Silibinin

• Silybin
• I silymarin
• 2,3-dihydro- 3-(4 -hydroxy-3 -methoxyphenyl) - 2 - (hydroxymethyl) -6 - ( 3,5,7 - trihydroxy -4- oxobenzopyran -2-yl ) benzodioxin
• (2R, 3R) -3,5,7 -trihydroxy- 2 - [( 2R, 3R ) -2 - (4-hydroxy -3-methoxyphenyl ) -3 - ( hydroxymethyl) - 2,3- dihydro- 1, 4 - benzodioxin -7 -yl]- chroman- 4-one ( IUPAC)

A05BA03

Colorless crystals

Antidote

Fixed

167 ° C ( as monohydrate)

• Soluble in acetone, ethyl acetate, methanol
• Slightly soluble in chloroform, insoluble in water

Attention

Template: Infobox chemical / molecular formula search available

Silibinin, silybin also, is the most pharmacologically active substance of the substance silymarin complex, which consists of the fruits of the milk thistle ( Silybum marianum ) is obtained. It is considered a lead compound for medicinally used milk thistle fruit extracts that are standardized in the active substance content of silibinin. Milk Thistle fruit extract to act protectively liver and strengthen the function of the liver.

Description and mechanisms of action

Chemically, silibinin, a diastereomeric mixture consisting of silybin A and silybin B, which differ in the configuration at C-2 '' and C-3 ''.

The isolated silibinin is in the treatment of liver poisoning by toxins of Amanita phalloides ( amatoxins ) such as amanitin and phalloidin used. These silibinin is partially combined with a β -lactam antibiotic used to support the antidote action. Pharmaceutically the water soluble disodium salt of the succinic acid ester of the silibinin, the silibinin C -2 ' ,3-bis ( hydrogen succinate ) disodium salt, are used as the treatment is performed by means of intravenous administration. Liver protective effect is due to the membrane - stabilizing properties of Silibinins. The inclusion of amatoxins in the liver cells is hampered and prevented their enterohepatic circulation. Silibinin engages in the transport mechanisms of hepatocytes by inhibiting the reuptake of amatoxins. It inhibits specifically the organic anion transporter OATP1B3 ( SLCO1B3 = ). A second mechanism of action is the inhibition of the secretion of TNF- α.

Since the introduction in the therapy of amanitinbedingten mushroom poisoning mortality has decreased to 5 to 12% with timely treatment, earlier the rate was 20 to 30 %.

Clinical tests also show success in the treatment of prostate cancer, which is explained by an inhibition of PSA secretion and inhibition of telomerase.

Trade names

Legalon SIL ® (Madaus ) (D, CH) Silimarit ® ( Bionorica ), a silymarin product