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 |
|---|---|---|
| A phase I study of hydralazine to demethylate and reactivate the expression of tumor suppressor genes. | 2005 Apr 29 |
|
| Liver inflammation and cytokine production, but not acute phase protein synthesis, accompany the adult liver progenitor (oval) cell response to chronic liver injury. | 2005 Aug |
|
| Harnessing natural diversity to probe metabolic pathways. | 2005 Dec |
|
| In vivo antihepatotoxic effects of Ligularia fischeri var. spiciformis and the identification of the active component, 3,4-dicaffeoylquinic acid. | 2005 Fall |
|
| Natural disruption of group 2 phospholipase A2 gene protects against choline-deficient ethionine-supplemented diet-induced acute pancreatitis and lung injury. | 2005 Jul |
|
| Oncostatin M induces an acute phase response but does not modulate the growth or maturation-status of liver progenitor (oval) cells in culture. | 2005 May 15 |
|
| Regional differences in gastrointestinal motility disturbances during acute necrotising pancreatitis. | 2005 Oct |
|
| 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 Oct |
|
| Reduced expression of the E-cadherin gene and its aberrant DNA methylation in hamster pancreatic tumors. | 2005 Oct 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 Oct 3 |
|
| Selection and characterization of L-ethionine resistant mutants of Trichosporon cutaneum. | 2005 Sep-Oct |
|
| 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 Aug |
|
| Effect of amino acids containing sulfur on dithiolopyrrolone antibiotic productions by Saccharothrix algeriensis NRRL B-24137. | 2006 Feb |
|
| Cytochrome P450 expression-induction profile and chemically mediated alterations of the WIF-B9 cell line. | 2006 Jan |
|
| Integrity of the methylation cycle is essential for mammalian neural tube closure. | 2006 Jul |
|
| Alterations in the Smad4 gene in hamster pancreatic duct adenocarcinomas and established cell lines. | 2006 Jul |
|
| Natural and directed biosynthesis of communesin alkaloids. | 2006 Mar |
|
| S-adenosyl methionine: A connection between nutritional and genetic risk factors for neurodegeneration in Alzheimer's disease. | 2006 Nov-Dec |
|
| Activation of nuclear factor kappa B and severe hepatic necrosis may mediate systemic inflammation in choline-deficient/ethionine-supplemented diet-induced pancreatitis. | 2006 Oct |
|
| Isolation, culture and immortalisation of hepatic oval cells from adult mice fed a choline-deficient, ethionine-supplemented diet. | 2007 |
|
| 6His-Eco29kI methyltransferase methylation site and kinetic mechanism characterization. | 2007 Aug |
|
| Therapeutic treatment with poly(ADP-ribose) polymerase inhibitors attenuates the severity of acute pancreatitis and associated liver and lung injury. | 2007 Aug |
|
| The Birt-Hogg-Dube and tuberous sclerosis complex homologs have opposing roles in amino acid homeostasis in Schizosaccharomyces pombe. | 2007 Aug 24 |
|
| Analysis of time-related metabolic fluctuations induced by ethionine in the rat. | 2007 Dec |
|
| Hepatic accumulation of Hedgehog-reactive progenitors increases with severity of fatty liver damage in mice. | 2007 Dec |
|
| Interferon-gamma exacerbates liver damage, the hepatic progenitor cell response and fibrosis in a mouse model of chronic liver injury. | 2007 Dec |
|
| Attenuated liver progenitor (oval) cell and fibrogenic responses to the choline deficient, ethionine supplemented diet in the BALB/c inbred strain of mice. | 2007 Jan |
|
| Characteristics of methionine production by an engineered Corynebacterium glutamicum strain. | 2007 Jul |
|
| Stem cells in the adult pancreas and liver. | 2007 Jun 1 |
|
| Hepatotoxin-induced hypertyrosinemia and its toxicological significance. | 2007 Mar |
|
| The use of animal models to study bacterial translocation during acute pancreatitis. | 2007 May |
|
| An expanded set of amino acid analogs for the ribosomal translation of unnatural peptides. | 2007 Oct 3 |
|
| An unusual S-adenosylmethionine synthetase gene from dinoflagellate is methylated. | 2007 Oct 4 |
|
| Misincorporation of amino acid analogues into proteins by biosynthesis. | 2008 |
|
| Total glutathione and glutathione reductase in bovine erythrocytes and liver biopsy. | 2008 Aug |
|
| A toxicogenomics approach for early assessment of potential non-genotoxic hepatocarcinogenicity of chemicals in rats. | 2008 Aug 19 |
|
| 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 Feb |
|
| 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 Feb |
|
| Synthetic biology of proteins: tuning GFPs folding and stability with fluoroproline. | 2008 Feb 27 |
|
| Attenuation of Biochemical Parameters in Streptozotocin-induced Diabetic Rats by Oral Administration of Extracts and Fractions of Cephalotaxus sinensis. | 2008 Jan |
|
| Random mutagenesis and recombination of sam1 gene by integrating error-prone PCR with staggered extension process. | 2008 Jul |
|
| X-ray structure of the [FeFe]-hydrogenase maturase HydE from Thermotoga maritima. | 2008 Jul 4 |
|
| Increased expression of Smad6 deteriorates murine acute experimental pancreatitis in two models. | 2008 Jun |
|
| Elucidating the mechanisms of cooperative calcium-calmodulin interactions: a structural systems biology approach. | 2008 Jun 2 |
|
| Norvaline is accumulated after a down-shift of oxygen in Escherichia coli W3110. | 2008 Oct 21 |
|
| C-kit inhibition by imatinib mesylate attenuates progenitor cell expansion and inhibits liver tumor formation in mice. | 2008 Sep |
|
| 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 Jan |
|
| Separation and determination of seleno amino acids using gas chromatography hyphenated with inductively coupled plasma mass spectrometry after hollow fiber liquid phase microextraction. | 2009 May |
|
| Ethyl pyruvate ameliorates liver injury secondary to severe acute pancreatitis. | 2009 May 15 |
|
| Superoxide dismutase activity as a measure of hepatic oxidative stress in cattle following ethionine administration. | 2009 Nov |
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
Sat Dec 16 08:52:43 GMT 2023
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Sat Dec 16 08:52:43 GMT 2023
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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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