Structure via PubChem · Public domain (PubChem)
silibinin A
Sign in to saveAlso known as silybin, Silymarin, Silybin A, Silybin A (constituent of milk thistle), Silymarin I, Silibinin, Flavobin, Karsil
Silibinin (INN), also known as silybin (both from Silybum, the generic name of the plant from which it is extracted), is the major active constituent of silymarin, a standardized extract of the milk thistle, containing a mixture of flavonolignans consisting of silibinin, isosilibinin, silychristin, silidianin, and others. Silibinin itself is a mixture of two diastereomers, silybin A and silybin B, in approximately equimolar ratio. Silibinin is used in pure forms as a medication, and more frequently as an active ingredient in milk thistle–derived herbal supplements.
Chemical data
- Formula
- C25H22O10
- Molecular weight
- 482.4 g/mol
- IUPAC name
- (2R,3R)-3,5,7-trihydroxy-2-[(2R,3R)-3-(4-hydroxy-3-methoxyphenyl)-2-(hydroxymethyl)-2,3-dihydro-1,4-benzodioxin-6-yl]-2,3-dihydrochromen-4-one
- SMILES
- COC1=C(C=CC(=C1)[C@@H]2[C@H](OC3=C(O2)C=C(C=C3)[C@@H]4[C@H](C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O
- InChIKey
- SEBFKMXJBCUCAI-HKTJVKLFSA-N
- XLogP
- 2.4
- Polar surface area
- 155 Ų
- H-bond donors
- 5
- H-bond acceptors
- 10
- Formal charge
- 0
via PubChem
Drug data · ChEMBL
- Max clinical phase
- Phase 3
- Molecule type
- Small molecule
- Indications
- hepatocellular carcinoma, immune system disease, hepatitis C virus infection, non-alcoholic fatty liver disease
via ChEMBL · EBI
Research
1,959 papers- Silibinin: a toxicologist's herbal medicine?Clinical toxicology (Philadelphia, Pa.) · 2022
- Silibinin attenuates ferroptosis in acute kidney injury by targeting FTH1.Redox biology · 2024
- Nano-soldiers Ameliorate Silibinin Delivery: A Review Study.Current drug delivery · 2020
- The Radiosensitizing Potentials of Silymarin/Silibinin in Cancer: A Systematic Review.Current medicinal chemistry · 2024
- Milk thistle (Silybum marianum): A concise overview on its chemistry, pharmacological, and nutraceutical uses in liver diseases.Phytotherapy research : PTR · 2018
via PubMed
Wikidata facts
- Mass
- 482.121297
Show 5 more facts
- chemical formula
- C₂₅H₂₂O₁₀
- canonical SMILES
- COC1=C(C=CC(=C1)C2C(OC3=C(O2)C=C(C=C3)C4C(C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O
- isomeric SMILES
- COC1=C(C=CC(=C1)[C@@H]2[C@H](OC3=C(O2)C=C(C=C3)[C@@H]4[C@H](C(=O)C5=C(C=C(C=C5O4)O)O)O)CO)O
- World Health Organisation international non-proprietary name
- silibinin
- has characteristic
- bitterness
via Wikidata · CC0
~7 min read
Encyclopedic overview
9 sectionsContents
- Medical uses
- Potential medical uses
- Pharmacology
- Toxicity
- Biotechnology
- Biosynthesis
- References
- Further reading
- External links
Silibinin (INN), also known as silybin (both from Silybum, the generic name of the plant from which it is extracted), is the major active constituent of silymarin, a standardized extract of the milk thistle, containing a mixture of flavonolignans consisting of silibinin, isosilibinin, silychristin, silidianin, and others. Silibinin itself is a mixture of two diastereomers, silybin A and silybin B, in approximately equimolar ratio. Silibinin is used in pure forms as a medication, and more frequently as an active ingredient in milk thistle–derived herbal supplements.
== Medical uses == For approved drug preparations and parenteral applications in the treatment of Amanita mushroom poisoning, the water-soluble silibinin-C-2',3-dihydrogensuccinate disodium salt is used. In 2012, the same compound also received Orphan Medicinal Product Designation for the prevention of recurrent hepatitis C in liver transplant recipients by the European Commission.
Excerpted from Wikipedia’s “silibinin A” article, available under the CC BY-SA 4.0 licence.