Back to products
Approved anticancer agents
Anticancer agents in trials
in preclinical trials
Anticancer molecular libraries
Other drug agents
Bio-reagents and biochemicals
MedKoo product information:
Description of silibinin: Silibinin (INN), also
known as silybin, is the major active constituent of silymarin,
standardized extract of the milk thistle seeds, containing mixture
of flavonolignans consisting of among others of silibinin,
isosilibinin, silicristin and silidianin. Silibinin itself is
mixture of two diastereomers Silibinin A and Silybinin B in
approximately equimolar ratio. Both in vitro and animal research
suggest that silibinin has hepatoprotective (antihepatotoxic)
properties that protect liver cells against toxins. Silibinin has
also demonstrated anti-cancer effects against human prostate
adenocarcinoma cells, estrogen-dependent and -independent human
breast carcinoma cells, human ectocervical carcinoma cells, human
colon cancer cells, and both small and nonsmall human lung carcinoma
MedKoo Code#: 202610
Chemical Formula: C25H22O10
Exact Mass: 482.12130
Molecular Weight: 482.44
Elemental Analysis: C, 62.24; H, 4.60; O,
Availability and price:
This agent is available through custom synthesis.
To inquire quotation and lead time or to ask questions, please send email to
email@example.com to describe your needs. A representative
will respond your email shortly. We offer big discount for orders of bulk quantities.
Product will be shipped with
supporting analytical data.
Information about this agent
Silibinin (INN), also known as silybin, is the major
active constituent of silymarin, the mixture of flavonolignans extracted
from blessed milk thistle. Poor water solubility and bioavailability of
silymarin led to the development of enhanced formulations. Silipide
(trade name Siliphos), a complex of silymarin and phosphatidylcholine
(lecithin), is about ten times more bioavailable than silymarin.
It has been also reported that silymarin inclusion complex with β-cyclodextrin
is much more soluble than silymarin itself. There have also been
prepared glycosides of silybin, which show better water solubility and
even stronger hepatoprotective effect. Silymarin, as other flavonoids,
has been shown to inhibit P-glycoprotein-mediated cellular efflux.
The modulation of P-glycoprotein activity may result in altered
absorption and bioavailability of drugs that are P-glycoprotein
substrates. It has been reported that silymarin inhibit cytochrome P450
enzymes and an interaction with drugs primarily cleared by P450s cannot
be excluded. [source:
Toxicity: The acute toxicity of silymarin and silybin
were investigated by oral and intravenous route in various animal
species. No mortality or any signs of adverse effects were observed
after silymarin at oral doses of 20 g/kg in mice and 1 g/kg in dogs. The
50% lethal dose (LD50) after intravenous infusion values are 400 mg/kg
in mice, 385 mg/kg in rats and 140 mg/kg in rabbits and dogs. These data
demonstrate that the acute toxicity of silymarin is very low [source:
1: Kaur M, Velmurugan B, Tyagi A, Agarwal C,
Singh RP, Agarwal R. Silibinin suppresses growth of human colorectal
carcinoma SW480 cells in culture and xenograft through down-regulation
of beta-catenin-dependent signaling. Neoplasia. 2010 May;12(5):415-24.
PubMed PMID: 20454513; PubMed Central PMCID: PMC2864479.
2: Duan W, Jin X, Li Q, Tashiro S, Onodera S, Ikejima T. Silibinin
induced autophagic and apoptotic cell death in HT1080 cells through a
reactive oxygen species pathway. J Pharmacol Sci. 2010;113(1):48-56.
Epub 2010 Apr 22. PubMed PMID: 20431246.
3: Wu K, Zeng J, Li L, Fan J, Zhang D, Xue Y, Zhu G, Yang L, Wang X, He
D. Silibinin reverses epithelial-to-mesenchymal transition in metastatic
prostate cancer cells by targeting transcription factors. Oncol Rep.
2010 Jun;23(6):1545-52. PubMed PMID: 20428808.
4: Li L, Zeng J, Gao Y, He D. Targeting silibinin in the
antiproliferative pathway. Expert Opin Investig Drugs. 2010
Feb;19(2):243-55. Review. PubMed PMID: 20047507.
5: Mateen S, Tyagi A, Agarwal C, Singh RP, Agarwal R. Silibinin inhibits
human nonsmall cell lung cancer cell growth through cell-cycle arrest by
modulating expression and function of key cell-cycle regulators. Mol
Carcinog. 2010 Mar;49(3):247-58. PubMed PMID: 19908243.
6: Kidd PM. Bioavailability and activity of phytosome complexes from
botanical polyphenols: the silymarin, curcumin, green tea, and grape
seed extracts. Altern Med Rev. 2009 Sep;14(3):226-46. Review. PubMed
7: Jung HJ, Park JW, Lee JS, Lee SR, Jang BC, Suh SI, Suh MH, Baek WK.
Silibinin inhibits expression of HIF-1alpha through suppression of
protein translation in prostate cancer cells. Biochem Biophys Res Commun.
2009 Dec 4;390(1):71-6. Epub 2009 Sep 22. PubMed PMID: 19778521.
8: Kaur M, Velmurugan B, Tyagi A, Deep G, Katiyar S, Agarwal C, Agarwal
R. Silibinin suppresses growth and induces apoptotic death of human
colorectal carcinoma LoVo cells in culture and tumor xenograft. Mol
Cancer Ther. 2009 Aug;8(8):2366-74. Epub 2009 Jul 28. PubMed PMID:
19638451; PubMed Central PMCID: PMC2728169.
9: Lin CJ, Sukarieh R, Pelletier J. Silibinin inhibits translation
initiation: implications for anticancer therapy. Mol Cancer Ther. 2009
Jun;8(6):1606-12. Epub 2009 Jun 9. PubMed PMID: 19509268.
10: Kim KW, Choi CH, Kim TH, Kwon CH, Woo JS, Kim YK. Silibinin inhibits
glioma cell proliferation via Ca2+/ROS/MAPK-dependent mechanism in vitro
and glioma tumor growth in vivo. Neurochem Res. 2009 Aug;34(8):1479-90.
Epub 2009 Mar 5. PubMed PMID: 19263218.
11: Bhatt RS, Bubley GJ. The challenge of herbal therapies for prostate
cancer. Clin Cancer Res. 2008 Dec 1;14(23):7581-2. Review. PubMed PMID:
12: Thongphasuk P, Stremmel W, Chamulitrat W. 2,3-dehydrosilybin is a
better DNA topoisomerase I inhibitor than its parental silybin.
Chemotherapy. 2009;55(1):42-8. Epub 2008 Nov 21. PubMed PMID: 19023201.
13: García-Maceira P, Mateo J. Silibinin inhibits hypoxia-inducible
factor-1alpha and mTOR/p70S6K/4E-BP1 signalling pathway in human
cervical and hepatoma cancer cells: implications for anticancer therapy.
Oncogene. 2009 Jan 22;28(3):313-24. Epub 2008 Nov 3. PubMed PMID:
14: Wang HJ, Tashiro S, Onodera S, Ikejima T. Inhibition of insulin-like
growth factor 1 receptor signaling enhanced silibinin-induced activation
of death receptor and mitochondrial apoptotic pathways in human breast
cancer MCF-7 cells. J Pharmacol Sci. 2008 Jul;107(3):260-9. PubMed PMID:
15: Zhou L, Liu P, Chen B, Wang Y, Wang X, Chiriva Internati M, Wachtel
MS, Frezza EE. Silibinin restores paclitaxel sensitivity to paclitaxel-resistant
human ovarian carcinoma cells. Anticancer Res. 2008
Mar-Apr;28(2A):1119-27. PubMed PMID: 18507063.
16: Deep G, Oberlies NH, Kroll DJ, Agarwal R. Identifying the
differential effects of silymarin constituents on cell growth and cell
cycle regulatory molecules in human prostate cancer cells. Int J Cancer.
2008 Jul 1;123(1):41-50. PubMed PMID: 18435416.
17: Huber A, Thongphasuk P, Erben G, Lehmann WD, Tuma S, Stremmel W,
Chamulitrat W. Significantly greater antioxidant anticancer activities
of 2,3-dehydrosilybin than silybin. Biochim Biophys Acta. 2008
May;1780(5):837-47. Epub 2008 Jan 3. PubMed PMID: 18222181.
18: Thongphasuk P, Stremmel W, Chamulitrat W. Potent direct or
TNF-alpha-promoted anticancer effects of 2,3-dehydrosilybin: comparison
study with silybin. Chemotherapy. 2008;54(1):23-30. Epub 2007 Dec 7.
PubMed PMID: 18063863.
19: Raina K, Agarwal R. Combinatorial strategies for cancer eradication
by silibinin and cytotoxic agents: efficacy and mechanisms. Acta
Pharmacol Sin. 2007 Sep;28(9):1466-75. Review. PubMed PMID: 17723180.
20: Jancová P, Anzenbacherová E, Papousková B, Lemr K, Luzná P,
Veinlichová A, Anzenbacher P, Simánek V. Silybin is metabolized by
cytochrome P450 2C8 in vitro. Drug Metab Dispos. 2007 Nov;35(11):2035-9.
Epub 2007 Aug 1. PubMed PMID: 17670841.
(Keyword; CAS#; MedKoo code#)