2-[bis(2-chloroethyl)amino]-1,3,2λ5-oxazaphosphinane-2,4-dione

• ChemBase ID: 176001
• Molecular Formular: C7H13Cl2N2O3P
• Molecular Mass: 275.069481
• Monoisotopic Mass: 274.00408428
• SMILES: C1COP(=O)(NC1=O)N(CCCl)CCCl
• Canonical SMILES: ClCCN(P1(=O)OCCC(=O)N1)CCCl
• InChI: InChI=1S/C7H13Cl2N2O3P/c8-2-4-11(5-3-9)15(13)10-7(12)1-6-14-15/h1-6H2,(H,10,12,13)
• InChIKey: VBMZHOCORXMDJU-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[bis(2-chloroethyl)amino]-1,3,2λ^5-oxazaphosphinane-2,4-dione
• IUPAC Traditional name: 2-[bis(2-chloroethyl)amino]-1,3,2λ^5-oxazaphosphinane-2,4-dione
• Synonyms: 2-[Bis(2-chloroethyl)amino]tetrahydro-4H-1,3,2-oxazaphosphorin-4-one 2-Oxide; 4-Ketocyclophosphamide; Asta 5160; NSC 139488; 4-Oxo Cyclophosphamide

Database IDs

• CAS Number: 27046-19-1
• PubChem SID: 164231911
• PubChem CID: 33676

CALCULATED PROPERTIES

• Acid pKa: 8.212085
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.089360364
• LogD (pH = 7.4): -0.14330393
• Log P: -0.08861311
• Molar Refractivity: 58.3912 cm^3
• Polarizability: 23.547577 Å^3
• Polar Surface Area: 58.64 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: White Solid
• Melting Point: 139-141°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under Inert Atmosphere

DETAILS

Toronto Research Chemicals - O849900

A minor metabolite of Cyclophosphamide

REFERENCES

• Juma, F., et al.: Br. J. Clin. Pharmacol., 10, 327 (1980)
• Powers, J., et al.: Cancer Res., 43, 1101 (1980)
• Hardy, R., et al.: Ther. Drug Monit., 9, 221 (1980)