SILIBININ A

Possibly Marketed Outside US

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

Structure Search

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

HIDE SMILES / InChI

Molecular Formula	C25H22O10
Molecular Weight	482.4362
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	0
Optical Activity	UNSPECIFIED

Description
Sources: https://www.squarepharma.com.bd/downloads/Silybin%20DS.PDF
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
response to oxidative stress 20 Target ID: GO:0006979 Sources: https://www.squarepharma.com.bd/downloads/Silybin%20DS.PDF	Modulator 828
Estrogen receptor beta 110 Target ID: CHEMBL3021 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14568570	Agonist 2678
P-glycoprotein 1 54 Target ID: CHEMBL4302 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17305535 \| https://www.ncbi.nlm.nih.gov/pubmed/15072439	Inhibitor 8297

Conditions

Condition	Modality	Highest Phase	Product
Liver cirrhosis 15 Sources: https://www.squarepharma.com.bd/downloads/Silybin%20DS.PDF https://www.ncbi.nlm.nih.gov/pubmed/28125040	Primary	Approved 8429	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
Hepatitis 8 Sources: https://www.squarepharma.com.bd/downloads/Silybin%20DS.PDF	Primary	Approved 8429	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
Gallbladder disease 13 Sources: http://www.naturesgardenonline.com/ns/DisplayMonograph.asp?storeID=4qv7af8nchqt8hx4xqu61nerl9mtecuf&DocID=bottomline-milkthistle	Primary	Approved 8429	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

Title	Date	PubMed
Inhibition of reverse transcriptases by flavonoids.	1989 Sep	2480745
Stimulatory effects of silibinin and silicristin from the milk thistle Silybum marianum on kidney cells.	1999 Sep	10454517
Hepatoprotective and antifibrotic effect of a new silybin-phosphatidylcholine-Vitamin E complex in rats.	2005 Nov	16169303
Antiparasitic activity of flavonoids and isoflavones against Cryptosporidium parvum and Encephalitozoon intestinalis.	2006 Jun	16684116
Effect of silibinin on the growth and progression of primary lung tumors in mice.	2006 Jun 21	16788158
MDR- and CYP3A4-mediated drug-herbal interactions.	2006 Mar 27	16442130
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	16777994
Increased expression of the MGMT repair protein mediated by cysteine prodrugs and chemopreventative natural products in human lymphocytes and tumor cell lines.	2007 Feb	16950796
Inhibition effect of flavonoids on monocarboxylate transporter 1 (MCT1) in Caco-2 cells.	2007 Nov	17976262
Hepatoprotective efficacy of certain flavonoids against microcystin induced toxicity in mice.	2007 Oct	17696131
AKR1C3 as a potential target for the inhibitory effect of dietary flavonoids.	2009 Mar 16	19007764
The protective effect of silibinin against mitomycin C-induced intrinsic apoptosis in human melanoma A375-S2 cells.	2009 Oct	19834285
Multiple effects of silymarin on the hepatitis C virus lifecycle.	2010 Jun	20512985
Silibinin and related compounds are direct inhibitors of hepatitis C virus RNA-dependent RNA polymerase.	2010 Mar	19962982
Capsaicin sensitizes malignant glioma cells to TRAIL-mediated apoptosis via DR5 upregulation and survivin downregulation.	2010 Mar	19939880
Identification of hepatoprotective flavonolignans from silymarin.	2010 Mar 30	20231449
Differential in vitro effects of intravenous versus oral formulations of silibinin on the HCV life cycle and inflammation.	2011 Jan 28	21297992
Protective effect of curcumin, silymarin and N-acetylcysteine on antitubercular drug-induced hepatotoxicity assessed in an in vitro model.	2012 Aug	22318308
Silibinin ameliorates arsenic induced nephrotoxicity by abrogation of oxidative stress, inflammation and apoptosis in rats.	2012 Dec	23070905
Synergistic effects of arsenic trioxide and silibinin on apoptosis and invasion in human glioblastoma U87MG cell line.	2012 Feb	21969006
Metabolic effects of silibinin in the rat liver.	2012 Jan 25	22137898
In vitro determination of anticryptosporidial activity of phytogenic extracts and compounds.	2012 Jul	22278729
Antiplasmodial activity of flavonol quercetin and its analogues in Plasmodium falciparum: evidence from clinical isolates in Bangladesh and standardized parasite clones.	2012 Jun	22215188
Silibinin potentially protects arsenic-induced oxidative hepatic dysfunction in rats.	2012 May	22229868
Silibinin as a potential therapeutic for sulfur mustard injuries.	2013 Dec 5	23810508
Silibinin inhibits hepatitis C virus entry into hepatocytes by hindering clathrin-dependent trafficking.	2013 Nov	23701235
The binding of silibinin to ERp57.	2014 Apr 25	24530445
Silibinin potentially attenuates arsenic-induced oxidative stress mediated cardiotoxicity and dyslipidemia in rats.	2014 Mar	24062023
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	24440808
Blockade of lipid accumulation by silibinin in adipocytes and zebrafish.	2015 Feb 5	25559859

Patents

Sample Use Guides

In Vivo Use Guide

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

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 `Fri Dec 15 19:01:35 UTC 2023` Edited by `admin` on `Fri Dec 15 19:01:35 UTC 2023`
Record UNII	33X338MNE4
Record Status	`Validated (UNII)`
Record Version

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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