Berberine
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Berberine
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CAS No:
2086-83-1
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Formula:
C20H18NO4
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Chemical Name:
Berberine
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Synonyms:
Benzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium,5,6-dihydro-9,10-dimethoxy-;Umbellatine;Berbinium,7,8,13,13a-tetradehydro-9,10-dimethoxy-2,3-(methylenedioxy)-;5,6-Dihydro-9,10-dimethoxybenzo[g]-1,3-benzodioxolo[5,6-a]quinolizinium;Berberine;Berbericine;Berberin;Umbellatin;Thalsine;Majarine;Berberone;100414-97-9;1361-59-7;11048-54-7;66414-49-1
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CAS No:
Description
Berberine is a natural alkaline, reduces apoptosis, with potent anti-oxidative and anti-inflammatory effect[1].
Solid
Berberine is an organic heteropentacyclic compound, an alkaloid antibiotic, a botanical anti-fungal agent and a berberine alkaloid. It has a role as an antilipemic drug, a hypoglycemic agent, an antioxidant, a potassium channel blocker, an antineoplastic agent, an EC 1.1.1.21 (aldehyde reductase) inhibitor, an EC 1.1.1.141 [15-hydroxyprostaglandin dehydrogenase (NAD(+))] inhibitor, an EC 1.13.11.52 (indoleamine 2,3-dioxygenase) inhibitor, an EC 1.21.3.3 (reticuline oxidase) inhibitor, an EC 2.1.1.116 [3'-hydroxy-N-methyl-(S)-coclaurine 4'-O-methyltransferase] inhibitor, an EC 3.1.1.4 (phospholipase A2) inhibitor, an EC 3.4.21.26 (prolyl oligopeptidase) inhibitor, an EC 3.4.14.5 (dipeptidyl-peptidase IV) inhibitor, an EC 3.1.3.48 (protein-tyrosine-phosphatase) inhibitor, an EC 3.1.1.7 (acetylcholinesterase) inhibitor, an EC 3.1.1.8 (cholinesterase) inhibitor, an EC 2.7.11.10 (IkappaB kinase) inhibitor, an EC 2.1.1.122 [(S)-tetrahydroprotoberberine N-methyltransferase] inhibitor, a geroprotector and a metabolite.|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.|Berberine is a quaternary ammonia compound found in many botanical products, including goldenseal, barberry and Oregon grape, which is used for its purported antioxidant and antimicrobial properties for a host of conditions, including obesity, diabetes, hyperlipidemia, heart failure, H. pylori infection and colonic adenoma prevention. Berberine has not been linked to serum aminotransferase elevations during therapy nor to instances of clinically apparent liver injury.|Berberine is a quaternary ammonium salt of an isoquinoline alkaloid and active component of various Chinese herbs, with potential antineoplastic, radiosensitizing, anti-inflammatory, anti-lipidemic and antidiabetic activities. Although the mechanisms of action through which berberine exerts its effects are not yet fully elucidated, upon administration this agent appears to suppress the activation of various proteins and/or modulate the expression of a variety of genes involved in tumorigenesis and inflammation, including, but not limited to transcription factor nuclear factor-kappa B (NF-kB), myeloid cell leukemia 1 (Mcl-1), B-cell lymphoma 2 (Bcl-2), B-cell lymphoma-extra large (Bcl-xl), cyclooxygenase (COX)-2, tumor necrosis factor (TNF), interleukin (IL)-6, IL-12, inducible nitric oxide synthase (iNOS), intercellular adhesion molecule-1 (ICAM-1), E-selectin, monocyte chemoattractant protein-1 (MCP-1), C-X-C motif chemokine 2 (CXCL2), cyclin D1, activator protein (AP-1), hypoxia-inducible factor 1 (HIF-1), signal transducer and activator of transcription 3 (STAT3), peroxisome proliferator-activated receptor (PPAR), arylamine N-acetyltransferase (NAT), and DNA topoisomerase I and II. The modulation of gene expression may induce cell cycle arrest and apoptosis, and inhibit cancer cell proliferation. In addition, berberine modulates lipid and glucose metabolism.
Characteristics
40.80000
3.6
Solid
1.2976 (rough estimate)
145 °C
43.48g/L(25 ºC)
LD50 orl-mus: 329 mg/kg YKKZAJ 82,726,62
Toxicity
Berberine has not been linked to serum enzyme elevations during therapy, although there have been few prospective studies in humans that have reported on its effects on laboratory test results in any detail. In published trials, berberine has appeared to be well tolerated with only minor and few adverse effects which have been similar in frequency among persons receiving placebo. Despite wide scale use as an herbal supplement, berberine has not been linked to published instances of clinically apparent liver injury. The frequency of hypersensitivity reactions to berberine is also not known.
Drug Information
Berberine is a quaternary ammonia compound found in many botanical products, including goldenseal, barberry and Oregon grape, which is used for its purported antioxidant and antimicrobial properties for a host of conditions, including obesity, diabetes, hyperlipidemia, heart failure, H. pylori infection and colonic adenoma prevention. Berberine has not been linked to serum aminotransferase elevations during therapy nor to instances of clinically apparent liver injury.
Herbal and Dietary Supplements
Berberine
Berberine Use and Manufacturing
Antiseptic drug.Treat intestinal infection caused from dysentery bacillus and E.coil
Computed Properties
Molecular Weight:336.4
XLogP3:3.6
Hydrogen Bond Acceptor Count:4
Rotatable Bond Count:2
Exact Mass:336.12358306
Monoisotopic Mass:336.12358306
Topological Polar Surface Area:40.8
Heavy Atom Count:25
Formal Charge:1
Complexity:488
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes
Drug Function and Efficacy
Exhibits broad-spectrum antibacterial activity by inhibiting bacterial DNA topoisomerase; activates AMPK signaling pathway to improve insulin resistance
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