Interesting facts from the world of organic chemistry
Arenas:
Lipitor
Arenes are aromatic hydrocarbons containing an aromatic nucleus in their structure. These are hydrocarbons that meet the aromaticity rule. They are aromatic if they have a delocalized π-electron system in the planar plane.
The name aromatic hydrocarbons is rather historical and was based on the fact that most arenes have a typical smell.
Lipitor (also known by other names: Cardyl, Edovin, Liprimar, Orbeos, Prevencor, Sortis, Tahor, Texzor and some others) is the trade name for a substance trivially called atorvastatin. It is a pharmaceutical, more precisely a drug, used as a dietary supplement to reduce the concentration of lipids. It mainly involves a reduction in the level of cholesterol and triglycerides in the blood serum. A remarkable feature of this substance is the fact that it performs the function of a safe drug, despite the presence of three benzene nuclei. Very often, compounds with one or more benzene nuclei are highly toxic and carcinogenic.
Picture above: Chemical structure of Lipitor.
Atorvastatin is used by patients suffering from primary hypercholesterolemia or with combined (mixed) hyperlipidemia (corresponding to types IIa and IIb of the Fredrickson classification) in cases where the response to diet and different non-drug measures do not provide satisfactory results. This compound serves not only as a medicine, but is also used in patients whose condition is considered to be highly critical, at the same time as prevention of the first cardiovascular event, e.g. heart attack.
The usual dosage is 10 mg once a day at the beginning, the maximum dose is around 80 mg in one daily dose.
Picture above: Atorvastatin in tablets as a medicine.
Industrial production of this patented compound is a semi-synthetic process. The process begins with the fermentation activity of Penicillium citricum (or Aspergillus terrus). In this way, lovastatin is prepared, which is subsequently converted into atorvastatin by the appropriate reaction steps.
Lovastatin can be found not only as a product of the mentioned fungi, but also in the fruiting bodies of Oyster Mushrooms (in amounts ranging from 0.4-2.7 wt.% in dry matter).
Sources:
1) MCMURRY J.: Organic Chemistry, Seventh Edition. Copyright © 2008, 2004 Brooks/Cole, a division of Thomson Learning, Inc. Kapitola 15 – Benzene and Aromaticity, page 516.
2) EUROPEAN MEDICINES AGENCY: Otázky a odpovědi týkající se přípravků Lipor a souvisejících názvů (…) [online]. Available from: http://www.ema.europa.eu/docs/cs_CZ/document_library/Referrals_document/Lipitor_30/WC500097035.pdf.
3) BIZUKOJC M., Marta PAWLAK a kol.: Effect of pH on biosynthesis of lovastatin and other secondary metabolites by Aspergillus terreus ATCC 20542. Journal of Biotechnology, Volume 162, Issues 2-3, 31th December 2012, Pages 253-261.