Rita Fabela

5th Hour
1/17/2010

Ibuprofen

Ibuprofen is an NSAID (non-steroidal anti-inflammatory drug). Non-

steroidal means they are not steroids, which often have similar effects. They
are generally non-narcotic. Along with ibuprofen, aspirin, and narpoxen
mainly because most of them are over the counter medications.The chemical
formula is C13H18O2. It's name comes from the nomenclature iso-butyl-
propanic-phenolic acid. It is also known as Nurofen, Advil, and Motrin. It is a
white powder that belongs to the propionic acid derivatives, with a melting
point of 74 to 77 degrees. It is slightly soluble in water and readily soluble in
organic solvents such as ethanol. Racemic Ibuprofen is usually used, still only
one form is active medicinally.
Ibuprofen was derived from propionic acid by the research arm of
Boots Group during the 1960s, discovered by Stewart Adams, with
colleagues Andrew RM Dunlop, John Nicholson, Jeffery Bruce Wilson & Colin
Burrows and was patented in 1961. The drug was launched as a treatment
for rheumatoid arthritis in the United Kingdom in 1969, and in the United
States in 1974. Famously, it is recorded that Dr. Adams initially tested his
drug on a hangover. He was subsequently awarded an OBE in 1987. Boots
was awarded the Queen's Award For Technical Achievement for the
development of the drug in the same year.
There have been many commercial and laboratory publications for the
synthesis of Ibuprofen. Two of the most popular ways to obtain Ibuprofen are
the Boot process and the Hoechst process. The Boot process is an older
commercial process developed by the Boot Pure Drug Company and the
Hoechst process is a newer process developed by the Hoechst Company.
Most of these routes to Ibuprofen begin with isobutylbenzene and use
Friedel-Crafts acylation. The Boot process requires six steps, while the
Hoechst process, with the assistance of catalysts, is completed in only three
steps.Cheminor Drugs have developed a process for an improved version of
ibuprofen based on chiral synthesis. The move is significant given that pure
S-Ibuprofen (the active form of ibuprofen) could near halve the regular
ibuprofen dosage, besides improving the side-effect profile.However the
human body can convert the inactive (R) form into the (S) form, so
eventually 100% of the ibuprofen taken becomes active. The process
discovered by Cheminor is therefore unlikely to have commercial
significance. It is generally used for relieving muscular and
skeletal pain. It also can be used as relieve postoperative pain and morning
stiffness and has been shown to slow down pulmonary decline in cystic
fibrosis sufferers. Ibuprofen blocks the production of prostaglandins. It can
cause pain and swelling. The prostaglandins are released to our brain and
can cause fever. Ibuprofen's painkilling effects immediately take effect after
dose is taken, but for the anti-inflammatory effects it can take a bit longer,
sometimes even a few weeks Ibuprofen can also have its side effects. The
most common are diarrhea, nausea, vomiting, dyspepsia, and any pain in the
stomach or intestines. But it can also cause dizziness, edema, hypertension,
and stomach inflammation, ulcers, rash, and worsening of asthma
symptoms. You also have to be careful if you are taking other medications
because you can cause a drug interaction. Causing one medication interferes
with the effects of another medication.
Like
acetylsalicylic acid (aspirin), another NSAID, and acetaminophen, ibuprofen
works by inhibiting the activity of a class of enzymes called cyclooxygenases
(COX). These enzymes are significant because they catalyze the synthesis of
prostaglandins, molecules that have both positive and negative effects in the
body. Prostaglandins are, for example, protective against the development of
stomach ulcers, but they can also mediate inflammation (as well as the pain
response). One of the
most interesting things about human COX enzymes is that there is more
than one of them—definitely two, and probably at least three. This is
important to our understanding of the therapeutic effects of ibuprofen,
aspirin, and acetaminophen. It had long been suspected that there was more
than one COX enzyme, but it was not until 1991 that evidence for the
existence of two forms, COX-1 and COX-2, materialized. It was then
recognized that COX-1 is present at near constant levels in the body under
all conditions (that is, it is a constitutive enzyme), whereas the levels of COX-
2 could increase in response to inflammatory conditions (i.e., it is an
inducible enzyme). This led to the idea that the side effects of ibuprofen and
aspirin (including stomach ulcers) probably arose from inhibition of the
constitutive COX-1 enzyme, whereas the therapeutic benefits arose from
inhibition of the inducible COX-2 enzyme.
Ibuprofen and aspirin both inhibit COX-1 and COX-2, but they do it in
different ways. Ibuprofen binds noncovalently to a COX enzyme and thus
competes with the enzyme's natural substrate. (This is referred to as
reversible inhibition.) On the other hand, aspirin forms a covalent bond to a
serine residue in the enzyme, and this bond cannot be broken. (This is called
irreversible inhibition.) Acetaminophen does not interact with either COX-1 or
COX-2, but it is now understood that it may interact with a newly identified
cyclooxygenase, COX-3. Selective targeting of the COX enzymes is an
exciting area of pharmacology, in which the challenge continues to be the
development of drugs that interact with specific COX enzymes.
To
sum it all up Ibuprofen has changed history in numerous ways. The one's
that stand out most are: in certain studies it has shown better results than a
placebo in the prevention of Alzheimer's disease when given in small
amounts over a long stretch of time. It has also shown to lower the risk or
sometimes even prevent Parkinson's disease, while other drugs like Aspirin
did not. A recent study has also shown that it works best compared to
common painkillers for kids with broken bones, bruises, and sprains. Most
commonly, it has allowed us to lessen or altogether eliminate any pains
mentioned such as headaches, toothaches, arthritis, and temporarily remove
fever.