ISOCORYNOXEINE

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-VKCGGMIFSA-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/25633191 | https://www.ncbi.nlm.nih.gov/pubmed/9437908 | https://www.ncbi.nlm.nih.gov/pubmed/25519834 | https://www.ncbi.nlm.nih.gov/pubmed/28534954 | https://www.ncbi.nlm.nih.gov/pubmed/18588343

Isocorynoxeine is one of four bioactive tetracyclic oxinole alkaloids which can be isolated from Uncaria hooks used in traditional Chinese and Kampo medicines. The traditional remedies are claimed to have sedative and anti-spasmodic effects, however, isocorynoxeine does not appear to cross the blood-brain barrier. It is suspected that one or more metabolites of isocorynoxeine produce the effect of lower blood pressure, vasodilation and protection against ischemic neural damage. Furthermore, isocoynoxine has also shown reduce the viability of multi-drug resistant cancer cells when used in conjunction with doxycycline

CNS Activity

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
nitric oxide metabolic process 2 Target ID: GO:0046209 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18588343	Inhibitor 8297		13.7 µM [IC50]

Conditions

Condition	Modality	Highest Phase	Product
Epilepsy 121 Sources: https://www.ncbi.nlm.nih.gov/pubmed/9437908	Primary	Natural Metabolite	Unknown Approved Use Unknown
Cell death due to ischemia 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/25519834	Primary	Natural Metabolite	Unknown Approved Use Unknown
Cancer multi-drug resistance 1 Sources: https://www.ncbi.nlm.nih.gov/pubmed/28534954	Secondary	Natural Metabolite	Unknown Approved Use Unknown

PubMed

Title	Date	PubMed

Patents

Sample Use Guides

In Vivo Use Guide

An oral dose of 40 mg/kg of isocorynoxeine was fed to rats. After dosing bile was drained and analyzed by LC-MS in order to identify metabolites of isocorynoxeine.

Route of Administration: Oral

In Vitro Use Guide

Isocorynooxeine and several metabolites were tested for the ability to protect against 3 mM glutamate-induced cell death in immortalized an HT22-cell line. HT22 cells were cultured in DMEM supplemented with 10% FBS at 37 deg-C in a 5% CO2 and 95% air atmosphere. Cells were incubated 24 hours before being treated with 1 - 100 micro-M of each test sample and 3 mM glutamate. Isocorynoxeine exhibited significant neuroprotective effects against glutamate-induced cell death at the maximum concentration of 100 micro-M. However little neuroprotection was observed for the tested metabolites.

Substance Class	Chemical Created by `admin` on `Sat Dec 16 09:45:11 UTC 2023` Edited by `admin` on `Sat Dec 16 09:45:11 UTC 2023`
Record UNII	J18B596D11
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ISOCORYNOXEINE

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'S,6'R,7'S,8'AS)-

Systematic Name

English

7-ISOCORYNOXEINE

Common Name

English

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

Common Name

English

Code System Code Type Description

PUBCHEM

3037448