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

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	HO4S
Molecular Weight	97.071
Charge	-1
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

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
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991 Jan-Feb	1710653
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
Screening of compounds for antimicrosporidial activity in vitro.	1998	9684323
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
Protective effect of berberine on cyclophosphamide-induced haemorrhagic cystitis in rats.	2001 May	11393582
Antimicrobial activity of berberine--a constituent of Mahonia aquifolium.	2002	12422513
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
Effect of berberine on interleukin 8 and monocyte chemotactic protein 1 expression in a human retinal pigment epithelial cell line.	2006	16391493
Berberine, a natural product, induces G1-phase cell cycle arrest and caspase-3-dependent apoptosis in human prostate carcinoma cells.	2006 Feb	16505103
Berberine enhances inhibition of glioma tumor cell migration and invasiveness mediated by arsenic trioxide.	2008 Feb 25	18294404
Antiosteoporotic chemical constituents from Er-Xian Decoction, a traditional Chinese herbal formula.	2008 Jul 23	18501540
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
Berberine attenuates lipopolysaccharide-induced impairments of intestinal glutamine transport and glutaminase activity in rat.	2011 Apr	21073932
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	21867779
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
Modulations of cytochrome P450 expression in diabetic mice by berberine.	2012 Mar 5	22342832
Berberine, a natural antidiabetes drug, attenuates glucose neurotoxicity and promotes Nrf2-related neurite outgrowth.	2013 Nov 1	23954465
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
Berberine promotes bone marrow-derived mesenchymal stem cells osteogenic differentiation via canonical Wnt/β-catenin signaling pathway.	2016 Jan 5	26478571

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.

Substance Class	Chemical Created by `admin` on `Fri Dec 15 17:23:00 GMT 2023` Edited by `admin` on `Fri Dec 15 17:23:00 GMT 2023`
Record UNII	69A4M9800W
Record Status	`Validated (UNII)`
Record Version

Download

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