ENECADIN

Investigational

Details

Stereochemistry	ACHIRAL
Molecular Formula	C21H28FN3O
Molecular Weight	357.4649
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

CC1=NC(=CC(OCCCCCN2CCCCC2)=N1)C3=CC=C(F)C=C3

InChI

InChIKey=SZSHJTJCJOWMHM-UHFFFAOYSA-N

InChI=1S/C21H28FN3O/c1-17-23-20(18-8-10-19(22)11-9-18)16-21(24-17)26-15-7-3-6-14-25-12-4-2-5-13-25/h8-11,16H,2-7,12-15H2,1H3

HIDE SMILES / InChI

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/16100702 | https://adisinsight.springer.com/drugs/800009089 | https://www.ncbi.nlm.nih.gov/pubmed/12676377 | https://www.ncbi.nlm.nih.gov/pubmed/15678048 | https://www.ncbi.nlm.nih.gov/pubmed/16187036 | https://clinicaltrials.gov/ct2/show/NCT00331721

Enecadin (NS 7 or ZK 228326) is a voltage-dependent sodium and calcium channel blocker. Enecadin is a neuroprotective agent demonstrated efficacy in animal models of ischemic injury of brain, spinal cord and retina. Enecadin was undergoing phase II development in stroke with PAION in Germany. Enecadin development has been discontinued.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Voltage-sensitive sodium channel 7 Target ID: CHEMBL2362985 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18377333	Blocker 555
Voltage-gated calcium channel 37 Target ID: CHEMBL2363032 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18377333	Blocker 555

PubMed

Title	Date	PubMed
Decreasing the infusion rate reduces the proarrhythmic risk of NS-7: confirming the relevance of short-term variability of repolarisation in predicting drug-induced torsades de pointes.	2005-06	15778734
NS-7, a novel Na+/Ca2+ channel blocker, prevents neurologic injury after spinal cord ischemia in rabbits.	2005-02	15678048
Neuroprotective effect of the novel Na+/Ca2+ channel blocker NS-7 on rat retinal ganglion cells.	2004-09-07	16187036
Neuroprotective effect of NS-7, a novel Na+ and Ca2+ channel blocker, in a focal ischemic model in the rat.	2003-04-18	12676377
Cardiac electrophysiological modulation by NS-7, a novel neuroprotective drug, of guinea pig ventricular muscles.	2003-01-17	12495782
Pharmacokinetics of the new pyrimidine derivative NS-7, a novel Na+/Ca2+ channel blocker. 2nd communication: tissue distributions, placental transfer and milk secretion of radioactivity after a single intravenous 14C-NS-7 injection to rats.	2003	14650361
Pharmacokinetics of the new pyrimidine derivative NS-7, a novel Na+/Ca2+ channel blocker. 1st communication: plasma concentrations and excretions after a single intravenous 14C-NS-7 injection to rats, dogs and monkeys.	2003	14558434
A novel voltage-sensitive Na(+) and Ca(2+) channel blocker, NS-7, prevents suppression of cyclic AMP-dependent protein kinase and reduces infarct area in the acute phase of cerebral ischemia in rat.	2002-01-04	11744000
Electrophysiological and neurochemical evidence for voltage-dependent Ca(2+) channel blockade by a novel neuroprotective agent NS-7.	2001-09	11589782
Reversal by NS-7, a neuroprotective compound, of the decrease in transcription factor CREB mRNA expression in rat brain after permanent middle cerebral artery occlusion.	2001-06-15	11403938
Effective plasma concentration of a novel Na+/Ca2+ channel blocker NS-7 for its cerebroprotective actions in rats with a transient middle cerebral artery occlusion.	2001-02	11160611
Cerebroprotective action of a Na+/Ca2+ channel blocker NS-7. II. Effect on the cerebral infarction, behavioral and cognitive impairments at the chronic stage of permanent middle cerebral artery occlusion in rats.	2001-01-26	11164780
Cerebroprotective action of a Na+/Ca2+ channel blocker NS-7. I. Effect on the cerebral infarction and edema at the acute stage of permanent middle cerebral artery occlusion in rats.	2001-01-26	11164779

Patents

Sample Use Guides

In Vitro Use Guide

In rat dorsal root ganglion neurones, NS-7 (0.3-100 microM) inhibited the whole-cell Ba(2+) currents (IBa) in a voltage-dependent manner, in which the compound more potently blocked the IBa elicited from the holding potential of -40 mV than that induced from -80 mV.

Name

Type

Language

Enecadin [WHO-DD]

Preferred Name

English

ENECADIN

Official Name

English

4-(4-FLUOROPHENYL)-2-METHYL-6-((5-(PIPERIDIN-1-YL)PENTYL)OXY)PYRIMIDINE

Systematic Name

English

enecadin [INN]

Common Name

English

Classification Tree Code System Code

NCI_THESAURUS

C1509