Fotemustine

Title: Fotemustine
CAS Registry Number: 92118-27-9
CAS Name: [1-[[[(2-Chloroethyl)nitrosoamino]carbonyl]amino]ethyl]phosphonic acid diethyl ester
Additional Names: (±)-diethyl [1-[3-(2-chloroethyl)-3-nitrosoureido]ethyl]phosphonate; 1-[N-(2-chloroethyl)-N-nitrosoureido]ethylphosphonic acid diethyl ester
Manufacturers' Codes: S-10036
Trademarks: Muphoran (Servier)
Molecular Formula: C9H19ClN3O5P
Molecular Weight: 315.69
Percent Composition: C 34.24%, H 6.07%, Cl 11.23%, N 13.31%, O 25.34%, P 9.81%
Literature References: Amino acid-linked nitrosourea alkylating agent. Prepn: G. Lavielle, C. Cudennec, FR 2536075; eidem, US 4567169 (1984, 1986 both to ADIR). Clinical evaluation in advanced cancers: D. Khayat et al., Cancer Res. 47, 6782 (1987); in disseminated malignant melanoma: D. Khayat et al., J. Natl. Cancer Inst. 80, 1407 (1988).
Properties: mp 85°.
Melting point: mp 85°
Therap-Cat: Antineoplastic.
Keywords: Antineoplastic; Alkylating Agents; Nitrosoureas.
Frangula Frangulin Fraxetin Fraxin Fredericamycin A

Fotemustine
Fotemustine.svg
Systematic (IUPAC) name
(RS)-diethyl (1-{[(2-chloroethyl)(nitroso)carbamoyl]amino}
ethyl)phosphonate
Clinical data
AHFS/Drugs.com International Drug Names
Legal status  ?
Identifiers
CAS number 92118-27-9 N
ATC code L01AD05
PubChem CID 104799
DrugBank DB04106
ChemSpider 94600 YesY
UNII GQ7JL9P5I2 YesY
KEGG D07255 YesY
ChEMBL CHEMBL549386 YesY
Chemical data
Formula C9H19ClN3O5P 
Mol. mass 315.691 g/mol
 N (what is this?)  (verify)

Fotemustine is a nitrosourea alkylating agent approved for use in the treatment of metastasising melanoma. A study[1] has shown that fotemustine produces improved response rates and but does not increase survival (over dacarbazine in the treatment of disseminated cutaneous melanoma. Median survival was 7.3 months with fotemustine versus 5.6 months with DTIC (P=.067). There was also toxicity prevalence in fotemustine arm. The main toxicity was grade 3 to 4 neutropenia (51% with fotemustine v 5% with DTIC) and thrombocytopenia (43% v 6%, respectively).