Name | DL-BUTHIONINE-[S,R]-SULFOXIMINE |
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 (2R)-2-amino-4-(S-butylsulfonimidoyl)butanoic acid |
CAS | 5072-26-4 |
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)/t7-,14?/m1/s1 |
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 |
Physical and Chemical Properties | Bioactive DL-Buthionine-Sulfoximine (BSO, DL-Buthionine-(S,R)-sulfoximine) is an inhibitor of glutathione (GSH) 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 |
Downstream Products | Ethyl 5-[3-(4,6-dimethoxy pyrimidyl-2-yl)ureido]methylpyrazolyl-4-carboxylic ester |
Reference Show more | 1. [IF=6.639] Xiao Zhang et al."ATP8B1 Knockdown Activated the Choline Metabolism Pathway and Induced High-Level Intracellular REDOX Homeostasis in Lung Squamous Cell Carcinoma."Cancers. 2022 Jan;14(3):835 |
storage conditions | 2-8°C |
solubility | H2O: 50 mg/mL, clear, colorless |
morphology | Fluffy Powder |
color | White |
Merck | 13,1520 |
BRN | 2367136 |
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 studies
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.
WGK Germany | 3 |
RTECS number | EK7713435 |
F | 10 |
customs code | 29309090 |
biological activity | DL-Buthionine-Sulfoximine (BSO, DL-Buthionine-(S,R)-sulfoximine) is an inhibitor of glutathione (GSH) synthesis. |
target | TargetValue GSH () |
Target | Value |
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 dos 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 tumour levels in both parental and multidrug-resistant tumors. |