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MedKoo Cat#: 524131 | Name: Acivicin
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Acivicin is an inhibitor of gamma-glutamyl transferase. It is a potent antineoplastic agent. Acivicin interferes with glutamate metabolism and inhibits glutamate dependent synthesis of enzymes, and is thereby potentially helpful in treatment of solid tumors.

Chemical Structure

Acivicin
Acivicin
CAS#42228-92-2

Theoretical Analysis

MedKoo Cat#: 524131

Name: Acivicin

CAS#: 42228-92-2

Chemical Formula: C5H7ClN2O3

Exact Mass: 178.0145

Molecular Weight: 178.57

Elemental Analysis: C, 33.63; H, 3.95; Cl, 19.85; N, 15.69; O, 26.88

Price and Availability

Size Price Availability Quantity
5mg USD 500.00 2 Weeks
10mg USD 850.00 2 Weeks
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Related CAS #
No Data
Synonym
Acivicin; Antibiotic AT-125; Antibiotic AT125; Antibiotic AT 125; NSC 163501; NSC163501; NSC-163501; U 42126; U42126; U-42126
IUPAC/Chemical Name
(S)-2-amino-2-((S)-3-chloro-4,5-dihydroisoxazol-5-yl)acetic acid
InChi Key
QAWIHIJWNYOLBE-OKKQSCSOSA-N
InChi Code
InChI=1S/C5H7ClN2O3/c6-3-1-2(11-8-3)4(7)5(9)10/h2,4H,1,7H2,(H,9,10)/t2-,4-/m0/s1
SMILES Code
ClC1=NO[C@@]([H])(C1)[C@@H](C(O)=O)N
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, not in water
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
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 178.57 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
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Bioanalysis. 2014 Apr;6(7):947-56. doi: 10.4155/bio.13.331. PubMed PMID: 24806903. 10: Ida T, Suzuki H, Fukuyama K, Hiratake J, Wada K. Structure of Bacillus subtilis γ-glutamyltranspeptidase in complex with acivicin: diversity of the binding mode of a classical and electrophilic active-site-directed glutamate analogue. Acta Crystallogr D Biol Crystallogr. 2014 Feb;70(Pt 2):607-14. doi: 10.1107/S1399004713031222. Epub 2014 Jan 31. PubMed PMID: 24531494; PubMed Central PMCID: PMC3940202. 11: Rosa JM, Dafre AL, Rodrigues AL. Antidepressant-like responses in the forced swimming test elicited by glutathione and redox modulation. Behav Brain Res. 2013 Sep 15;253:165-72. doi: 10.1016/j.bbr.2013.07.009. Epub 2013 Jul 11. PubMed PMID: 23850355. 12: Ki MR, Yun NR, Hwang SY. Glutamine-induced production and secretion of Helicobacter pylori gamma-glutamyltranspeptidase at low pH and its putative role in glutathione transport. J Microbiol Biotechnol. 2013 Apr;23(4):467-72. PubMed PMID: 23568200. 13: Stephan J, Franke J, Ehrenhofer-Murray AE. Chemical genetic screen in fission yeast reveals roles for vacuolar acidification, mitochondrial fission, and cellular GMP levels in lifespan extension. Aging Cell. 2013 Aug;12(4):574-83. doi: 10.1111/acel.12077. Epub 2013 Apr 23. PubMed PMID: 23521895. 14: Geier EG, Schlessinger A, Fan H, Gable JE, Irwin JJ, Sali A, Giacomini KM. Structure-based ligand discovery for the Large-neutral Amino Acid Transporter 1, LAT-1. Proc Natl Acad Sci U S A. 2013 Apr 2;110(14):5480-5. doi: 10.1073/pnas.1218165110. Epub 2013 Mar 18. PubMed PMID: 23509259; PubMed Central PMCID: PMC3619328. 15: Willoughby LF, Schlosser T, Manning SA, Parisot JP, Street IP, Richardson HE, Humbert PO, Brumby AM. An in vivo large-scale chemical screening platform using Drosophila for anti-cancer drug discovery. Dis Model Mech. 2013 Mar;6(2):521-9. doi: 10.1242/dmm.009985. Epub 2012 Sep 20. PubMed PMID: 22996645; PubMed Central PMCID: PMC3597034. 16: Dahboul F, Leroy P, Maguin Gate K, Boudier A, Gaucher C, Liminana P, Lartaud I, Pompella A, Perrin-Sarrado C. Endothelial γ-glutamyltransferase contributes to the vasorelaxant effect of S-nitrosoglutathione in rat aorta. PLoS One. 2012;7(9):e43190. doi: 10.1371/journal.pone.0043190. Epub 2012 Sep 11. PubMed PMID: 22984412; PubMed Central PMCID: PMC3439434. 17: Tamborini L, Pinto A, Smith TK, Major LL, Iannuzzi MC, Cosconati S, Marinelli L, Novellino E, Lo Presti L, Wong PE, Barrett MP, De Micheli C, Conti P. Synthesis and biological evaluation of CTP synthetase inhibitors as potential agents for the treatment of African trypanosomiasis. ChemMedChem. 2012 Sep;7(9):1623-34. doi: 10.1002/cmdc.201200304. Epub 2012 Aug 2. PubMed PMID: 22865834; PubMed Central PMCID: PMC3744939. 18: Wang Y, Zalups RK, Barfuss DW. Luminal transport of thiol S-conjugates of methylmercury in isolated perfused rabbit renal proximal tubules. Toxicol Lett. 2012 Sep 3;213(2):203-10. doi: 10.1016/j.toxlet.2012.07.003. Epub 2012 Jul 16. PubMed PMID: 22800651; PubMed Central PMCID: PMC3423585. 19: Yoshida T, Nasu H, Namba E, Ubukata O, Yamashita M. Discovery of a compound that acts as a bacterial PyrG (CTP synthase) inhibitor. J Med Microbiol. 2012 Sep;61(Pt 9):1280-5. doi: 10.1099/jmm.0.046052-0. Epub 2012 Jun 14. PubMed PMID: 22700553. 20: Kwiecień I, Iciek M, Włodek L. Acceleration of anaerobic cysteine transformations to sulfane sulfur consequent to γ-glutamyl transpeptidase inhibition. ScientificWorldJournal. 2012;2012:253724. doi: 10.1100/2012/253724. Epub 2012 Apr 30. PubMed PMID: 22629124; PubMed Central PMCID: PMC3353287.