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Details

Stereochemistry ACHIRAL
Molecular Formula C21H21ClN4O3
Molecular Weight 412.869
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of NIZOFENONE

SMILES

CCN(CC)CC1=NC=CN1C2=C(C=C(C=C2)[N+]([O-])=O)C(=O)C3=C(Cl)C=CC=C3

InChI

InChIKey=WZGBZLHGOVJDET-UHFFFAOYSA-N
InChI=1S/C21H21ClN4O3/c1-3-24(4-2)14-20-23-11-12-25(20)19-10-9-15(26(28)29)13-17(19)21(27)16-7-5-6-8-18(16)22/h5-13H,3-4,14H2,1-2H3

HIDE SMILES / InChI

Molecular Formula C21H21ClN4O3
Molecular Weight 412.869
Charge 0
Count
MOL RATIO 1 MOL RATIO (average)
Stereochemistry ACHIRAL
Additional Stereochemistry No
Defined Stereocenters 0 / 0
E/Z Centers 0
Optical Activity NONE

Description

Nizofenone (Ekonal, Midafenone) is a neuroprotective drug which protects neurons from death following cerebral anoxia (interruption of oxygen supply to the brain). It might thus be useful in the treatment of acute neurological conditions such as stroke. Nizofenone ameliorates various pathophysiologic events during ischemia, such as ATP depletion, lactate accumulation, glutamate release, free fatty acid liberation, edema, and neuronal degeneration; in particular, ischemia-induced excessive glutamate release has been completely blocked by this drug. This drug has also radical-scavenging action, comparable to vitamin E, and inhibits oxygen radical-induced lipid peroxidation. The potent cerebroprotective effect of nizofenone has been demonstrated in various experimental models of cerebral hypoxia, ischemia (focal and global), ischemia-reperfusion, and infarction. The clinical efficacy of nizofenone has been proved by pioneering double-blind studies in acute subarachnoid hemorrhage patients. Nizofenone is clinically used for preventing the delayed ischemic neurologic deficits due to late vasospasm following subarachnoid hemorrhage.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

PubMed

Sample Use Guides

In Vivo Use Guide
Nizofenone (1 mg/kg, i.v.) - to treat brain ischemia in cats
Route of Administration: Intravenous
In Vitro Use Guide
In spontaneously firing pacemaker cells, nizofenone (above 1 uM) decreased the heart rate. Above 3 uM, nizofenone reduced the maximum upstroke velocity, the amplitude of the action potential and the slope of the phase 4 depolarization, and prolonged the action potential duration at 50% repolarization in rabbit sino-atrial node.
Substance Class Chemical
Record UNII
7A2NOC3R88
Record Status Validated (UNII)
Record Version