CORYNOXEINE

Possibly Marketed Outside US

First approved in 2021

Details

Stereochemistry	ABSOLUTE
Molecular Formula	C22H26N2O4
Molecular Weight	382.4528
Optical Activity	UNSPECIFIED
Defined Stereocenters	4 / 4
E/Z Centers	1
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

[H][C@@]12C[C@@H]([C@H](CN1CC[C@]23C(=O)NC4=CC=CC=C34)C=C)C(=C/OC)\C(=O)OC

InChI

InChIKey=MUVGVMUWMAGNSY-KAXDATADSA-N

InChI=1S/C22H26N2O4/c1-4-14-12-24-10-9-22(17-7-5-6-8-18(17)23-21(22)26)19(24)11-15(14)16(13-27-2)20(25)28-3/h4-8,13-15,19H,1,9-12H2,2-3H3,(H,23,26)/b16-13+/t14-,15-,19-,22+/m0/s1

HIDE SMILES / InChI

Molecular Formula	C22H26N2O4
Molecular Weight	382.4528
Charge	0
Count

Stereochemistry	ABSOLUTE
Additional Stereochemistry	No
Defined Stereocenters	4 / 4
E/Z Centers	1
Optical Activity	UNSPECIFIED

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/18981576
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/24522518

Corynoxeine is a compound isolated from Uncaria rhynchophylla, a traditional Chinese herb that has been applied to the treatment of convulsive disorders in China. Corynoxeine was found to inhibit PDGF-BB-induced activation of ERK1/2 and vascular smooth muscle cells proliferation. Corynoxeine found to induce autophagy in different neuronal cell lines, including N2a and SHSY-5Y cells and may have potential application for the prevention or treatment of Parkinson's disease.

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Mitogen-activated protein kinase; ERK1/ERK2 2 Target ID: CHEMBL1907606 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18981576	Inhibitor 8297

Conditions

Condition	Modality	Targets	Highest Phase	Product
Parkinson's disease 226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/24522518	Preventing		Basic research	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed
Corynoxeine isolated from the hook of Uncaria rhynchophylla inhibits rat aortic vascular smooth muscle cell proliferation through the blocking of extracellular signal regulated kinase 1/2 phosphorylation.	2008 Nov	18981576
The blood-brain barrier permeability of geissoschizine methyl ether in Uncaria hook, a galenical constituent of the traditional Japanese medicine yokukansan.	2011 Jul	21442303
Corynoxine, a natural autophagy enhancer, promotes the clearance of alpha-synuclein via Akt/mTOR pathway.	2014 Jun	24522518

Patents

Sample Use Guides

In Vivo Use Guide

In a rat PK study, Yokukansan (a traditional Japanese medicine, containing corynoxeine) was administered orally at 1 or 4 g/kg.

Route of Administration: Oral

In Vitro Use Guide

Vascular smooth muscle cells (VSMCs) were seeded in 12-well culture plates at 5x104 cells/ml and cultured in DMEM with 10% FBS at 37 °C for 24 h. Under these conditions, the cells reached ca. 70% confluence. VSMCs were pre-cultured in serum-free medium in the presence and absence of corynoxeine (5 - 50mM) for 24 h and then stimulated with 50 ng/ml PDGF-BB. The cells were trypsinized and counted using hemocytometer after 24 h.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:31:30 GMT 2023` Edited by `admin` on `Sat Dec 16 09:31:30 GMT 2023`
Record UNII	27KIC0Q2VA
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

CORYNOXEINE

Common Name

English

SPIRO(3H-INDOLE-3,1'(5'H)-INDOLIZINE)-7'-ACETIC ACID, 6'-ETHENYL-1,2,2',3',6',7',8',8'A-OCTAHYDRO-.ALPHA.-(METHOXYMETHYLENE)-2-OXO-, METHYL ESTER, (.ALPHA.E,1'R,6'R,7'S,8'AS)-

Systematic Name

English

CORYNOXEIN

Common Name

English

.DELTA.18-RHYNCHOPHYLLINE

Common Name

English

CORYNOXAN-16-CARBOXYLIC ACID, 16,17,18,19-TETRADEHYDRO-17-METHOXY-2-OXO-, METHYL ESTER, (7.BETA.,16E,20.ALPHA.)-

Common Name

English

.DELTA.18-RHYNCOPHYLLINE

Common Name

English

Code System Code Type Description

EPA CompTox

DTXSID001318311