Carmustine

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Contents

Carmustine (BCNU or bis-chloronitrosourea, BiCNU, Gliadel)

Effective Against

Several types of Brain cancer (including glioma, glioblastoma multiforme, medulloblastoma and astrocytoma), multiple myeloma and lymphoma (Hodgkin's and non-Hodgkin)

Carmustine is a highly lipophilic nitrosourea compound which undergoes hydrolysis in vivo to form reactive metabolites. These metabolites cause alkylation and cross-linking of DNA and RNA. Other biologic effects include inhibition of DNA repair, de-novo purine synthesis and some cell cycle phase-specificity. Nitrosoureas generally lack cross-resistance with other alkylating agents.

Cost

From Sigma-Aldrich: 53.40 USD (25mg) or 179 USD (100mg)

Reported Routes of Synthesis

Please reference Vardnayan, R and Hruby, V. Synthesis of Essential Drugs. Elsevier:2006. pg. 400 for a short synthesis.




Image:CarmustineSynthesis2.jpg

Kar, Ashutosh. Medicinal Chemistry. New Age International: 2005. pg. 687

Cost of Starting Materials and Selected Reagents:
Starting Material 1,3-bis(2-chloroethyl)urea pricing not available from Sigma-Aldrich
Sodium nitrite from Sigma-Aldrich: 84.1 USD (25 g)
Formic acid (1 M in H2O) from Sigma-Aldrich: 124 USD (100 mL)




Image:CarmustineSynthesis3.jpg

Bregnedal, Peter (Allerod, DK), Buus, Jorn L. M. (Bjaeverskov, DK). 1983. 2-Chloroethyl urea derivatives. United States. Kefalas, A/s (Copenhagen-Valby, DK). 4384140

Cost of Reagents:
Sodium Amide from Sigma-Aldrich: 30.4 USD (25 g)
Lithium aluminum hydride from Sigma-Aldrich: 28.5 USD (10 g)
Aluminum chloride from Sigma-Aldrich: 85.3 USD (5 g)
3-Chloropropionamide from Sigma-Aldrich: 28.7 USD (5 g)

Submitted Syntheses