BERBERINE BISULFATE

First approved in 2023

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H18NO4.HO4S
Molecular Weight	433.432
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS([O-])(=O)=O.COC1=C(OC)C2=C(C=C1)C=C3C4=CC5=C(OCO5)C=C4CC[N+]3=C2

InChI

InChIKey=JISRTQBQFQMSLG-UHFFFAOYSA-M

InChI=1S/C20H18NO4.H2O4S/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;1-5(2,3)4/h3-4,7-10H,5-6,11H2,1-2H3;(H2,1,2,3,4)/q+1;/p-1

HIDE SMILES / InChI

Description
Sources: http://www.webmd.com/vitamins-supplements/ingredientmono-1126-berberine.aspx?activeingredientid=1126&activeingredientname=berberine
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

Targets

Primary Target	Pharmacology	Condition	Potency
DNA topoisomerase I 59 Target ID: CHEMBL1781 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19686830	Inhibitor 8297
cell cycle arrest 14 Target ID: GO:0007050 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19686830	Activator 1430
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19686830	Activator 1430

Conditions

Condition	Modality	Highest Phase	Product
Type 2 diabetes mellitus 259 Sources: https://examine.com/supplements/berberine/	Primary	Phase III 656	Unknown Approved Use Unknown
Colorectal adenoma 7 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26397137	Primary	Phase III 656	Unknown Approved Use Unknown
Ulcerative colitis 123 Sources: https://www.ncbi.nlm.nih.gov/pubmed/27587080	Primary	Phase IV 63	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Screening for new compounds with antiherpes activity.	1984 Oct	6517562
HIV-1 and HIV-2 reverse transcriptases: a comparative study of sensitivity to inhibition by selected natural products.	1992 May 29	1376118
Effect of long-term administration of berberine on scopolamine-induced amnesia in rats.	1997 Jul	9268086
[Determination of berberine in human serum by reversed-phase high performance liquid chromatography].	1997 Sep	15739507
The effect of Kampo formulae on bone resorption in vitro and in vivo. I. Active constituents of Tsu-kan-gan.	1998 Dec	9881647
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	9784149
Analysis of coptisine, berberine and palmatine in adulterated Chinese medicine by capillary electrophoresis-electrospray ion trap mass spectrometry.	2000 Jan 14	10670817
Potential antimutagenic activity of berberine, a constituent of Mahonia aquifolium.	2002 Feb 19	11943071
Inhibitory effect of berberine on tert-butyl hydroperoxide-induced oxidative damage in rat liver.	2002 Nov	12415430
[Inhibitory action of berberine on glucose absorption].	2003 Dec	15040083
Search of chemical scaffolds for novel antituberculosis agents.	2005 Apr	15809316
Berberine, a natural product, induces G1-phase cell cycle arrest and caspase-3-dependent apoptosis in human prostate carcinoma cells.	2006 Feb	16505103
Combination of simvastatin with berberine improves the lipid-lowering efficacy.	2008 Aug	18640378
Effect of berberine on expression of hepatocyte nuclear factor-4alpha in rats with fructose-induced insulin resistance.	2008 Jun	18563319
Studies on alkaloids binding to GC-rich human survivin promoter DNA using positive and negative ion electrospray ionization mass spectrometry.	2008 Mar	17968851
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	19080170
Berberine inhibits SREBP-1-related clozapine and risperidone induced adipogenesis in 3T3-L1 cells.	2010 Dec	20564506
[Controlling effect of berberine on in vitro synthesis and metabolism of steroid hormones in insulin resistant ovary].	2010 Feb	20462044
Cytotoxicity of berberine on human cervical carcinoma HeLa cells through mitochondria, death receptor and MAPK pathways, and in-silico drug-target prediction.	2010 Sep	20656010
Effect of traditional Chinese medicinal herbs on Candida spp. from patients with HIV/AIDS.	2011 Apr	21441482
Antitumor effects of the combination of cholesterol reducing drugs.	2011 Jul	21491092
Protective effect of berberine on antioxidant enzymes and positive transcription elongation factor b expression in diabetic rat liver.	2011 Mar	20828602
Berberine protects against lipopolysaccharide-induced intestinal injury in mice via alpha 2 adrenoceptor-independent mechanisms.	2011 Nov	21963898
Structure-activity studies of some berberine analogs as inhibitors of Toxoplasma gondii.	2012 Apr 15	22425568
Alteration of hepatic glutathione peroxidase and superoxide dismutase expression in streptozotocin-induced diabetic mice by berberine.	2012 Aug	22775417
Modulations of cytochrome P450 expression in diabetic mice by berberine.	2012 Mar 5	22342832
Mechanism study of goldenseal-associated DNA damage.	2013 Jul 31	23747414
Berberine protects liver from ethanol-induced oxidative stress and steatosis in mice.	2014 Dec	25455889
Palmatine activates AhR and upregulates CYP1A activity in HepG2 cells but not in human hepatocytes.	2014 Jun	24583342
Kinetics and molecular docking studies of cholinesterase inhibitors derived from water layer of Lycopodiella cernua (L.) Pic. Serm. (II).	2015 Oct 5	26297990

Patents

Sample Use Guides

In Vivo Use Guide

500 mg of berberine 2-3 times daily for up to 3 months

Route of Administration: Oral

In Vitro Use Guide

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.

Name

Type

Language

BERBERINE BISULFATE

Common Name

English

BERBERINE BISULPHATE

Common Name

English

BERBERINE ACID SULFATE

Common Name

English

Berberine hemisulfate [WHO-DD]

Common Name

English

BERBERINE ACID SULPHATE

Common Name

English

BENZO(G)-1,3-BENZODIOXOLO(5,6-A)QUINOLIZINIUM, 5,6-DIHYDRO-9,10-DIMETHOXY-, SULFATE (1:1)

Systematic Name

English

BENZO(G)-1,3-BENZODIOXOLO(5,6-A)QUINOLIZINIUM, 5,6-DIHYDRO-9,10-DIMETHOXY-, SULPHATE (1:1)

Systematic Name

English

NSC-150444

Code

English

BERBERINE ACID SULFATE [MI]

Common Name

English

Code System Code Type Description

NSC

150444