Identification
- Generic Name
- Berberine
- DrugBank Accession Number
- DB04115
- Background
An alkaloid from Hydrastis canadensis L., Berberidaceae. It is also found in many other plants. It is relatively toxic parenterally, but has been used orally for various parasitic and fungal infections and as antidiarrheal.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Berberine (DB04115)
- Weight
- Average: 336.3612
Monoisotopic: 336.123583069 - Chemical Formula
- C20H18NO4
- Synonyms
- Not Available
Pharmacology
- Indication
Not Available
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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
Target Actions Organism UBaculoviral IAP repeat-containing protein 5 Not Available Humans UHTH-type transcriptional regulator QacR Not Available Staphylococcus haemolyticus - Absorption
Not Available
- Volume of distribution
Not Available
- Protein binding
Not Available
- Metabolism
- Not Available
- Route of elimination
Not Available
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
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Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
- 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.Not Available
- 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 Berberine chloride UOT4O1BYV8 633-65-8 VKJGBAJNNALVAV-UHFFFAOYSA-M Berberine sulfate anhydrous FST3E667FF 316-41-6 OJVABJMSSDUECT-UHFFFAOYSA-L
Categories
- Drug Categories
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as protoberberine alkaloids and derivatives. These are alkaloids with a structure based on a protoberberine moiety, which consists of a 5,6-dihydrodibenzene moiety fused to a quinolizinium and forming 5,6-Dihydrodibenzo(a,g)quinolizinium skeleton.
- Kingdom
- Organic compounds
- Super Class
- Alkaloids and derivatives
- Class
- Protoberberine alkaloids and derivatives
- Sub Class
- Not Available
- Direct Parent
- Protoberberine alkaloids and derivatives
- Alternative Parents
- Isoquinolines and derivatives / Benzodioxoles / Anisoles / Alkyl aryl ethers / Pyridinium derivatives / Heteroaromatic compounds / Oxacyclic compounds / Azacyclic compounds / Acetals / Organopnictogen compounds show 3 more
- Substituents
- Acetal / Alkyl aryl ether / Anisole / Aromatic heteropolycyclic compound / Azacycle / Benzenoid / Benzodioxole / Ether / Heteroaromatic compound / Hydrocarbon derivative show 12 more
- Molecular Framework
- Aromatic heteropolycyclic compounds
- External Descriptors
- organic heteropentacyclic compound, berberine alkaloid, alkaloid antibiotic, botanical anti-fungal agent (CHEBI:16118) / Alkaloids, Isoquinoline alkaloids (C00757) / a small molecule (BERBERINE)
- Affected organisms
- Not Available
Chemical Identifiers
- UNII
- 0I8Y3P32UF
- CAS number
- 2086-83-1
- InChI Key
- YBHILYKTIRIUTE-UHFFFAOYSA-N
- InChI
- InChI=1S/C20H18NO4/c1-22-17-4-3-12-7-16-14-9-19-18(24-11-25-19)8-13(14)5-6-21(16)10-15(12)20(17)23-2/h3-4,7-10H,5-6,11H2,1-2H3/q+1
- IUPAC Name
- 16,17-dimethoxy-5,7-dioxa-13lambda5-azapentacyclo[11.8.0.0^{2,10}.0^{4,8}.0^{15,20}]henicosa-1(21),2,4(8),9,13,15,17,19-octaen-13-ylium
- SMILES
- COC1=CC=C2C=C3C4=CC5=C(OCO5)C=C4CC[N+]3=CC2=C1OC
References
- Synthesis Reference
Christopher W. Grote, Frank W. Moser, John E. Johnson, JR., "Berberine compounds and processes for the preparation of berberine compounds." U.S. Patent US20100081821, issued April 01, 2010.
US20100081821- General References
- Not Available
- External Links
- Human Metabolome Database
- HMDB0003409
- KEGG Drug
- D00092
- KEGG Compound
- C00757
- PubChem Compound
- 2353
- PubChem Substance
- 46506051
- ChemSpider
- 2263
- BindingDB
- 50203126
- 1437
- ChEBI
- 16118
- ChEMBL
- CHEMBL295124
- ZINC
- ZINC000003779067
- Therapeutic Targets Database
- DNC000385
- PharmGKB
- PA165860812
- PDBe Ligand
- BER
- Wikipedia
- Berberine
- PDB Entries
- 1jum / 2qvd / 3bti / 3d6y / 3np6 / 3r6r / 3vw2 / 4dbk / 5y0v / 6jwd … show 8 more
Clinical Trials
- Clinical Trials
Phase Status Purpose Conditions Count 4 Completed Treatment Berberine / Coronavirus Disease 2019 (COVID‑19) 1 4 Completed Treatment Chronic Kidney Disease (CKD) / Diabetes Mellitus 1 4 Completed Treatment Dyspepsia / Gastric Cancer / Gastritis Chronic / Helicobacter Pylori Infection 1 4 Completed Treatment Dyspepsia / Gastritis / Peptic Ulcer 2 4 Completed Treatment Gastric Cancer / Gastric Ulcer / Gastritis / Gastritis Chronic / Helicobacter Pylori Infection 1 4 Completed Treatment Gastritis Chronic / Helicobacter Pylori Infection 1 4 Not Yet Recruiting Prevention Syndrome, Metabolic 1 4 Not Yet Recruiting Treatment (NAFLD) / Obesity / Obesity, Abdominal 1 4 Not Yet Recruiting Treatment Diabetes, Autoimmune / Type 1 Diabetes Mellitus 1 4 Not Yet Recruiting Treatment Dyslipidemia / Hypertension / Impaired Glucose Tolerance / Obesity, Abdominal 1
Pharmacoeconomics
- Manufacturers
- Not Available
- Packagers
- Not Available
- Dosage Forms
- Not Available
- Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Solid
- Experimental Properties
Property Value Source melting point (°C) 145 °C PhysProp - Predicted Properties
Property Value Source Water Solubility 0.000354 mg/mL ALOGPS logP -0.18 ALOGPS logP -1.3 Chemaxon logS -6 ALOGPS pKa (Strongest Basic) -4.4 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 4 Chemaxon Hydrogen Donor Count 0 Chemaxon Polar Surface Area 40.8 Å2 Chemaxon Rotatable Bond Count 2 Chemaxon Refractivity 93.52 m3·mol-1 Chemaxon Polarizability 36.92 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
Property Value Probability Human Intestinal Absorption - 0.5 Blood Brain Barrier + 0.9279 Caco-2 permeable + 0.8726 P-glycoprotein substrate Non-substrate 0.6002 P-glycoprotein inhibitor I Non-inhibitor 0.8782 P-glycoprotein inhibitor II Non-inhibitor 0.8435 Renal organic cation transporter Inhibitor 0.6035 CYP450 2C9 substrate Non-substrate 0.876 CYP450 2D6 substrate Non-substrate 0.5937 CYP450 3A4 substrate Substrate 0.6738 CYP450 1A2 substrate Inhibitor 0.9107 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Inhibitor 0.8933 CYP450 2C19 inhibitor Non-inhibitor 0.7463 CYP450 3A4 inhibitor Non-inhibitor 0.5873 CYP450 inhibitory promiscuity High CYP Inhibitory Promiscuity 0.9003 Ames test Non AMES toxic 0.9132 Carcinogenicity Non-carcinogens 0.9539 Biodegradation Not ready biodegradable 0.8408 Rat acute toxicity 2.7834 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.8367 hERG inhibition (predictor II) Non-inhibitor 0.8734
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Targets
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- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Zinc ion binding
- Specific Function
- Multitasking protein that has dual roles in promoting cell proliferation and preventing apoptosis. Component of a chromosome passage protein complex (CPC) which is essential for chromosome alignmen...
- Gene Name
- BIRC5
- Uniprot ID
- O15392
- Uniprot Name
- Baculoviral IAP repeat-containing protein 5
- Molecular Weight
- 16388.555 Da
References
- Wang Z, Guo X, Liu Z, Cui M, Song F, Liu S: Studies on alkaloids binding to GC-rich human survivin promoter DNA using positive and negative ion electrospray ionization mass spectrometry. J Mass Spectrom. 2008 Mar;43(3):327-35. [Article]
- Kind
- Protein
- Organism
- Staphylococcus haemolyticus
- Pharmacological action
- Unknown
- General Function
- Transcription factor activity, sequence-specific dna binding
- Specific Function
- Transcriptional repressor of qacA. Binds to IR1, an unusually long 28 bp operator, which is located downstream from the qacA promoter and overlaps its transcription start site. QacR is induced from...
- Gene Name
- qacR
- Uniprot ID
- P0A0N5
- Uniprot Name
- HTH-type transcriptional regulator QacR
- Molecular Weight
- 22174.175 Da
References
- Crystal Binding Structure [Link]
Drug created at June 13, 2005 13:24 / Updated at June 12, 2020 16:52