Chelerythrine hydrosulfate

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H18NO4.HO4S
Molecular Weight	445.442
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

OS([O-])(=O)=O.COC1=CC=C2C3=CC=C4C=C5OCOC5=CC4=C3[N+](C)=CC2=C1OC

InChI

InChIKey=ZKALVUWQQPLSDA-UHFFFAOYSA-M

InChI=1S/C21H18NO4.H2O4S/c1-22-10-16-13(6-7-17(23-2)21(16)24-3)14-5-4-12-8-18-19(26-11-25-18)9-15(12)20(14)22;1-5(2,3)4/h4-10H,11H2,1-3H3;(H2,1,2,3,4)/q+1;/p-1

HIDE SMILES / InChI

Molecular Formula	C21H18NO4
Molecular Weight	348.3719
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: https://www.ncbi.nlm.nih.gov/pubmed/24380291 | https://www.ncbi.nlm.nih.gov/pubmed/2244923 | https://www.ncbi.nlm.nih.gov/pubmed/12702731 | https://www.ncbi.nlm.nih.gov/pubmed/16936897 | http://www.google.com.pg/patents/WO2002013803A2

Chelerythrine is a kind of benzo[c] phenanthridine alkaloids, which is widely found in plant of Fumariaceae, Papaveraceae, Ranunculaceae and Rutaceae families. Chelerythrine is a potent and specific inhibitor of protein kinase C. In addition chelerythrine inhibits pro-survival protein Bcl(XL) thereby inducing apoptosis. It exerts antitumor properties.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Protein kinase C (PKC) 44 Target ID: CHEMBL2093867 Sources: https://www.ncbi.nlm.nih.gov/pubmed/2244923	Inhibitor 8297	0.7 µM [Ki]
Apoptosis regulator Bcl-X 8 Target ID: CHEMBL4625 Sources: https://www.ncbi.nlm.nih.gov/pubmed/17011577 \| https://www.ncbi.nlm.nih.gov/pubmed/12702731	Inhibitor 8297
Peroxisome proliferator-activated receptor gamma 111 Target ID: CHEMBL235 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26183621	Modulator 828	566.0 nM [IC50]
DNA 278 Target ID: CHEMBL2311221 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28509993 \| https://www.ncbi.nlm.nih.gov/pubmed/28102286	Binding Agent 1064
Protein kinase C (PKC) 44 Target ID: CHEMBL2093867 Sources: https://adisinsight.springer.com/drugs/800013523	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Cancer 592 Sources: http://www.google.com.pg/patents/WO2002013803A2 http://adisinsight.springer.com/drugs/800013523 https://www.ncbi.nlm.nih.gov/pubmed/28515445 https://www.ncbi.nlm.nih.gov/pubmed/28399187	Primary		Preclinical	Unknown Approved Use Unknown
Pain 614 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11786500 https://www.ncbi.nlm.nih.gov/pubmed/28842814 https://www.ncbi.nlm.nih.gov/pubmed/26515544 https://www.ncbi.nlm.nih.gov/pubmed/14768516	Primary		Preclinical	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Interaction of benzo[c]phenanthridine and protoberberine alkaloids with animal and yeast cells.	2001	11504450
Inhibition of calcium-independent luminal uptake of L-dopa by calmodulin antagonists in immortalized rat capillary cerebral endothelial cells.	2001	11352497
Metalloproteinase activity in growth plate chondrocyte cultures is regulated by 1,25-(OH)(2)D(3) and 24,25-(OH)(2)D(3) and mediated through protein kinase C.	2001 Apr	11334710
Receptor-stimulated phospholipase A(2) liberates arachidonic acid and regulates neuronal excitability through protein kinase C.	2001 Apr	11287487
Ischemic preconditioning upregulates vascular endothelial growth factor mRNA expression and neovascularization via nuclear translocation of protein kinase C epsilon in the rat ischemic myocardium.	2001 Apr 13	11304492
Hormonal regulation of phospholipase D activity in Ca(2+) transporting cells of rabbit connecting tubule and cortical collecting duct.	2001 Apr 23	11336804
Characterisation using FLIPR of human vanilloid VR1 receptor pharmacology.	2001 Apr 6	11301059
Evidence for two mechanisms of amino acid osmolyte release from hippocampal slices.	2001 Aug	11512036
Diminished alpha1-adrenergic-mediated contraction and translocation of PKC in senescent rat heart.	2001 Aug	11454560
Effect of platelet-activating factor on gastrin release from cultured rabbit G-cells.	2001 Feb	11284466
Evidence for a role of protein kinase C in FGF signal transduction in the developing chick limb bud.	2001 Jul	11493562
Role of protein kinase C in the reduction of infarct size by N-methyl-1-deoxynojirimycin, an alpha-1,6-glucosidase inhibitor.	2001 Jul	11429386
Activation of extracellular signal-regulated kinase in trabecular meshwork cells.	2001 Jul	11428860
Histamine increases interstitial adenosine concentration via activation of ecto-5'-nucleotidase in rat hearts in vivo.	2001 Jul	11408527
Differential effects of protein kinase C on human vascular smooth muscle cell proliferation and migration.	2001 Jul	11406504
Heat shock prevents simulated ischemia-induced apoptosis in renal tubular cells via a PKC-dependent mechanism.	2001 Jul	11404313
ANG II-mediated inhibition of neuronal delayed rectifier K+ current: role of protein kinase C-alpha.	2001 Jul	11401823
Chelerythrine and genistein inhibit the endothelin-1-induced increase in myofilament Ca(2+) sensitivity in rabbit ventricular myocytes.	2001 Jul 20	11476754
Inhibition of acetylcholine-activated K(+) current by chelerythrine and bisindolylmaleimide I in atrial myocytes from mice.	2001 Jul 27	11672559
A new diprenyl coumarin and alkaloids from the bark of Zanthoxylum dimorphophyllum (Rutaceae).	2001 Jul-Aug	11531078
Protein kinase A- and C-dependent modulation of murine inducible nitric oxide synthase.	2001 Jun	11642342
Vasopressin-induced protein kinase C-dependent superoxide generation contributes to atp-sensitive potassium channel but not calcium-sensitive potassium channel function impairment after brain injury.	2001 Jun	11387506
Inhibition of carbachol stimulated acid secretion by interleukin 1beta in rabbit parietal cells requires protein kinase C.	2001 Jun	11358895
Protein kinase C and intracellular calcium are required for amphetamine-mediated dopamine release via the norepinephrine transporter in undifferentiated PC12 cells.	2001 Jun	11356924
Protein phosphorylation in mitochondria from human placenta.	2001 May	11373154
Protein kinase C regulation of dopamine transporter initiated by nicotinic receptor activation in slices of rat prefrontal cortex.	2001 May	11331413
CAMKII inhibition in the parabrachial nuclei elicits conditioned taste aversion in rats.	2001 May	11300732
Anti-adrenergic effect of adenosine on Na(+)-Ca(2+) exchange current recorded from guinea-pig ventricular myocytes.	2001 May	11292391
Responsiveness of canine bronchial vasculature to excitatory stimuli and to cooling.	2001 May	11290517
Protein kinase C inhibition abrogates hepatic ischemic preconditioning responses.	2001 May 15	11341790
Capsaicin potentiates 1,25-dihydoxyvitamin D3- and all-trans retinoic acid-induced differentiation of human promyelocytic leukemia HL-60 cells.	2001 May 25	11408028
Involvement of protein kinase C and tyrosine kinase in lipopolysaccharide-induced anorexia.	2001 May-Jun	11420064
Differentiation of bipolar CG-4 line oligodendrocytes is associated with regulation of CREB, MAP kinase and PKC signalling pathways.	2001 Nov	11672834
Activation of PKC decreases myocardial O2 consumption and increases contractile efficiency in rats.	2001 Nov	11668082
Mechanisms of the apoptotic and necrotic actions of trimethyltin in cerebellar granule cells.	2001 Nov	11606804
Novel role of macrophage migration inhibitory factor in angiotensin II regulation of neuromodulation in rat brain.	2001 Nov	11606427
Adenosine A(2A) and A(2B) receptor activation of erythropoietin production.	2001 Nov	11592940
Death by protein kinase C inhibitor: a stressful event.	2001 Oct	11603920
Endothelium-derived endothelin-1 reduces cerebral artery sensitivity to nitric oxide by a protein kinase C-independent pathway.	2001 Oct	11588325
Role of Na(+)/H(+) exchanger during O(2) deprivation in mouse CA1 neurons.	2001 Oct	11546657
Regulation and distribution of MAdCAM-1 in endothelial cells in vitro.	2001 Oct	11546645
Characterization of the signal transduction pathways mediating morphine withdrawal-stimulated c-fos expression in hypothalamic nuclei.	2001 Oct 26	11698063
Stimulatory effect of phenylephrine on the secretion of beta-endorphin from rat adrenal medulla in vitro.	2001 Oct 8	11695703
The lysophospholipids sphingosine-1-phosphate and lysophosphatidic acid enhance survival during hypoxia in neonatal rat cardiac myocytes.	2001 Sep	11549349
Src and multiple MAP kinase activation in cardiac hypertrophy and congestive heart failure under chronic pressure-overload: comparison with acute mechanical stretch.	2001 Sep	11549343
Role of calcineurin in insulin-like growth factor-1-induced hypertrophy of cultured adult rat ventricular myocytes.	2001 Sep	11548882
Mechanism of action of angiotensin II in human isolated subcutaneous resistance arteries.	2001 Sep	11522611
Regulation of ATP-sensitive K(+) channels by protein kinase C in murine colonic myocytes.	2001 Sep	11502563
Induction of osteoblast differentiation indexes by PTHrP in MG-63 cells involves multiple signaling pathways.	2001 Sep	11500304
A diacylglycerol-activated Ca2+ channel in PC12 cells (an adrenal chromaffin cell line) correlates with expression of the TRP-6 (transient receptor potential) protein.	2001 Sep 15	11535132

Patents

Sample Use Guides

In Vivo Use Guide

Mice injected i.p. with chelerythrine 1-10 mg/kg

Route of Administration: Intraperitoneal

In Vitro Use Guide

10 ug/mL of chelerythrine is capable of inducing apoptosis in Dalton's lymphoma (DL) cells.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 19:16:07 GMT 2023` Edited by `admin` on `Sat Dec 16 19:16:07 GMT 2023`
Record UNII	RC5FDY3X64
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

Chelerythrine hydrosulfate

Common Name

English

[1,3]Benzodioxolo[5,6-c]phenanthridinium, 1,2-dimethoxy-12-methyl-, sulfate (1:1)

Systematic Name

English

1,2-Dimethoxy-12-methyl-[1,3]dioxolo[4′,5′:4,5]benzo[1,2-c]phenanthridin-12-ium hydrogensulfate

Systematic Name

English

Chelerythrine hydrosulfate [WHO-DD]

Common Name

English

Code System Code Type Description

FDA UNII

RC5FDY3X64

Created by admin on Sat Dec 16 19:16:07 GMT 2023 , Edited by admin on Sat Dec 16 19:16:07 GMT 2023

PRIMARY

PUBCHEM

13394150

Created by admin on Sat Dec 16 19:16:07 GMT 2023 , Edited by admin on Sat Dec 16 19:16:07 GMT 2023

PRIMARY

CAS

53144-45-9

Created by admin on Sat Dec 16 19:16:07 GMT 2023 , Edited by admin on Sat Dec 16 19:16:07 GMT 2023

PRIMARY

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					E3B045W6X0

CHELERYTHRINE

PARENT -> SALT/SOLVATE

Amount:

Related Record Type Details


					E3B045W6X0

CHELERYTHRINE

ACTIVE MOIETY

Amount:

Details

SMILES

InChI

DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/24380291 | https://www.ncbi.nlm.nih.gov/pubmed/2244923 | https://www.ncbi.nlm.nih.gov/pubmed/12702731 | https://www.ncbi.nlm.nih.gov/pubmed/16936897 | http://www.google.com.pg/patents/WO2002013803A2

CNS Activity

Originator

Approval Year

Targets

Conditions

Approved Use

Approved Use

PubMed

Patents

Sample Use Guides

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/24380291 | https://www.ncbi.nlm.nih.gov/pubmed/2244923 | https://www.ncbi.nlm.nih.gov/pubmed/12702731 | https://www.ncbi.nlm.nih.gov/pubmed/16936897 | http://www.google.com.pg/patents/WO2002013803A2