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

• ChemBase ID: 165524
• Molecular Formular: C5H12ClN2O2P
• Molecular Mass: 198.587741
• Monoisotopic Mass: 198.03249194
• SMILES: C1COP(=O)(NC1)NCCCl
• Canonical SMILES: ClCCNP1(=O)NCCCO1
• InChI: InChI=1S/C5H12ClN2O2P/c6-2-4-8-11(9)7-3-1-5-10-11/h1-5H2,(H2,7,8,9)
• InChIKey: DZKGMGPLDJOVCX-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(2-chloroethyl)amino]-1,3,2λ^5-oxazaphosphinan-2-one
• IUPAC Traditional name: 3-dechloroethylifosfamide
• Synonyms: N-(2-Chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-Oxide; 2-(2-Chloroethylamino)tetrahydro-2H-1,3,2-oxazaphosphorine 2-oxide; 3-Dechloroethylifosfamide; Asta 4968; Dechloroethylcyclophosphamide; Monochloroethylcyclophosphamide; N-Dechloroethyl Cyclophosphamide

Database IDs

• CAS Number: 36761-83-8
• PubChem SID: 162259657
• PubChem CID: 114861

CALCULATED PROPERTIES

• Acid pKa: 12.733573
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): -0.7916182
• LogD (pH = 7.4): -0.79162
• Log P: -0.7916182
• Molar Refractivity: 44.2381 cm^3
• Polarizability: 17.82817 Å^3
• Polar Surface Area: 50.36 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - D226400

A metabolite of Cyclophosphamide (C988580).

REFERENCES

• Bohnenstengel, F., et al.: Eur. J. Clin. Pharmacol., 51, 297 (1996)
• Busse, D., et al.: J. Clin. Oncol., 15, 188 (1996)
• Roy, P., et al.: Drug Metab. Dispos., 27, 655 (1996)