Mafosfamide

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

MedKoo CAT#: 205978

CAS#: 88859-04-5

Description: Mafosfamide 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.


Chemical Structure

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Mafosfamide
CAS# 88859-04-5

Theoretical Analysis

MedKoo Cat#: 205978
Name: Mafosfamide
CAS#: 88859-04-5
Chemical Formula: C9H19Cl2N2O5PS2
Exact Mass: 399.98501
Molecular Weight: 401.26732
Elemental Analysis: C, 26.94; H, 4.77; Cl, 17.67; N, 6.98; O, 19.94; P, 7.72; S, 15.98

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Synonym: Z-7557; Z7557; Z 7557; Mafosfamide

IUPAC/Chemical Name: 2-((2-(bis(2-chloroethyl)amino)-2-oxido-1,3,2-oxazaphosphinan-4-yl)thio)ethanesulfonic acid

InChi Key: BSGICWROEOGEDW-UHFFFAOYSA-N

InChi Code: InChI=1S/C9H20Cl2N2O5PS2/c10-2-4-13(5-3-11)19(14)12-9(1-6-18-19)20-7-8-21(15,16)17/h9,12,19H,1-8H2,(H,15,16,17)/q-1

SMILES Code: [O-]P1(N(CCCl)CCCl)OCCC(SCCS(=O)(O)=O)N1

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, not in water

Shelf Life: >5 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

Preparing Stock Solutions

The following data is based on the product molecular weight 401.26732 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

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1: Rico MJ, Matar P, Scharovsky OG. Modulation of IL-10/IL-10R expression by mafosfamide, a derivative of 4-hydroxycyclophosphamide, in a rat B-cell lymphoma. Biocell. 2012 Aug;36(2):91-5. PubMed PMID: 23185784.

2: 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. 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). J Neurooncol. 2012 Sep;109(3):565-71. doi: 10.1007/s11060-012-0929-x. Epub 2012 Jul 13. PubMed PMID: 22790443; PubMed Central PMCID: PMC3529096.

3: Harati K, Chromik AM, Bulut D, Goertz O, Hahn S, Hirsch T, Klein-Hitpass L, Lehnhardt M, Uhl W, Daigeler A. TRAIL and taurolidine enhance the anticancer activity of doxorubicin, trabectedin and mafosfamide in HT1080 human fibrosarcoma cells. Anticancer Res. 2012 Jul;32(7):2967-84. PubMed PMID: 22753761.

4: Mazur L, Opydo-Chanek M, Stojak M, Wojcieszek K. Mafosfamide as a new anticancer agent: preclinical investigations and clinical trials. Anticancer Res. 2012 Jul;32(7):2783-9. Review. PubMed PMID: 22753738.

5: Goldstein M, Roos WP, Kaina B. Apoptotic death induced by the cyclophosphamide analogue mafosfamide in human lymphoblastoid cells: contribution of DNA replication, transcription inhibition and Chk/p53 signaling. Toxicol Appl Pharmacol. 2008 May 15;229(1):20-32. doi: 10.1016/j.taap.2008.01.001. Epub 2008 Jan 17. PubMed PMID: 18289623.

6: Jacob E, Scorsone K, Blaney SM, D'Argenio DZ, Berg SL. Synergy of karenitecin and mafosfamide in pediatric leukemia, medulloblastoma, and neuroblastoma cell lines. Pediatr Blood Cancer. 2008 Apr;50(4):757-60. PubMed PMID: 17849472; PubMed Central PMCID: PMC2975705.

7: Kobylinska A, Bednarek J, Blonski JZ, Hanausek M, Walaszek Z, Robak T, Kilianska ZM. In vitro sensitivity of B-cell chronic lymphocytic leukemia to cladribine and its combinations with mafosfamide and/or mitoxantrone. Oncol Rep. 2006 Dec;16(6):1389-95. PubMed PMID: 17089066.

8: McNiece I, Civin C, Harrington J, Kellner J, Malehorn M, Turney J, Barber J, Jones R. Ex vivo expansion of mafosfamide-purged PBPC products. Cytotherapy. 2006;8(5):459-64. PubMed PMID: 17050250.

9: Tsaryk R, Fabian K, Thacker J, Kaina B. Xrcc2 deficiency sensitizes cells to apoptosis by MNNG and the alkylating anticancer drugs temozolomide, fotemustine and mafosfamide. Cancer Lett. 2006 Aug 8;239(2):305-13. Epub 2005 Nov 18. PubMed PMID: 16298473.

10: Chamberlain MC. Mafosfamide: a new intra-CSF chemotherapy? J Clin Oncol. 2005 Oct 20;23(30):7748-9; author reply 7749. PubMed PMID: 16234539.



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