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MedKoo Cat#: 585435 | Name: XK 469

Description:

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

XK 469 is a quinoxaline anti-tumor agent that mediates its effects by topoisomerase IIB inhibition.

Chemical Structure

XK 469
XK 469
CAS#157434-99-6

Theoretical Analysis

MedKoo Cat#: 585435

Name: XK 469

CAS#: 157434-99-6

Chemical Formula: C17H12ClN2NaO4

Exact Mass: 366.0383

Molecular Weight: 366.73

Elemental Analysis: C, 55.68; H, 3.30; Cl, 9.67; N, 7.64; Na, 6.27; O, 17.45

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
XK 469; XK469; XK-469
IUPAC/Chemical Name
sodium;2-[4-(7-chloroquinoxalin-2-yl)oxyphenoxy]propanoate
InChi Key
OJENKXNXJPNEPU-UHFFFAOYSA-M
InChi Code
InChI=1S/C17H13ClN2O4.Na/c1-10(17(21)22)23-12-3-5-13(6-4-12)24-16-9-19-14-7-2-11(18)8-15(14)20-16;/h2-10H,1H3,(H,21,22);/q;+1/p-1
SMILES Code
CC(OC1=CC=C(OC2=NC3=CC(Cl)=CC=C3N=C2)C=C1)C([O-])=O.[Na+]
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
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 366.73 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: Burton RD, Hieronymus T, Chamem T, Heim D, Anderson S, Zhu X, Hutzler JM. Assessment of the Biotransformation of Low-Turnover Drugs in the HµREL Human Hepatocyte Coculture Model. Drug Metab Dispos. 2018 Nov;46(11):1617-1625. doi: 10.1124/dmd.118.082867. Epub 2018 Aug 22. PubMed PMID: 30135244. 2: Sinha BK, Kumar A, Mason RP. Nitric oxide inhibits ATPase activity and induces resistance to topoisomerase II-poisons in human MCF-7 breast tumor cells. Biochem Biophys Rep. 2017 Apr 20;10:252-259. doi: 10.1016/j.bbrep.2017.04.011. eCollection 2017 Jul. PubMed PMID: 28955753; PubMed Central PMCID: PMC5614683. 3: Xia QH, Hu W, Li C, Wu JF, Yang L, Han XM, Shen YM, Li ZY, Li X. Design, synthesis, biological evaluation and molecular docking study on peptidomimetic analogues of XK469. Eur J Med Chem. 2016 Nov 29;124:311-325. doi: 10.1016/j.ejmech.2016.08.010. Epub 2016 Aug 9. PubMed PMID: 27597408. 4: Huang CJ, Lee CL, Yang SH, Chien CC, Huang CC, Yang RN, Chang CC. Upregulation of the growth arrest-specific-2 in recurrent colorectal cancers, and its susceptibility to chemotherapy in a model cell system. Biochim Biophys Acta. 2016 Jul;1862(7):1345-53. doi: 10.1016/j.bbadis.2016.04.010. Epub 2016 Apr 13. PubMed PMID: 27085973. 5: Ramírez J, Kim TW, Liu W, Myers JL, Mirkov S, Owzar K, Watson D, Mulkey F, Gamazon ER, Stock W, Undevia S, Innocenti F, Ratain MJ. A pharmacogenetic study of aldehyde oxidase I in patients treated with XK469. Pharmacogenet Genomics. 2014 Feb;24(2):129-32. doi: 10.1097/FPC.0000000000000023. PubMed PMID: 24300566; PubMed Central PMCID: PMC3901533. 6: Hutzler JM, Yang YS, Albaugh D, Fullenwider CL, Schmenk J, Fisher MB. Characterization of aldehyde oxidase enzyme activity in cryopreserved human hepatocytes. Drug Metab Dispos. 2012 Feb;40(2):267-75. doi: 10.1124/dmd.111.042861. Epub 2011 Oct 26. PubMed PMID: 22031625. 7: Kakodkar NC, Peddinti R, Kletzel M, Tian Y, Guerrero LJ, Undevia SD, Geary D, Chlenski A, Yang Q, Salwen HR, Cohn SL. The quinoxaline anti-tumor agent (R+)XK469 inhibits neuroblastoma tumor growth. Pediatr Blood Cancer. 2011 Jan;56(1):164-7. doi: 10.1002/pbc.22639. PubMed PMID: 20860039; PubMed Central PMCID: PMC4116189. 8: Zientek M, Jiang Y, Youdim K, Obach RS. In vitro-in vivo correlation for intrinsic clearance for drugs metabolized by human aldehyde oxidase. Drug Metab Dispos. 2010 Aug;38(8):1322-7. doi: 10.1124/dmd.110.033555. Epub 2010 May 5. PubMed PMID: 20444863. 9: Yong WP, Kim TW, Undevia SD, Innocenti F, Ratain MJ. R(+)XK469 inhibits hydroxylation of S-warfarin by CYP2C9. Eur J Cancer. 2009 Jul;45(11):1904-8. doi: 10.1016/j.ejca.2009.04.032. Epub 2009 May 21. PubMed PMID: 19464879; PubMed Central PMCID: PMC2758059. 10: Ling ZH, Ding ZH. [Mechanisms of G2/M cycle arrest induced by topo IIalpha and II beta inhibitors in H460 cells]. Nan Fang Yi Ke Da Xue Xue Bao. 2008 Dec;28(12):2187-90. Chinese. PubMed PMID: 19114353. 11: Reiners JJ Jr, Kleinman M, Joiakim A, Mathieu PA. The chemotherapeutic agents XK469 (2-{4-[(7-chloro-2-quinoxalinyl)oxy]phenoxy}propionic acid) and SH80 (2-{4-[(7-bromo-2-quinolinyl)oxy]phenoxy}propionic acid) inhibit cytokinesis and promote polyploidy and induce senescence. J Pharmacol Exp Ther. 2009 Mar;328(3):796-806. doi: 10.1124/jpet.108.144808. Epub 2008 Dec 9. PubMed PMID: 19066341; PubMed Central PMCID: PMC2682258. 12: Undevia SD, Innocenti F, Ramirez J, House L, Desai AA, Skoog LA, Singh DA, Karrison T, Kindler HL, Ratain MJ. A phase I and pharmacokinetic study of the quinoxaline antitumour Agent R(+)XK469 in patients with advanced solid tumours. Eur J Cancer. 2008 Aug;44(12):1684-92. doi: 10.1016/j.ejca.2008.05.018. Epub 2008 Jul 21. PubMed PMID: 18650079; PubMed Central PMCID: PMC2731567. 13: Stock W, Undevia SD, Bivins C, Ravandi F, Odenike O, Faderl S, Rich E, Borthakur G, Godley L, Verstovsek S, Artz A, Wierda W, Larson RA, Zhang Y, Cortes J, Ratain MJ, Giles FJ. A phase I and pharmacokinetic study of XK469R (NSC 698215), a quinoxaline phenoxypropionic acid derivative, in patients with refractory acute leukemia. Invest New Drugs. 2008 Aug;26(4):331-8. doi: 10.1007/s10637-008-9129-0. Epub 2008 Apr 19. PubMed PMID: 18425419; PubMed Central PMCID: PMC4905709. 14: Bayes M, Rabasseda X, Prous JR. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2007 Apr;29(3):231-45. PubMed PMID: 17520107. 15: Pourpak A, Landowski TH, Dorr RT. Ethonafide-induced cytotoxicity is mediated by topoisomerase II inhibition in prostate cancer cells. J Pharmacol Exp Ther. 2007 Jun;321(3):1109-17. Epub 2007 Mar 9. PubMed PMID: 17351106. 16: Kessel D, Reiners JJ Jr, Hazeldine ST, Polin L, Horwitz JP. The role of autophagy in the death of L1210 leukemia cells initiated by the new antitumor agents, XK469 and SH80. Mol Cancer Ther. 2007 Jan;6(1):370-9. PubMed PMID: 17237296; PubMed Central PMCID: PMC2877038. 17: Alousi AM, Boinpally R, Wiegand R, Parchment R, Gadgeel S, Heilbrun LK, Wozniak AJ, DeLuca P, LoRusso PM. A phase 1 trial of XK469: toxicity profile of a selective topoisomerase IIbeta inhibitor. Invest New Drugs. 2007 Apr;25(2):147-54. Epub 2006 Nov 11. PubMed PMID: 17103044. 18: Zhang Y, Hua Y, Benbrook DM, Covey JM, Dai G, Liu Z, Chan KK. High performance liquid chromatographic analysis and preclinical pharmacokinetics of the heteroarotinoid antitumor agent, SHetA2. Cancer Chemother Pharmacol. 2006 Nov;58(5):561-9. Epub 2006 Mar 14. PubMed PMID: 16534614. 19: Zhao CH, Chen Y, Ding J, Duan WH. [Design and synthesis of quinoxaline derivatives and their antitumor activities]. Yao Xue Xue Bao. 2005 Sep;40(9):814-9. Chinese. PubMed PMID: 16342683. 20: Hazeldine ST, Polin L, Kushner J, White K, Corbett TH, Horwitz JP. Synthesis and biological evaluation of conformationally constrained analogs of the antitumor agents XK469 and SH80. Part 5. Bioorg Med Chem. 2006 Apr 1;14(7):2462-7. Epub 2005 Dec 5. PubMed PMID: 16337128.