Mycophenolic acid

• (E) -6 - ( 4-hydroxy -6-methoxy -7-methyl -3-oxo -1 ,3- dihydroisobenzofuran -5-yl )-4- methylhex -4- enoic acid (IUPAC)
• Acidum mycophenolicum (Latin )

L04AA06

White to off- white crystalline powder

Immunosuppressants

Selective, uncompetitive and reversible inhibitor of IMPDH

141 ° C (needles from hot water )

4.5

Almost insoluble in cold water; slightly soluble in ethanol; moderately soluble in diethyl ether and chloroform; slightly soluble in toluene

Attention

352 mg · kg -1 ( LD50, rat, oral)

Template: Infobox chemical / molecular formula search available

Mycophenolic acid was the first, well-characterized example of an antibiotic. It was in 1893 by Bartolomeo Gosio isolated and crystallized. He observed that it inhibited anthrax in their growth.

Gosio examined actually the vitamin deficiency disease pellagra, the cause of which he suspected a fungal infection of corn. He isolated a mold, which he held for Penicillium glaucum, which is likely, however, have acted to Penicillium brevicompactum. From filtrates of this organism he isolated a substance with phenolic properties, together with iron (III ) chloride solutions give a blue to violet color. He gave him no name, because he thought he was p- Hydroxyhydrozimtsäure. The substance inhibited the development of anthrax, as Gosio provisionally announced in 1893. In 1896 he summarized his findings together again.

When, after the discovery of penicillin began a hunt for other antibiotics mycophenolic acid has been rediscovered at least twice. The co-discoverer of Penicillin Howard Florey recognized Gosios performance but with the words: " mycophenolic acid enjoys the distinction of being the first antibiotic produced by a mold to be Crystallised ". The correct structure was elucidated in 1952 by Birkinshaw. Except against bacteria acts mycophenolic acid also against fungi, viruses, and against tumor cells. It has been used clinically for the treatment of psoriasis.

Mycophenolic acid selectively inhibits inosine monophosphate dehydrogenase, the enzyme which is responsible for the formation of DNA in cells of importance, particularly in lymphocytes. By mycophenolic acid inhibits the production of new DNA, it reduces the proliferation rate of lymphocytes and thus acts immunosuppressive. An ester of mycophenolic acid, mycophenolate mofetil which is used for suppression of organ rejection after renal and heart transplantation. After administration produced in the body from the ester again free mycophenolic acid.