CAS 5072-26-4|D,L-Buthionine-(S,R)-sulfoximine
| Common Name | D,L-Buthionine-(S,R)-sulfoximine | ||
|---|---|---|---|
| CAS Number | 5072-26-4 | Molecular Weight | 222.30500 |
| Density | 1.29g/cm3 | Boiling Point | 382.3ºC at 760 mmHg |
| Molecular Formula | C8H18N2O3S | Melting Point | 215ºC (dec.)(lit.) |
| MSDS | ChineseUSA | Flash Point | 185ºC |
| Symbol | GHS07 | Signal Word | Warning |
Names
| Name | S-butyl-DL-homocysteine (S,R)-sulfoximine |
|---|---|
| Synonym | More Synonyms |
D,L-Buthionine-(S,R)-sulfoximine BiologicalActivity
| Description | D,L-Buthionine-(S,R)-sulfoximine is a potent inhibitor of glutamylcysteine synthetase biosynthesis. |
|---|---|
| Related Catalog | Signaling Pathways >>Others >>OthersResearch Areas >>Cancer |
| Target | glutamylcysteine synthetase[1] |
| In Vitro | 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[1]. |
| In Vivo | 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[2]. |
| Animal Admin | Mice[2] D,L-Buthionine-(S,R)-sulfoximine is dissolved in sterile 0.9% saline, filtered through a 0.2-p.m polysulfone membrane filter, and administered by 48-h continuous iv. infusion at a dose of 300 mg/kg/day and 600 mg/kg/day starting at 24 h before doxorubicin administration. In vivo GSH levels after treatment with D,L-Buthionine-(S,R)-sulfoximine at a dose of 300 mg/kg and 600 mg/kg for 24 h as an iv. continuous infusion in munine plasma and in tumor tissue of HT1080 and HT1080/DR4 xenografts is measured[2]. |
| References | [1]. Griffith OW, et al. Potent and specific inhibition of glutathione synthesis by buthionine sulfoximine (S-n-butyl homocysteine sulfoximine). J Biol Chem. 1979 Aug 25;254(16):7558-60. [2]. Vanhoefer U, et al. d,l-buthionine-(S,R)-sulfoximine potentiates in vivo the therapeutic efficacy of doxorubicin against multidrug resistance protein-expressing tumors. Clin Cancer Res. 1996 Dec;2(12):1961-8. |
Chemical & Physical Properties
| Density | 1.29g/cm3 |
|---|---|
| Boiling Point | 382.3ºC at 760 mmHg |
| Melting Point | 215ºC (dec.)(lit.) |
| Molecular Formula | C8H18N2O3S |
| Molecular Weight | 222.30500 |
| Flash Point | 185ºC |
| Exact Mass | 222.10400 |
| PSA | 112.62000 |
| LogP | 2.30100 |
| Index of Refraction | 1.537 |
| InChIKey | KJQFBVYMGADDTQ-UHFFFAOYSA-N |
| SMILES | CCCCS(=N)(=O)CCC(N)C(=O)O |
| Storage condition | 2-8°C |
| Water Solubility | H2O: 50 mg/mL, clear, colorless |
Toxicological Information
CHEMICAL IDENTIFICATION |
ACUTE TOXICITY DATA - TYPE OF TEST :
- TDLo - Lowest published toxic dose
- ROUTE OF EXPOSURE :
- Intraperitoneal
- DOSE :
- 1 gm/kg
- SEX/DURATION :
- female 1 day(s) pre-mating
- TOXIC EFFECTS :
- Reproductive - Maternal Effects - ovaries, fallopian tubes Reproductive - Maternal Effects - other effects
- REFERENCE :
- REPTED Reproductive Toxicology. (Pergamon Press Inc., Maxwell House, Fairview Park, Elmsford, NY 10523) V.1- 1987- Volume(issue)/page/year: 6,133,1992
Safety Information
| Symbol | GHS07 |
|---|---|
| Signal Word | Warning |
| Hazard Statements | H315-H319-H335 |
| Precautionary Statements | P305 + P351 + P338 |
| Personal Protective Equipment | dust mask type N95 (US);Eyeshields;Gloves |
| Hazard Codes | Xi |
| Risk Phrases | 36/37/38 |
| Safety Phrases | 26-36 |
| RIDADR | NONH for all modes of transport |
| WGK Germany | 3 |
| RTECS | EK7713435 |
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Synonyms
| 2-amino-4-(butylsulfonimidoyl)butanoic acid |
| DL-Buthionine (S,R)-sulfoximine |
| EINECS 246-685-1 |
| MFCD00070309 |
| D,L-Buthionine-(S,R)-sulfoximine |
