Question

Find information on:

1. epinephrine

2. cholic acid

3. ibuprofen (both enantiomers)

4. naproxen

To get full credit (4 pts) you must: 1. Give molecular formula and structure

2. Identify each carbon’s hybridization

3. Identify one stereocenter and it’s configuration

4. Identify the molecule’s importance and/or application

Answer 1

EPINEPHRINE:

Epinephrine, also known as adrenaline, is a medication, hormone and neurotransmitter. As a medication it is used for a number of conditions including: anaphylaxis, cardiac arrest, and superficial bleeding.Inhaled epinephrine may be used to improve the symptoms of croup. It may also be used for asthma when other treatments are not effective. It is given intravenously, by injection into a muscle, by inhalation, or by injection just under the skin.

CHOLIC ACID:

Cholic acid, also known as 3α,7α,12α-trihydroxy-5β-cholan-24-oic acid is a primary bile acid that is insoluble in water (soluble in alcohol and acetic acid), it is a white crystalline substance. Salts of cholic acid are called cholates. Cholic acid, along with chenodeoxycholic acid, is one of the two major bile acids produced by the liver, where it is synthesized from cholesterol. These two major bile acids are roughly equal in concentration in humans. Derivatives are made from cholyl-CoA, which exchanges its CoA with either glycine, or taurine, yielding glycocholic and taurocholic acid, respectively.

Cholic acid downregulates cholesterol-7-α-hydroxylase (rate-limiting step in bile acid synthesis), and cholesterol does the opposite. This is why chenodeoxycholic acid, and not cholic acid, can be used to treat gallstones (because decreasing bile acid synthesis would supersaturate the stones even more).

Cholic acid and chenodeoxycholic acid are the most important human bile acids. Other species may synthesize different bile acids as their predominant primary bile acids.

IBUPROFEN:

Ibuprofen, from isobutylphenylpropanoic acid, is a nonsteroidal anti-inflammatory drug (NSAID) used for relieving pain, helping with fever and reducing inflammation. About 60% of people improve with any given NSAID and it is recommended that if one does not work that another should be tried. Ibuprofen might be considered a weaker anti-inflammatory than other NSAIDs.

Compared to other NSAIDs it may have fewer side effects such as gastrointestinal bleeding. At low doses it does not appear to increase the risk of myocardial infarction; however, at higher doses it may. It may result in worsened asthma.

Like other NSAIDs, it works by inhibiting the synthesis of prostaglandins, which are fat-like molecules derived from arachidonic acid, which are involved in mediating inflammation (swelling), pain, and fever. It achieves this effect on prostaglandin synthesis by inhibiting cyclooxygenase, an enzyme that is present in various tissues of the body.

NAPROXEN:

naproxen is a non-selective COX inhibitor; usually sold as the sodium salt, is a nonsteroidal anti-inflammatory drug (NSAID) of the propionic acid class (which puts it in the same class asibuprofen) and is commonly used for relief of a wide variety of pain, fever, swelling and stiffness.

It is the preferred NSAID for long-term use in people with a high risk of cardiovascular (for example, heart attacks or strokes) complications, due to its relatively low risk of causing such complications. Naproxen has an intermediate risk of causing stomach ulcers as compared with ibuprofen, which is low risk, and indometacin, which is high risk. In order to reduce the risk of stomach ulceration, it is often combined with a proton-pump inhibitor (a medication that reduces the production of stomach acid) during long-term treatment, in those with pre-existing stomach ulcers, or a history of developing stomach ulcers while on NSAID.