Buthionine sulfoximine

Buthionine sulfoximine (BSO) is a sulfoximine derivative which reduces levels of glutathione and is being investigated as an adjunct with chemotherapy 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 oxidative antiparasitic drugs.[2]

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
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.156.351
MeSH Buthionine+sulfoximine
UNII
  • InChI=1S/C8H18N2O3S/c1-2-3-5-14(10,13)6-4-7(9)8(11)12/h7,10H,2-6,9H2,1H3,(H,11,12) checkY
    Key: KJQFBVYMGADDTQ-UHFFFAOYSA-N checkY
  • InChI=1/C8H18N2O3S/c1-2-3-5-14(10,13)6-4-7(9)8(11)12/h7,10H,2-6,9H2,1H3,(H,11,12)
    Key: KJQFBVYMGADDTQ-UHFFFAOYAW
  • CCCCS(=N)(=O)CCC(C(=O)O)N
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).
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Infobox references

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. doi:10.2174/156802612798919187. PMID 22196271.
  2. "Definition of buthionine sulfoximine - National Cancer Institute Drug Dictionary". 2011-02-02.


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