Perzinfotel | EAA-090 | WAY-126090 | CAS#144912-63-0 | NMDA receptor antagonist

MedKoo Cat#: 329440 | Name: Perzinfotel

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Perzinfotel, also known as EAA-090; WAY-126090, is a NMDA receptor antagonist potentially for the treatment of diabetic neuropathic pain. EAA-090 inhibited [(3)H]3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid binding to NMDA receptors with IC(50) value of 28 nM. IC(50) values for inhibition of current induced by 10 microM NMDA was 477nM.

Chemical Structure

Perzinfotel

CAS#144912-63-0

Theoretical Analysis

MedKoo Cat#: 329440

Name: Perzinfotel

CAS#: 144912-63-0

Chemical Formula: C9H13N2O5P

Exact Mass: 260.0562

Molecular Weight: 260.19

Elemental Analysis: C, 41.55; H, 5.04; N, 10.77; O, 30.75; P, 11.90

Price and Availability

Size	Price	Availability	Quantity
10mg	USD 450.00
20mg	USD 650.00
50mg	USD 1,250.00

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Related CAS #

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Synonym

Perzinfotel; EAA-090; WAY-126090; EAA090; WAY126090.

IUPAC/Chemical Name

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

InChi Key

BDABGOLMYNHHTR-UHFFFAOYSA-N

InChi Code

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)

SMILES Code

O=C(C1=C2NCCCN1CCP(O)(O)=O)C2=O

Appearance

Solid powder

Purity

>98% (or refer to the Certificate of Analysis)

Shipping Condition

Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition

Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility

Soluble in DMSO

Shelf Life

>2 years if stored properly

Drug Formulation

This drug may be formulated in DMSO

Stock Solution Storage

0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code

2934.99.9001

More Info

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Perzinfotel (EAA-090) is a potent, selective, and competitive NMDA receptor antagonist.

In vitro activity:

Two novel N-methyl-d-aspartate (NMDA) antagonists with unique chemical structures, EAA-090 (2-[8,9-dioxo-2, 6-diazabicyclo[5.2.0]non-1(7)-en2-yl]ethylphosphonic acid) and EAB-318 (R-alpha-amino-5-chloro-1-(phosphonomethyl)-1H-benzimidazole-2-propanoic acid hydrochloride), were compared with CGS-19755 (Selfotel) in ligand binding, electrophysiology, and neuroprotection assays. CGS-19755, EAA-090 and EAB-318 inhibited [(3)H]3-(2-carboxypiperazin-4-yl)propyl-1-phosphonic acid binding to NMDA receptors with IC(50) values of 55, 28, and 7.9 nM, respectively. EAA-090 was 10 times more potent at blocking NR2A-versus NR2B- or NR2C-containing NMDA receptors. Reference: J Pharmacol Exp Ther. 2004 Aug;310(2):563-70. https://pubmed.ncbi.nlm.nih.gov/15075380/

In vivo activity:

TBD

	Solvent	mg/mL	mM
Solubility
	DMSO	20.8	80.06
	Water	5.9	22.60

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 260.19 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Concentration / Solvent Volume / Mass	1 mg	5 mg	10 mg
1 mM	1.15 mL	5.76 mL	11.51 mL
5 mM	0.23 mL	1.15 mL	2.3 mL
10 mM	0.12 mL	0.58 mL	1.15 mL
50 mM	0.02 mL	0.12 mL	0.23 mL

Formulation protocol:

Sun L, Chiu D, Kowal D, Simon R, Smeyne M, Zukin RS, Olney J, Baudy R, Lin S. Characterization of two novel N-methyl-D-aspartate antagonists: EAA-090 (2-[8,9-dioxo-2,6-diazabicyclo [5.2.0]non-1(7)-en2-yl]ethylphosphonic acid) and EAB-318 (R-alpha-amino-5-chloro-1-(phosphonomethyl)-1H-benzimidazole-2-propanoic acid hydrochloride). J Pharmacol Exp Ther. 2004 Aug;310(2):563-70. doi: 10.1124/jpet.104.066092. Epub 2004 Apr 9. PMID: 15075380.

In vitro protocol:

In vivo protocol:

TBD

1: Henle F, Dehmel M, Leemhuis J, Fischer C, Meyer DK. Role of GluN2A and GluN2B subunits in the formation of filopodia and secondary dendrites in cultured hippocampal neurons. Naunyn Schmiedebergs Arch Pharmacol. 2012 Feb;385(2):171-80. doi: 10.1007/s00210-011-0701-3. PubMed PMID: 22033802. 2: Budsberg SC, Torres BT, Zwijnenberg RJ, Eppler CM, Clark JD, Cathcart CJ, Reynolds LR, Al-Nadaf S. Effect of perzinfotel and a proprietary phospholipase A(2) inhibitor on kinetic gait and subjective lameness scores in dogs with sodium urate-induced synovitis. Am J Vet Res. 2011 Jun;72(6):757-63. doi: 10.2460/ajvr.72.6.757. PubMed PMID: 21627521. 3: Zwijnenberg RJ, L del Rio C, Pollet RA, Muir WW. Effects of perzinfotel, butorphanol tartrate, and a butorphanol-perzinfotel combination on the minimum alveolar concentration of isoflurane in cats. Am J Vet Res. 2010 Nov;71(11):1270-6. doi: 10.2460/ajvr.71.11.1270. PubMed PMID: 21034317. 4: Zwijnenberg RJ, del Rio CL, Pollet RA, Muir WW. 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. Am J Vet Res. 2010 Jun;71(6):604-9. doi: 10.2460/ajvr.71.6.604. PubMed PMID: 20513173. 5: Ueyama Y, Lerche P, Eppler CM, Muir WW. Effects of intravenous administration of perzinfotel, fentanyl, and a combination of both drugs on the minimum alveolar concentration of isoflurane in dogs. Am J Vet Res. 2009 Dec;70(12):1459-64. doi: 10.2460/ajvr.70.12.1459. PubMed PMID: 19951116. 6: Baudy RB, Butera JA, Abou-Gharbia MA, Chen H, Harrison B, Jain U, Magolda R, Sze JY, Brandt MR, Cummons TA, Kowal D, Pangalos MN, Zupan B, Hoffmann M, May M, Mugford C, Kennedy J, Childers WE Jr. Prodrugs of perzinfotel with improved oral bioavailability. J Med Chem. 2009 Feb 12;52(3):771-8. doi: 10.1021/jm8011799. PubMed PMID: 19146418. 7: Kushiro T, Wiese AJ, Eppler MC, Muir WW 3rd. Effects of perzinfotel on the minimum alveolar concentration of isoflurane in dogs. Am J Vet Res. 2007 Dec;68(12):1294-9. PubMed PMID: 18052733. 8: Arias RL, Bowlby MR. Pharmacological characterization of antiepileptic drugs and experimental analgesics on low magnesium-induced hyperexcitability in rat hippocampal slices. Brain Res. 2005 Jun 21;1047(2):233-44. PubMed PMID: 15907811. 9: Brandt MR, Cummons TA, Potestio L, Sukoff SJ, Rosenzweig-Lipson S. Effects of the N-methyl-D-aspartate receptor antagonist perzinfotel [EAA-090; [2-(8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)-ethyl]phosphonic acid] on chemically induced thermal hypersensitivity. J Pharmacol Exp Ther. 2005 Jun;313(3):1379-86. PubMed PMID: 15764736. 10: Sun L, Chiu D, Kowal D, Simon R, Smeyne M, Zukin RS, Olney J, Baudy R, Lin S. Characterization of two novel N-methyl-D-aspartate antagonists: EAA-090 (2-[8,9-dioxo-2,6-diazabicyclo [5.2.0]non-1(7)-en2-yl]ethylphosphonic acid) and EAB-318 (R-alpha-amino-5-chloro-1-(phosphonomethyl)-1H-benzimidazole-2-propanoic acid hydrochloride). J Pharmacol Exp Ther. 2004 Aug;310(2):563-70. PubMed PMID: 15075380. 11: Kinney WA, Abou-Gharbia M, Garrison DT, Schmid J, Kowal DM, Bramlett DR, Miller TL, Tasse RP, Zaleska MM, Moyer JA. Design and synthesis of [2-(8,9-dioxo-2,6-diazabicyclo[5.2.0]non-1(7)-en-2-yl)-ethyl]phosphonic acid (EAA-090), a potent N-methyl-D-aspartate antagonist, via the use of 3-cyclobutene-1,2-dione as an achiral alpha-amino acid bioisostere. J Med Chem. 1998 Jan 15;41(2):236-46. PubMed PMID: 9457246.