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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 of SILIBININ A

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
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

2000
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

2000
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

2000
PubMed

PubMed

TitleDatePubMed
MDR- and CYP3A4-mediated drug-herbal interactions.
2006 Mar 27
Identification of hepatoprotective flavonolignans from silymarin.
2010 Mar 30
Synergistic effects of arsenic trioxide and silibinin on apoptosis and invasion in human glioblastoma U87MG cell line.
2012 Feb
Silibinin potentially protects arsenic-induced oxidative hepatic dysfunction in rats.
2012 May
Blockade of lipid accumulation by silibinin in adipocytes and zebrafish.
2015 Feb 5
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 Fri Dec 15 19:01:35 GMT 2023
Edited
by admin
on Fri Dec 15 19:01:35 GMT 2023
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 Fri Dec 15 19:01:36 GMT 2023 , Edited by admin on Fri Dec 15 19:01:36 GMT 2023
PRIMARY
PUBCHEM
31553
Created by admin on Fri Dec 15 19:01:36 GMT 2023 , Edited by admin on Fri Dec 15 19:01:36 GMT 2023
PRIMARY
EPA CompTox
DTXSID8026018
Created by admin on Fri Dec 15 19:01:36 GMT 2023 , Edited by admin on Fri Dec 15 19:01:36 GMT 2023
PRIMARY
NSC
651520
Created by admin on Fri Dec 15 19:01:36 GMT 2023 , Edited by admin on Fri Dec 15 19:01:36 GMT 2023
PRIMARY
ECHA (EC/EINECS)
245-302-5
Created by admin on Fri Dec 15 19:01:36 GMT 2023 , Edited by admin on Fri Dec 15 19:01:36 GMT 2023
PRIMARY
CAS
22888-70-6
Created by admin on Fri Dec 15 19:01:36 GMT 2023 , Edited by admin on Fri Dec 15 19:01:36 GMT 2023
PRIMARY
MERCK INDEX
m9941
Created by admin on Fri Dec 15 19:01:36 GMT 2023 , Edited by admin on Fri Dec 15 19:01:36 GMT 2023
PRIMARY
SMS_ID
300000005280
Created by admin on Fri Dec 15 19:01:36 GMT 2023 , Edited by admin on Fri Dec 15 19:01:36 GMT 2023
PRIMARY
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