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Drug Details

General Information of the Drug (ID: DR1651)
Name
Buthionine sulfoximine
Synonyms
BUTHIONINE SULFOXIMINE; 5072-26-4; Buthionine sulphoximine; DL-Buthionine-[S,R]-sulfoximine; Butionine sulfoximine; Buthionine sulfoxamine; D,L-Buthionine-(S,R)-sulfoximine; DL-Buthionine-sulfoximine; Buthionine-S,R-sulfoximine; 2-Amino-4-(S-butylsulfonimidoyl)butanoic acid; 2-Amino-4-(butylsulfonimidoyl)butanoic acid; DL-Buthionine-(S,R)-sulfoximine; Butanoic acid, 2-amino-4-(S-butylsulfonimidoyl)-; CHEBI:28714; DL-butathionine-(S,R)-sulfoximine; MFCD00070309; NSC326231; NSC381100; L-Buthionine-(S,R)-sulfoximine; S-butyl-DL-homocysteine (S,R)-sulfoximine; S-Butyl-DL-homocysteine-[S,R]-sulfoximine; 2-amino-4-(S-butylsulfonimidoyl)butyric acid; NSC 326231; BRN 2367136; Buthione sulfoximine; DL-Buthionine (S,R)-sulfoximine, 99%; 71765-30-5; NSC 381100; DL-Buthionine-S,R-sulfoximine; l-buthionine (s,r)-sulfoximine; dl-buthionine (s,r)-sulfoximine; NSC-381100; BSO; Sulfoximine, S-(3-amino-3-carboxypropyl)-S-butyl-; Lopac0_000231; SCHEMBL62033; BSPBio_002464; SPECTRUM1505108; dl-Buthionine(S,R)-sulfoximine; CHEMBL1256575; CHEMBL1627290; DTXSID6044434; CHEBI:176510; HMS3260P03; BCP24029; BCP27775; Tox21_500231; s2433; STL328818; AKOS022106364; CCG-204326; DB12870; LP00231; MCULE-8178742509; SDCCGSBI-0050219.P003; NCGC00015148-03; NCGC00015148-04; NCGC00015148-05; NCGC00015148-06; NCGC00015148-07; NCGC00015148-13; NCGC00093696-01; NCGC00093696-02; NCGC00093696-03; NCGC00260916-01; AS-67962; NCI60_002827; HY-106376; CS-0025687; EU-0100231; FT-0624379; FT-0627738; FT-0663956; ST51012445; DL-Buthionine-sulfoximine, >=99.0% (TLC); 2-Amino-4-(butylsulfonimidoyl)butanoic acid #; B 2640; C04543; SR-01000075713; Q5002519; SR-01000075713-1; 2-amino-4-[butyl(imino)oxo-??-sulfanyl]butanoic acid; BRD-A04020513-001-01-9; D,L-Buthionine-(S,R)-sulfoximine (Butionine sulfoximine)
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Molecular Type
Small molecule
Disease Malaria [ICD-11: 1F40] Investigative [1]
Structure
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2D MOL

3D MOL

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Formula
C8H18N2O3S
PubChem CID
21157
Canonical SMILES
CCCCS(=N)(=O)CCC(C(=O)O)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)
InChIKey
KJQFBVYMGADDTQ-UHFFFAOYSA-N
CAS Number
CAS 5072-26-4
ChEBI ID
CHEBI:28714
TTD Drug ID
D0Z6VR
DrugBank ID
DB12870
Combinatorial Therapeutic Effect(s) Validated Clinically or Experimentally
    α. A List of Natural Product(s) Able to Enhance the Efficacy of This Drug
          Arsenic trioxide      Realgar and orpiment     Click to Show/Hide the Molecular Data of This NP
                 Achieving Therapeutic Synergy     Click to Show/Hide
                    Representative Experiment Reporting the Effect of This Combination [2]
                    Detail(s)  Combination Info  click to show the detail info of this combination
                    Molecule(s)
                    Regulation
Up-regulation Expression BID  Molecule Info 
Pathway MAP
Down-regulation Expression CASP3  Molecule Info 
Pathway MAP
Up-regulation Expression CASP8  Molecule Info 
Pathway MAP
Down-regulation Phosphorylation ERK1  Molecule Info 
Pathway MAP
Up-regulation Phosphorylation JNK1  Molecule Info 
Pathway MAP
Up-regulation Phosphorylation p38 beta  Molecule Info 
Pathway MAP
Up-regulation Cleavage PARP1  Molecule Info 
Pathway MAP
Down-regulation Expression TRAIL-R2  Molecule Info 
Pathway MAP
                    In-vitro Model NB4 CVCL_0005 Acute promyelocytic leukemia Homo sapiens
U-937 CVCL_0007 Adult acute monocytic leukemia Homo sapiens
Namalwa CVCL_0067 EBV-related Burkitt lymphoma Homo sapiens
Jurkat CVCL_0065 T acute lymphoblastic leukemia Homo sapiens
                    Experimental
                    Result(s)
Buthionine Sulfoximine enhancement of arsenic trioxide-induced apoptosis in leukemia cells is mediated via activation of c-Jun NH2-terminal kinase and up-regulation of death receptors.
Target and Pathway
Target(s) Glutamate-cysteine ligase modifier (GCLM)  Molecule Info  [1]
KEGG Pathway Glutathione metabolism Click to Show/Hide
2 Metabolic pathways
Pathwhiz Pathway Glutamate Metabolism Click to Show/Hide
2 Glutathione Metabolism
3 Cysteine Metabolism
WikiPathways Transcriptional activation by NRF2 Click to Show/Hide
2 NRF2 pathway
3 Nuclear Receptors Meta-Pathway
4 Metabolism of amino acids and derivatives
5 Trans-sulfuration and one carbon metabolism
6 Trans-sulfuration pathway
7 Phase II conjugation
8 Glutathione metabolism
References
Reference 1 Novel molecular targets for antimalarial chemotherapy. Int J Antimicrob Agents. 2007 Jul;30(1):4-10.
Reference 2 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. Cancer Res. 2006 Dec 1;66(23):11416-23.
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Cite NPCDR
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Correspondence

X. N. Sun, Y. T. Zhang, Y. Zhou, X. C. Lian, L. L. Yan, T. Pan, T. Jin, H. Xie, Z. M. Liang, W. Q. Qiu, J. X. Wang, Z. R. Li, F. Zhu*, X. B. Sui*. NPCDR: natural product-based drug combination and its disease-specific molecular regulation. Nucleic Acids Research. 50(D1): 1324-1333 (2020). PMID: 34664659

Prof. Feng ZHU  (zhufeng@zju.edu.cn)

College of Pharmaceutical Sciences, Zhejiang University, Hangzhou, China


Prof. Xinbing SUI  (hzzju@hznu.edu.cn)

School of Pharmacy and Department of Medical Oncology, the Affiliated Hospital of Hangzhou Normal University, Hangzhou Normal University, Hangzhou, China