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Buthionine sulfoximine

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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
CAS Number
3D model (JSmol)
ChEBI
ChemSpider
ECHA InfoCard 100.156.351 Edit this at Wikidata
MeSH Buthionine+sulfoximine
PubChem CID
UNII
CompTox Dashboard (EPA)
InChI
  • 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)Key: KJQFBVYMGADDTQ-UHFFFAOYSA-N
  • 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
SMILES
  • CCCCS(=N)(=O)CCC(C(=O)O)N
Properties
Chemical formula 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 , 100 kPa). ☒N verify (what is  ?) Infobox references
Chemical compound

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. 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.

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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