Details
| Stereochemistry | MIXED |
| Molecular Formula | C8H18N2O3S |
| Molecular Weight | 222.305 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCS(=N)(=O)CCC(N)C(O)=O
InChI
InChIKey=KJQFBVYMGADDTQ-UHFFFAOYSA-N
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)
| Molecular Formula | C8H18N2O3S |
| Molecular Weight | 222.305 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
Buthionine sulfoximine (BSO) is a selective inhibitor of γ-glutamylcysteine synthetase (γ-GCS), the rate-limiting enzyme in glutathione (GSH) synthesis. In cancer cells, glutathione depletion significantly increased cytotoxicity via oxidative stress. In addition, in neuroblastoma cells susceptible to Buthionine sulfoximine treatment, DNA damage and cell apoptosis occurred via ROS production. Buthionine sulfoximine plus melphalan was effective in treatment for patients with recurrent/refractory neuroblastoma. Buthionine sulfoximine may also be used to increase the sensitivity of parasites to oxidative antiparasitic drugs. Buthionine sulfoximine has been shown to increase the efficacy of nifurtimox against T. cruzi and has also been shown to be an effective modulator of GSH-mediated chemoresistance by increasing the in vitro cytotoxicity of alkylating agents and radiation. Buthionine sulfoximine has been tested in animal studies and in human phase I trials for adults with solid tumors, with documented clinical responses in patients with melanoma, ovarian carcinoma and small cell carcinoma of the lung treated with the combination of Buthionine sulfoximine and melphalan.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| An improved model of acetaminophen-induced fulminant hepatic failure in dogs. | 1992 Feb |
|
| CYP2E1-mediated oxidative stress induces collagen type I expression in rat hepatic stellate cells. | 1999 Oct |
|
| Hepatocellular response to chemical stress in CD-1 mice: induction of early genes and gamma-glutamylcysteine synthetase. | 2000 Aug |
|
| Induction of oxidative stress by glutathione depletion causes severe hypertension in normal rats. | 2000 Jul |
|
| [Effect of thiabendazole (TBZ) on glutathione (GSH) and GSH related enzymes in mice liver]. | 2000 Sep |
|
| Inducers of gamma-glutamylcysteine synthetase and their effects on glutathione synthetase expression. | 2000 Sep 7 |
|
| A novel model of acetaminophen-induced acute hepatic failure in rabbits. | 2002 Aug |
|
| Mediation of cadmium-induced oxidative damage and glucose-6-phosphate dehydrogenase expression through glutathione depletion. | 2003 |
|
| Synthesis and antifilarial evaluation of N1,Nn- xylofuranosylated diaminoalkanes. | 2003 Apr 17 |
|
| Metallothionein 2A induction by zinc protects HEPG2 cells against CYP2E1-dependent toxicity. | 2003 Feb 15 |
|
| Oxidative modulation of the glutathione-redox couple enhances lipopolysaccharide-induced interleukin 12 P40 production by a mouse macrophage cell line, J774A.1. | 2003 Mar |
|
| Synergy between sulforaphane and selenium in the induction of thioredoxin reductase 1 requires both transcriptional and translational modulation. | 2003 Mar |
|
| Role of glutathione in dimethylarsinic acid-induced apoptosis. | 2004 Aug 1 |
|
| Mistargeted MRPdeltaF728 mutant is rescued by intracellular GSH. | 2004 Dec 3 |
|
| The gamma-glutamylcysteine synthetase and glutathione regulate asbestos-induced expression of activator protein-1 family members and activity. | 2004 Nov 1 |
|
| N-acetylcysteine enhances multidrug resistance-associated protein 1 mediated doxorubicin resistance. | 2004 Oct |
|
| Two major branches of anti-cadmium defense in the mouse: MTF-1/metallothioneins and glutathione. | 2005 |
|
| Heme oxygenase-2 protects against glutathione depletion-induced neuronal apoptosis mediated by bilirubin and cyclic GMP. | 2005 Apr |
|
| Inhibition of interferon-gamma signaling by a mercurio-substituted dihydropsoralen in murine keratinocytes. | 2005 Dec 5 |
|
| The responses of Ht22 cells to oxidative stress induced by buthionine sulfoximine (BSO). | 2005 Feb 12 |
|
| Manganese potentiates in vitro production of proinflammatory cytokines and nitric oxide by microglia through a nuclear factor kappa B-dependent mechanism. | 2005 Mar |
|
| Selenoprotein W as molecular target of methylmercury in human neuronal cells is down-regulated by GSH depletion. | 2005 May 20 |
|
| Arsenite enhances tumor necrosis factor-alpha-induced expression of vascular cell adhesion molecule-1. | 2005 Nov 15 |
|
| Schisandrin B-induced increase in cellular glutathione level and protection against oxidant injury are mediated by the enhancement of glutathione synthesis and regeneration in AML12 and H9c2 cells. | 2006 |
|
| Buthionine sulfoximine enhancement of arsenic trioxide-induced apoptosis in leukemia and lymphoma cells is mediated via activation of c-Jun NH2-terminal kinase and up-regulation of death receptors. | 2006 Dec 1 |
|
| Piceatannol upregulates endothelial heme oxygenase-1 expression via novel protein kinase C and tyrosine kinase pathways. | 2006 Feb |
|
| Oxidative stress induces phosphoenolpyruvate carboxykinase expression in H4IIE cells. | 2006 Sep |
|
| Expression and function of cystine/glutamate transporter in neutrophils. | 2007 Apr |
|
| Effect of various radical generators on insulin-dependent regulation of hepatic gene expression. | 2007 Jan |
|
| Chalcone inhibits the activation of NF-kappaB and STAT3 in endothelial cells via endogenous electrophile. | 2007 Mar 20 |
|
| Curcumin-induced GADD153 upregulation: modulation by glutathione. | 2007 May 15 |
|
| Activation of nuclear factor (erythroid-2 like) factor 2 by toxic bile acids provokes adaptive defense responses to enhance cell survival at the emergence of oxidative stress. | 2007 Nov |
|
| Boric acid inhibits LPS-induced TNF-alpha formation through a thiol-dependent mechanism in THP-1 cells. | 2008 |
|
| Decreased glutathione levels potentiate the apoptotic efficacy of selenium: possible involvement of p38 and JNK MAPKs--in vitro studies. | 2008 Feb |
|
| Changes in antioxidant defense systems induced by thiram in V79 Chinese hamster fibroblasts. | 2008 Feb |
|
| Activation of Nrf2-mediated oxidative stress response in macrophages by hypochlorous acid. | 2008 Feb 1 |
|
| NF-kappaB and AP-1 are key signaling pathways in the modulation of NAD(P)H:quinone oxidoreductase 1 gene by mercury, lead, and copper. | 2008 Jul-Aug |
|
| The hepatotoxic metabolite of acetaminophen directly activates the Keap1-Nrf2 cell defense system. | 2008 Oct |
|
| Involvement of oxidative stress and activation of aryl hydrocarbon receptor in elevation of CYP1A1 expression and activity in lung cells and tissues by arsenic: an in vitro and in vivo study. | 2009 Feb |
|
| Transcription factor Nrf2 mediates an adaptive response to sulforaphane that protects fibroblasts in vitro against the cytotoxic effects of electrophiles, peroxides and redox-cycling agents. | 2009 Jun 15 |
|
| Early sensing and gene expression profiling under a low dose of cadmium exposure. | 2009 Mar |
Patents
| Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 07:03:08 GMT 2023
by
admin
on
Sat Dec 16 07:03:08 GMT 2023
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| Record UNII |
LW4108Q0BV
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| Record Status |
Validated (UNII)
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| Record Version |
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| Classification Tree | Code System | Code | ||
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FDA ORPHAN DRUG |
209705
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NCI_THESAURUS |
C2130
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FDA ORPHAN DRUG |
213205
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| Code System | Code | Type | Description | ||
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28714
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100000172386
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DTXSID6044434
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LW4108Q0BV
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D019328
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DB12870
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381100
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m2798
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PRIMARY | Merck Index | ||
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21157
Created by
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BUTHIONINE SULFOXIMINE
Created by
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5072-26-4
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admin on Sat Dec 16 07:03:08 GMT 2023 , Edited by admin on Sat Dec 16 07:03:08 GMT 2023
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| Related Record | Type | Details | ||
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ACTIVE MOIETY |
