Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C6H13NO2S |
Molecular Weight | 163.238 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCSCC[C@@H](N)C(O)=O
InChI
InChIKey=GGLZPLKKBSSKCX-RXMQYKEDSA-N
InChI=1S/C6H13NO2S/c1-2-10-4-3-5(7)6(8)9/h5H,2-4,7H2,1H3,(H,8,9)/t5-/m1/s1
Molecular Formula | C6H13NO2S |
Molecular Weight | 163.238 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
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). Ethionine is a far more potent inhibitor of RNA synthesis than of protein synthesis. While both stereoisomers were active, the L isomer was a more potent inhibitor of RNA synthesis than was the D isomer. In male mice, 3 hr after 20 mg/kg L-ethionine, RNA synthesis was inhibited 80%, while after D-ethionine it was inhibited only 51%. Ethionine was a potent inhibitor of wool growth in sheep; the L- and D-isomers appeared equally effective. Because of these pharmacological effects, ethionine is highly toxic and is a potent carcinogen. L and D-ethionine have being shown to be equally effective in producing tissue damage in rats and mice. The L- and ID-isomers of ethionine
are equally effective in producing pancreatic
and renal changes in the rat as well
as fatty infiltration of the liver and pancreatic
damage in the albino mouse.
Originator
Sources: https://www.ncbi.nlm.nih.gov/pubmed/13699975
Curator's Comment: Ethionine was first synthesized by Dyer in 1938
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL3976 Sources: https://www.ncbi.nlm.nih.gov/pubmed/19263194 |
|||
Target ID: P53634|||Q7Z3G7 Gene ID: 1075.0 Gene Symbol: CTSC Target Organism: Homo sapiens (Human) Sources: https://www.ncbi.nlm.nih.gov/pubmed/19263194 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/890687
The acute, 7-day LD50 in Swiss mice of D-ethionine administered intraperitoneally, was determined as 185 mg/kg with 95% confidence limits of 163 and 210 mg/kg.
Route of Administration:
Intraperitoneal
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19263194
20 mM L-ethionine and D-ethionine enhanced the activities
of prolidase I and prolidase II from normal human erythrocytes, and prolidase
activity in erythrocyte lysates from a patient with prolidase
deficiency against the iminodipeptides tested. The enhancing effect of D-ethionine was more significant than that of L-ethionine.
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 08:52:43 GMT 2023
by
admin
on
Sat Dec 16 08:52:43 GMT 2023
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Record UNII |
91GB0NN2T6
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Record Status |
Validated (UNII)
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Record Version |
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