BERBERINE CHLORIDE

First approved in 2023

Details

Stereochemistry	ACHIRAL
Molecular Formula	C20H18NO4.Cl
Molecular Weight	371.814
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

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

InChI

InChIKey=VKJGBAJNNALVAV-UHFFFAOYSA-M

InChI=1S/C20H18NO4.ClH/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/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
Evaluation of natural products as inhibitors of human immunodeficiency virus type 1 (HIV-1) reverse transcriptase.	1991 Jan-Feb	1710653
Effect of long-term administration of berberine on scopolamine-induced amnesia in rats.	1997 Jul	9268086
Differential inhibitory effects of protoberberines on sterol and chitin biosyntheses in Candida albicans.	1999 May	10382888
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
Fluorescence assay based on preconcentration by a self-ordered ring using berberine as a model analyte.	2002 Nov 1	12433089
[Inhibitory action of berberine on glucose absorption].	2003 Dec	15040083
Effect of berberine on expression of hepatocyte nuclear factor-4alpha in rats with fructose-induced insulin resistance.	2008 Jun	18563319
Berberine inhibits SREBP-1-related clozapine and risperidone induced adipogenesis in 3T3-L1 cells.	2010 Dec	20564506
Effect of traditional Chinese medicinal herbs on Candida spp. from patients with HIV/AIDS.	2011 Apr	21441482
Synthesis of 9-substituted derivatives of berberine as anti-HIV agents.	2011 Apr	21295891
Characterization of protoberberine analogs employed as novel human P2X7 receptor antagonists.	2011 Apr 15	21320518
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
Hepatoprotective activity of berberine is mediated by inhibition of TNF-α, COX-2, and iNOS expression in CCl(4)-intoxicated mice.	2011 Feb 4	21095217
Antitumor effects of the combination of cholesterol reducing drugs.	2011 Jul	21491092
Berberine protects against lipopolysaccharide-induced intestinal injury in mice via alpha 2 adrenoceptor-independent mechanisms.	2011 Nov	21963898
The formation and stabilization of a novel G-quadruplex in the 5'-flanking region of the relaxin gene.	2012	22363579
Structure-activity studies of some berberine analogs as inhibitors of Toxoplasma gondii.	2012 Apr 15	22425568
Modulations of cytochrome P450 expression in diabetic mice by berberine.	2012 Mar 5	22342832
Berberine attenuates bleomycin induced pulmonary toxicity and fibrosis via suppressing NF-κB dependant TGF-β activation: a biphasic experimental study.	2013 May 23	23523906
Multiple mechanisms of cell death induced by chelidonine in MCF-7 breast cancer cell line.	2014 Nov 5	25265580
The neuroprotective effect of berberine in mercury-induced neurotoxicity in rats.	2015 Aug	25600690

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 CHLORIDE

Common Name

English

Berberine hydrochloride [WHO-DD]

Common Name

English

5,6-DIHYDRO-9,10-DIMETHOXYBENZO(G)-1,3-BENZODIOXOLO(5,6-A)QUINOLIZINIUM CHLORIDE

Systematic Name

English

BERBERINE HYDROCHLORIDE

Common Name

English

BERBERINUM

Common Name

English

NSC-646666

Code

English

NSC-163088

Code

English

BERBERINUM [HPUS]

Common Name

English

BERBERINE CHLORIDE [USP-RS]

Common Name

English

Code System Code Type Description

CAS

633-65-8