Buthionine sulfoximine
-
Buthionine sulfoximine
structure -
-
CAS No:
5072-26-4
-
Formula:
C8H18N2O3S
-
Chemical Name:
Buthionine sulfoximine
-
Synonyms:
Butanoic acid,2-amino-4-(S-butylsulfonimidoyl)-;Sulfoximine,S-(3-amino-3-carboxypropyl)-S-butyl-;Sulfoximine,3-amino-3-carboxypropyl butyl;2-Amino-4-(S-butylsulfonimidoyl)butanoic acid;Butionine sulfoximine;Buthionine sulfoximine;DL-Buthionine (S,R)-sulfoximine;NSC 381100;71765-30-5
-
CAS No:
Description
D,L-Buthionine-(S,R)-sulfoximine is a potent inhibitor of glutamylcysteine synthetase biosynthesis.
S-butyl-DL-homocysteine (S,R)-sulfoximine is a sulfoximide that is the sulfoximine derivative of an analogue of DL-methionine in which the S-methyl group is replaced by S-butyl. It has a role as an EC 6.3.2.2 (glutamate--cysteine ligase) inhibitor and a ferroptosis inducer. It contains a D-buthionine-(S,R)-sulfoximine and a L-buthionine-(S,R)-sulfoximine.|Buthionine Sulfoximine has been used in trials studying the treatment of Neuroblastoma and Melanoma (Skin).|A synthetic amino acid that depletes glutathione by irreversibly inhibiting gamma-glutamylcysteine synthetase. Inhibition of this enzyme is a critical step in glutathione biosynthesis. It has been shown to inhibit the proliferative response in human T-lymphocytes and inhibit macrophage activation. (J Biol Chem 1995;270(33):1945-7)
Safety Information
NONH for all modes of transport
3
36/37/38
26-36
EK7713435
Xi
P305 + P351 + P338
H315-H319-H335
|Warning|H315 (100%): Causes skin irritation [Warning Skin corrosion/irritation]|P261, P264, P271, P280, P302+P352, P304+P340, P305+P351+P338, P312, P321, P332+P313, P337+P313, P362, P403+P233, P405, and P501|Aggregated GHS information provided by 39 companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Drug Information
Antimetabolites that are useful in cancer chemotherapy. (See all compounds classified as Antimetabolites, Antineoplastic.)|Drugs used to protect against ionizing radiation. They are usually of interest for use in radiation therapy but have been considered for other purposes, e.g. military. (See all compounds classified as Radiation-Protective Agents.)|Drugs used to potentiate the effectiveness of radiation therapy in destroying unwanted cells. (See all compounds classified as Radiation-Sensitizing Agents.)|Drugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033) (See all compounds classified as Antimetabolites.)|Compounds or agents that combine with an enzyme in such a manner as to prevent the normal substrate-enzyme combination and the catalytic reaction. (See all compounds classified as Enzyme Inhibitors.)
Buthionine Sulfoximine
Buthionine sulfoximine Use and Manufacturing
A potent and specific inhibitor of alpha-glutamyl cysteine synthetase Biological tool for depletion of glutathione.
Computed Properties
Molecular Weight:222.31
XLogP3:-0.6
Hydrogen Bond Donor Count:3
Hydrogen Bond Acceptor Count:5
Rotatable Bond Count:7
Exact Mass:222.10381361
Monoisotopic Mass:222.10381361
Topological Polar Surface Area:113
Heavy Atom Count:14
Complexity:284
Undefined Atom Stereocenter Count:2
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes