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Silibinin



Silibinin
Systematic (IUPAC) name
3,5,7-trihydroxy-2-(3-(3-hydroxy-4-methoxyphenyl)-2-
(hydroxymethyl)-2,3-dihydrobenzo[b][1,4]dioxin-6-yl)chroman-4-one
Identifiers
CAS number 22888-70-6
ATC code  ?
PubChem 31553
Chemical data
Formula C25H22O10 
Mol. mass 482.44 g/mol
Pharmacokinetic data
Bioavailability  ?
Metabolism  ?
Half life  ?
Excretion  ?
Therapeutic considerations
Pregnancy cat.

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Legal status
Routes  ?

Silibinin (INN, also known as silybin, trade name Legalon) is the major active constituent of silymarin, the mixture of flavonolignans extracted from blessed milk thistle (Silybum marianum). It is used in the treatment and prevention of liver diseases because of its hepatoprotective (antihepatotoxic) properties. Clinical tests have also shown its ability to protect against certain types of cancer (skin and prostate), probably due to its antioxidant properties.[citation needed]

Chemically modified silibinin, silibinin dihydrogen disuccinate disodium (trade name Legalon SIL) a solution for injection, is used in treatment of severe intoxications with hepatotoxic substances, such as death cap (Amanita phalloides) poisoning.

Additional recommended knowledge

Contents

Pharmacology

Poor water solubility and bioavailability of silymarin led to the development of enhanced formulations. Silipide (trade name Siliphos), a complex of silymarin and phosphatidylcholine (lecithin), is about ten times more bioavailable than silymarin. It has been also reported that silymarin inclusion complex with β-cyclodextrin is much more soluble than silymarin itself. There have also been prepared glycosides of silybin, which show better water solubility and even stronger hepatoprotective effect.

Silymarin, as other flavonoids, has been shown to inhibit P-gp-mediated cellular efflux.[citation needed] The modulation of P-gp- activity may result in altered absorption and bioavailability of drugs that are P-gp- substrates. It has been reported that silymarin inhibit cytochrome P450 enzymes and an interaction with drugs primarily cleared by P450s cannot be excluded.[citation needed]

Toxicity

The acute toxicity of silymarin and silybin were investigated by oral and intravenous route in various animal species. No mortality or any signs of adverse effects were observed after silymarin at oral doses of 20 g/kg in mice and 1 g/kg in dogs. The 50% lethal dose (LD50) after intravenous infusion values are 400 mg/kg in mice, 385 mg/kg in rats and 140 mg/kg in rabbits and dogs. These data demonstrate that the acute toxicity of silymarin is very low. Similarly, its subacute and chronic toxicity are very low; the compound is also devoid of embryotoxic potential.[citation needed]

Complementary and alternative medicine

Silymarin is among the popular complementary medicine for the treatment of cancer. Its use has included treatment of varicose veins, menstrual problems, depression, and low breast milk production. However, the most valuable use of milk thistle-derived silymarin is as a liver supporter to prevent and treat cirrhosis, chronic hepatitis, and gall bladder problems. A recent study suggested that silymarin may help diabetic patients by assisting in blood sugar control.[citation needed]

References

  • Morazzoni P., Bombardelli E. (1994). Silybum marianum (cardus marianus) Fitoterapia 66:3-42.
  • Saller R., Meier R., Brignoli R. (2001) The use of silymarin in the treatment of liver diseases. Drugs, 61(14), 2035-63.
  • Huseini, H.F: The Efficacy of Silybum marianum (L.) Gaertn. (Silymarin) in the Treatment of Type II Diabetes: A Randomized, Double-blind, Placebo-controlled, Clinical Trial. Phytotherapy Research.
 
This article is licensed under the GNU Free Documentation License. It uses material from the Wikipedia article "Silibinin". A list of authors is available in Wikipedia.
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