Silybin A
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Also known as NSC-651520Silibinin aSilymarin iSID17388738SID50086851SID144204621SID170466469SID144207953Silybin ASilibininSilybinSILIBININ(+)-Silybin ASILYBIN_SILIBININSilymarin
Summary
Silybin A (CHEMBL431701) is a phase-3 clinical-stage small-molecule antineoplastic agent; indicated across 14 conditions including hepatitis c virus infection and proteinuria.
At a glance
- Status: Max clinical phase 3 (not approved)
- Modality: Small molecule
- Indications: 14 conditions
- Clinical trials: 54
- Chemistry: 482.4 Da · C25H22O10
Identifiers
Drug identity and classification
| Field | Value |
|---|---|
| ChEMBL ID | CHEMBL431701 |
| Name | Silybin A |
| Type | Small molecule |
| Max phase | 3 |
| FDA approved | no |
| PubChem CID | 31553 |
| ChEBI | CHEBI:9144 |
| Molecular formula | C25H22O10 |
| Molecular weight | 482.4 |
| InChIKey | SEBFKMXJBCUCAI-HKTJVKLFSA-N |
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
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
ChEBI definition: A flavonolignan isolated from milk thistle, Silybum marianum, that has been shown to exhibit antioxidant and antineoplastic activities.
Pharmacological roles (ChEBI): antioxidant, antineoplastic agent, hepatoprotective agent.
Other ChEBI roles (chemical / environmental): plant metabolite.
Also known as: NSC-651520, Silibinin a, Silybin a, Silymarin i, Silybin A, SID17388738, SID50086851, SID144204621, SID170466469, SID144207953, silybin A, Silybin A; Silibinin
Patent coverage: 2,900 distinct patent families (6,297 SureChEMBL compound mentions), from 3 matched compound structure(s). One matched structure accounts for 6,036 (96%) of the total. Mentions count patents naming the compound (not distinct inventions), so promiscuous / reference molecules inflate the mention figure — families are the dedup metric.
Targets
Targets
Broader ChEMBL bioactivity targets: 14 (assay-derived). Sample: Tyrosyl-DNA phosphodiesterase 1, Solute carrier family 2, facilitated glucose transporter member 4, Prelamin-A/C, Solute carrier organic anion transporter family member 1B1, Solute carrier organic anion transporter family member 1B3, Solute carrier organic anion transporter family member 2B1, Thyrotropin receptor, Polyunsaturated fatty acid lipoxygenase ALOX15, Cytochrome P450 2C9, Cytochrome P450 3A4.
Bioactivity
ChEMBL activities: 9 potent at pChembl ≥ 5 of 17 total. Top 30 by potency (10 = 0.1 nM, 6 = 1 µM):
| Target | pChembl | Type | Value | Unit | Activity ID |
|---|---|---|---|---|---|
| LMNA | 7.75 | Potency | 17.8 | nM | CHEMBL_ACT_3652553 |
| TDP1 | 5.7 | Potency | 1995 | nM | CHEMBL_ACT_3931746 |
| TSHR | 5.6 | Potency | 2512 | nM | CHEMBL_ACT_3934130 |
| TSHR | 5.6 | Potency | 2512 | nM | CHEMBL_ACT_4727379 |
| SLCO1B3 | 5.57 | IC50 | 2700 | nM | CHEMBL_ACT_15451341 |
| SLCO2B1 | 5.35 | IC50 | 4500 | nM | CHEMBL_ACT_15451344 |
| SLCO1B1 | 5.01 | IC50 | 9700 | nM | CHEMBL_ACT_15451338 |
| CYP3A4 | 5 | Potency | 10000 | nM | CHEMBL_ACT_4993960 |
| CYP3A4 | 5 | Potency | 10000 | nM | CHEMBL_ACT_5062831 |
Target pathways
No target-pathway data for this drug (no mapped target genes).
Indications & clinical
Indications
14 indications (0 at ChEMBL trial phase 4). Phase below is the highest clinical-trial phase recorded for this drug against each disease — not the molecule’s overall approval status (that is in the Summary).
| Indication | Trial phase | MONDO | EFO |
|---|---|---|---|
| hepatitis C virus infection | 3 | MONDO:0005231 | EFO:0003047 |
| proteinuria | 3 | MONDO:0003634 | HP:0000093 |
| depressive disorder | 3 | MONDO:0002050 | MONDO:0002050 |
| atrial fibrillation | 3 | MONDO:0004981 | EFO:0000275 |
| metabolic dysfunction-associated steatotic liver disease | 2 | MONDO:0013209 | EFO:0003095 |
| chronic hepatitis C virus infection | 2 | MONDO:0005354 | EFO:0004220 |
| hepatitis E virus infection | 2 | MONDO:0005788 | EFO:0007303 |
| hepatitis A virus infection | 2 | MONDO:0005790 | EFO:0007305 |
| neoplasm | 2 | MONDO:0005070 | MONDO:0004992 |
| viral hepatitis | 2 | MONDO:0006011 | EFO:0004196 |
| type 2 diabetes mellitus | 2 | MONDO:0005148 | MONDO:0005148 |
| hepatocellular carcinoma | 1 | MONDO:0007256 | EFO:0000182 |
| immune system disorder | 1 | MONDO:0005046 | EFO:0000540 |
1 further indication record had no mapped disease name (EFO/MeSH-only) or were duplicates, and are omitted.
Clinical trials
Total trials: 54.
Phase distribution
| Phase | Trials |
|---|---|
| PHASE2 | 14 |
| Not specified | 13 |
| PHASE4 | 8 |
| PHASE1 | 8 |
| PHASE2/PHASE3 | 5 |
| PHASE3 | 5 |
| PHASE1/PHASE2 | 1 |
Top trials by phase / activity
| NCT | Phase | Status | Title |
|---|---|---|---|
| NCT02973295 | PHASE4 | WITHDRAWN | Silymarin in NAFLD |
| NCT03130634 | PHASE4 | COMPLETED | The Efficacy of Silymarin as Adjuvant Therapy on Colorectal Cancer Patients Undergoing FOLFIRI Treatment |
| NCT03538327 | PHASE4 | COMPLETED | Effects of Silybin in Hypertensive Patients |
| NCT04490967 | PHASE4 | UNKNOWN | Silymarin Cream Versus Salicylic Acid in Treatment of Acne Vulgaris |
| NCT04816682 | PHASE4 | COMPLETED | Silymarin in COVID-19 Patients Admitted to Hospital With Elevated Liver Enzymes |
| NCT05042245 | PHASE4 | COMPLETED | The Efficacy and Safety of Ornithine Aspartic Acid Granules in NAFLD Against Silymarin Capsules |
| NCT05099601 | PHASE4 | UNKNOWN | Silymarin Cream Versus Combined Silymarin Cream and Microneedling in Treatment of Melasma |
| NCT05666765 | PHASE4 | UNKNOWN | Comparison Between Isotretinoin, Silymarin and Both in the Treatment of Acne Vulgaris |
| NCT00755950 | PHASE2/PHASE3 | TERMINATED | Randomized Placebo-controlled Trial Evaluating the Safety and Efficacy of Silymarin Treatment in Patients With Acute Viral Hepatitis |
| NCT00999349 | PHASE2/PHASE3 | UNKNOWN | Therapeutic Effects of Silymarin in Patients With B-thalassemia Major |
| NCT01049178 | PHASE2/PHASE3 | WITHDRAWN | Randomized Controlled Trial of Silymarin in Asthma |
| NCT01091324 | PHASE3 | UNKNOWN | Dextromethorphan and Silymarin in Chronic Kidney Disease (CKD) Patients |
| NCT01258686 | PHASE3 | COMPLETED | Clinical Study With Silymarin in the Patients With Chronic Hepatitis C Infection Who Failed Conventional Antiviral Therapy |
| NCT01829178 | PHASE2/PHASE3 | COMPLETED | Evaluation of Effects of Silymarin on Cisplatin Induced Nephrotoxicity in Upper Gastrointestinal Adenocarcinoma |
| NCT04394208 | PHASE3 | UNKNOWN | Silymarin in COVID-19 Pneumonia |
| NCT05595109 | PHASE2/PHASE3 | UNKNOWN | Role of Silymarin in Chemotherapy Toxicity and Cognition Improvement in Breast Cancer Patients |
| NCT05631041 | PHASE3 | UNKNOWN | Effect of Silymarin in Metastatic Colorectal Cancer Patients |
| NCT06114719 | PHASE3 | COMPLETED | Silymarin for the Prevention of Atrial Fibrillation After Cardiac Surgery |
| NCT06213857 | PHASE2 | RECRUITING | Beneficial Effect of Silymarin in Ulcerative Colitis |
| NCT07001150 | PHASE2 | RECRUITING | Role of Silymarin in Neuroprotection and Symptom Management in Parkinson’s Disease |
| NCT07572552 | PHASE2 | NOT_YET_RECRUITING | Clinical Study Evaluating the Efficacy and Safety of Fenofibrates Versus Silymarin in Adult Patients With Sepsis |
| NCT00055718 | PHASE2 | COMPLETED | Silymarin (Milk Thistle Extract) in Treating Patients With Acute Lymphoblastic Leukemia Who Are Receiving Chemotherapy |
| NCT00246363 | PHASE1/PHASE2 | COMPLETED | A Clinical Research Study Designed To Determine If Treatment of Hepatitis C With Milk Thistle is More Effective Than No Treatment In Patients Infected With Both HIV And Hepatitis C |
| NCT00680342 | PHASE2 | COMPLETED | Phase II Trial of Silymarin for Patients With Chronic Hepatitis C Who Have Failed Conventional Antiviral Treatment |
| NCT00680407 | PHASE2 | COMPLETED | Phase II Trial of Silymarin for Non-Cirrhotic Patients With Non-Alcoholic Steatohepatitis |
| NCT00684268 | PHASE2 | COMPLETED | Intravenous Silibinin in Combination With Peg-interferon and Ribavirin in Nonresponders |
| NCT00915681 | PHASE2 | TERMINATED | Intravenous Milk Thistle (Silibinin-Legalon) for Hepatic Failure Induced by Amatoxin/Amanita Mushroom Poisoning |
| NCT01292161 | PHASE2 | COMPLETED | Effects of Silybum Marianum on Treatment of Patients With Chronic Hepatitis C |
| NCT01518933 | PHASE2 | TERMINATED | Effect of LEGALON SIL on Hepatitis C Virus Recurrence in Stable Liver Transplanted Patients |
| NCT01535092 | PHASE2 | TERMINATED | Legalon SIL for the Treatment of HCV Recurrence in Liver Transplanted Patients |
| NCT01816490 | PHASE2 | COMPLETED | THISTLE - The HIV-HCV Silibinin Trial |
| NCT03982849 | PHASE2 | COMPLETED | Comparison of Topical Silymarin With Hydroquinone in the Treatment of Melasma |
| NCT06425705 | PHASE2 | COMPLETED | Impact of Silymarin Adjunct Therapy on Proteinuria in Type 2 Diabetic Patients on RAS Inhibitors |
| NCT07058090 | PHASE1 | NOT_YET_RECRUITING | Comparison of the Outcome of Treatment With Silymarin or N-Aceylcysteine in Patients Taking Anti-Tuberculous Drugs for Tuberculosis at a Tertiary Care Hospital , Karachi |
| NCT00065741 | PHASE1 | COMPLETED | Botanical/Drug Interactions in HIV: Glucuronidation |
| NCT00389376 | PHASE1 | COMPLETED | Phase I Trial of Silymarin for Chronic Liver Diseases |
| NCT01018615 | PHASE1 | COMPLETED | Safety, Metabolism, and Antioxidant Activity of Silymarin and Green Tea Extract in Patients With Chronic Hepatitis C |
| NCT01129570 | PHASE1 | COMPLETED | Siliphos in Advanced Hepatocellular Carcinoma |
| NCT01752153 | PHASE1 | COMPLETED | Immunomodulatory Effects of Silymarin in Patients With Beta-Thalassemia Major |
| NCT02633696 | PHASE1 | COMPLETED | Study to Investigate the Absolute Bioavailability of Oral Sylibin |
Clinical evidence (CIViC)
No CIViC predictive evidence (expected for non-precision-medicine drugs).
Pharmacology
Pharmacogenomics
No CPIC/DPWG dosing guideline, but PharmGKB curates 1 clinical and 1 variant annotation(s) for this drug (gene-keyed; see PharmGKB).
Related molecules
Related molecules
No competitor molecules sharing a primary target (ChEMBL phase ≥2 or PubChem drug-class).