NICANARTINE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C23H33NO2
Molecular Weight	355.5136
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC(C)(C)C1=CC(CCCOCC2=CN=CC=C2)=CC(=C1O)C(C)(C)C

InChI

InChIKey=YNBBIPPQHYZTQF-UHFFFAOYSA-N

InChI=1S/C23H33NO2/c1-22(2,3)19-13-17(14-20(21(19)25)23(4,5)6)10-8-12-26-16-18-9-7-11-24-15-18/h7,9,11,13-15,25H,8,10,12,16H2,1-6H3

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Description
Sources: https://adisinsight.springer.com/drugs/800004102

Nicanartine [MRZ 3124] is an antioxidant and cholesterol-lowering agent that was under development with Merz + Co. (later Merz Pharma) in Germany. Development of nicanartine for the treatment of atherosclerosis and reperfusion injury was discontinued at the phase I stage.

Originator

Approval Year

PubMed

Title	Date	PubMed
[Study of lipid peroxidation inhibition in human blood by several endogenous and exogenous compounds].	2000-10	11060406
Chain-breaking antioxidants and ferriheme-bound drugs are synergistic inhibitors of erythrocyte membrane peroxidation.	1998-02	9645396
Effect of the antioxidant Nicanartine on the proliferative and inflammatory response after experimental balloon angioplasty.	1998	9894928
Effects of the new antioxidant nicanartine in an experimental model of atherosclerosis.	1996-10	8931887

Patents

Sample Use Guides

In Vivo Use Guide

In order to study the contribution of oxidant stress to the pathogenesis of experimental diabetic retinopathy, male streptozotocin diabetic Lewis rats were treated nicanartine (80 mg/kg) by oral supplementation for 6 months

Route of Administration: Oral

In Vitro Use Guide

Nicanartine concentration dependently reduced LPO and H2O2 production already at a concentration of 1 uM, whereas LC and LM amplified CL and WB-CL were not affected. EROD and END were concentration dependently diminished starting at 1 uM, and ECOD already at 0.1 uM.

Name

Type

Language

nicanartine [INN]

Preferred Name

English

NICANARTINE

Official Name

English

2,6-DI-TERT-BUTYL-4-(3-(3-PYRIDYLMETHOXY)PROPYL)PHENOL

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C29703