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Details

Stereochemistry ACHIRAL
Molecular Formula C9H13N2O5P
Molecular Weight 260.1837
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of PERZINFOTEL

SMILES

OP(O)(=O)CCN1CCCNC2=C1C(=O)C2=O

InChI

InChIKey=BDABGOLMYNHHTR-UHFFFAOYSA-N
InChI=1S/C9H13N2O5P/c12-8-6-7(9(8)13)11(3-1-2-10-6)4-5-17(14,15)16/h10H,1-5H2,(H2,14,15,16)

HIDE SMILES / InChI

Description

Perzinfotel (EAA-090) is a novel squaric acid amide derivative that has been identified as a potential treatment for ischemic brain damage resulting from stroke. EAA-090 is a competitive inhibitor at the NMDA-selective subtype of the glutamate receptor. The compound demonstrates potent inhibitory activity in both in vitro and in vivo models of NMDA-induced excitotoxicity and provides neuroprotective efficacy in several animal models of stroke. EAA-090 is unique among competitive NMDA antagonists in displaying a clear separation between predicted efficacious dose and doses that induce PCP-like psychotomimetic side effects in both animals and humans. This unique profile makes EAA-090 an exciting candidate for assessing the neuroprotective potential of the competitive NMDA mechanism.

CNS Activity

Originator

Approval Year

Targets

Primary TargetPharmacologyConditionPotency
28.0 nM [IC50]

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown
Palliative
Unknown

Cmax

ValueDoseCo-administeredAnalytePopulation
1210 ng/mL
50 mg single, oral
MIDOSTAURIN unknown
Homo sapiens

AUC

ValueDoseCo-administeredAnalytePopulation
15700 ng × h/mL
50 mg single, oral
MIDOSTAURIN unknown
Homo sapiens

T1/2

ValueDoseCo-administeredAnalytePopulation
20 h
50 mg single, oral
MIDOSTAURIN unknown
Homo sapiens

Funbound

ValueDoseCo-administeredAnalytePopulation
0.2%
MIDOSTAURIN plasma
Homo sapiens

Doses

AEs

Drug as perpetrator​

Drug as victim

Tox targets

PubMed

Sample Use Guides

In Vivo Use Guide
30-100 mg/kg orally (rats) 10-30 mg/kg intravenous (dogs)
Route of Administration: Oral
In Vitro Use Guide
IC50 28 nM (inhibited [(3)H]3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid binding to NMDA receptors). IC50 477 nM (decreased the duration of spontaneous synaptic currents and inhibited NMDA-activated currents in rat hippocampal neurons).