PERZINFOTEL

Investigational

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

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 Target	Pharmacology	Condition	Potency
NMDA selective glutamate receptor complex 1	Antagonist 2,778		28.0 nM [IC50]

Conditions

Condition	Modality	Targets	Highest Phase	Product
Stroke 144	Primary		Preclinical	Unknown
Neuropathic pain 26	Palliative		Phase II 1,132	Unknown

C_max

Value	Dose	Co-administered	Analyte	Population
1210 ng/mL	50 mg single, oral		MIDOSTAURIN unknown	Homo sapiens

AUC

Value	Dose	Co-administered	Analyte	Population
15700 ng × h/mL	50 mg single, oral		MIDOSTAURIN unknown	Homo sapiens

T_1/2

Value	Dose	Co-administered	Analyte	Population
20 h	50 mg single, oral		MIDOSTAURIN unknown	Homo sapiens

F_unbound

Value	Dose	Co-administered	Analyte	Population
0.2%			MIDOSTAURIN plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
50 mg 2 times / day steady, oral Recommended	unhealthy, 47 years (range: 18-60 years) n = 345	Disc. AE: Renal insufficiency...
50 mg 2 times / day steady, oral Recommended	unhealthy, 47 years (range: 18-60 years) n = 345	Disc. AE: Transaminases increased, Rash...
300 mg 2 times / day multiple, oral Highest studied dose	unhealthy, adult n = 29

Showing 1 to 3 of 3 entries

Previous1Next

AEs

Show entries

AE	Significance	Dose	Population
Renal insufficiency	grade 3-4, 2 patients Disc. AE	50 mg 2 times / day steady, oral Recommended	unhealthy, 47 years (range: 18-60 years) n = 345
Arrhythmia	2 patients Disc. AE	50 mg 2 times / day steady, oral Recommended	unhealthy, 47 years (range: 18-60 years) n = 345
Myocardial ischemia	2 patients Disc. AE	50 mg 2 times / day steady, oral Recommended	unhealthy, 47 years (range: 18-60 years) n = 345
Nausea	2 patients Disc. AE	50 mg 2 times / day steady, oral Recommended	unhealthy, 47 years (range: 18-60 years) n = 345
Rash	3 patients Disc. AE	50 mg 2 times / day steady, oral Recommended	unhealthy, 47 years (range: 18-60 years) n = 345

Showing 1 to 5 of 7 entries

Previous1 2Next

Overview

CYP3A4	CYP2C9	CYP2D6	hERG
substrate 1,737	inhibitor 1,767 inducer 389	inhibitor 1,852 substrate 1,217	inhibitor 1,612

OverviewOther

Other Inhibitor	Other Substrate	Other Inducer
CYP1A2 1,524 CYP2C8 911 CYP2C19 1,478 CYP2E1 882 CYP2A6 707 CYP2B6 810 CYP3A4/5 278 P-gp 1,461 BCRP 699 MRP2 383 OATP1B1 788 OATP1B3 706 OAT1 599 OAT3 642	CYP1A2 1,054 CYP2A6 543 CYP2B6 664 CYP2C8 693 CYP2C19 991 CYP2E1 667 CYP3A5 395 CYP1A1 349 CYP3A 191 P-gp 1,537 MRP2 205	CYP1A2 701 CYP2B6 547 CYP2C8 168 CYP2C19 293 CYP3A 129 MRP2 111

Drug as perpetrator

Show entries

Target	Modality	Activity	Metabolite
CYP2A6 739	inhibitor 3,277	no
CYP2A6 739	inhibitor 3,277	no	CGP52421 1
CYP2A6 739	inhibitor 3,277	no	CGP62221 1
CYP2B6 1,001	inhibitor 3,277	no
CYP2B6 1,001	inhibitor 3,277	no	CGP52421 1

Showing 1 to 5 of 60 entries

Previous1 2 3 4 5…12Next

Drug as victim

Show entries

Target	Modality	Activity	Metabolite
CYP3A4 1,737	substrate 3,367	major	CGP52421 1
CYP3A4 1,737	substrate 3,367	major	CGP62221 1
CYP1A2 1,054	substrate 3,367	no
CYP2A6 543	substrate 3,367	no
CYP2B6 664	substrate 3,367	no

Showing 1 to 5 of 18 entries

Previous1 2 3 4Next

Tox targets

Show entries

Target	Modality	Activity	Metabolite	Clinical evidence
hERG 1,647	inhibitor 1,626

Showing 1 to 1 of 1 entries

Previous1Next

Sourcing

Sourcing

Show entries

Vendor/Aggregator	ID	URL
Chem Scene	CS-0014908	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0014908
Compound Cloud	6918236
MedChem Express	HY-19168	https://www.medchemexpress.com/search.html?q=HY-19168&ft=&fa=&fp=
MuseChem	I008642	https://www.musechem.com/product/I008642.html
eMolecules	36772575	https://orderbb.emolecules.com/search/#?query=36772575

Showing 1 to 5 of 6 entries

Previous1 2Next

PubMed

Show entries

Title	Date	PubMed
Effects of perzinfotel on the minimum alveolar concentration of isoflurane in dogs when administered as a preanesthetic via various routes or in combination with butorphanol.	2010 Jun	20513173
Effects of perzinfotel, butorphanol tartrate, and a butorphanol-perzinfotel combination on the minimum alveolar concentration of isoflurane in cats.	2010 Nov	21034317

Showing 1 to 2 of 2 entries

Previous1Next

Patents

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).

Show entries

Name

Type

Language

PERZINFOTEL

Official Name

English

EAA-090

Code

English

perzinfotel [INN]

Common Name

English

[2-(8,9-Dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)ethyl]phosphonic acid

Systematic Name

English

PERZINFOTEL [USAN]

Common Name

English

Showing 1 to 5 of 6 entries

Previous1 2Next

Show entries

Classification Tree

Code System

Code

Protective Agent

NCI_THESAURUS

C1509

Showing 1 to 1 of 1 entries

Previous1Next

Show entries

Code System

Code

Type

Description

INN

8492

PRIMARY

EPA CompTox

DTXSID70162846

PRIMARY

USAN

PP-87

PRIMARY

CAS

144912-63-0

PRIMARY

PUBCHEM

6918236

PRIMARY

Showing 1 to 5 of 11 entries

Previous1 2 3Next

ACTIVE MOIETY


					FX5AUU7Z8T

PERZINFOTEL

SMILES

InChI

CNS Activity

Originator

Approval Year

Targets

Conditions

Cmax

AUC

T1/2

Funbound

Doses

AEs

Overview

OverviewOther

Drug as perpetrator​

Drug as victim

Tox targets

Sourcing

PubMed

Patents

Sample Use Guides

C_max

T_1/2

F_unbound

Drug as perpetrator