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MedKoo Cat#: 145577 | Name: EAPB-0503

Description:

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

EAPB-0503 is a imidazoquinoxaline and Imiquimod analog. EAPB0503 selectively downregulates HDM2 expression and activates the p53 pathway in NPM1c expressing cells, resulting in apoptosis.

Chemical Structure

EAPB-0503
EAPB-0503
CAS#1140627-77-5

Theoretical Analysis

MedKoo Cat#: 145577

Name: EAPB-0503

CAS#: 1140627-77-5

Chemical Formula: C18H16N4O

Exact Mass: 304.1300

Molecular Weight: 304.35

Elemental Analysis: C, 71.04; H, 5.30; N, 18.41; O, 5.26

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
EAPB-0503; EAPB0503; EAPB 0503;
IUPAC/Chemical Name
1-(3-methoxyphenyl)-N-methylimidazo[1,2-a]quinoxalin-4-amine
InChi Key
PLJRXCRNKAGLBD-UHFFFAOYSA-N
InChi Code
1S/C18H16N4O/c1-19-17-18-20-11-16(12-6-5-7-13(10-12)23-2)22(18)15-9-4-3-8-14(15)21-17/h3-11H,1-2H3,(H,19,21)
SMILES Code
CNC1=NC2=C(C=CC=C2)N3C(=CN=C13)C4=CC=CC(OC)=C4
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 304.35 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.

Recalculate based on batch purity %
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
1: Skayneh H, Jishi B, Hleihel R, Hamie M, El Hajj R, Deleuze-Masquefa C, Bonnet PA, El Sabban M, El Hajj H. EAPB0503, an Imidazoquinoxaline Derivative Modulates SENP3/ARF Mediated SUMOylation, and Induces NPM1c Degradation in NPM1 Mutant AML. Int J Mol Sci. 2022 Mar 22;23(7):3421. doi: 10.3390/ijms23073421. PMID: 35408798; PMCID: PMC8998649. 2: El Hajj R, Bou Youness H, Lachaud L, Bastien P, Masquefa C, Bonnet PA, El Hajj H, Khalifeh I. EAPB0503: An Imiquimod analog with potent in vitro activity against cutaneous leishmaniasis caused by Leishmania major and Leishmania tropica. PLoS Negl Trop Dis. 2018 Nov 21;12(11):e0006854. doi: 10.1371/journal.pntd.0006854. PMID: 30462645; PMCID: PMC6248897. 3: Saliba J, Deleuze-Masquéfa C, Iskandarani A, El Eit R, Hmadi R, Mahon FX, Bazarbachi A, Bonnet PA, Nasr R. EAPB0503, a novel imidazoquinoxaline derivative, inhibits growth and induces apoptosis in chronic myeloid leukemia cells. Anticancer Drugs. 2014 Jul;25(6):624-32. doi: 10.1097/CAD.0000000000000084. PMID: 24463483. 4: Nabbouh AI, Hleihel RS, Saliba JL, Karam MM, Hamie MH, Wu HJM, Berthier CP, Tawil NM, Bonnet PA, Deleuze-Masquefa C, El Hajj HA. Imidazoquinoxaline derivative EAPB0503: A promising drug targeting mutant nucleophosmin 1 in acute myeloid leukemia. Cancer. 2017 May 1;123(9):1662-1673. doi: 10.1002/cncr.30515. Epub 2017 Jan 5. PMID: 28055106. 5: Chouchou A, Aubert-Pouëssel A, Dorandeu C, Zghaib Z, Cuq P, Devoisselle JM, Bonnet PA, Bégu S, Deleuze-Masquefa C. Lipid nanocapsules formulation and cellular activities evaluation of a promising anticancer agent: EAPB0503. Int J Pharm Investig. 2017 Oct-Dec;7(4):155-163. doi: 10.4103/jphi.JPHI_53_17. PMID: 29692974; PMCID: PMC5903019. 6: Khier S, Gattacceca F, El Messaoudi S, Lafaille F, Deleuze-Masquéfa C, Bompart J, Cooper JF, Solassol I, Pinguet F, Bonnet PA, Bressolle FM. Metabolism and pharmacokinetics of EAPB0203 and EAPB0503, two imidazoquinoxaline compounds previously shown to have antitumoral activity on melanoma and T-lymphomas. Drug Metab Dispos. 2010 Oct;38(10):1836-47. doi: 10.1124/dmd.110.034579. Epub 2010 Jul 21. PMID: 20660102. 7: Lafaille F, Solassol I, Enjalbal C, Bertrand B, Doulain PE, Vappiani J, Bonnet PA, Deleuze-Masquéfa C, Bressolle FM. Structural characterization of in vitro metabolites of the new anticancer agent EAPB0503 by liquid chromatography- tandem mass spectrometry. J Pharm Biomed Anal. 2014 Jan;88:429-40. doi: 10.1016/j.jpba.2013.09.015. Epub 2013 Oct 5. PMID: 24176748. 8: Courbet A, Bec N, Constant C, Larroque C, Pugniere M, El Messaoudi S, Zghaib Z, Khier S, Deleuze-Masquefa C, Gattacceca F. Imidazoquinoxaline anticancer derivatives and imiquimod interact with tubulin: Characterization of molecular microtubule inhibiting mechanisms in correlation with cytotoxicity. PLoS One. 2017 Aug 10;12(8):e0182022. doi: 10.1371/journal.pone.0182022. PMID: 28797090; PMCID: PMC5552358. 9: Zghaib Z, Guichou JF, Vappiani J, Bec N, Hadj-Kaddour K, Vincent LA, Paniagua-Gayraud S, Larroque C, Moarbess G, Cuq P, Kassab I, Deleuze-Masquéfa C, Diab-Assaf M, Bonnet PA. New imidazoquinoxaline derivatives: Synthesis, biological evaluation on melanoma, effect on tubulin polymerization and structure-activity relationships. Bioorg Med Chem. 2016 Jun 1;24(11):2433-2440. doi: 10.1016/j.bmc.2016.04.004. Epub 2016 Apr 1. PMID: 27094151. 10: Khier S, Moarbess G, Deleuze-Masquefa C, Solassol I, Margout D, Pinguet F, Bonnet PA, Bressolle FM. Quantitation of imidazo[1,2-a]quinoxaline derivatives in human and rat plasma using LC/ESI-MS. J Sep Sci. 2009 May;32(9):1363-73. doi: 10.1002/jssc.200800668. PMID: 19399864. 11: Chouchou A, Marion B, Enjalbal C, Roques C, Cuq P, Bonnet PA, Bressolle- Gomeni FMM, Deleuze-Masquéfa C. Liquid chromatography-electrospray ionization- tandem mass spectrometry method for quantitative estimation of new imiqualine leads with potent anticancer activities in rat and mouse plasma. Application to a pharmacokinetic study in mice. J Pharm Biomed Anal. 2018 Jan 30;148:369-379. doi: 10.1016/j.jpba.2017.10.025. Epub 2017 Oct 24. PMID: 29111492. 12: Chouchou A, Patinote C, Cuq P, Bonnet PA, Deleuze-Masquéfa C. Imidazo[1,2-a]quinoxalines Derivatives Grafted with Amino Acids: Synthesis and Evaluation on A375 Melanoma Cells. Molecules. 2018 Nov 15;23(11):2987. doi: 10.3390/molecules23112987. PMID: 30445763; PMCID: PMC6278480.

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