Mafosfamide

Mafosfamide

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 ASTA-Z-7557
Identifiers
CAS Number	88859-04-5  N
3D model (JSmol)	Interactive image
ChemSpider	16736958  Y
MeSH	Mafosfamide
PubChem CID	104746
UNII	5970HH9923  Y
CompTox Dashboard (EPA)	DTXSID90905075
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)/t9-,19-/m1/s1 Y Key: PBUUPFTVAPUWDE-AYLIAGHASA-N Y 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
SMILES O=P1(N[C@@H](CCO1)SCCS(O)(=O)=O)N(CCCl)CCCl
Properties
Chemical formula	C9H19Cl2N2O5PS2
Molar mass	401.25 g·mol−1
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). N  verify  (what is  YN ?) Infobox references

Mafosfamide (INN; development code ASTA-Z-7557) 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]

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.

Further reading

• Prous, J. R. (1983). "ASTA-Z-7557". Drugs of the Future. 8 (10): 839. doi:10.1358/dof.1983.008.10.61900. ISSN   0377-8282.