91390-37-3

Basic information

• Product Name: 1-(2-fluoroethyl)-3-[(1S,2R)-2-hydroxycyclohexyl]-1-nitrosourea
• CAS NO: 91390-37-3
• Molecular Formula: C₉H₁₆FN₃O₃
• Molecular Weight: 233.24
• Mol File: 91390-37-3.mol
• Article Data: 1

Chemical Properties

• Density: 1.42g/cm³
• Refractive Index: 1.572
• CAS DataBase Reference: 1-(2-fluoroethyl)-3-[(1S,2R)-2-hydroxycyclohexyl]-1-nitrosourea(CAS DataBase Reference)
• NIST Chemistry Reference: 1-(2-fluoroethyl)-3-[(1S,2R)-2-hydroxycyclohexyl]-1-nitrosourea(91390-37-3)
• EPA Substance Registry System: 1-(2-fluoroethyl)-3-[(1S,2R)-2-hydroxycyclohexyl]-1-nitrosourea(91390-37-3)

Safety Data

• Hazardous Substances Data: 91390-37-3(Hazardous Substances Data)

Usage

Chemical class

Nitrosoureas

Potency

Potent alkylating agent

Antineoplastic properties

Inhibits the growth of cancer cells

Mechanism of action

DNA cross-linking

Effect on cancer cells

Prevents replication and transcription, leading to cell death

Cancer types treated

Brain tumors, melanoma, and lymphomas

Administration method

Injection

Dose-limiting toxicities

Myelosuppression and gastrointestinal disturbances

Side effects

Potential for severe side effects

Research status

Active research in oncology for treatment of certain malignancies

Upstream product

• 931-16-8 (+/-)-trans-2-aminocyclohexanol 
• 91390-33-9 2-nitrophenyl (2-fluoroethyl)nitrosocarbamate 

Relevant articles and documents

Studies on Synthesis and Anticancer Activity of Selected N-(2-Fluoroethyl)-N-nitrosoureas

An activated carbamate, 2-nitrophenyl (2-fluoroethyl)nitrosocarbamate (3), was used to advantage in the synthesis of the water-soluble (2-fluoroethyl)nitrosoureas 6a-d from 2-aminoethanol, (1α,2β,3α)-2-amino-1,3-cyclohexanediol, cis-2-hydroxycyclohexanol, and 2-amino-2-deoxy-D-glucose.In a variation of this method, 2,4,5-trichlorophenyl (2-fluoroethyl)carbamate (4) was used to prepare the urea from which the essentially water-insoluble N'-(2,6-dioxo-3-piperidinyl)-N-(2-fluoroethyl)-N-nitrosourea (6e) was derived.The anticancer activity of these nitrosoureas was determined against the murine tumors B16 melanoma and Lewis lung carcinoma and found to be significant and comparable to their chloroethyl counterparts.On the basis of results from both systems, the dihydroxycyclohexyl derivative 6b may be the most effective.