Misplaced Pages

4-Hydroxycyclophosphamide

Identifiers
IUPAC name 2--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
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
(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.

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.

This antineoplastic or immunomodulatory drug article is a stub. You can help Misplaced Pages by expanding it.

• v
• t
• e

• Antineoplastic and immunomodulating drug stubs
• Organochlorides
• IARC Group 1 carcinogens
• Oxazaphosphinans
• Nitrogen mustards
• Phosphorodiamidates
• Chloroethyl compounds