Buthionine Sulphoximine
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MedKoo CAT#: 206723

CAS#: 5072-26-4

Description: Buthionine Sulphoximine, also known as NSC-326231, is a gamma-glutamylcysteine synthetase inhibitor potentially for the treatment of solid tumors.


Price and Availability

Size Price Shipping out time Quantity
50mg USD 150 2 Weeks
100mg USD 250 2 Weeks
200mg USD 450 2 Weeks
500mg USD 650 2 Weeks
1g USD 850 2 Weeks
2g USD 1450 2 Weeks
5g USD 2150 2 Weeks
Inquire bulk and customized quantity

Pricing updated 2020-10-22. Prices are subject to change without notice.

Buthionine Sulphoximine, purity > 98%, is in stock. Current shipping out time is about 2 weeks after order is received. CoA, QC data and MSDS documents are available in one week after order is received.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 206723
Name: Buthionine Sulphoximine
CAS#: 5072-26-4
Chemical Formula: C8H18N2O3S
Exact Mass: 222.1038
Molecular Weight: 222.303
Elemental Analysis: C, 43.22; H, 8.16; N, 12.60; O, 21.59; S, 14.42


Synonym: NSC-326231; BSO; Buthionine Sulphoximine; DL-Buthionine-(S,R)-sulfoximine.

IUPAC/Chemical Name: 2-amino-4-(butylsulfonimidoyl)butanoic acid

InChi Key: KJQFBVYMGADDTQ-UHFFFAOYSA-N

InChi Code: InChI=1S/C8H18N2O3S/c1-2-3-5-14(10,13)6-4-7(9)8(11)12/h7,10H,2-6,9H2,1H3,(H,11,12)

SMILES Code: N[C@@H](CCS(CCCC)(=O)=N)C(O)=O


Technical Data

Appearance:
Solid powder

Purity:
>98% (or refer to the Certificate of Analysis)

Shipping Condition:
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition:
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility:
Soluble in DMSO

Shelf Life:
>2 years if stored properly

Drug Formulation:
This drug may be formulated in DMSO

Stock Solution Storage:
0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code:
2934.99.9001


References

1: Park MH, Kim SY, Moon C, Bae YC, Moon JI, Moon C. Differential cell death and Bcl-2 expression in the mouse retina after glutathione decrease by systemic D,L-buthionine sulphoximine administration. Mol Cells. 2013 Mar;35(3):235-42. doi: 10.1007/s10059-013-2276-y. Epub 2013 Feb 18. PubMed PMID: 23430084; PubMed Central PMCID: PMC3887915.

2: Vukovic V, Nicklee T, Hedley DW. Differential effects of buthionine sulphoximine in hypoxic and non-hypoxic regions of human cervical carcinoma xenografts. Radiother Oncol. 2001 Jul;60(1):69-73. PubMed PMID: 11410306.

3: Hanada K, Mukasa Y, Nomizo Y, Ogata H. Effect of buthionine sulphoximine, glutathione and methimazole on the renal disposition of cisplatin and on cisplatin-induced nephrotoxicity in rats: pharmacokinetic-toxicodynamic analysis. J Pharm Pharmacol. 2000 Dec;52(12):1483-90. PubMed PMID: 11197076.

4: Lockhart B, Jones C, Cuisinier C, Villain N, Peyroulan D, Lestage P. Inhibition of L-homocysteic acid and buthionine sulphoximine-mediated neurotoxicity in rat embryonic neuronal cultures with alpha-lipoic acid enantiomers. Brain Res. 2000 Feb 14;855(2):292-7. PubMed PMID: 10677603.

5: Chattopadhyay A, Deb S, Chatterjee A. Modulation of the clastogenic activity of gamma-irradiation in buthionine sulphoximine-mediated glutathione depleted mammalian cells. Int J Radiat Biol. 1999 Oct;75(10):1283-91. PubMed PMID: 10549605.

6: Li XM, Metzger G, Filipski E, Lemaigre G, Lévi F. Modulation of nonprotein sulphydryl compounds rhythm with buthionine sulphoximine: relationship with oxaliplatin toxicity in mice. Arch Toxicol. 1998 Sep;72(9):574-9. PubMed PMID: 9806429.

7: Nagasaki H, Nakano H, Boudjema K, Jaeck D, Alexandre E, Baek Y, Kitamura N, Yamaguchi M, Kumada K. Efficacy of preconditioning with N-acetylcysteine against reperfusion injury after prolonged cold ischaemia in rats liver in which glutathione had been reduced by buthionine sulphoximine. Eur J Surg. 1998 Feb;164(2):139-46. PubMed PMID: 9537722.

8: Anderson CP, Tsai J, Chan W, Park CK, Tian L, Lui RM, Forman HJ, Reynolds CP. Buthionine sulphoximine alone and in combination with melphalan (L-PAM) is highly cytotoxic for human neuroblastoma cell lines. Eur J Cancer. 1997 Oct;33(12):2016-9. PubMed PMID: 9516845.

9: Dizdar N, Kullman A, Kågedal B, Arstrand K. Effects on interstitial glutathione, cysteine and 5-S-cysteinyldopa of buthionine sulphoximine in human melanoma transplants. Melanoma Res. 1997 Aug;7(4):322-8. PubMed PMID: 9293482.

10: Chattopadhyay A, Choudhury S, Chatterjee A. Modulation of the clastogenic activity of bleomycin by reduced-glutathione, glutathione-ester and buthionine sulphoximine. Mutagenesis. 1997 Jul;12(4):221-5. PubMed PMID: 9237765.

11: Sarma L, Devasagayam TP, Mohan H, Mittal JP, Kesavan PC. Mechanisms of protection by buthionine sulphoximine against gamma-ray-induced micronuclei in polychromatic erythrocytes of mouse bone marrow. Int J Radiat Biol. 1996 May;69(5):633-43. PubMed PMID: 8648251.

12: Schneider E, Yamazaki H, Sinha BK, Cowan KH. Buthionine sulphoximine-mediated sensitisation of etoposide-resistant human breast cancer MCF7 cells overexpressing the multidrug resistance-associated protein involves increased drug accumulation. Br J Cancer. 1995 Apr;71(4):738-43. PubMed PMID: 7710938; PubMed Central PMCID: PMC2033716.

13: Terradez P, Asensi M, Lasso de la Vega MC, Puertes IR, Viña J, Estrela JM. Depletion of tumour glutathione in vivo by buthionine sulphoximine: modulation by the rate of cellular proliferation and inhibition of cancer growth. Biochem J. 1993 Jun 1;292 ( Pt 2):477-83. PubMed PMID: 8503882; PubMed Central PMCID: PMC1134234.

14: Riley RJ, Spielberg SP, Leeder JS. A comparative study of the toxicity of chemically reactive xenobiotics towards adherent cell cultures: selective attenuation of menadione toxicity by buthionine sulphoximine pretreatment. J Pharm Pharmacol. 1993 Apr;45(4):263-7. PubMed PMID: 8098365.

15: Brittebo EB, Darnerud PO, Eriksson C, Brandt I. Nephrotoxicity and covalent binding of 1,1-dichloroethylene in buthionine sulphoximine-treated mice. Arch Toxicol. 1993;67(9):605-12. PubMed PMID: 8311687.

16: Jin YZ, Ding L, Shen ZF, Cai RM, Xu LM, Yang JK, Jin XQ, Lu WQ, Xu JF. Effects of glutathione depletion using buthionine sulphoximine on the cytotoxicity in mammalian cells and human tumor cells in vitro. Chin Med J (Engl). 1992 Aug;105(8):647-50. PubMed PMID: 1458967.

17: Polhuijs M, Lankhaar G, Mulder GJ. Relationship between glutathione content in liver and glutathione conjugation rate in the rat in vivo. Effect of buthionine sulphoximine pretreatment on conjugation of the two 2-bromoisovalerylurea enantiomers during intravenous infusion. Biochem J. 1992 Jul 15;285 ( Pt 2):401-4. PubMed PMID: 1637334; PubMed Central PMCID: PMC1132802.

18: Mizutani T, Yoshida K, Ito K, Kawazoe S. Sex difference in the nephrotoxicity of thiabendazole in mice depleted of glutathione by treatment with DL-buthionine sulphoximine. Food Chem Toxicol. 1992 Mar;30(3):247-50. PubMed PMID: 1618448.

19: VanSteenhouse JL, Fettman MJ, Gould DH. The effect of glutathione depletion by buthionine sulphoximine on 1-cyano-3,4-epithiobutane toxicity. Food Chem Toxicol. 1991 Mar;29(3):153-7. PubMed PMID: 2032656.

20: Wong RS, Basas RA, Ling CC. Enhancement of SR 2508 (etanidazole) radiosensitization by buthionine sulphoximine at low-dose-rate irradiation. Int J Radiat Biol. 1991 Jan;59(1):133-43. PubMed PMID: 1671060.