Mafosfamide

• CAT Number: I000009
• CAS Number: 88859-04-5
• Molecular Formula: C9H19Cl2N2O5PS2
• Molecular Weight: 401.254
• Purity: ≥95%
• Synonyms: Z-7557; Z7557; Z 7557; Mafosfamide
• Storage: Store at -20°C
• IUPAC Name: 2-[[2-[bis(2-chloroethyl)amino]-2-oxo-1,3,2$l^{5}
• InChI: InChI=1S/C9H19Cl2N2O5PS2/c10-2-4-13(5-3-11)19(14)12-9(1-6-18-19)20-7-8-21(15,16)17/h9H,1-8H2,(H,12,14)(H,15,16,17)
• InChIKey: PBUUPFTVAPUWDE-UHFFFAOYSA-N
• SMILES: C1COP(=O)(NC1SCCS(=O)(=O)O)N(CCCl)CCCl

Mafosfamide(cas 88859-04-5) is a synthetic oxazaphosphorine derivative with antineoplastic properties. Mafosfamide alkylates DNA, forming DNA cross-links and inhibiting DNA synthesis. Although closely related to cyclophosphamide, mafosfamide, unlike cyclophosphamide, does not require hepatic activation to generate its active metabolite 4-hydroxy-cyclophosphamide; accordingly, mafosfamide is potentially useful in the intrathecal treatment of neoplastic meningitis.

Reference

1:Selective ALDH3A1 inhibition by benzimidazole analogues increase mafosfamide sensitivity in cancer cells. Parajuli B, Fishel ML, Hurley TD.J Med Chem. 2014 Jan 23;57(2):449-61. doi: 10.1021/jm401508p. Epub 2014 Jan 10. PMID: 24387105 Free PMC Article2:Shiga toxin 1, as DNA repair inhibitor, synergistically potentiates the activity of the anticancer drug, mafosfamide, on raji cells. Brigotti M, Arfilli V, Carnicelli D, Rocchi L, Calcabrini C, Ricci F, Pagliaro P, Tazzari PL, Alfieri RR, Petronini PG, Sestili P.Toxins (Basel). 2013 Feb 21;5(2):431-44. doi: 10.3390/toxins5020431. PMID: 23430607 Free PMC Article3:Modulation of IL-10/IL-10R expression by mafosfamide, a derivative of 4-hydroxycyclophosphamide, in a rat B-cell lymphoma. Rico MJ, Matar P, Scharovsky OG.Biocell. 2012 Aug;36(2):91-5. PMID: 23185784 4:Pilot study of systemic and intrathecal mafosfamide followed by conformal radiation for infants with intracranial central nervous system tumors: a pediatric brain tumor consortium study (PBTC-001). Blaney SM, Kocak M, Gajjar A, Chintagumpala M, Merchant T, Kieran M, Pollack IF, Gururangan S, Geyer R, Phillips P, McLendon RE, Packer R, Goldman S, Banerjee A, Heideman R, Boyett JM, Kun L.J Neurooncol. 2012 Sep;109(3):565-71. doi: 10.1007/s11060-012-0929-x. Epub 2012 Jul 13. PMID: 22790443 Free PMC Article5:TRAIL and taurolidine enhance the anticancer activity of doxorubicin, trabectedin and mafosfamide in HT1080 human fibrosarcoma cells. Harati K, Chromik AM, Bulut D, Goertz O, Hahn S, Hirsch T, Klein-Hitpass L, Lehnhardt M, Uhl W, Daigeler A.Anticancer Res. 2012 Jul;32(7):2967-84. PMID: 22753761 6:Mafosfamide as a new anticancer agent: preclinical investigations and clinical trials. Mazur L, Opydo-Chanek M, Stojak M, Wojcieszek K.Anticancer Res. 2012 Jul;32(7):2783-9. Review. PMID: 22753738 7:Apoptotic death induced by the cyclophosphamide analogue mafosfamide in human lymphoblastoid cells: contribution of DNA replication, transcription inhibition and Chk/p53 signaling. Goldstein M, Roos WP, Kaina B.Toxicol Appl Pharmacol. 2008 May 15;229(1):20-32. doi: 10.1016/j.taap.2008.01.001. Epub 2008 Jan 17. PMID: 18289623 8:Synergy of karenitecin and mafosfamide in pediatric leukemia, medulloblastoma, and neuroblastoma cell lines. Jacob E, Scorsone K, Blaney SM, D/’Argenio DZ, Berg SL.Pediatr Blood Cancer. 2008 Apr;50(4):757-60. PMID: 17849472 Free PMC Article9:In vitro sensitivity of B-cell chronic lymphocytic leukemia to cladribine and its combinations with mafosfamide and/or mitoxantrone. Kobylinska A, Bednarek J, Blonski JZ, Hanausek M, Walaszek Z, Robak T, Kilianska ZM.Oncol Rep. 2006 Dec;16(6):1389-95. PMID: 17089066 10:Ex vivo expansion of mafosfamide-purged PBPC products. McNiece I, Civin C, Harrington J, Kellner J, Malehorn M, Turney J, Barber J, Jones R.Cytotherapy. 2006;8(5):459-64. PMID: 17050250