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Showing posts with label Buthionine Sulphoximine. Show all posts
Showing posts with label Buthionine Sulphoximine. Show all posts

Wednesday, 11 May 2016

Buthionine Sulphoximine

Skeletal formula of buthionine sulfoximine
Buthionine Sulphoximine
NDA Filed in china
A gamma-glutamylcysteine synthetase inhibitor potentially for the treatment of solid tumors.
 NSC-326231; BSO
CAS No. 5072-26-4
BUTHIONINE SULFOXIMINE; DL-Buthionine-[S,R]-sulfoximine; 5072-26-4; Buthionine sulfoxamine; Buthionine-S,R-sulfoximine; Buthione sulfoximine;
Molecular Formula:C8H18N2O3S
Molecular Weight:222.30512 g/mol
Buthionine sulfoximine (BSO) is a sulfoximine which reduces levels of glutathione and is being investigated as an adjunct withchemotherapy in the treatment of cancer.[1] The compound inhibits gamma-glutamylcysteine synthetase, the enzyme required in the first step of glutathione synthesis. Buthionine sulfoximine may also be used to increase the sensitivity of parasites to oxidativeantiparasitic drugs.[2]
Buthionine sulphoximine is an oncolytic agent in early clinical development at the National Cancer Institute (NCI) for the treatment of neuroblastoma in pediatric patients in combination with melphalan and bone marrow or peripheral stem cell transplantation.



Methionine and buthionine sulfoximines: Syntheses under mild and safe imidation/oxidation conditions
Advanced Synthesis&Catalysis (2014), 356, (10), 2209-2213


Thumbnail image of graphical abstract
Methionine and buthionine sulfoximines (MSO and BSO) are non-natural amino acids known to inhibit the biosynthesis of glutathione (GSH). The current syntheses of these biologically active molecules involve harsh reaction conditions and the use of hazardous reagents for the sulfur imidation. Here, improved syntheses of MSO and BSO are presented including safe and mild one-pot imidation/oxidation sequences and single-step deprotections of three different functionalities.

Methionine and Buthionine Sulfoximines: Syntheses under Mild and Safe Imidation/Oxidation Conditions

  1. Laura Buglioni,
  2. Vincent Bizet and
  3. Carsten Bolm*
DOI: 10.1002/adsc.201400354



  1.  Defty, CL; Marsden, JR (2012). "Melphalan in regional chemotherapy for locally recurrent metastatic melanoma.". Current topics in medicinal chemistry 12 (1): 53–60. PMID 22196271.
  2.  "Definition of buthionine sulfoximine - National Cancer Institute Drug Dictionary".
Buthionine sulfoximine
Skeletal formula of buthionine sulfoximine
Ball-and-stick model of buthionine sulfoximine as a zwitterion
IUPAC name
2-amino-4-(butylsulfonimidoyl)butanoic acid
Other names
CAS Number5072-26-4 
ChEBICHEBI:28714 Yes
ChemSpider19896 Yes
Jmol 3D modelInteractive image
Chemical formulaC8H18N2O3S
Molar mass222.305 g/mol
Density1.29 g/mL
Melting point215 °C (419 °F; 488 K)
Boiling point382.3 °C (720.1 °F; 655.5 K)
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

////NSC-326231,  BSO, 5072-26-4, Butionine sulfoximine, Neuroblastoma