diethyl (1-{[N-(2-chloroethyl)-N'-oxohydrazinecarbonyl]amino}ethyl)phosphonate

• ChemBase ID: 154568
• Molecular Formular: C9H19ClN3O5P
• Molecular Mass: 315.691021
• Monoisotopic Mass: 315.07508503
• SMILES: CCOP(=O)(C(C)NC(=O)N(CCCl)N=O)OCC
• Canonical SMILES: ClCCN(C(=O)NC(P(=O)(OCC)OCC)C)N=O
• InChI: InChI=1S/C9H19ClN3O5P/c1-4-17-19(16,18-5-2)8(3)11-9(14)13(12-15)7-6-10/h8H,4-7H2,1-3H3,(H,11,14)
• InChIKey: YAKWPXVTIGTRJH-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: diethyl (1-{[N-(2-chloroethyl)-N'-oxohydrazinecarbonyl]amino}ethyl)phosphonate
• IUPAC Traditional name: fotemustine
• Synonyms: Mustophorane; (+-)-Diethyl (1-(3-(2-chloroethyl)-3-nitrosoureido)ethyl)phosphonate; Muphoran; P-[1-[[[(2-Chloroethyl)nitrosoamino]carbonyl]amino]ethyl]-phosphonic acid diethyl ester; S 10036; Fotemustine; Diethyl (1-(3-(2-chloroethyl)-3-nitrosoureido)ethyl)phosphonate

Database IDs

• CAS Number: 92118-27-9
• MDL Number: MFCD00866278
• PubChem SID: 162248706
• PubChem CID: 104799

CALCULATED PROPERTIES

• Acid pKa: 11.064619
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): 1.281335
• LogD (pH = 7.4): 1.2812502
• Log P: 1.2813362
• Molar Refractivity: 71.4238 cm^3
• Polarizability: 27.539778 Å^3
• Polar Surface Area: 97.3 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: H2O: ≥1 mg/mL
• Apperance: light yellow powder

Safety Information

• Storage Condition: protect from light
• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 3
• Risk Statements: 40
• Safety Statements: 36/37
• GHS Pictograms: GHS08
• GHS Signal Word: Warning
• GHS Hazard statements: H351
• GHS Precautionary statements: P281
• Storage Temperature: 2-8°C

Product Information

• Purity: ≥98% (HPLC); 95+%
• Empirical Formula (Hill Notation): C9H19ClN3O5P

DETAILS

Sigma Aldrich - F7307

Biochem/physiol Actions
Fotemustine is a third generation nitrosourea, chloroethylating agent used in the treatment of glioma and malignant melanoma.