2-[bis(2-chloroethyl)amino](4,4,5,5-2H4)-1,3,2λ5-oxazaphosphinan-2-one

• ChemBase ID: 165245
• Molecular Formular: C7H15Cl2N2O2P
• Molecular Mass: 261.085961
• Monoisotopic Mass: 260.02481972
• SMILES: C1COP(=O)(NC1)N(CCCl)CCCl
• Canonical SMILES: ClCCN(P1(=O)NCCCO1)CCCl
• InChI: InChI=1S/C7H15Cl2N2O2P/c8-2-5-11(6-3-9)14(12)10-4-1-7-13-14/h1-7H2,(H,10,12)
• InChIKey: CMSMOCZEIVJLDB-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[bis(2-chloroethyl)amino](4,4,5,5-^2H₄)-1,3,2λ^5-oxazaphosphinan-2-one
• IUPAC Traditional name: 2-[bis(2-chloroethyl)amino](4,4,5,5-^2H₄)-1,3,2λ^5-oxazaphosphinan-2-one
• Synonyms: N,N-Bis(2-chloroethyl)tetrahydro-4,5-d2-2H-1,3,2-oxazaphosphorin-2-amine 2-Oxide; Cycloblastin-d4; Cyclostin-d4; Cytoxan-d4; Endoxan-d4; Genoxal-d4; Hexadrin-d4; Mitoxan-d4; NSC 26271-d4; Cyclophosphamide-d4

Database IDs

• CAS Number: 173547-45-0
• PubChem SID: 162259378
• PubChem CID: 10801618

CALCULATED PROPERTIES

• Acid pKa: 12.076543
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): 0.09654615
• LogD (pH = 7.4): 0.096539564
• Log P: 0.096547686
• Molar Refractivity: 58.4781 cm^3
• Polarizability: 23.373837 Å^3
• Polar Surface Area: 41.57 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Alcohol; Benzene; Chloroform; Dioxane; Ethylene Glycol
• Apperance: White to Off-White Solid
• Melting Point: 41-45°C

Safety Information

• Storage Condition: -20°C Freezer

DETAILS

Toronto Research Chemicals - C988582

It is a cytotoxic nitrogen mustard derivative widely used in cancer chemotherapy. It cross-links DNA, causes strand breakage, and induces mutations. Its clinical activity is associated with a decrease in aldehyde dehydrogenase 1 (ALDH1) activity. This sub

REFERENCES

• Wheeler, A.G., et al.: Toxicol. Appl. Pharmacol., 4, 324 (1962)
• Fraiser, L.H., et al.: Drugs, 42, 781 (1962)
• Colvin, O.M., et al.: Curr. Pharmaceut. Design, 5, 555 (1962)