2-[bis(2-chloroethyl)amino]-4-hydroperoxy-1,3,2λ5-oxazaphosphinan-2-one

• ChemBase ID: 170058
• Molecular Formular: C7H15Cl2N2O4P
• Molecular Mass: 293.084761
• Monoisotopic Mass: 292.01464896
• SMILES: C1COP(=O)(NC1OO)N(CCCl)CCCl
• Canonical SMILES: ClCCN(P1(=O)OCCC(N1)OO)CCCl
• InChI: InChI=1S/C7H15Cl2N2O4P/c8-2-4-11(5-3-9)16(13)10-7(15-12)1-6-14-16/h7,12H,1-6H2,(H,10,13)
• InChIKey: VPAWVRUHMJVRHU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[bis(2-chloroethyl)amino]-4-hydroperoxy-1,3,2λ^5-oxazaphosphinan-2-one
• IUPAC Traditional name: 4-hydroperoxycyclophosphamide
• Synonyms: 2-[Bis(2-chloroethyl)amino]tetrahydro-2-oxido-2H-1,3,2-oxazaphosphorin-4-yl Hydroperoxide; 4-Hydroperoxycyclofosfamide; Asta 6496; 4-Hydroperoxy Cyclophosphamide

Database IDs

• CAS Number: 39800-16-3
• PubChem SID: 164225968
• PubChem CID: 38347

CALCULATED PROPERTIES

• Acid pKa: 10.253673
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): 0.3919943
• LogD (pH = 7.4): 0.3914613
• Log P: 0.3920025
• Molar Refractivity: 60.4446 cm^3
• Polarizability: 24.85185 Å^3
• Polar Surface Area: 71.03 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane
• Apperance: White Solid

Safety Information

• Storage Condition: Hygroscopic, -86°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - H714675

A metabolite of Cyclophosphamide. Antineoplastic; bone marrow purging agent.

REFERENCES

• Takamizawa, A., et al.: J. Med. Chem., 18, 376 (1975)
• Jones, R.J., et al.: J. Hematother., 1, 343 (1975)
• Biggs, D., et al.: Prog. Clin. Biol. Res., 389, 9 (1975)