AUTHOR OF THIS BLOG

DR ANTHONY MELVIN CRASTO, WORLDDRUGTRACKER

Buthionine Sulphoximine

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May 112016
 

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.

DATA

STR1

STR1

1H NMR

 

STR1

13C NMR

 

Synthesis

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

Abstract

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

http://onlinelibrary.wiley.com/doi/10.1002/adsc.201400354/abstract

References

  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.png

Buthionine sulfoximine
Skeletal formula of buthionine sulfoximine
Ball-and-stick model of buthionine sulfoximine as a zwitterion
Names
IUPAC name

2-amino-4-(butylsulfonimidoyl)butanoic acid
Other names

BSO
Identifiers
5072-26-4 
ChEBI CHEBI:28714 Yes
ChemSpider 19896 Yes
Jmol 3D model Interactive image
MeSH Buthionine+sulfoximine
PubChem 21157
Properties
C8H18N2O3S
Molar mass 222.305 g/mol
Density 1.29 g/mL
Melting point 215 °C (419 °F; 488 K)
Boiling point 382.3 °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

CCCCS(=N)(=O)CCC(C(=O)O)N

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