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5072-26-4

5072-26-4 structure
5072-26-4 structure
  • Name: D,L-Buthionine-(S,R)-sulfoximine
  • Chemical Name: S-butyl-DL-homocysteine (S,R)-sulfoximine
  • CAS Number: 5072-26-4
  • Molecular Formula: C8H18N2O3S
  • Molecular Weight: 222.30500
  • Catalog: Research Areas Cancer
  • Create Date: 2019-01-25 21:58:11
  • Modify Date: 2025-09-01 11:55:18
  • D,L-Buthionine-(S,R)-sulfoximine is a potent inhibitor of glutamylcysteine synthetase biosynthesis.
Name S-butyl-DL-homocysteine (S,R)-sulfoximine
Synonyms 2-amino-4-(butylsulfonimidoyl)butanoic acid
DL-Buthionine (S,R)-sulfoximine
EINECS 246-685-1
MFCD00070309
D,L-Buthionine-(S,R)-sulfoximine
Description D,L-Buthionine-(S,R)-sulfoximine is a potent inhibitor of glutamylcysteine synthetase biosynthesis.
Related Catalog
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.
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
Storage condition 2-8°C
Water Solubility H2O: 50 mg/mL, clear, colorless

CHEMICAL IDENTIFICATION

RTECS NUMBER :
EK7713435
CHEMICAL NAME :
Butanoic acid, 2-amino-4-(S-butylsulfonimidoyl)-
CAS REGISTRY NUMBER :
5072-26-4
LAST UPDATED :
199612
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C8-H18-N2-O3-S
MOLECULAR WEIGHT :
222.34

HEALTH HAZARD DATA

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
Symbol GHS07
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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