Carboxycyclophosphamide

Carboxycyclophosphamide
Names

IUPAC name 3-({amino[bis(2-chloroethyl)amino]phosphoryl}oxy)propanoic acid
Other names Carboxyphosphamide
Identifiers
CAS Number	22788-18-7
ChemSpider	29229
Jmol interactive 3D	Image
PubChem	31515
InChI InChI=1S/C7H15Cl2N2O4P/c8-2-4-11(5-3-9)16(10,14)15-6-1-7(12)13/h1-6H2,(H2,10,14)(H,12,13) Key: QLAKAJLYYGOZQL-UHFFFAOYSA-N InChI=1/C7H15Cl2N2O4P/c8-2-4-11(5-3-9)16(10,14)15-6-1-7(12)13/h1-6H2,(H2,10,14)(H,12,13) Key: QLAKAJLYYGOZQL-UHFFFAOYAS
SMILES C(COP(=O)(N)N(CCCl)CCCl)C(=O)O
Properties
Chemical formula	C₇H₁₅Cl₂N₂O₄P
Molar mass	293.084762
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
Infobox references

Carboxycyclophosphamide is an inactive metabolite of the cytotoxic antineoplastic drug cyclophosphamide. In the metabolic pathway of cyclophosphamide inactivation it first metabolizes to 4-hydroxycyclophosphamide, then partially tautomerizes into aldophosphamide. Aldophosphamide then, in turn, is oxidized into carboxycyclophosphamide by the enzyme ALDH (aldehyde dehydrogenase).^[1]

References

↑ Dockham PA, Lee MO, Sladek NE. Identification of human liver aldehyde dehydrogenases that catalyze the oxidation of aldophosphamide and retinaldehyde. Biochem Pharmacol. 1992 Jun 9;43(11):2453-69

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