Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C20H18NO4.Cl.2H2O |
| Molecular Weight | 407.845 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
O.O.[Cl-].COC1=C(OC)C2=C(C=C1)C=C3C4=CC5=C(OCO5)C=C4CC[N+]3=C2
InChI
InChIKey=NWMNHQUPWGJEKI-UHFFFAOYSA-M
InChI=1S/C20H18NO4.ClH.2H2O/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;1H;2*1H2/q+1;;;/p-1
| Molecular Formula | C20H18NO4 |
| Molecular Weight | 336.3612 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | H2O |
| Molecular Weight | 18.0153 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | ClH |
| Molecular Weight | 36.461 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including:
https://examine.com/supplements/berberine/ | https://www.ncbi.nlm.nih.gov/pubmed/19686830 | https://www.ncbi.nlm.nih.gov/pubmed/25610485
Curator's Comment: description was created based on several sources, including:
https://examine.com/supplements/berberine/ | https://www.ncbi.nlm.nih.gov/pubmed/19686830 | https://www.ncbi.nlm.nih.gov/pubmed/25610485
Berberine, an alkaloid isolated from Rhizoma Coptidis, is known to have a wide array of therapeutic effects including antimicrobial, antineoplastic, and hepatoprotective effects. It is found in several plants including European barberry, goldenseal, goldthread, Oregon grape, phellodendron, and tree tumeric. Berberine seems to slightly reduce blood sugar levels in people with diabetes. Berberine might lower blood pressure. Berberine is possibly safe for most adults for short-term use when taken by mouth or applied to the skin.
CNS Activity
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Screening for new compounds with antiherpes activity. | 1984 Oct |
|
| Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase. | 1991 Jan-Feb |
|
| HIV-1 and HIV-2 reverse transcriptases: a comparative study of sensitivity to inhibition by selected natural products. | 1992 May 29 |
|
| The effect of Kampo formulae on bone resorption in vitro and in vivo. I. Active constituents of Tsu-kan-gan. | 1998 Dec |
|
| Antitubercular natural products: berberine from the roots of commercial Hydrastis canadensis powder. Isolation of inactive 8-oxotetrahydrothalifendine, canadine, beta-hydrastine, and two new quinic acid esters, hycandinic acid esters-1 and -2. | 1998 Oct |
|
| Differential inhibitory effects of protoberberines on sterol and chitin biosyntheses in Candida albicans. | 1999 May |
|
| Analysis of coptisine, berberine and palmatine in adulterated Chinese medicine by capillary electrophoresis-electrospray ion trap mass spectrometry. | 2000 Jan 14 |
|
| Potential antimutagenic activity of berberine, a constituent of Mahonia aquifolium. | 2002 Feb 19 |
|
| Inhibitory effect of berberine on tert-butyl hydroperoxide-induced oxidative damage in rat liver. | 2002 Nov |
|
| Search of chemical scaffolds for novel antituberculosis agents. | 2005 Apr |
|
| Effect of berberine on interleukin 8 and monocyte chemotactic protein 1 expression in a human retinal pigment epithelial cell line. | 2006 |
|
| Berberine, a natural product, induces G1-phase cell cycle arrest and caspase-3-dependent apoptosis in human prostate carcinoma cells. | 2006 Feb |
|
| Combination of simvastatin with berberine improves the lipid-lowering efficacy. | 2008 Aug |
|
| Effect of berberine on expression of hepatocyte nuclear factor-4alpha in rats with fructose-induced insulin resistance. | 2008 Jun |
|
| Studies on alkaloids binding to GC-rich human survivin promoter DNA using positive and negative ion electrospray ionization mass spectrometry. | 2008 Mar |
|
| Anti-diabetic effects of cinnamaldehyde and berberine and their impacts on retinol-binding protein 4 expression in rats with type 2 diabetes mellitus. | 2008 Nov 5 |
|
| Effect of berberine on the antioxidant status, ultrastructural modifications and protein bound carbohydrates in azoxymethane-induced colon cancer in rats. | 2009 Feb 12 |
|
| Cytotoxicity of berberine on human cervical carcinoma HeLa cells through mitochondria, death receptor and MAPK pathways, and in-silico drug-target prediction. | 2010 Sep |
|
| Berberine attenuates lipopolysaccharide-induced impairments of intestinal glutamine transport and glutaminase activity in rat. | 2011 Apr |
|
| Berberine down-regulates the Th1/Th2 cytokine gene expression ratio in mouse primary splenocytes in the absence or presence of lipopolysaccharide in a preventive manner. | 2011 Dec |
|
| The formation and stabilization of a novel G-quadruplex in the 5'-flanking region of the relaxin gene. | 2012 |
|
| Alteration of hepatic glutathione peroxidase and superoxide dismutase expression in streptozotocin-induced diabetic mice by berberine. | 2012 Aug |
|
| Modulations of cytochrome P450 expression in diabetic mice by berberine. | 2012 Mar 5 |
|
| The potential effect of berberine in mercury-induced hepatorenal toxicity in albino rats. | 2014 Jul |
|
| Palmatine activates AhR and upregulates CYP1A activity in HepG2 cells but not in human hepatocytes. | 2014 Jun |
Sample Use Guides
500 mg of berberine 2-3 times daily for up to 3 months
Route of Administration:
Oral
Berberine acted cytotoxically on both tumour cell lines. The melanoma B16 cells were much more sensitive to berberine treatment than the U937 cells. The value of IC(100) was below 100 ug/ml for the U937 cells and below 1 ug/ml for the B16 cells. As for both cell lines under the long-term influence the values of IC(50) were found to be less than 4 ug/ml.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 01:07:38 GMT 2023
by
admin
on
Sat Dec 16 01:07:38 GMT 2023
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| Record UNII |
266464AEJZ
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| Record Status |
Validated (UNII)
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| Record Version |
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PRIMARY | Merck Index |
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ANHYDROUS->SOLVATE |
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ACTIVE MOIETY |