A γ-glutamylcysteine synthetase inhibitor
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D,L-Buthionine-(S,R)-Sulfoximine

Item No. 23691

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
2-amino-4-(S-butylsulfonimidoyl)-butanoic acid
CAS Number
5072-26-4
Synonyms
  • NSC 381100
Molecular Formula
C8H18N2O3S
Formula Weight
222.3
Purity
≥95%
Formulation
A solid
Solubility(Learn about Variance in Solubility)
Water: Slightly soluble
SMILES
O=S(CCCC)(CCC(N)C(O)=O)=N
InChi Code
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)
InChi Key
KJQFBVYMGADDTQ-UHFFFAOYSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    250 mg

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    Cayman Chemical
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    Product Description

    D,L-Buthionine-(S,R)-sulfoximine is an inhibitor of γ-glutamylcysteine synthetase that induces 100% inhibition at a concentration of 10 μM in an enzyme assay.1 It is selective for γ-glutamylcysteine synthetase, lacking activity at glutamine synthetase at concentrations up to 500 μM. D,L-Buthionine-(S,R)-sulfoximine (32 mmol/kg, i.p.) reduces renal glutathione in mice without inducing abnormal behavior or convulsions. It has antiparasitic activity, eliminating T. brucei from the bloodstream of infected mice via depletion of intratrypanosomal glutathione and induction of oxidative stress at a dose of 4 mmol/kg.2 D,L-Buthionine-(S,R)-sulfoximine is an isomeric mixture of L-buthionine-S-sulfoxime, L-buthionine-R-sulfoxime, D-buthionine-S-sulfoxime, and D-buthionine-R-sulfoxime.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Griffith, O.W., and Meister, A. Potent and specific inhibition of glutathione synthesis by buthionine sulfoximine (S-n-butyl homocysteine sulfoximine). The Journal of Biological Chemisty 254(16), 7558-7560 (1979).

    2. Arrick, B.A., Griffith, O.W., and Cerami, A. Inhibition of glutathione synthesis as a chemotherapeutic strategy for trypanosomiasis. J. Exp. Med. 153(3), 720-725 (1981).