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Buthionine Sulphoximine

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Skeletal formula of buthionine sulfoximine

Buthionine Sulphoximine

NDA Filed in china

A gamma-glutamylcysteine synthetase inhibitor potentially for the treatment of solid tumors.

 NSC-326231; BSO

CAS No. 5072-26-4

BUTHIONINE SULFOXIMINE; DL-Buthionine-[S,R]-sulfoximine; 5072-26-4; Buthionine sulfoxamine; Buthionine-S,R-sulfoximine; Buthione sulfoximine;

Molecular Formula: C8H18N2O3S
Molecular Weight: 222.30512 g/mol

Buthionine sulfoximine (BSO) is a sulfoximine which reduces levels of glutathione and is being investigated as an adjunct withchemotherapy 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 oxidativeantiparasitic drugs.[2]

Buthionine sulphoximine is an oncolytic agent in early clinical development at the National Cancer Institute (NCI) for the treatment of neuroblastoma in pediatric patients in combination with melphalan and bone marrow or peripheral stem cell transplantation.

DATA

STR1

STR1

1H NMR

STR1

13C NMR

Synthesis

Methionine and buthionine sulfoximines: Syntheses under mild and safe imidation/oxidation conditions
Advanced Synthesis&Catalysis (2014), 356, (10), 2209-2213

Abstract

Thumbnail image of graphical abstract

Methionine and buthionine sulfoximines (MSO and BSO) are non-natural amino acids known to inhibit the biosynthesis of glutathione (GSH). The current syntheses of these biologically active molecules involve harsh reaction conditions and the use of hazardous reagents for the sulfur imidation. Here, improved syntheses of MSO and BSO are presented including safe and mild one-pot imidation/oxidation sequences and single-step deprotections of three different functionalities.

Methionine and Buthionine Sulfoximines: Syntheses under Mild and Safe Imidation/Oxidation Conditions

  1. Laura Buglioni,
  2. Vincent Bizet and
  3. Carsten Bolm*

DOI: 10.1002/adsc.201400354

http://onlinelibrary.wiley.com/doi/10.1002/adsc.201400354/abstract

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”.

BUTHIONINE SULFOXIMINE.png

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
5072-26-4 
ChEBI CHEBI:28714 Yes
ChemSpider 19896 Yes
Jmol 3D model Interactive image
MeSH Buthionine+sulfoximine
PubChem 21157
Properties
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).

////NSC-326231,  BSO, 5072-26-4, Butionine sulfoximine, Neuroblastoma

CCCCS(=N)(=O)CCC(C(=O)O)N


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DR ANTHONY CRASTO

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DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO Ph.D

DR ANTHONY MELVIN CRASTO, Born in Mumbai in 1964 and graduated from Mumbai University, Completed his Ph.D from ICT, 1991,Matunga, Mumbai, India, in Organic Chemistry, The thesis topic was Synthesis of Novel Pyrethroid Analogues, Currently he is working with GLENMARK PHARMACEUTICALS LTD, Research Centre as Principal Scientist, Process Research (bulk actives) at Mahape, Navi Mumbai, India. Total Industry exp 29 plus yrs, Prior to joining Glenmark, he has worked with major multinationals like Hoechst Marion Roussel, now Sanofi, Searle India Ltd, now RPG lifesciences, etc. He has worked with notable scientists like Dr K Nagarajan, Dr Ralph Stapel, Prof S Seshadri etc, He did custom synthesis for major multinationals in his career like BASF, Novartis, Sanofi, etc., He has worked in Discovery, Natural products, Bulk drugs, Generics, Intermediates, Fine chemicals, Neutraceuticals, GMP, Scaleups, etc, he is now helping millions, has 9 million plus hits on Google on all Organic chemistry websites. His friends call him worlddrugtracker. His New Drug Approvals, Green Chemistry International, All about drugs, Eurekamoments, Organic spectroscopy international, etc in organic chemistry are some most read blogs He has hands on experience in initiation and developing novel routes for drug molecules and implementation them on commercial scale over a 29 year tenure till date Aug 2016, Around 30 plus products in his career. He has good knowledge of IPM, GMP, Regulatory aspects, he has several International patents published worldwide . He has good proficiency in Technology transfer, Spectroscopy, Stereochemistry, Synthesis, Polymorphism etc., He suffered a paralytic stroke/ Acute Transverse mylitis in Dec 2007 and is 90 %Paralysed, He is bound to a wheelchair, this seems to have injected feul in him to help chemists all around the world, he is more active than before and is pushing boundaries, He has 9 million plus hits on Google, 2.5 lakh plus connections on all networking sites, 25 Lakh plus views on dozen plus blogs, He makes himself available to all, contact him on +91 9323115463, email amcrasto@gmail.com, Twitter, @amcrasto , He lives and will die for his family, 90% paralysis cannot kill his soul., Notably he has 13 lakh plus views on New Drug Approvals Blog in 212 countries......https://newdrugapprovals.wordpress.com/ , He appreciates the help he gets from one and all, Friends, Family, Glenmark, Readers, Wellwishers, Doctors, Drug authorities, His Contacts, Physiotherapist, etc

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