Coptisine chloride

Details

Stereochemistry	ACHIRAL
Molecular Formula	C19H14NO4.Cl
Molecular Weight	355.772
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[Cl-].C1OC2=C(O1)C=C3C(CC[N+]4=C3C=C5C=CC6=C(OCO6)C5=C4)=C2

InChI

InChIKey=LUXPUVKJHVUJAV-UHFFFAOYSA-M

InChI=1S/C19H14NO4.ClH/c1-2-16-19(24-10-21-16)14-8-20-4-3-12-6-17-18(23-9-22-17)7-13(12)15(20)5-11(1)14;/h1-2,5-8H,3-4,9-10H2;1H/q+1;/p-1

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25079795 | https://www.ncbi.nlm.nih.gov/pubmed/26228628 | https://www.ncbi.nlm.nih.gov/pubmed/26134304

Coptisine (COP), a protoberberine alkaloid, is widely found in Chinese medicinal plants (family Berberidaceae, Ranunculaceae and Papaveraceae). It is reported that COP has a wide range of pharmacological and biological activities, including antibacterial, hypoglycemic, anti-tumorigenic, and gastric-mucous membrane protection. Considerable attention has been focused on its activity against central nervous system disorders, such as improving the symptoms of Alzheimer’s disease and even preventing its onset, by exerting antidepressant effects as a potent type A monoamine oxidase inhibitor. Coptisine was found to be an efficient uncompetitive Indoleamine 2,3-dioxygenase inhibitor. Coptisine is a potent inhibitor of human organic cation transporters.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Apoptosis 155 Target ID: map04210 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165459	Activator 1430
ERK1 and ERK2 cascade 8 Target ID: GO:0070371 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165459	Inhibitor 8297
Solute carrier family 22 member 1 18 Target ID: CHEMBL5685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26134304	Inhibitor 8297	0.9 µM [IC50]
Solute carrier family 22 member 2 8 Target ID: CHEMBL1743122 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26134304	Inhibitor 8297	2.3 µM [IC50]
Solute carrier family 22 member 3 6 Target ID: CHEMBL2073673 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26134304	Inhibitor 8297	2.3 µM [IC50]
Indoleamine 2,3-dioxygenase 19 Target ID: CHEMBL4685 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25079795	Inhibitor 8297	6.3 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Colon cancer 62 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28165459	Primary	Preclinical	Unknown Approved Use Unknown
Breast cancer 434 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25081696	Primary	Basic research	Unknown Approved Use Unknown
Non-small cell lung cancer 206 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28351307	Primary	Basic research	Unknown Approved Use Unknown
Osteosarcoma 22 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24607417	Primary	Preclinical	Unknown Approved Use Unknown
Hepatoma 3 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14756686	Primary	Basic research	Unknown Approved Use Unknown
Leukemia 87 Sources: https://www.ncbi.nlm.nih.gov/pubmed/14756686	Primary	Basic research	Unknown Approved Use Unknown
Alzheimer’s disease 272 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25079795	Primary	Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
[The effects of kampo-formulation and the constituting crude drugs, prescribed for the treatment of peptic ulcer on H,K-ATPase activity].	2001 Feb	11218732
In vitro cytotoxicity of the protoberberine-type alkaloids.	2001 Jul	11473418
Sheathless capillary electrophoresis/electrospray mass spectrometry using a carbon-coated tapered fused-silica capillary with a beveled edge.	2001 Nov 1	11721903
[Study on the solubility changes of Rhizoma Coptidis' main chemical constituents influenced by the proportion of Rhizoma Coptidis and Fructus Evodiae].	2003 Jul	15139107
Structural elucidation and identification of alkaloids in Rhizoma Coptidis by electrospray ionization tandem mass spectrometry.	2004 Nov	15532075
Improved detection of Coptidis alkaloids by field-amplified sample stacking in capillary electrophoresis.	2004 Sep 21	15351046
[Studies on the alkaloids from herb of Corydalis adunca].	2005 Nov	16468373
[Qualitative and quantitative determination of the main components of huanglianjiedu decoction by HPLC-UV/MS].	2006 Apr	16856488
Bioavailabilty and pharmacokinetics of four active alkaloids of traditional Chinese medicine Yanhuanglian in rats following intravenous and oral administration.	2006 Jun 16	16644173
Disruption of nucleocytoplasmic trafficking of cyclin D1 and topoisomerase II by sanguinarine.	2006 Mar 2	16512916
Selective inhibition of vascular smooth muscle cell proliferation by coptisine isolated from Coptis rhizoma, one of the crude drugs composing Kampo medicines Unsei-in.	2006 May	16635741
Simultaneous analysis of alkaloids from Zanthoxylum nitidum by high performance liquid chromatography-diode array detector-electrospray tandem mass spectrometry.	2006 Sep 18	16730156
High performance liquid chromatography-mass spectrometry analysis of protoberberine alkaloids in medicine herbs.	2007 Apr	17536728
Simultaneous quantification of three alkaloids of Coptidis Rhizoma in rat urine by high-performance liquid chromatography: application to pharmacokinetic study.	2007 Dec	17891749
Antimicrobial properties of berberines alkaloids in Coptis chinensis Franch by microcalorimetry.	2008 Apr 24	17804078
[Studies on chemical constituents in the anti-myocardial ischemia effective fraction of Corydalis yanhusuo].	2008 Nov	19260272
Anti-Alzheimer and antioxidant activities of Coptidis Rhizoma alkaloids.	2009 Aug	19652386
Bear bile: dilemma of traditional medicinal use and animal protection.	2009 Jan 12	19138420
A rapid and simple determination of protoberberine alkaloids in Rhizoma Coptidis by 1H NMR and its application for quality control of commercial prescriptions.	2009 Jul 12	19345543
Simultaneous determination of 11 active components in two well-known traditional Chinese medicines by HPLC coupled with diode array detection for quality control.	2009 May 1	19264437
Selective regulation of multidrug resistance protein in vascular smooth muscle cells by the isoquinoline alkaloid coptisine.	2010	20410605
Simultaneous determination of seven main alkaloids of Chelidonium majus L. by ultra-performance LC with photodiode-array detection.	2010 Apr	20183823
Quality assurance for Chinese herbal formulae: standardization of IBS-20, a 20-herb preparation.	2010 Feb 22	20175906
JinQi-Jiangtang tablet, a Chinese patent medicine, for pre-diabetes: a randomized controlled trial.	2010 Mar 10	20214831

Patents

Sample Use Guides

In Vivo Use Guide

Mice: 50,100 or 150mg/kg body weight daily

Route of Administration: Oral

In Vitro Use Guide

In HCT-116 cells, Coptisine exhibited cell cytotoxicity at a high rate (IC50 was 27.13 μg/mL vs 282.2 μg/mL in human colorectal epithelial cells FHC). Besides, Coptisine (2.5 μg/mL) decreased the survival rate of cells time-dependently .

Name

Type

Language

Coptisine chloride

Common Name

English

Coptisine hydrochloride

Common Name

English

Bis[1,3]benzodioxolo[5,6-a:4′,5′-g]quinolizinium, 6,7-dihydro-, chloride (1:1)

Systematic Name

English

NSC-119754

Code

English

Berbinium, 7,8,13,13a-tetradehydro-2,3:9,10-bis(methylenedioxy)-, chloride

Systematic Name

English

Code System Code Type Description

FDA UNII

4RSB8UY88E