Silibinin

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Silibinin
File:Silibinin skeletal.svg
File:Silibinin 3D.png
Systematic (IUPAC) name
(2R,3R)-3,5,7-trihydroxy-
2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)
-2,3-dihydrobenzo[b][1,4]dioxin-6-yl]chroman-4-one
Identifiers
CAS Number 22888-70-6
ATC code A05BA03 (WHO)
PubChem CID 31553
Chemical data
Formula C25H22O10
Molar mass 482.44 g/mol[[Script error: No such module "String".]]
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Silibinin (INN), also known as silybin, is the major active constituent of silymarin, the mixture of flavonolignans extracted from blessed milk thistle (Silybum marianum) consisting of silibinin A and B, isosibilinin A and B, silicristin, silidianin. Both in vitro and animal research suggest that silibinin has hepatoprotective (antihepatotoxic) properties that protect liver cells against toxins.[1][2] Silibinin has also demonstrated anti-cancer effects against human prostate adenocarcinoma cells, estrogen-dependent and -independent human breast carcinoma cells, human ectocervical carcinoma cells, human colon cancer cells, and both small and nonsmall human lung carcinoma cells.[3][4][5][6]

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.[7]

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.[citation needed] It has been also reported[who?] that silymarin inclusion complex with β-cyclodextrin is much more soluble than silymarin itself[citation needed]. There have also been prepared glycosides of silybin, which show better water solubility and even stronger hepatoprotective effect[citation needed].

Silymarin, as other flavonoids, has been shown to inhibit P-glycoprotein-mediated cellular efflux.[8] 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.[citation needed]

Similarly, its subacute and chronic toxicity are very low; the compound is also devoid of embryotoxic potential.[citation needed]

Complementary and alternative medicine

A recent study suggested that silymarin may help patients with type II diabetes by assisting in blood sugar control.[9]

References

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  • 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. doi:10.2165/00003495-200161140-00003. PMID 11735632. 

External links

de:Silibinin

fr:Silibinine pl:Sylibina pt:Silibinina

zh:水飛薊
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  6. Sharma G, Singh RP, Chan DC, Agarwal R (2003). "Silibinin induces growth inhibition and apoptotic cell death in human lung carcinoma cells". Anticancer Res. 23 (3B): 2649–55. PMID 12894553. 
  7. Mitchell, T (2009). "Intravenous Milk Thistle (Silibinin-Legalon) for Hepatic Failure Induced by Amatoxin/Amanita Mushroom Poisoning". (Clinical study). 
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