Mafosfamide

Mafosfamide (INN) is an oxazaphosphorine (cyclophosphamide-like) alkylating agent under investigation as a chemotherapeutic. It is metabolized by cytochrome P450 into 4-hydroxycyclophosphamide, which is then converted into aldophosphamide, which, in turn yields the cytotoxic metabolites phosphoramide mustard and acrolein.[1]

Mafosfamide
Skeletal formula
Ball-and-stick model
Names
IUPAC name
2-{(2-[bis(2-chloroethyl)amino]-2-oxido-1,3,2-oxazaphosphinan-4-yl}thio)ethanesulfonic acid
Other names
2-{[2-[bis(2-chloroethyl)amino]-2-oxo-1-oxa-3-aza-2λ5-phosphacyclohex-4-yl}sulfanyl]ethanesulfonic acid
Identifiers
3D model (JSmol)
ChemSpider
MeSH Mafosfamide
UNII
  • 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)/t9-,19-/m1/s1 checkY
    Key: PBUUPFTVAPUWDE-AYLIAGHASA-N checkY
  • InChI=1/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)/t9-,19-/m1/s1
    Key: PBUUPFTVAPUWDE-AYLIAGHABO
  • O=P1(N[C@@H](CCO1)SCCS(O)(=O)=O)N(CCCl)CCCl
Properties
C9H19Cl2N2O5PS2
Molar mass 401.269 g/mol
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references

Several Phase I trials have been completed.[2][3]

References
  1. Ludeman SM. The chemistry of the metabolites of cyclophosphamide. Curr Pharm Des. 1999 Aug;5(8):627-43. PMID 10469895
  2. "Intrathecal Mafosfamide". ClinicalTrials.gov. U.S. National Institutes of Health. August 21, 2006. Retrieved 2007-07-13. ClinicalTrials.gov Identifier NCT00062881.
  3. "Mafosfamide in Treating Patients With Progressive or Refractory Meningeal Tumors". ClinicalTrials.gov. U.S. National Institutes of Health. February 20, 2007. Retrieved 2007-07-13. ClinicalTrials.gov Identifier NCT00031928.
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