This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.
Identification
- Summary
Silibinin is a flavonolignan with hepatoprotective effects used to treat toxic liver damage and as an adjunct in the management of chronic conditions such as cirrhosis and hepatitis.
- Generic Name
- Silibinin
- DrugBank Accession Number
- DB09298
- Background
Silibinin is the major active constituent of silymarin, a standardized extract of the milk thistle seeds, containing a mixture of flavonolignans consisting of silibinin, isosilibinin, silicristin, silidianin and others. Silibinin is presented as a mixture of two diastereomers, silybin A and silybin B, which are found in an 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 in vitro 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 cells.
- Type
- Small Molecule
- Groups
- Experimental, Investigational
- Structure
Structure for Silibinin (DB09298)
- Weight
- Average: 482.441
Monoisotopic: 482.121296908 - Chemical Formula
- C25H22O10
- Synonyms
- Silibinin
- Silibinin A
- Silibinina
- Silibinine
- Silibininum
- Silybin A
- Silybin A (constituent of milk thistle)
- Silymarin I
Pharmacology
- Indication
Currently being tested as a treatment of severe intoxications with hepatotoxic substances, such as death cap (Amanita phalloides) poisoning.
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Treatment of Acute hepatitis •••••••••••• •••••• Treatment of Acute hepatitis •••••••••••• ••••••• Treatment of Acute hepatitis •••••••••••• ••••••• •••••• Treatment of Amanita poisoning •••••••••••• •••••••••• ••••••• ••• •••••••• Treatment of Clinical deterioration of the liver •••••••••••• ••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- Pharmacodynamics
Not Available
- Mechanism of action
- Not Available
- Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
Hover over products below to view reaction partners
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir The metabolism of Abacavir can be decreased when combined with Silibinin. Acetaminophen The metabolism of Acetaminophen can be decreased when combined with Silibinin. Acetazolamide The excretion of Silibinin can be decreased when combined with Acetazolamide. Acetylsalicylic acid The excretion of Silibinin can be decreased when combined with Acetylsalicylic acid. Acyclovir The excretion of Silibinin can be decreased when combined with Acyclovir. - Food Interactions
- Not Available
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Silibinin dihemisuccinate disodium 57LSQ377IE 1265089-66-4 Not applicable - International/Other Brands
- Legalon
- Mixture Products
Name Ingredients Dosage Route Labeller Marketing Start Marketing End Region Image HEPAVITE CAPSULE Silibinin (70 mg) + Nicotinamide (12 mg) + Calcium pantothenate (8 mg) + Pyridoxine hydrochloride (4 mg) + Riboflavin (4 mg) + Thiamine mononitrate (5 mg) Capsule Oral Y.S.P. INDUSTRIES (M) SDN BHD 2020-09-08 Not applicable Malaysia 
Shine Hepavite Forte Capsule Silibinin (150 mg) + Nicotinamide (12 mg) + Calcium pantothenate (8 mg) + Pyridoxine hydrochloride (4 mg) + Riboflavin (4 mg) + Thiamine mononitrate (3.9 mg) Capsule Oral Y.S.P. INDUSTRIES (M) SDN BHD 2020-09-08 Not applicable Malaysia SIMEPAR CAPSULES Silibinin (70 mg) + Cyanocobalamin (1.2 µg) + Nicotinamide (12 mg) + Calcium pantothenate (8 mg) + Pyridoxine hydrochloride (4 mg) + Riboflavin (4 mg) + Thiamine hydrochloride (4 mg) Capsule Oral MEPHARM (MALAYSIA) SDN BHD 2020-09-08 Not applicable Malaysia
Categories
- ATC Codes
- A05BA03 — Silymarin
- Drug Categories
- Alimentary Tract and Metabolism
- Antineoplastic Agents
- Antineoplastic Agents, Phytogenic
- Antioxidants
- Benzopyrans
- Bile and Liver Therapy
- Biological Factors
- Chromones
- Compounds used in a research, industrial, or household setting
- Flavonoids
- Flavonolignans
- Heterocyclic Compounds, Fused-Ring
- Liver Therapy
- Liver Therapy, Lipotropics
- OAT1/SLC22A6 inhibitors
- OAT1/SLC22A6 Substrates
- OAT3/SLC22A8 Substrates
- OATP1B1/SLCO1B1 Inhibitors
- OATP1B3 inhibitors
- Organic Anion Transporting Polypeptide 2B1 Inhibitors
- Protective Agents
- Pyrans
- UGT1A1 Inhibitors
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as flavonolignans. These are non-conventional lignans that derived from flavonoids. They are characterized by a p-dioxin ring substituted at one carbon atom by a C3C6 (phenylpropan) group and fused to the B-ring of the 2-phenylchromene moiety.
- Kingdom
- Organic compounds
- Super Class
- Lignans, neolignans and related compounds
- Class
- Flavonolignans
- Sub Class
- Not Available
- Direct Parent
- Flavonolignans
- Alternative Parents
- 3-hydroxyflavonoids / 5-hydroxyflavonoids / 7-hydroxyflavonoids / Flavanonols / Phenylbenzo-1,4-dioxanes / Chromones / Methoxyphenols / Benzo-1,4-dioxanes / Phenoxy compounds / Anisoles show 13 more
- Substituents
- 1-benzopyran / 1-hydroxy-2-unsubstituted benzenoid / 1-hydroxy-4-unsubstituted benzenoid / 2-phenylbenzo-1,4-dioxane / 3-hydroxyflavonoid / 5-hydroxyflavonoid / 7-hydroxyflavonoid / Alcohol / Alkyl aryl ether / Anisole show 34 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- aromatic ether, polyphenol, benzodioxine, flavonolignan (CHEBI:9144)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 33X338MNE4
- CAS number
- 22888-70-6
- InChI Key
- SEBFKMXJBCUCAI-HKTJVKLFSA-N
- InChI
- 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
- 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]-3,4-dihydro-2H-1-benzopyran-4-one
- SMILES
- [H][C@@]1(OC2=C(O[C@@H]1CO)C=CC(=C2)[C@@]1([H])OC2=C(C(O)=CC(O)=C2)C(=O)[C@@H]1O)C1=CC(OC)=C(O)C=C1
References
- General References
- Not Available
- External Links
- KEGG Drug
- D08515
- KEGG Compound
- C07610
- PubChem Compound
- 31553
- PubChem Substance
- 310265190
- ChemSpider
- 29263
- BindingDB
- 50084982
- 155067
- ChEBI
- 9144
- ChEMBL
- CHEMBL431701
- ZINC
- ZINC000002033589
- PharmGKB
- PA166129539
- Wikipedia
- Silibinin
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Completed Prevention Breast Cancer 1 4 Completed Treatment Chronic Liver Disease 1 4 Completed Treatment Coronavirus Disease 2019 (COVID‑19) / Liver Disease 1 4 Completed Treatment Hepatitis 1 4 Completed Treatment Metastatic Colorectal Cancer (CRC) 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
Form Route Strength Capsule, coated Oral 15000000 mg Powder, for suspension Oral 1 g Tablet, delayed release Oral 150 mg Capsule Oral Suspension Oral 1 g Granule, effervescent Oral 200 MG Syrup Oral 1 % Capsule, coated Oral 70 mg Capsule Oral 200 mg Granule, effervescent Oral Tablet Oral 200 MG Capsule, coated Oral 150 mg Tablet Oral Capsule Oral Tablet, coated Oral 140 mg Tablet, coated Oral 70 mg Powder 528.5 mg Capsule Oral 70 mg Capsule Oral 140 mg - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
- Not Available
- Predicted Properties
Property Value Source Water Solubility 0.0926 mg/mL ALOGPS logP 2.35 ALOGPS logP 2.63 Chemaxon logS -3.7 ALOGPS pKa (Strongest Acidic) 7.75 Chemaxon pKa (Strongest Basic) -3 Chemaxon Physiological Charge 0 Chemaxon Hydrogen Acceptor Count 10 Chemaxon Hydrogen Donor Count 5 Chemaxon Polar Surface Area 155.14 Å2 Chemaxon Rotatable Bond Count 4 Chemaxon Refractivity 120.29 m3·mol-1 Chemaxon Polarizability 48.41 Å3 Chemaxon Number of Rings 5 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter No Chemaxon Veber's Rule No Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
- Not Available
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 244.7851847 predictedDarkChem Lite v0.1.0 [M-H]- 244.5758847 predictedDarkChem Lite v0.1.0 [M-H]- 205.31447 predictedDeepCCS 1.0 (2019) [M+H]+ 247.6761847 predictedDarkChem Lite v0.1.0 [M+H]+ 245.7987847 predictedDarkChem Lite v0.1.0 [M+H]+ 207.20988 predictedDeepCCS 1.0 (2019) [M+Na]+ 245.0341847 predictedDarkChem Lite v0.1.0 [M+Na]+ 212.8214 predictedDeepCCS 1.0 (2019)
Enzymes
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- No
- Actions
- Inhibitor
- General Function
- Steroid binding
- Specific Function
- UDPGT is of major importance in the conjugation and subsequent elimination of potentially toxic xenobiotics and endogenous compounds. This isoform glucuronidates bilirubin IX-alpha to form both the...
- Gene Name
- UGT1A1
- Uniprot ID
- P22309
- Uniprot Name
- UDP-glucuronosyltransferase 1-1
- Molecular Weight
- 59590.91 Da
References
- Williams JA, Hyland R, Jones BC, Smith DA, Hurst S, Goosen TC, Peterkin V, Koup JR, Ball SE: Drug-drug interactions for UDP-glucuronosyltransferase substrates: a pharmacokinetic explanation for typically observed low exposure (AUCi/AUC) ratios. Drug Metab Dispos. 2004 Nov;32(11):1201-8. doi: 10.1124/dmd.104.000794. Epub 2004 Aug 10. [Article]
Transporters
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- SubstrateInhibitor
- Curator comments
- This is based on the findings of in vitro studies using human OAT1 expressed on MDCK cells.
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Involved in the renal elimination of endogenous and exogenous organic anions. Functions as organic anion exchanger when the uptake of one molecule of organic anion is coupled with an efflux of one ...
- Gene Name
- SLC22A6
- Uniprot ID
- Q4U2R8
- Uniprot Name
- Solute carrier family 22 member 6
- Molecular Weight
- 61815.78 Da
References
- VanWert AL, Gionfriddo MR, Sweet DH: Organic anion transporters: discovery, pharmacology, regulation and roles in pathophysiology. Biopharm Drug Dispos. 2010 Jan;31(1):1-71. doi: 10.1002/bdd.693. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as pravastatin, taurocholate, methotrexate, dehydroepiandrosterone sulfate, 17-beta-glucuronosyl estradiol, estrone sulfate, prostagland...
- Gene Name
- SLCO1B1
- Uniprot ID
- Q9Y6L6
- Uniprot Name
- Solute carrier organic anion transporter family member 1B1
- Molecular Weight
- 76447.99 Da
References
- Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent uptake of organic anions such as 17-beta-glucuronosyl estradiol, taurocholate, triiodothyronine (T3), leukotriene C4, dehydroepiandrosterone sulfate (DHEAS), methotre...
- Gene Name
- SLCO1B3
- Uniprot ID
- Q9NPD5
- Uniprot Name
- Solute carrier organic anion transporter family member 1B3
- Molecular Weight
- 77402.175 Da
References
- Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Actions
- Inhibitor
- General Function
- Sodium-independent organic anion transmembrane transporter activity
- Specific Function
- Mediates the Na(+)-independent transport of organic anions such as taurocholate, the prostaglandins PGD2, PGE1, PGE2, leukotriene C4, thromboxane B2 and iloprost.
- Gene Name
- SLCO2B1
- Uniprot ID
- O94956
- Uniprot Name
- Solute carrier organic anion transporter family member 2B1
- Molecular Weight
- 76709.98 Da
References
- Karlgren M, Vildhede A, Norinder U, Wisniewski JR, Kimoto E, Lai Y, Haglund U, Artursson P: Classification of inhibitors of hepatic organic anion transporting polypeptides (OATPs): influence of protein expression on drug-drug interactions. J Med Chem. 2012 May 24;55(10):4740-63. doi: 10.1021/jm300212s. Epub 2012 May 15. [Article]
Drug created at October 30, 2015 20:42 / Updated at February 02, 2024 22:52