Evofosfamide - CAS 918633-87-1
Catalog number: B0084-460516
Category: Inhibitor
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Evofosfamide is a hypoxia-activated prodrug consisting of a 2-nitroimidazole phosphoramidate conjugate with potential antineoplastic activity. The 2-nitroimidazole moiety of hypoxia-activated prodrug TH-302 acts as a hypoxic trigger, releasing the DNA-alkylating dibromo isophosphoramide mustard moiety within hypoxic regions of tumors. Normoxic tissues may be spared due to the hypoxia-specific activity of this agent, potentially reducing systemic toxicity.
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B0084-460516 50 mg $499 In stock
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> 98%
Off-White to Pale Yellow Solid
TH-302; TH 302; TH302; 2-bromo-N-[(2-bromoethylamino)-[(3-methyl-2-nitroimidazol-4-yl)methoxy]phosphoryl]ethanamine
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1.Hypoxia-Activated Prodrug TH-302 Targets Hypoxic Bone Marrow Niches in Preclinical Leukemia Models.
Benito J1, Ramirez MS2, Millward NZ3, Velez J1, Harutyunyan KG1, Lu H1, Shi YX1, Matre P1, Jacamo R1, Ma H1, Konoplev S4, McQueen T1, Volgin A5, Protopopova M6, Mu H1, Lee J2, Bhattacharya PK7, Marszalek JR6, Davis RE8, Bankson JA2, Cortes JE1, Hart CP9, Clin Cancer Res. 2016 Apr 1;22(7):1687-98. doi: 10.1158/1078-0432.CCR-14-3378. Epub 2015 Nov 24.
PURPOSE: To characterize the prevalence of hypoxia in the leukemic bone marrow, its association with metabolic and transcriptional changes in the leukemic blasts and the utility of hypoxia-activated prodrug TH-302 in leukemia models.
2.Anticancer efficacy of the hypoxia-activated prodrug evofosfamide (TH-302) in osteolytic breast cancer murine models.
Liapis V1, Zinonos I1, Labrinidis A1, Hay S1, Ponomarev V2, Panagopoulos V1, Zysk A1, DeNichilo M1, Ingman W3,4, Atkins GJ5, Findlay DM5, Zannettino AC6, Evdokiou A1. Cancer Med. 2016 Mar;5(3):534-45. doi: 10.1002/cam4.599. Epub 2016 Jan 9.
Tumor hypoxia is a major cause of treatment failure for a variety of malignancies. However, hypoxia offers treatment opportunities, exemplified by the development of compounds that target hypoxic regions within tumors. Evofosfamide (TH-302) is a prodrug created by the conjugation of 2-nitroimidazole to bromo-isophosphoramide mustard (Br-IPM). When evofosfamide is delivered to hypoxic regions, the DNA cross-linking effector, Br-IPM, is released. This study assessed the cytotoxic activity of evofosfamide in vitro and its antitumor activity against osteolytic breast cancer either alone or in combination with paclitaxel in vivo. A panel of human breast cancer cell lines were treated with evofosfamide under hypoxia and assessed for cell viability. Osteolytic MDA-MB-231-TXSA cells were transplanted into the mammary fat pad, or into tibiae of mice, allowed to establish and treated with evofosfamide, paclitaxel, or both. Tumor burden was monitored using bioluminescence, and cancer-induced bone destruction was measured using micro-CT.
3.Comparison of hypoxia-activated prodrug evofosfamide (TH-302) and ifosfamide in preclinical non-small cell lung cancer models.
Sun JD1, Liu Q1, Ahluwalia D1, Ferraro DJ1, Wang Y1, Jung D1, Matteucci MD1, Hart CP1. Cancer Biol Ther. 2016 Apr 2;17(4):371-80. doi: 10.1080/15384047.2016.1139268. Epub 2016 Jan 28.
Evofosfamide (TH-302) is a hypoxia-activated prodrug of the cytotoxin bromo-isophosphoramide. In hypoxic conditions Br-IPM is released and alkylates DNA. Ifosfamide is a chloro-isophosphoramide prodrug activated by hepatic Cytochrome P450 enzymes. Both compounds are used for the treatment of cancer. Ifosfamide has been approved by the FDA while evofosfamide is currently in the late stage of clinical development. The purpose of this study is to compare efficacy and safety profile of evofosfamide and ifosfamide in preclinical non-small cell lung cancer H460 xenograft models. Immunocompetent CD-1 mice and H460 tumor-bearing immunocompromised nude mice were used to investigate the safety profile. The efficacy of evofosfamide or ifosfamide, alone, and in combination with docetaxel or sunitinib was compared in ectopic and intrapleural othortopic H460 xenograft models in animals exposed to ambient air or different oxygen concentration breathing conditions.
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CAS 918633-87-1 Evofosfamide

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