Transcript Organic Compound proj

ORGANIC COMPOUND
- IBUPROFEN
C13H18O2
BRAND NAMES: ADVIL, GENPRIL, MIDOL IB, MOTRIN IB, PROPRINAL, SMART SENSE
CHILDREN'S IBUPROFEN
Emma Van Der Mark
History of
Ibuprofen
In the 1960s Ibuprofen was developed by the British drug
manufacturer and retailer Boots Laboratories as a result of
research in the 1950 and 1960s to find a safer, more powerful
alternative to aspirin. A team led by Stewart Adams, part of
Boots, discovered that carboxylic acid was the agent in
aspirin that gave the anti-inflammatory property. Therefore
after synthesizing and testing more than 600 compounds
created from these acids, the most active was chosen for a
clinical trial. After they found it to be ineffective to treat
rheumatoid arthritis they tried other compounds and ended
up finding that ibuprofen was the most effective and useful
compound. Adams initial idea was to use ibuprofen as a cure
for hangovers but in 1969 in the United Kingdom it was
released as a treatment for rheumatoid arthritis. Then, later in
the early 1980s ibuprofen was available for over the counter
uses in the United States and United Kingdom. As a result of
the development of ibuprofen, Boots was awarded the
Queens Award for Technical Achievement in 1987.
Out of the many commercial and biological ways to synthesize
How its
synthesized
commercially and
biologically
Ibuprofen, the two most popular ways are by the Boot process and
the Hoechst process. The Boot process which was created by the Boot
Pure Drug Company is an older commercial process compared to the
Hoechst process, created by the Hoechst Company. Not only is the
Boot process older but it also requires 6 steps compared to the
Hoechst process which only requires 3 steps as a result of the added
catalysts. Many of the ways used to synthesize Ibuprofen start off
with isobutylbenzene and use Friedel-Crafts acylation (a substitution
that allows the synthesis of monoacylated products in the reaction.)
Cheminor Drugs, a pharmaceutical company, has developed a new
process using chiral synthesis to form an improved version of
ibuprofen. By using the chiral synthesis, the pure S-Ibuprofen (the
active form of ibuprofen) could almost halve the normal dosage of
ibuprofen and also greatly improves on the potential side effects of
taking this drug.
Properties of
Ibuprofen
Ibuprofen is an organic compound in the class of propionic
acid derivatives.
Melting point
74-77°C
Molecular Weight
206.28082 g/mol
Formal Charge
0
Isotope Atom Count
0
Topological Polar Surface Area 37.3 A²
systematic name: 2-(4-isobutylphenyl)propanoic acid
Physical Description
Solid
Colour
Colourless, white crystalline
stable solid
Odor
Characteristic odor
Solubility
• Very soluble in alcohol
• Slightly soluble in water
Water solubility
21 mg/L (at 25°C)
Stability
Stable
pKa
4.91
Uses and side
effects of
Ibuprofen
Ibuprofen is a non-steroidal antiinflammatory drug (NSAID)
that reduces hormones that
cause pain in the body.
Ibuprofen is used to reduce
fever, relieve pain or
inflammation caused by
conditions such as headache,
muscle aches, menstrual cramps,
minor injuries or arthritis.
Although ibuprofen doesn't have very severe side
effects, there are still minor ones that are commonly
associated with ibuprofen.
Common ibuprofen side effects may include:
upset stomach, mild heartburn, nausea, vomiting;
bloating, gas, diarrhea, constipation;
dizziness, headache, nervousness;
mild itching or rash; or
ringing in your ears.
The gastrointestinal related side effects are caused
by the ibuprofen stopping the enzyme that produces
prostaglandins. This results in stomach irritation
because there would be no decrease in stomach acid
and no increase in stomach mucus secretion.
Uncommon, more severe side effects include:
Fatal heart attack or stroke (after long-term use or
high doses);
Stomach or intestinal bleeding;
Taking ibuprofen within the last 3 months of
pregnancy could harm the baby
Bibliographie
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