4-Hydroxycyclophosphamide

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4-Hydroxycyclophosphamide is in the class of oxazaphosphorine compounds, and is the main, active metaboliteofcyclophosphamide 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]

4-Hydroxycyclophosphamide
Identifiers

IUPAC name 2-[bis(2-Chloroethyl)amino]-4-hydroxy-2H1,3,2-oxazaphosphinan-2-one
CAS Number	40277-05-2^N
PubChem CID	99735
ChemSpider	90110^N
UNII	1XBF4E50HS
ChEMBL	ChEMBL731^N
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)^N Key:RANONBLIHMVXAJ-UHFFFAOYSA-N^N
^NY (what is this?) (verify)

References

^ 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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Retrieved from "https://en.wikipedia.org/w/index.php?title=4-Hydroxycyclophosphamide&oldid=1172449540" Last edited on 27 August 2023, at 04:43

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