Details
| Stereochemistry | RACEMIC |
| Molecular Formula | C6H13NO2S |
| Molecular Weight | 163.238 |
| Optical Activity | ( + / - ) |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CCSCCC(N)C(O)=O
InChI
InChIKey=GGLZPLKKBSSKCX-UHFFFAOYSA-N
InChI=1S/C6H13NO2S/c1-2-10-4-3-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)
| Molecular Formula | C6H13NO2S |
| Molecular Weight | 163.238 |
| Charge | 0 |
| Count |
|
| Stereochemistry | RACEMIC |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 1 |
| E/Z Centers | 0 |
| Optical Activity | ( + / - ) |
Ethionine is a non-proteinogenic amino acid structurally related to methionine, with an ethyl group in place of the methyl group. Ethionine is an antimetabolite and methionine antagonist. It prevents amino acid incorporation into proteins and interferes with cellular use of adenosine triphosphate (ATP). DL-Ethionine is a racemic mixture of the anti-methylation agent L-Ethionine and its enantiomer D-Ethionine. DL-Ethionine is used as a dietary supplement to accelerate cholangiocarcinogenesis in vivo. D-Ethionine and D,L-ethionine strongly
enhanced the activity of prolidase II compared with
L-ethionine. DL-Ethionine is used to induce oxidative stress in liver to study the levels and activities of anti-oxidative enzymes and compounds such as glutathione. As a therapeutic agent in the treatment of
malignant tumors of man, ethionine had no demonstrable efficacy. No changes in the appearance of tumor cells were noted after its administration, even when marked effects on other tissues were evident. The distressing toxicity of ethionine prevented further extension of the investigation.
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| Superoxide dismutase activity as a measure of hepatic oxidative stress in cattle following ethionine administration. | 2009-11 |
|
| Ethyl pyruvate ameliorates liver injury secondary to severe acute pancreatitis. | 2009-05-15 |
|
| Separation and determination of seleno amino acids using gas chromatography hyphenated with inductively coupled plasma mass spectrometry after hollow fiber liquid phase microextraction. | 2009-05 |
|
| Risperidone attenuates local and systemic inflammatory responses to ameliorate diet-induced severe necrotic pancreatitis in mice: it may provide a new therapy for acute pancreatitis. | 2009-01 |
|
| Norvaline is accumulated after a down-shift of oxygen in Escherichia coli W3110. | 2008-10-21 |
|
| C-kit inhibition by imatinib mesylate attenuates progenitor cell expansion and inhibits liver tumor formation in mice. | 2008-09 |
|
| A toxicogenomics approach for early assessment of potential non-genotoxic hepatocarcinogenicity of chemicals in rats. | 2008-08-19 |
|
| Total glutathione and glutathione reductase in bovine erythrocytes and liver biopsy. | 2008-08 |
|
| X-ray structure of the [FeFe]-hydrogenase maturase HydE from Thermotoga maritima. | 2008-07-04 |
|
| Random mutagenesis and recombination of sam1 gene by integrating error-prone PCR with staggered extension process. | 2008-07 |
|
| Elucidating the mechanisms of cooperative calcium-calmodulin interactions: a structural systems biology approach. | 2008-06-02 |
|
| Increased expression of Smad6 deteriorates murine acute experimental pancreatitis in two models. | 2008-06 |
|
| Synthetic biology of proteins: tuning GFPs folding and stability with fluoroproline. | 2008-02-27 |
|
| Bone marrow-derived cells fuse with hepatic oval cells but are not involved in hepatic tumorigenesis in the choline-deficient ethionine-supplemented diet rat model. | 2008-02 |
|
| Reduced expression of the Rassf1a gene and its aberrant DNA methylation in pancreatic duct adenocarcinomas induced by N-nitrosobis(2-oxopropyl)amine in hamsters. | 2008-02 |
|
| Attenuation of Biochemical Parameters in Streptozotocin-induced Diabetic Rats by Oral Administration of Extracts and Fractions of Cephalotaxus sinensis. | 2008-01 |
|
| Misincorporation of amino acid analogues into proteins by biosynthesis. | 2008 |
|
| Analysis of time-related metabolic fluctuations induced by ethionine in the rat. | 2007-12 |
|
| Hepatic accumulation of Hedgehog-reactive progenitors increases with severity of fatty liver damage in mice. | 2007-12 |
|
| Interferon-gamma exacerbates liver damage, the hepatic progenitor cell response and fibrosis in a mouse model of chronic liver injury. | 2007-12 |
|
| An unusual S-adenosylmethionine synthetase gene from dinoflagellate is methylated. | 2007-10-04 |
|
| An expanded set of amino acid analogs for the ribosomal translation of unnatural peptides. | 2007-10-03 |
|
| The Birt-Hogg-Dube and tuberous sclerosis complex homologs have opposing roles in amino acid homeostasis in Schizosaccharomyces pombe. | 2007-08-24 |
|
| 6His-Eco29kI methyltransferase methylation site and kinetic mechanism characterization. | 2007-08 |
|
| Therapeutic treatment with poly(ADP-ribose) polymerase inhibitors attenuates the severity of acute pancreatitis and associated liver and lung injury. | 2007-08 |
|
| Characteristics of methionine production by an engineered Corynebacterium glutamicum strain. | 2007-07 |
|
| Stem cells in the adult pancreas and liver. | 2007-06-01 |
|
| The use of animal models to study bacterial translocation during acute pancreatitis. | 2007-05 |
|
| Hepatotoxin-induced hypertyrosinemia and its toxicological significance. | 2007-03 |
|
| Attenuated liver progenitor (oval) cell and fibrogenic responses to the choline deficient, ethionine supplemented diet in the BALB/c inbred strain of mice. | 2007-01 |
|
| Isolation, culture and immortalisation of hepatic oval cells from adult mice fed a choline-deficient, ethionine-supplemented diet. | 2007 |
|
| S-adenosyl methionine: A connection between nutritional and genetic risk factors for neurodegeneration in Alzheimer's disease. | 2006-12-22 |
|
| Activation of nuclear factor kappa B and severe hepatic necrosis may mediate systemic inflammation in choline-deficient/ethionine-supplemented diet-induced pancreatitis. | 2006-10 |
|
| Hepatic oval cell response to the choline-deficient, ethionine supplemented model of murine liver injury is attenuated by the administration of a cyclo-oxygenase 2 inhibitor. | 2006-08 |
|
| Integrity of the methylation cycle is essential for mammalian neural tube closure. | 2006-07 |
|
| Alterations in the Smad4 gene in hamster pancreatic duct adenocarcinomas and established cell lines. | 2006-07 |
|
| Natural and directed biosynthesis of communesin alkaloids. | 2006-03 |
|
| Effect of amino acids containing sulfur on dithiolopyrrolone antibiotic productions by Saccharothrix algeriensis NRRL B-24137. | 2006-02 |
|
| Cytochrome P450 expression-induction profile and chemically mediated alterations of the WIF-B9 cell line. | 2006-01 |
|
| Selection and characterization of L-ethionine resistant mutants of Trichosporon cutaneum. | 2005-12-03 |
|
| Harnessing natural diversity to probe metabolic pathways. | 2005-12 |
|
| Reduced expression of the E-cadherin gene and its aberrant DNA methylation in hamster pancreatic tumors. | 2005-10-14 |
|
| Effects of R-102444 and its active metabolite R-96544, selective 5-HT2A receptor antagonists, on experimental acute and chronic pancreatitis: Additional evidence for possible involvement of 5-HT2A receptors in the development of experimental pancreatitis. | 2005-10-03 |
|
| Regional differences in gastrointestinal motility disturbances during acute necrotising pancreatitis. | 2005-10 |
|
| Inhibition of adult liver progenitor (oval) cell growth and viability by an agonist of the peroxisome proliferator activated receptor (PPAR) family member gamma, but not alpha or delta. | 2005-10 |
|
| Liver inflammation and cytokine production, but not acute phase protein synthesis, accompany the adult liver progenitor (oval) cell response to chronic liver injury. | 2005-08 |
|
| Natural disruption of group 2 phospholipase A2 gene protects against choline-deficient ethionine-supplemented diet-induced acute pancreatitis and lung injury. | 2005-07 |
|
| Oncostatin M induces an acute phase response but does not modulate the growth or maturation-status of liver progenitor (oval) cells in culture. | 2005-05-15 |
|
| A phase I study of hydralazine to demethylate and reactivate the expression of tumor suppressor genes. | 2005-04-29 |
|
| In vivo antihepatotoxic effects of Ligularia fischeri var. spiciformis and the identification of the active component, 3,4-dicaffeoylquinic acid. | 2005 |
Patents
Sample Use Guides
In Vivo Use Guide
Curator's Comment: Humans: Six patients with far-advanced neoplastic disease were treated with ethionine. Ethionine was given orally in doses that ranged from 0.67 to 15 gm. per day. https://www.ncbi.nlm.nih.gov/pubmed/13199763
Rats fed with a low protein diet for 11 days received daily intraperitoneal administration of DL-ethionine (20 mg/100 g) for the last 4 days of the diet.
Route of Administration:
Intraperitoneal
| Substance Class |
Chemical
Created
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admin
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Edited
Mon Mar 31 22:21:22 GMT 2025
by
admin
on
Mon Mar 31 22:21:22 GMT 2025
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| Record UNII |
92AK1Y27MZ
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| Record Status |
Validated (UNII)
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| Record Version |
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m5062
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