Buthionine sulfoximine

Buthionine sulfoximine

Names
IUPAC name 2-amino-4-(butylsulfonimidoyl)butanoic acid
Other names BSO
Identifiers
CAS Number	5072-26-4
3D model (Jmol)	Interactive image
ChEBI	CHEBI:28714
ChemSpider	19896
ECHA InfoCard	100.156.351
MeSH	Buthionine+sulfoximine
PubChem	21157
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 [77 °F], 100 kPa).
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Infobox references

Buthionine sulfoximine (BSO) is a sulfoximine 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]

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".