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07-SEPTEMBER-2008 03:17:44 - Silibinin Redirected from Silymarin Silibinin Systematic IUPAC name 3,5,7-trihydroxy-2-3-3-hydroxy-4-methoxyphenyl-2- hydroxymethyl-2,3-dihydrobenzob1,4dioxin-6-ylchroman-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. ? Legal status Routes ? Silibinin INN, also known as silybin, 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. Contents 1 Pharmacology 2 Toxicity 3 Complementary and alternative medicine 4 References 5 External Links 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-glycoprotein-mediated cellular efflux.1 The modulation of P-glycoprotein activity may result in altered absorption and bioavailability of drugs that are P-glycoprotein 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 patients with type II diabetes by assisting in blood sugar control.2 References ^ Zhou S, Lim LY, Chowbay B. Herbal modulation of P-glycoprotein. Drug Metabolism Reviews. 2004 Feb;361:57-104. PMID 15072439 ^ Huseini HF, Larijani B, Heshmat R, Fakhrzadeh H, Radjabipour B, Toliat T, Raza M. 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. 2006 Dec;2012:1036-9. PMID 17072885 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, 6114, 2035-63. External Links Review of the Quality of Evidence for Milk Thistle Use from MayoClinic.com Intravenous Milk Thistle Compound Used to Save Victims of Poisonous Mushrooms MeSH Silymarin Retrieved from http://en..org/wiki/Silibinin Categories: Antidotes | Antioxidants | FlavonoidsHidden categories: All articles with statements | Articles with statements since April 2007 Views Article Discussion this page History Personal tools Log in / create account Navigation Main page Contents Featured content Current events Random article Search Go Search Interaction Community portal Recent changes Contact Donate to Help Toolbox What links here Related changes Upload file Special pages Printable version Permanent link Cite this page Languages Deutsch Français 中文 This page was last modified on 18 June 2008, at 23:19
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