Date published: 2025-10-15

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Acivicin (CAS 42228-92-2)

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Alternate Names:
αS-amino-3-chloro-4,5S-dihydro-5-isoxazoleacetic acid; (αS,5S)-α-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetic Acid; [S-(R*,R*)]-α-Amino-3-chloro-4,5-dihydro-5-isoxazoleacetic Acid; AT 125; Antibiotic AT 125; NSC 163501; U 42126; (+)-Acivicin
Application:
Acivicin is an inhibitor of GGT used for solid tumor research
CAS Number:
42228-92-2
Purity:
≥97%
Molecular Weight:
178.57
Molecular Formula:
C5H7ClN2O3
Supplemental Information:
This is classified as a Dangerous Good for transport and may be subject to additional shipping charges.
For Research Use Only. Not Intended for Diagnostic or Therapeutic Use.
* Refer to Certificate of Analysis for lot specific data.

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Acivicin is an antineoplastic antibiotic believed to act by interfering with glutamine metabolism which has been researched in a variety of solid tumor samples. Acivicin is an irreversible inhibitor of GGT (gamma-glutamyl transpeptidase) ID50 = 0.54 mM. Additionally, it inhibits the enzymatic conversion of leukotriene C4 to leukotriene D4 and the bioactivation and release of nitric oxide from GSNO6. Also, studies show anti-tumor and anti-metastatic activity and blocks H. Pylori GGT-induced T-cell inhibition.


Acivicin (CAS 42228-92-2) References

  1. Inhibition of gamma-glutamyl transpeptidase or cysteine S-conjugate beta-lyase activity blocks the nephrotoxicity of cisplatin in mice.  |  Townsend, DM. and Hanigan, MH. 2002. J Pharmacol Exp Ther. 300: 142-8. PMID: 11752109
  2. gamma-Glutamyl transpeptidase overexpression increases metastatic growth of B16 melanoma cells in the mouse liver.  |  Obrador, E., et al. 2002. Hepatology. 35: 74-81. PMID: 11786961
  3. Inhibition of gamma-glutamyl transpeptidase activity decreases intracellular cysteine levels in cervical carcinoma.  |  Ruoso, P. and Hedley, DW. 2004. Cancer Chemother Pharmacol. 54: 49-56. PMID: 15034755
  4. Effects of probenecid and acivicin on potassium dichromate-induced acute nephrotoxicity in mice.  |  De Ceaurriz, J. and Ban, M. 1991. Toxicol Lett. 59: 139-45. PMID: 1684453
  5. Inhibition of T-cell proliferation by Helicobacter pylori gamma-glutamyl transpeptidase.  |  Schmees, C., et al. 2007. Gastroenterology. 132: 1820-33. PMID: 17484877
  6. Prevention of central nervous system toxicity of the antitumor antibiotic acivicin by concomitant infusion of an amino acid mixture.  |  Williams, MG., et al. 1990. Cancer Res. 50: 5475-80. PMID: 2386952
  7. Distribution of gamma-glutamyl transpeptidase in the mouse epididymis and its response to acivicin.  |  Agrawal, YP., et al. 1989. J Reprod Fertil. 86: 185-93. PMID: 2569039
  8. Effects of acivicin and dichloroallyl lawsone upon pyrimidine biosynthesis in mouse L1210 leukemia cells.  |  Kemp, AJ., et al. 1986. J Biol Chem. 261: 14891-5. PMID: 3771555
  9. The inhibition of gamma-glutamyl transpeptidase from human pancreatic carcinoma cells by (alpha S,5S)-alpha-amino-3-chloro-4,5-dihydro-5-isoxazoleacetic acid (AT-125; NSC-163501).  |  Allen, L., et al. 1980. Res Commun Chem Pathol Pharmacol. 27: 175-82. PMID: 6102405
  10. Excretion of cysteine and gamma-glutamylcysteine moieties in human and experimental animal gamma-glutamyl transpeptidase deficiency.  |  Griffith, OW. and Meister, A. 1980. Proc Natl Acad Sci U S A. 77: 3384-7. PMID: 6106190
  11. Effects of acivicin and dipyridamole on hepatoma 3924A cells.  |  Zhen, YS., et al. 1983. Cancer Res. 43: 1616-9. PMID: 6831407
  12. Biochemical pharmacology of acivicin in rat hepatoma cells.  |  Lui, MS., et al. 1982. Biochem Pharmacol. 31: 3469-73. PMID: 7150366
  13. Sex- and age-related mouse toxicity and disposition of the amino acid antitumor agent, acivicin.  |  McGovren, JP., et al. 1981. J Pharmacol Exp Ther. 216: 433-40. PMID: 7205622
  14. S-Nitrosoglutathione as a substrate for gamma-glutamyl transpeptidase.  |  Hogg, N., et al. 1997. Biochem J. 323 (Pt 2): 477-81. PMID: 9163341

Ordering Information

Product NameCatalog #UNITPriceQtyFAVORITES

Acivicin, 1 mg

sc-200498B
1 mg
$102.00

Acivicin, 5 mg

sc-200498C
5 mg
$408.00

Acivicin, 10 mg

sc-200498
10 mg
$642.00

Acivicin, 25 mg

sc-200498D
25 mg
$1275.00

What is the solubility in PBS?

Asked by: SCchem16
Thank you for your question. This chemical, Acivicin (CAS 42228-92-2), is soluble in PBS (pH 7.2) at ~1.4 mg/ml.
Answered by: Chemical Support 2
Date published: 2017-03-06

For the IC50 data listed (HIV-1(RF): IC50 = > 15.2 uM), do you have a reference for this, or know if it is a measure of GGT inhibition in HIV-1?

Asked by: two2igm05
Thank you for your question. Yes, we have a reference for that IC50 data: https://chemdb.niaid.nih.gov/CellularDetails.aspx?AIDSNO=010581&pn=0 Please contact Technical Service for more information regarding this chemical.
Answered by: Tech Service 9
Date published: 2016-12-15
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Rated 5 out of 5 by from Exactly what we wantFast shipment and exactly what we wanted! High quality standard.
Date published: 2022-04-15
Rated 5 out of 5 by from Solbu et alSolbu et al. (PubMed ID 15716335) used Acivicin to inhibit the activity of the PIG enzyme. -SCBT Publication Review
Date published: 2015-06-24
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Acivicin is rated 5.0 out of 5 by 2.
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