4-Hydroxycyclophosphamide

4-Hydroxycyclophosphamide
Identifiers
	IUPAC name 2-[bis(2-Chloroethyl)amino]-4-hydroxy-2H1,3,2-oxazaphosphinan-2-one;
CAS Number	40277-05-2 ;
PubChem CID	99735;
ChemSpider	90110 ;
UNII	1XBF4E50HS;
ChEMBL	ChEMBL731 ;
CompTox Dashboard (EPA)	DTXSID90960669 ;
Chemical and physical data
Formula	C7H15Cl2N2O3P
Molar mass	277.08 g·mol−1
3D model (JSmol)	Interactive image;
	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

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

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