Name | 2-amino-4-(S-butylsulfonimidoyl)butanoic acid |
Synonyms | buthioninesulfoxamine buthioninesulfoximine DL-BUTHIONINE-SULFOXIMINE DL-BUTHIONINE (S,R)-SULPHOXIME DL-BUTHIONINE-[S,R]-SULFOXIMINE DL-BUTHIONINE (R,S)-SULFOXIMINE 2-amino-4-(s-butylsulfonimidoyl)butanoicacid 2-amino-4-(s-butylsulfonimidoyl)-butanoicaci 2-amino-4-(S-butylsulfonimidoyl)butanoic acid |
CAS | 5072-26-4 71765-30-5 83730-53-4 |
EINECS | 628-045-7 |
InChI | InChI=1/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 |
Molar Mass | 222.31 |
Density | 1.29±0.1 g/cm3(Predicted) |
Melting Point | 215°C (dec.)(lit.) |
Boling Point | 382.3±52.0 °C(Predicted) |
Flash Point | 185°C |
Solubility | H2O: 50mg/mL, clear, colorless |
Vapor Presure | 6.64E-07mmHg at 25°C |
Appearance | Fluffy Powder |
Color | White |
Merck | 13,1520 |
BRN | 2367136 |
Storage Condition | 2-8°C |
Refractive Index | 1.537 |
MDL | MFCD00067000 |
Use | Inhibition of γ-glutamylcysteine synthetase (a key enzyme in glutathione synthesis). |
In vitro study | Buthionine sulfoximine is an analogs of methionine sulfoximine and inhibits gamma-glutamylcysteine synthetase about 20 times more effectively than prothionine sulfoximine and at least 100 times more effectively than methionine sulfoximine. |
In vivo study | Treatment of mice bearing HT1080 and HT1080/DR4 xenografts with a continuous i.v infusion of nontoxic doses of D,L-Buthionine-(S,R)-sulfoximine (300 and 600 mg/kg/day) produce a 60% reduction of GSH plasma levels and greater than 95 % reduction in GSH tumor levels in both parental and multidrug-resistant tumors. |
Hazard Symbols | Xi - Irritant |
Risk Codes | 36/37/38 - Irritating to eyes, respiratory system and skin. |
Safety Description | S26 - In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. S36 - Wear suitable protective clothing. |
WGK Germany | 3 |
RTECS | EK7713435 |
FLUKA BRAND F CODES | 10 |
HS Code | 29309090 |
Reference Show more | 1. Li, Bingqiang, et al. "A dual pH-and reduction-responsive anticancer drug delivery system based on PEG–SS–poly (amino acid) block copolymer." RSC advances 7.48 (2017): 30242-30249. 2. [IF=3.361] Bingqiang Li et al."A dual pH- and reduction-responsive anticancer drug delivery system based on PEG–SS–poly(amino acid) block copolymer."Rsc Adv. 2017 Jun;7(48):30242-30249 3. [IF=3.239] Gang Luo et al."The mechanism of N-acetyl-l-cysteine in improving the secretion of porcine follicle-stimulating hormone in Pichia pastoris."Yeast. 2021 Nov;38(11):601-611 |