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Unformatted text preview: e who are allergic to aspirin or who cannot take aspirin due to
aspirin's side effect of irritating the mucous membranes of the digestive tract. Once again, Bayer
was first with the next effective analgesic, phenacetin, which was prepared from p-aminophenol,
a by-product of the manufacture of another compound made by Bayer. For a number of years,
phenacetin, which had very good analgesic and antipyretic properties, was used as a component
of APC tablets, an analgesic preparation that contained aspirin, phenacetin, and caffeine.
However, phenacetin has now been supplanted by acetaminophen, which is easier to produce.
Acetaminophen is the sole analgesic component in over-the-counter products such as Tylenol
and Datril. (Interestingly, even acetanilide, a simpler analogue of phenacetin and acetaminophen
also has analgesic effects.) However, acetaminophen and phenacetin also have a side effect.
They cause a type of anemia called methemoglobinemia. While it does not seem to be a major
problem, certain people are more susceptible to this anemia and should avoid use of products
containing acetaminophen. Acetaminophen is also used as one of the analgesic components in
combination analgesics such as Excedrin, which contains aspirin, acetaminophen, and caffeine. NH2 NHCOCH3 NHCOCH3 NHCOCH3 O
H3 C O
p -aminophenol OCH2 CH3
phenacetin OH CH3
N N CH3 acetaminophen acetanilide caffeine More recently, another compound has become popular as an over-the-counter product. This is
the compound ibuprofen, which is principally an anti-inflammatory compound. It also has
analgesic and antipyretic properties, and was first marketed under the trade name Motrin. It is
more effective than aspirin as an analgesic and requires lower doses to achieve the same pain
relief. It also has effectiveness over a wider dose range than does aspirin. Like the other
analgesics, ibuprofen does have some side effects, and people who are allergic to aspirin often
cannot take ibuprofen. People with kidney disease, ulcers, hypertension, and heart disease are
also advised not to take ibuprofen. CO2H Ibuprofen Each tablet or c...
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