Carboxycyclophosphamide

Last updated
Carboxycyclophosphamide
Carboxycyclophosphamide.svg
Names
Preferred IUPAC name
3-({Amino[bis(2-chloroethyl)amino]phosphoryl}oxy)propanoic acid
Other names
Carboxyphosphamide
Identifiers
3D model (JSmol)
ChemSpider
PubChem CID
UNII
  • 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
  • C(COP(=O)(N)N(CCCl)CCCl)C(=O)O
Properties
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).

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

  1. ↑ Dockham, PA; Lee, MO; Sladek, NE (1992). "Identification of human liver aldehyde dehydrogenases that catalyze the oxidation of aldophosphamide and retinaldehyde". Biochem Pharmacol. 43 (11): 2453–69. doi:10.1016/0006-2952(92)90326-e. PMID   1610409.
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