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

• ChemBase ID: 179351
• Molecular Formular: C9H18Cl3N2O2P
• Molecular Mass: 323.584181
• Monoisotopic Mass: 322.0171475
• SMILES: O1CCCN(P1(=O)N(CCCl)CCCl)CCCl
• Canonical SMILES: ClCCN(P1(=O)OCCCN1CCCl)CCCl
• InChI: InChI=1S/C9H18Cl3N2O2P/c10-2-6-13-5-1-9-16-17(13,15)14(7-3-11)8-4-12/h1-9H2
• InChIKey: UMKFEPPTGMDVMI-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[bis(2-chloroethyl)amino]-3-(2-chloroethyl)-1,3,2λ^5-oxazaphosphinan-2-one
• IUPAC Traditional name: trofosfamide
• Synonyms: N,N,3-Tris(2-chloroethyl)tetrahydro-2H-1,3,2-oxazaphosphorin-2-amine 2-Oxide; Ixoten; NSC 109723; Trifosfamide; Trilofosfamida; Trilophosphamide; Triphosphamide; Trisfosfamide; Trophosphamide; Z 4828; Trofosfamide

Database IDs

• CAS Number: 22089-22-1
• PubChem SID: 164235261
• PubChem CID: 65702

CALCULATED PROPERTIES

• H Acceptors: 2
• H Donor: 0
• LogD (pH = 5.5): 0.98471165
• LogD (pH = 7.4): 0.98471355
• Log P: 0.9847136
• Molar Refractivity: 72.7181 cm^3
• Polarizability: 28.919548 Å^3
• Polar Surface Area: 32.78 Å^2
• Rotatable Bonds: 7
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Methanol
• Apperance: Off-White Low Melting Solid
• Melting Point: 47-49°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - T892000

Antineoplastic; one derivative of of cyclophosphamide (NSC-26271).

REFERENCES

• Potel, J., et al.: Arzneim.-Forsch., 21, 1250 (1971)
• Bria, E., et al.: Cancer Treat. Rev., 32, 583 (1971)
• Faivre, S., et al.: J. Clin. Oncol., 24, 25 (2006).