Acivicin is an analog of glutamine. It is an inhibitor of gamma-glutamyl transferase.
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IUPAC name
(2S)-Amino[(5S)-3-chloro-4,5-dihydro-1,2-oxazol-5-yl]ethanoic acid
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Other names
Antibiotic AT 125
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3D model (JSmol)
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ChEBI |
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PubChem CID
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CompTox Dashboard (EPA)
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Properties | |
C5H7ClN2O3 | |
Molar mass | 178.574 |
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).
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Infobox references
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It is a fermentation product of Streptomyces sviceus.[1] It interferes with glutamate metabolism and inhibits glutamate dependent synthesis of enzymes, and is thereby potentially helpful in treatment of solid tumors.[2]
After its discovery in 1972, acivicin was studied as an anti-cancer agent, but trials were unsuccessful due to toxicity.[3]
An in vitro study showed that Acivicin at a concentration of 5 μM Acivicin inhibited by 78% the growth of human pancreatic carcinoma cells (MIA PaCa-2) after 72 hours in continuous culture. It was also found that acivicin at a concentration of 450 μM irreversibly inactivated MIA PaCa-2 γ-glutamyl transpeptidase (10 nmol/min/106 cells) with an inactivation half-life of 80 minutes.[1]
Phase I dose escalating studies conducted in 23 cancer patients administered acivicin with a concomitant 96-h i.v. infusion of a mixture of 16 amino acids showed reversible, dose-limiting CNS toxicity, characterized by lethargy, confusion and decreased mental status.