Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C25H22O10 |
Molecular Weight | 482.4362 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 4 / 4 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COC1=CC(=CC=C1O)[C@H]2OC3=CC(=CC=C3O[C@@H]2CO)[C@H]4OC5=C(C(=O)[C@@H]4O)C(O)=CC(O)=C5
InChI
InChIKey=SEBFKMXJBCUCAI-HKTJVKLFSA-N
InChI=1S/C25H22O10/c1-32-17-6-11(2-4-14(17)28)24-20(10-26)33-16-5-3-12(7-18(16)34-24)25-23(31)22(30)21-15(29)8-13(27)9-19(21)35-25/h2-9,20,23-29,31H,10H2,1H3/t20-,23+,24-,25-/m1/s1
DescriptionCurator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/17305535 | http://www.webmd.com/heart-disease/milk-thistle-benefits-and-side-effects#1
Curator's Comment: description was created based on several sources, including:
https://www.ncbi.nlm.nih.gov/pubmed/17305535 | http://www.webmd.com/heart-disease/milk-thistle-benefits-and-side-effects#1
Silymarin, a plant-derived flavonoid from the plant Silybum marianum, is considered the most potential drug to treat almost all kind of liver diseases, particularly alcoholic liver disease, acute and chronic viral hepatitis and toxins-mediated liver dysfunctions. The main component of the silymarin complex is silybin, synonymous with silibinin, sometimes incorrectly called silybinin, which is a mixture of two diastereomers A and B in approximately 1:1 proportion. The drug possess hepatoprotective and antioxidant activity. The hepatoprotective effect is due to stimulation of synthesis of structural and functional proteins and phospholipids, as well as acceleration of the regeneration of hepatocytes. Antioxidant effect is determined by interaction of bioflavones with free radicals in the liver and its detoxication. In such manner the process of peroxidation of the lipids is interrupted and further liver destruction is prevented. Side effect is a mild laxative effect has occasionally been observed.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0006979 |
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Target ID: CHEMBL3021 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14568570 |
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Target ID: CHEMBL4302 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Milk Thistle Approved UseIt is indicated for the treatment of jaundice, chronic inflammatory liver conditions, i.e. hepatitis, alcoholic liver damage and hepatic cirrhosis. Launch Date2000 |
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Primary | Milk Thistle Approved UseIt is indicated for the treatment of jaundice, chronic inflammatory liver conditions, i.e. hepatitis, alcoholic liver damage and hepatic cirrhosis. Launch Date2000 |
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Primary | Milk Thistle Approved UseIt is indicated for the treatment of jaundice, chronic inflammatory liver conditions, i.e. hepatitis, alcoholic liver damage and hepatic cirrhosis. Launch Date2000 |
PubMed
Title | Date | PubMed |
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Inhibition of reverse transcriptases by flavonoids. | 1989 Sep |
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Silibinin prevents cholestasis-associated retrieval of the bile salt export pump, Bsep, in isolated rat hepatocyte couplets: possible involvement of cAMP. | 2005 Apr 1 |
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Antiparasitic activity of flavonoids and isoflavones against Cryptosporidium parvum and Encephalitozoon intestinalis. | 2006 Jun |
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Effect of silibinin on the growth and progression of primary lung tumors in mice. | 2006 Jun 21 |
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Increased expression of the MGMT repair protein mediated by cysteine prodrugs and chemopreventative natural products in human lymphocytes and tumor cell lines. | 2007 Feb |
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Inhibition effect of flavonoids on monocarboxylate transporter 1 (MCT1) in Caco-2 cells. | 2007 Nov |
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Hepatoprotective efficacy of certain flavonoids against microcystin induced toxicity in mice. | 2007 Oct |
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AKR1C3 as a potential target for the inhibitory effect of dietary flavonoids. | 2009 Mar 16 |
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The protective effect of silibinin against mitomycin C-induced intrinsic apoptosis in human melanoma A375-S2 cells. | 2009 Oct |
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Multiple effects of silymarin on the hepatitis C virus lifecycle. | 2010 Jun |
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Silibinin and related compounds are direct inhibitors of hepatitis C virus RNA-dependent RNA polymerase. | 2010 Mar |
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Differential in vitro effects of intravenous versus oral formulations of silibinin on the HCV life cycle and inflammation. | 2011 Jan 28 |
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Protective effect of curcumin, silymarin and N-acetylcysteine on antitubercular drug-induced hepatotoxicity assessed in an in vitro model. | 2012 Aug |
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Synergistic effects of arsenic trioxide and silibinin on apoptosis and invasion in human glioblastoma U87MG cell line. | 2012 Feb |
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Metabolic effects of silibinin in the rat liver. | 2012 Jan 25 |
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In vitro determination of anticryptosporidial activity of phytogenic extracts and compounds. | 2012 Jul |
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Silibinin potentially protects arsenic-induced oxidative hepatic dysfunction in rats. | 2012 May |
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Silibinin inhibits hepatitis C virus entry into hepatocytes by hindering clathrin-dependent trafficking. | 2013 Nov |
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The binding of silibinin to ERp57. | 2014 Apr 25 |
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Silibinin induces apoptosis of HT29 colon carcinoma cells through early growth response-1 (EGR-1)-mediated non-steroidal anti-inflammatory drug-activated gene-1 (NAG-1) up-regulation. | 2014 Mar 25 |
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Blockade of lipid accumulation by silibinin in adipocytes and zebrafish. | 2015 Feb 5 |
Sample Use Guides
70 mg or 140 mg capsule should be taken 3 times daily. The medication should be continued until the relief of the symptoms according to the advice of a physician.
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17305535
Silybin at pharmacologically achievable in vivo concentrations (0.02–20 uM) increased insulin-like growth factorbinding protein 3 (IGFBP-3) accumulation in androgenindependent prostate cancer PC-3 cells in conditioned medium and caused a dose-dependent increase of IGFBP-3 mRNA abundance with a 9-fold increase over baseline at 20 uM concentration.
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SUBSTANCE RECORD