4-Hydroxycyclophosphamide

4-Hydroxycyclophosphamide

Systematic (IUPAC) name
2-[Bis(2-chloroethyl)amino]-4-hydroxy-2H1,3,2-oxazaphosphinan-2-one
Identifiers
CAS Number	40277-05-2
PubChem	CID 99735
ChemSpider	90110
ChEMBL	CHEMBL731
Chemical data
Formula	C7H15Cl2N2O3P
Molar mass	277.08 g·mol^−1
SMILES OC1CCOP(=O)(N1)N(CCCl)CCCl
InChI 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) Key:RANONBLIHMVXAJ-UHFFFAOYSA-N
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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. The chemistry of the metabolites of cyclophosphamide. Curr Pharm Des. 1999 Aug;5(8):627-43. PMID 10469895