| Name | Silibinin | ||
| PubChem CID | 31553 | ||
| Molecular Weight | 482.4g/mol | ||
| Synonyms |
2,3 Dehydrosilybin, 2,3-dehydrosilybin, Alepa forte, Alepa-forte, Ardeyhepan, Cefasilymarin, durasilymarin, Hepa loges, Hepa Merz Sil, hepa-loges, Hepa-Merz Sil, HepaBesch, Hepar Pasc, Hepar-Pasc, Heparsyx, Heplant, Lagosa, legalon forte, silibin, silibinin, Silibinin A, Silibinin B, silybin, silybin A, silybin B, silybinin |
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| Formula | C₂₅H₂₂O₁₀ | ||
| 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 | ||
| 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 | ||
| InChIKey | SEBFKMXJBCUCAI-HKTJVKLFSA-N | ||
| CAS Number | 65666-07-1 | ||
| ChEMBL ID | CHEMBL431701 | ||
| ChEBI ID | CHEBI:9144 | ||
| Herb ID | HBIN044028 | ||
| Drug Bank ID | DB09298 | ||
| KEGG ID | C07610 | ||
| Toxicity | Organism | Test Type | Route(Dose) |
| rat | LD50 | intraperitoneal(165 mg/kg) | |
| mouse | LD50 | intraperitoneal(254 mg/kg) | |
| rat | LD50 | oral(322 mg/kg) | |
| Structure | 
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Download
2D
MOL
3D
MOL
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| Chineses Pinyin | ShuiFeiJi | ||
| Use Part | Achene | ||
| Habitat | JiangSu, Shaanxi, BeiJing | ||
| Flavor | Bitter | ||
| Meridian Tropism | Liver, Gallbladder | ||
| Species |
>Kingdom: Viridiplantae
-->Phylum: Streptophyta
-->Class: Equisetopsida
-->Order: Asterales
-->Family: Asteraceae
-->Genus: Silybum
-->Species: Silybum marianum
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| Pair Name | Silibinin, Metformin | |||
| Partner Name | Metformin | |||
| Disease Info | [ICD-11: 2C60] | Breast cancer | Investigative | |
| Biological Phenomena | Induction-->Proliferation | |||
| Gene Regulation | Down-regulation | Expression | CCND1 | hsa595 |
| Down-regulation | Expression | TERT | hsa7015 | |
| In Vitro Model | T-47D | Invasive breast carcinoma of no special type | Homo sapiens (Human) | CVCL_0553 |
| Result | The results provide evidence that synergistic antiproliferative effects of MET and SIL, linking to the down-regulation of Cyclin D1 and hTERT genes, and propose that MET+SIL may have therapeutic value in breast cancer therapy. | |||
| Pair Name | Silibinin, Sorafenib | |||
| Partner Name | Sorafenib | |||
| Disease Info | [ICD-11: 2C12] | Hepatocellular carcinoma | Investigative | |
| Biological Phenomena | Induction-->Apoptosis | |||
| Gene Regulation | Down-regulation | Phosphorylation | AKT1 | hsa207 |
| Down-regulation | Expression | BCL2 | hsa596 | |
| Up-regulation | Cleavage | CASP3 | hsa836 | |
| Down-regulation | Expression | KLF4 | hsa9314 | |
| Down-regulation | Phosphorylation | MAPK1 | hsa5594 | |
| Down-regulation | Phosphorylation | MAPK14 | hsa1432 | |
| Down-regulation | Expression | MCL1 | hsa4170 | |
| Down-regulation | Expression | NANOG | hsa79923 | |
| Up-regulation | Cleavage | PARP1 | hsa142 | |
| Down-regulation | Phosphorylation | STAT3 | hsa6774 | |
| In Vitro Model | BEL-7404 | Human papillomavirus-related cervical adenocarcinoma | Homo sapiens (Human) | CVCL_6568 |
| Result | These results suggested that silibinin improved the efficacy of sorafenib in HCC therapy, indicating a clinical promising therapeutic strategy for HCC patients. | |||
| Pair Name | Silibinin, Paclitaxel | |||
| Partner Name | Paclitaxel | |||
| Disease Info | [ICD-11: 2B72] | Gastric cancer | Investigative | |
| Biological Phenomena | Induction-->Blockade of cell cycle in G2/M phase | |||
| Gene Regulation | Up-regulation | Expression | BAX | hsa581 |
| Down-regulation | Expression | BCL2 | hsa596 | |
| Up-regulation | Cleavage | CASP3 | hsa836 | |
| Up-regulation | Cleavage | CASP8 | hsa841 | |
| Down-regulation | Expression | CCNB1 | hsa891 | |
| Down-regulation | Expression | CDC25C | hsa995 | |
| Down-regulation | Expression | CDK1 | hsa983 | |
| Up-regulation | Expression | FAS | hsa355 | |
| Up-regulation | Cleavage | PARP1 | hsa142 | |
| In Vitro Model | BGC-823 | Human papillomavirus-related cervical adenocarcinoma | Homo sapiens (Human) | CVCL_3360 |
| SGC-7901 | Human papillomavirus-related cervical adenocarcinoma | Homo sapiens (Human) | CVCL_0520 | |
| AGS | Gastric adenocarcinoma | Homo sapiens (Human) | CVCL_0139 | |
| Result | Synergistic apoptotic effects of silibinin in enhancing paclitaxel toxicity in human gastric cancer cell lines | |||
| Pair Name | Silibinin, Paclitaxel | |||
| Partner Name | Paclitaxel | |||
| Disease Info | [ICD-11: 2C73] | Ovarian cancer | Investigative | |
| Gene Regulation | Up-regulation | Expression | CDKN1A | hsa1026 |
| Up-regulation | Expression | TP53 | hsa7157 | |
| In Vitro Model | SK-OV-3 | Ovarian serous cystadenocarcinoma | Homo sapiens (Human) | CVCL_0532 |
| Result | Our results showed that combination of chemotherapy drugs of silibinin and paclitaxel can be more efficient in treatment of ovarian cancer cells. | |||
| Pair Name | Silibinin, Doxorubicin | |||
| Partner Name | Doxorubicin | |||
| Disease Info | [ICD-11: 2C12] | Hepatocellular carcinoma | Investigative | |
| Biological Phenomena | Induction-->Blockade of cell cycle in G2/M phase | |||
| Gene Regulation | Up-regulation | Expression | CDC25C | hsa995 |
| Down-regulation | Activity | CDK1 | hsa983 | |
| Up-regulation | Expression | CHEK1 | hsa1111 | |
| Up-regulation | Expression | MS4A1 | hsa931 | |
| In Vitro Model | Hep-G2 | Hepatoblastoma | Homo sapiens (Human) | CVCL_0027 |
| In Vivo Model | An orthotopic rat model of HCC was used, in which subcutaneously injected Morris hepatoma (MH)-3924A cells (5×10⁶) in syngeneic ACI rats (Harlan, USA) led to formation of a subcutaneous tumor within 14 days. | |||
| Result | Inhibitory effects of Silibinin combined with doxorubicin in hepatocellular carcinoma; an in vivo study | |||
| Pair Name | Silibinin, Trichostatin A | |||
| Partner Name | Trichostatin A | |||
| Disease Info | [ICD-11: 2C25] | Lung cancer | Investigative | |
| Biological Phenomena | Induction-->Blockade of cell cycle in G2/M phase | |||
| Gene Regulation | Down-regulation | Expression | BCL2 | hsa596 |
| Down-regulation | Expression | BCL-xL | hsa598 | |
| Down-regulation | Expression | BIRC5 | hsa332 | |
| Down-regulation | Expression | CCNB1 | hsa891 | |
| Up-regulation | Expression | CDKN1A | hsa1026 | |
| Down-regulation | Expression | MCL1 | hsa4170 | |
| Down-regulation | Expression | POLD1 | hsa5424 | |
| Down-regulation | Expression | XIAP | hsa331 | |
| In Vitro Model | NCI-H1299 | Lung large cell carcinoma | Homo sapiens (Human) | CVCL_0060 |
| NCI-H358 | Minimally invasive lung adenocarcinoma | Homo sapiens (Human) | CVCL_1559 | |
| NCI-H322 | Minimally invasive lung adenocarcinoma | Homo sapiens (Human) | CVCL_1556 | |
| In Vivo Model | Six week old athymic (nu/nu) male nude mice were subcutaneously injected with about three million exponentially growing H1299 cells mixed with equal volume (1:1) of matrigel on the right flank of each mouse. | |||
| Result | Combinations of TSA with silibinin synergistically augmented the cytotoxic effects of the single agent, which was associated with a dramatic increase in p21 (Cdkn1a) | |||
| Pair Name | Silibinin, Trichostatin A | |||
| Partner Name | Trichostatin A | |||
| Disease Info | [ICD-11: 2C10] | Pancreatic cancer | Investigative | |
| Biological Phenomena | Induction-->Blockade of cell cycle in G2/M phase | |||
| Gene Regulation | Down-regulation | Expression | BIRC5 | hsa332 |
| Down-regulation | Expression | CCNA2 | hsa890 | |
| In Vitro Model | BxPC-3 | Pancreatic ductal adenocarcinoma | Homo sapiens (Human) | CVCL_0186 |
| PaTu 8988s | Pancreatic adenocarcinoma | Homo sapiens (Human) | CVCL_1846 | |
| PANC-1 | Pancreatic ductal adenocarcinoma | Homo sapiens (Human) | CVCL_0480 | |
| Capan-2 | Pancreatic ductal adenocarcinoma | Homo sapiens (Human) | CVCL_0026 | |
| Result | Combination of HDAC inhibitor TSA and silibinin induces cell cycle arrest and apoptosis by targeting survivin and cyclinB1/Cdk1 in pancreatic cancer cells | |||
| Pair Name | Silibinin, Neratinib | |||
| Partner Name | Neratinib | |||
| Disease Info | [ICD-11: 2C60] | Breast cancer | Investigative | |
| Biological Phenomena | Induction-->Ferroptosis | |||
| Gene Regulation | Up-regulation | Expression | ROS1 | hsa6098 |
| In Vitro Model | 4T1 | Malignant neoplasms of the mouse mammary gland | Mus musculus (Mouse) | CVCL_0125 |
| MDA-MB-231 | Breast adenocarcinoma | Homo sapiens (Human) | CVCL_0062 | |
| Result | N-S Alb NPs had the ability to promote "mixed" type cell death, showed promise in enhancing the payload capabilities and targeting in TNBC. | |||
| Pair Name | Silibinin, Regorafenib | |||
| Partner Name | Regorafenib | |||
| Disease Info | [ICD-11: 2B91] | Colorectal cancer | Investigative | |
| Biological Phenomena | Induction-->ROS generation | |||
| Gene Regulation | Down-regulation | Expression | AKT1 | hsa207 |
| Down-regulation | Expression | MTOR | hsa2475 | |
| Down-regulation | Expression | PIK3CA | hsa5290 | |
| In Vitro Model | SW48 | Colon adenocarcinoma | Homo sapiens (Human) | CVCL_1724 |
| HCT 15 | Colon adenocarcinoma | Homo sapiens (Human) | CVCL_0292 | |
| SW480 | Colon adenocarcinoma | Homo sapiens (Human) | CVCL_0546 | |
| Result | The present study suggests that silybin in combination with regorafenib is a promising strategy for treatment of metastatic colorectal patients. | |||
| No. | Title | Href |
|---|---|---|
| 1 | Regorafenib in combination with silybin as a novel potential strategy for the treatment of metastatic colorectal cancer. Oncotarget. 2017 Aug 7;8(40):68305-68316. doi: 10.18632/oncotarget.20054. | Click |
| 2 | Synergistic Anti-proliferative Effects of Metformin and Silibinin Combination on T47D Breast Cancer Cells via hTERT and Cyclin D1 Inhibition. Drug Res (Stuttg). 2018 Dec;68(12):710-716. doi: 10.1055/a-0631-8046. | Click |
| 3 | Combined treatment with sorafenib and silibinin synergistically targets both HCC cells and cancer stem cells by enhanced inhibition of the phosphorylation of STAT3/ERK/AKT. Eur J Pharmacol. 2018 Aug 5;832:39-49. doi: 10.1016/j.ejphar.2018.05.027. | Click |
| 4 | Synergistic apoptotic effects of silibinin in enhancing paclitaxel toxicity in human gastric cancer cell lines. Mol Med Rep. 2018 Aug;18(2):1835-1841. doi: 10.3892/mmr.2018.9129. | Click |
| 5 | Enhancement of anticancer activity by silibinin and paclitaxel combination on the ovarian cancer. Artif Cells Nanomed Biotechnol. 2018 Nov;46(7):1483-1487. doi: 10.1080/21691401.2017.1374281. | Click |
| 6 | Inhibitory effects of Silibinin combined with doxorubicin in hepatocellular carcinoma; an in vivo study. J BUON. 2016 Jul-Aug;21(4):917-924. | Click |
| 7 | Epigenetic modifications and p21-cyclin B1 nexus in anticancer effect of histone deacetylase inhibitors in combination with silibinin on non-small cell lung cancer cells. Epigenetics. 2012 Oct;7(10):1161-72. doi: 10.4161/epi.22070. | Click |
| 8 | Combination of HDAC inhibitor TSA and silibinin induces cell cycle arrest and apoptosis by targeting survivin and cyclinB1/Cdk1 in pancreatic cancer cells. Biomed Pharmacother. 2015 Aug;74:257-64. doi: 10.1016/j.biopha.2015.08.017. | Click |
| 9 | Genipin-crosslinked albumin nanoparticles containing neratinib and silibinin: A dual-death therapy for triple negative breast cancer. Int J Pharm. 2023 Dec 15;648:123570. doi: 10.1016/j.ijpharm.2023.123570. | Click |
