4-Hydroxycyclophosphamide
Identifiers
  • 2-[bis(2-Chloroethyl)amino]-4-hydroxy-2H1,3,2-oxazaphosphinan-2-one
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC7H15Cl2N2O3P
Molar mass277.08 g·mol−1
3D model (JSmol)
  • OC1CCOP(=O)(N1)N(CCCl)CCCl
  • InChI=1S/C7H15Cl2N2O3P/c8-2-4-11(5-3-9)15(13)10-7(12)1-6-14-15/h7,12H,1-6H2,(H,10,13) ☒N
  • Key:RANONBLIHMVXAJ-UHFFFAOYSA-N ☒N
 ☒NcheckY (what is this?)  (verify)

4-Hydroxycyclophosphamide is in the class of oxazaphosphorine compounds, and is the main, active metabolite of cyclophosphamide and of mafosfamide after they partially metabolized by cytochrome P450. It is then partially tautomerized into aldophosphamide, which, in turn, easily enters live cells and then is partially detoxified into inactive carboxycyclophosphamide by the enzyme ALDH, but partially is hydrolyzed by another cell's enzyme phosphatase to the two directly cytotoxic metabolites - phosphoramide mustard and acrolein.[1]

References

  1. ↑ Ludeman SM (August 1999). "The chemistry of the metabolites of cyclophosphamide". Current Pharmaceutical Design. 5 (8): 627–43. doi:10.2174/1381612805666230110215458. PMID 10469895.
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