L-ethionine is an S-ethylhomocysteine that has S-configuration at the chiral centre. It has a role as an antimetabolite and a carcinogenic agent. It is an enantiomer of a D-ethionine.
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
P261, P264, P264+P265, P271, P280, P302+P352, P304+P340, P305+P351+P338, P319, P321, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 39 reports by companies from 2 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Hazards SummaryCauses diffuse hepatitis and acute renal failure in acute oral studies of rats; Causes hepatitis in 35-day constant oral studies of rats; [RTECS] A hepatotoxin; [HSDB] A skin and strong eye irritant; Targets the liver; [Sigma-Aldrich MSDS]
Hazard Classes and CategoriesSkin Irrit. 2 (100%)
Safety & protection
Disposal Methods · 1 item
SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.
Toxicology
Interactions · 4 items
DL-METHIONINE @ 0.6-0.8% IN DIET FED SIMULTANEOUSLY WITH ETHIONINE PREVENTS DEVELOPMENT OF LIVER TUMORS /IN RATS/. /ETHIONINE/
IN RATS...LABELLING IN VIVO OF LIVER PROTEINS BY TRITIATED DIMETHYLNITROSAMINE WAS...LARGELY INHIBITED BY...ETHIONINE... /ETHIONINE/
Chemistry & industry
Pharmacology
Mechanism of Action · 2 items
/ETHIONINE/ INHIBITS THE INCORPORATION OF METHIONINE AND GLYCINE INTO RAT PROTEIN IN VIVO AND THE CONVERSION OF METHIONINE INTO CYSTEINE. ETHIONINE IS DEETHYLATED, AND THE ETHYL GROUP APPEARS IN ANALOGUES OF METABOLITES KNOWN TO PARTICIPATE IN TRANSMETHYLATION REACTIONS, EG ETHYL CHOLINE. IN THE RAT IT IS ITSELF INCORPORATED INTO ABNORMAL PROTEINS COMPETITIVELY, BUT ITS AFFINITY IS ONLY 1/600 THAT OF METHIONINE. /ETHIONINE/
... The mechanism by which ethionine induces fatty liver is thought to be due to the inhibition of synthesis of very low density lipoprotein. ... The synthesis of lipoprotein is correlated with liver estradiol receptor concn, /an examination/ of the effect of ethionine on estradiol receptor concn in rat liver /was examined/. Estradiol receptor concn in both cytosolic and nuclear fractions were greatly decr by a single injection of ethionine at a dose of 0.5 mg/kg bw. In particular, the decr in nuclear receptor concn was observed a few hr after the injection and correlated with the decr in triglyceride content in the very low density lipoprotein fraction. /Data suggests/ that liver estradiol receptor is involved in the pathogenesis of ethionine induced fatty liver of rats.
Metabolism/Metabolites · 3 items
S-ADENOSYLETHIONINE IS A SUGGESTED ALKYLATING METABOLITE OF CARCINOGEN ETHIONINE. /FROM TABLE/
ETHIONINE IS BIOACTIVATED IN LIVER TO S-ADENOSYL-L-ETHIONINE, WHICH CAN ETHYLATE MACROMOLECULES CAUSING CELL ABNORMALITIES. ADENOSYLETHIONINE IS CHEM STABLE & CAN PENETRATE TO EMBRYONIC TISSUES & CAUSE TERATOGENIC EFFECTS.
IN URINE OF TREATED RATS, 4 PRINCIPAL ETHIONINE EXCRETORY PRODUCTS WERE IDENTIFIED...N-ACETYLETHIONINE SULFOXIDE, S-ADENOSYLETHIONINE, ETHIONINE SULFOXIDE, & FREE ETHIONINE.
MeSH Pharmacological ClassificationDrugs that are chemically similar to naturally occurring metabolites, but differ enough to interfere with normal metabolic pathways. (From AMA Drug Evaluations Annual, 1994, p2033)
Absorption, Distribution and ExcretionIN RAT KIDNEY RADIOACTIVITY WAS MAINLY LOCALIZED IN MEDULLA FOLLOWING INJECTION WITH (14)C-ETHIONINE, WHEREAS (14)C-METHIONINE WAS HOMOGENEOUSLY DISTRIBUTED THROUGHOUT WHOLE PARENCHYMA IN RATS.
1 gm/kg · rat,LD,intraperitoneal,> 1gm/kg (1000mg/kg),LIVER: OTHER CHANGESLIVER: CHANGES IN LIVER WEIGHT,Acta Pathologica Japonica. Vol. 39, Pg. 281, 1989.
...TUMOR OF THE IRIS HAS BEEN OBSERVED IN RATS' EYES AFTER REPEATED SYSTEMIC ADMIN IN COMBINATION WITH N-2-FLUORENYLACETAMIDE.
The effects of SA3443, a novel disulfide cmpd on acute liver injuries induced by carbon tetrachloride, D-galactosamine and DL-ethionine were studied in rats or mice. SA3443 (100-300 mg/kg, po) significantly suppressed the incr of serum transaminase activity and liver triglyceride content in the carbon tetrachloride or DL-ethionine induced model. ...
Adverse EffectsOccupational hepatotoxin - Secondary hepatotoxins: the potential for toxic effect in the occupational setting is based on cases of poisoning by human ingestion or animal experimentation.
Human Toxicity Excerpts · 2 items
WHEN GIVEN ORALLY TO SMALL SERIES OF PATIENTS WITH FAR ADVANCED NEOPLASIAS IN DOSES OF 0.67 TO 45 G/DAY (TOTAL DOSES 9.7 TO 55 G), ETHIONINE PRODUCED THE FOLLOWING SYMPTOMS WHEN THE DIET WAS DEFICIENT IN METHIONINE: IMPAIRMENT OF LIVER FUNCTION, PROTEINURIA, HEMATURIA, DERMATITIS, LEUKOPENIA, THROMBOCYTOPENIA AND DIARRHEA. DETERIORATION OF MENTAL STATUS & FRANK TOXIC PSYCHOSIS ... ALSO OCCURRED.
These agents /including ethionine/ cause hepatic damage by interfering with essential metabolic pathways, which leads to cytotoxic (necrosis or steatosis) and/or cholestatic (biliary stasis) injury patterns. /Ethionine/
Non-Human Toxicity Excerpts · 5 items
ETHIONINE, A HEPATOCARCINOGEN, ETHYLATED CELLULAR CONSTITUENTS OF LIVER INCL DNA ON PROLONGED FEEDING TO RATS. SUGGESTED MECHANISM INVOLVES S-ADENOSYL-L-ETHIONINE AS /ETHYL/ DONOR... HOWEVER.../EXPECTATION /WOULD BE/ THAT 5-ETHYLCYTOSINE WOULD BE FORMED IN DNA... ONLY ETHYLATED BASE DETECTED WAS 7-ETHYLGUANINE.
OPTIMAL INDUCTION OF /RAT/ LIVER TUMORS REQUIRES CONTINUOUS FEEDING OF SYNTHETIC DL-ETHIONINE (0.25% IN DIET) FOR...5 MO. ... THOUGH ETHIONINE CAUSES ACUTE DEGENERATIVE LESIONS IN PANCREATIC ACINI & PREVENTS ALLOXAN DIABETES, NO PANCREATIC TUMORS...REPORTED. /DL-FORM/
CHEM TERATOGENS THAT REQUIRE METAB OR BIOACTIVATION TO ELECTROPHILIC REACTANTS INCL...ETHIONINE... MOST FREQUENTLY IT IS LIVER THAT PRODUCES VARIETY OF ELECTROPHILIC REACTANTS THAT, LIKE ALKYLATING AGENTS, COVALENTLY BIND TO MACROMOLECULES.
ETHIONINE...INTERFERENCE WITH METHIONINE FOR AVAILABLE ATP LEADS TO DIMINUTION OF LIPOPROTEIN-TRANSPORT MOLECULES & RETENTION OF FAT.
For more Non-Human Toxicity Excerpts (Complete) data for (L)-ETHIONINE (15 total), please visit the HSDB record page.
Antidote and Emergency TreatmentL-METHIONINE IS ANTAGONISTIC TO THE EFFECTS OF ETHIONINE.
Safety data
PPE
dust mask type N95 (US), Eyeshields, Gloves
wgk
3
tsca
TSCA listed
rtecs
ES6825300
hs_code
2930.90.4950
Toxicity
rat,LD,intraperitoneal,> 1gm/kg (1000mg/kg),LIVER: OTHER CHANGESLIVER: CHANGES IN LIVER WEIGHT,Acta Pathologica Japonica. Vol. 39, Pg. 281, 1989.
risk_code
36/37/38
Signal word
Warning
Symbol(GHS)
GHS07
hazard_code
Xi
safety_code
26
Storage Class
11 - Combustible Solids
target organs
Respiratory system
Hazard statements
H315-H319-H335
Hazard Classifications
Eye Irrit. 2Skin Irrit. 2STOT SE 3
Precautionary statements
P261-P264-P271-P280-P302+P352-P305+P351+P338
Hazardous Substances Data
13073-35-3(Hazardous Substances Data)
Uses & manufacturing
Uses · 3 items
An antimetabolite and methionine antagonist that interferes with amino acid incorporation into proteins and with cellular ATP utilization. It also produces liver neoplasms. [ChemIDplus] Toxic analogue of the essential amino acid methionine; Produced by various microorganisms such as E. coli; Used as an experimental carcinogen and in biological research; Not commercially produced in the US; [HSDB]
EXPTL CARCINOGEN
BIOLOGICAL RESEARCH CHEMICAL
U.S. Exports · 2 items
(1977) No Data
(1979) No Data
U.S. Imports · 2 items
(1977) No Data
(1979) No Data
U.S. Production · 3 items
(1977) NOT PRODUCED COMMERCIALLY IN US
(1979) NOT PRODUCED COMMERCIALLY IN US
(1992) No data
Methods of Manufacturing · 2 items
REACTION OF ETHANETHIOL WITH ACROLEIN FOLLOWED BY TREATMENT WITH HYDROGEN CYANIDE & AMMONIA AND HYDROLYSIS
...FROM ETHANETHIOL & ACROLEIN, PURIFICATION VIA ZN SALT: NORTON US PATENT 2,840,587 (1958 TO DOW). PREPN OF DL-...& L-FORM: ARMSTRONG, LEWIS, J ORG CHEM 16, 749 (1951).
General Manufacturing Information · 3 items
L-Homocysteine, S-ethyl-: INACTIVE
.../ETHIONINE/ WAS SYNTHESIZED AS AN ANTIMETABOLITE TO L-METHIONINE & USED IN STUDY OF TRANSMETHYLATION REACTIONS IN RELATION TO THE BIOCHEMISTRY OF THIS ESSENTIAL AMINO ACID.
ETHIONINE...THE TOXIC ANALOGUE OF AMINO ACID METHIONINE, IS PRODUCED BY E COLI & VARIOUS OTHER MICROORGANISMS.
Applications
UsesEthionine-induced inhibition of protein synthesis and lowering of ATP level in the liver.
