracetamol is a metabolite of phenacetin with similar analgesic and antipyretic effects, but the new formulation hasn't been found to have phenacetin's carcinogenicity.
Phenacetin is now being widely used as a
cutting agent to adulterate illegally supplied
cocaine due to the similar physical features of the two drugs.
Safety
Phenacetin, and products containing phenacetin have been shown in an
animal model to be
carcinogenic. In humans, many case reports have implicated products containing phenacetin in urothelial neoplasms, especially
transitional cell carcinoma of the
renal pelvis. In one prospective series, phenacetin was associated with an increased risk of death due to urologic or renal diseases, death due to cancers, and death due to cardiovascular diseases.
In addition, people with
glucose-6-phosphate dehydrogenase deficiency may experience acute
hemolysis while taking this drug. Acute hemolysis is possible in the case of patients who develop an
IgM response to Phenacetin leading to immune complexes that bind to
erythrocytes in blood. The erythrocytes are then lysed when the complexes activate the
complement cascade.
Chronic use of phenacetin is known to lead to
renal papillary necrosis. This is a condition which results in destruction of some or all of the
renal papillae in the kidneys.
Notes and references
Further Information
Get more info on 'Phenacetin'.
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