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Details

Stereochemistry ABSOLUTE
Molecular Formula C25H22O10
Molecular Weight 482.4371
Optical Activity UNSPECIFIED
Defined Stereocenters 4 / 4
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of SILIBININ A

SMILES

COc1cc(ccc1O)[C@]2([H])[C@@]([H])(CO)Oc3ccc(cc3O2)[C@]4([H])[C@]([H])(C(=O)c5c(cc(cc5O4)O)O)O

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

HIDE SMILES / InChI

Molecular Formula C25H22O10
Molecular Weight 482.4371
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 4 / 4
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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

TargetsConditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Milk Thistle

Approved Use

It is indicated for the treatment of jaundice, chronic inflammatory liver conditions, i.e. hepatitis, alcoholic liver damage and hepatic cirrhosis.

Launch Date

9.7666558E11
Primary
Milk Thistle

Approved Use

It is indicated for the treatment of jaundice, chronic inflammatory liver conditions, i.e. hepatitis, alcoholic liver damage and hepatic cirrhosis.

Launch Date

9.7666558E11
Primary
Milk Thistle

Approved Use

It is indicated for the treatment of jaundice, chronic inflammatory liver conditions, i.e. hepatitis, alcoholic liver damage and hepatic cirrhosis.

Launch Date

9.6880322E11
PubMed

PubMed

TitleDatePubMed
Stimulatory effects of silibinin and silicristin from the milk thistle Silybum marianum on kidney cells.
1999 Sep
Silybin inactivates cytochromes P450 3A4 and 2C9 and inhibits major hepatic glucuronosyltransferases.
2004 Jun
Silibinin prevents cholestasis-associated retrieval of the bile salt export pump, Bsep, in isolated rat hepatocyte couplets: possible involvement of cAMP.
2005 Apr 1
Inhibition of rat liver UDP-glucuronosyltransferase by silymarin and the metabolite silibinin-glucuronide.
2005 Jun 24
Hepatoprotective and antifibrotic effect of a new silybin-phosphatidylcholine-Vitamin E complex in rats.
2005 Nov
Effects of silymarin flavonolignans and synthetic silybin derivatives on estrogen and aryl hydrocarbon receptor activation.
2005 Nov 5
Antiparasitic activity of flavonoids and isoflavones against Cryptosporidium parvum and Encephalitozoon intestinalis.
2006 Jun
Effect of silibinin on the growth and progression of primary lung tumors in mice.
2006 Jun 21
MDR- and CYP3A4-mediated drug-herbal interactions.
2006 Mar 27
Silibinin activates p53-caspase 2 pathway and causes caspase-mediated cleavage of Cip1/p21 in apoptosis induction in bladder transitional-cell papilloma RT4 cells: evidence for a regulatory loop between p53 and caspase 2.
2006 Nov
Increased expression of the MGMT repair protein mediated by cysteine prodrugs and chemopreventative natural products in human lymphocytes and tumor cell lines.
2007 Feb
Inhibition effect of flavonoids on monocarboxylate transporter 1 (MCT1) in Caco-2 cells.
2007 Nov
Hepatoprotective efficacy of certain flavonoids against microcystin induced toxicity in mice.
2007 Oct
AKR1C3 as a potential target for the inhibitory effect of dietary flavonoids.
2009 Mar 16
The protective effect of silibinin against mitomycin C-induced intrinsic apoptosis in human melanoma A375-S2 cells.
2009 Oct
Multiple effects of silymarin on the hepatitis C virus lifecycle.
2010 Jun
Silibinin and related compounds are direct inhibitors of hepatitis C virus RNA-dependent RNA polymerase.
2010 Mar
Capsaicin sensitizes malignant glioma cells to TRAIL-mediated apoptosis via DR5 upregulation and survivin downregulation.
2010 Mar
Identification of hepatoprotective flavonolignans from silymarin.
2010 Mar 30
Differential in vitro effects of intravenous versus oral formulations of silibinin on the HCV life cycle and inflammation.
2011 Jan 28
Synergistic effects of arsenic trioxide and silibinin on apoptosis and invasion in human glioblastoma U87MG cell line.
2012 Feb
Metabolic effects of silibinin in the rat liver.
2012 Jan 25
In vitro determination of anticryptosporidial activity of phytogenic extracts and compounds.
2012 Jul
Antiplasmodial activity of flavonol quercetin and its analogues in Plasmodium falciparum: evidence from clinical isolates in Bangladesh and standardized parasite clones.
2012 Jun
Silibinin potentially protects arsenic-induced oxidative hepatic dysfunction in rats.
2012 May
Silibinin as a potential therapeutic for sulfur mustard injuries.
2013 Dec 5
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
Patents

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
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.
Substance Class Chemical
Created
by admin
on Sat Jun 26 03:34:10 UTC 2021
Edited
by admin
on Sat Jun 26 03:34:10 UTC 2021
Record UNII
33X338MNE4
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
SILIBININ A
Common Name English
SILYBIN A (CONSTITUENT OF MILK THISTLE) [DSC]
Common Name English
NSC-651520
Code English
SILYBIN A [MI]
Common Name English
4H-1-BENZOPYRAN-4-ONE, 2-((2R,3R)-2,3-DIHYDRO-3-(4-HYDROXY-3-METHOXYPHENYL)-2-(HYDROXYMETHYL)-1,4-BENZODIOXIN-6-YL)-2,3-DIHYDRO-3,5,7-TRIHYDROXY-, (2R,3R)-
Systematic Name English
SILYBIN A
Common Name English
SILYMARIN I
Common Name English
Code System Code Type Description
FDA UNII
33X338MNE4
Created by admin on Sat Jun 26 03:34:10 UTC 2021 , Edited by admin on Sat Jun 26 03:34:10 UTC 2021
PRIMARY
PUBCHEM
31553
Created by admin on Sat Jun 26 03:34:10 UTC 2021 , Edited by admin on Sat Jun 26 03:34:10 UTC 2021
PRIMARY
EPA CompTox
22888-70-6
Created by admin on Sat Jun 26 03:34:10 UTC 2021 , Edited by admin on Sat Jun 26 03:34:10 UTC 2021
PRIMARY
ECHA (EC/EINECS)
245-302-5
Created by admin on Sat Jun 26 03:34:10 UTC 2021 , Edited by admin on Sat Jun 26 03:34:10 UTC 2021
PRIMARY
CAS
22888-70-6
Created by admin on Sat Jun 26 03:34:10 UTC 2021 , Edited by admin on Sat Jun 26 03:34:10 UTC 2021
PRIMARY
MERCK INDEX
M9941
Created by admin on Sat Jun 26 03:34:10 UTC 2021 , Edited by admin on Sat Jun 26 03:34:10 UTC 2021
PRIMARY
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