Details
| Stereochemistry | ABSOLUTE |
| Molecular Formula | C5H10NO2S.Na |
| Molecular Weight | 171.193 |
| Optical Activity | UNSPECIFIED |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
[Na+].CSCC[C@H](N)C([O-])=O
InChI
InChIKey=IREPZTZSVPKCAR-WCCKRBBISA-M
InChI=1S/C5H11NO2S.Na/c1-9-3-2-4(6)5(7)8;/h4H,2-3,6H2,1H3,(H,7,8);/q;+1/p-1/t4-;/m0./s1
| Molecular Formula | Na |
| Molecular Weight | 22.98976928 |
| Charge | 1 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
| Molecular Formula | C5H10NO2S |
| Molecular Weight | 148.203 |
| Charge | -1 |
| Count |
|
| Stereochemistry | ABSOLUTE |
| Additional Stereochemistry | No |
| Defined Stereocenters | 1 / 1 |
| E/Z Centers | 0 |
| Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.drugs.com/cdi/methionine.html | http://www.rxlist.info/cons/me-500.html | https://www.ncbi.nlm.nih.gov/pubmed/5124307 | https://www.ncbi.nlm.nih.gov/pubmed/14505437
Curator's Comment: description was created based on several sources, including
https://www.drugs.com/cdi/methionine.html | http://www.rxlist.info/cons/me-500.html | https://www.ncbi.nlm.nih.gov/pubmed/5124307 | https://www.ncbi.nlm.nih.gov/pubmed/14505437
Methionine is an non-polar, aliphatic, essential α-amino acid that is used in the biosynthesis of proteins. High levels of methionine can be found in eggs, sesame seeds, Brazil nuts, fish, meats and some other plant seeds; methionine is also found in cereal grains. Most fruits and vegetables contain very little of it. Most legumes are also low in methionine. However, it is the combination of methionine and cystine which is considered for completeness of a protein. There is scientific evidence that restricting methionine consumption can increase lifespans in some animals. However, since methionine is an essential amino acid, it cannot be entirely removed from animals' diets without disease or death occurring over time. For example, rats fed a diet without methionine developed steatohepatitis (fatty liver), anemia and lost two thirds of their body weight over 5 weeks. Administration of methionine ameliorated the pathological consequences of methionine deprivation.
CNS Activity
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2111450 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | MEONINE Approved UseIt is used to make the urine more acidic. Making the urine more acidic helps to relieve skin irritation in incontinent (loss of bladder control) adults and diaper rash in infants. This medicine also helps to control strong urine odor. |
|||
| Primary | Me-500 Approved UseUnknown |
|||
| Primary | Unknown Approved UseUnknown |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
2.1 μg/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30873855/ |
40 mg/kg single, oral dose: 40 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
METHIONINE plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
AUC
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
17.81 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30873855/ |
40 mg/kg single, oral dose: 40 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
METHIONINE plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
T1/2
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
3.36 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/30873855/ |
40 mg/kg single, oral dose: 40 mg/kg route of administration: Oral experiment type: SINGLE co-administered: |
METHIONINE plasma | Rattus norvegicus population: HEALTHY age: ADULT sex: FEMALE food status: FASTED |
Doses
| Dose | Population | Adverse events |
|---|---|---|
3 g 2 times / day multiple, oral Studied dose Dose: 3 g, 2 times / day Route: oral Route: multiple Dose: 3 g, 2 times / day Sources: |
unhealthy, 31-62 |
Disc. AE: Gastrointestinal symptom NOS... AEs leading to discontinuation/dose reduction: Gastrointestinal symptom NOS (8.3%) Sources: |
3 g 2 times / day multiple, oral Studied dose Dose: 3 g, 2 times / day Route: oral Route: multiple Dose: 3 g, 2 times / day Sources: |
unhealthy, 42.5 |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| Gastrointestinal symptom NOS | 8.3% Disc. AE |
3 g 2 times / day multiple, oral Studied dose Dose: 3 g, 2 times / day Route: oral Route: multiple Dose: 3 g, 2 times / day Sources: |
unhealthy, 31-62 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 1.9 A x-ray study shows closed flap conformation in crystals of tethered HIV-1 PR. | 2001-04-01 |
|
| COMT-dependent protection of dopaminergic neurons by methionine, dimethionine and S-adenosylmethionine (SAM) against L-dopa toxicity in vitro. | 2001-03-02 |
|
| Axon terminals containing CGRP-immunoreactivity form synapses with CRF- and Met-enkephalin-immunopositive neurons in the laterodorsal division of the bed nucleus of the stria terminalis in the rat. | 2001-03-02 |
|
| Kinetics of the reactions of hypochlorous acid and amino acid chloramines with thiols, methionine, and ascorbate. | 2001-03-01 |
|
| Relative reactivities of N-chloramines and hypochlorous acid with human plasma constituents. | 2001-03-01 |
|
| Thermodynamics of the helix-coil transition: Binding of S15 and a hybrid sequence, disulfide stabilized peptide to the S-protein. | 2001-03-01 |
|
| Crystallization and preliminary X-ray crystallographic studies of recombinant human betaine-homocysteine S-methyltransferase. | 2001-03 |
|
| Structure of the M148Q mutant of rusticyanin at 1.5 A: a model for the copper site of stellacyanin. | 2001-03 |
|
| Synthesis of active high mannose-type lipoprotein lipase in human adipose tissues. | 2001-03 |
|
| Inhibitory effect of reactive oxygen species on angiotensin I-converting enzyme (kininase II). | 2001-03 |
|
| The effects of oral methionine and homocysteine on endothelial function. | 2001-03 |
|
| Evidence against oxidative stress as mechanism of endothelial dysfunction in methionine loading model. | 2001-03 |
|
| Steroidogenic acute regulatory protein expression is dependent upon post-translational effects of cAMP-dependent protein kinase A. | 2001-02-28 |
|
| Extracellular amino acid profiles in the paraventricular nucleus of the rat hypothalamus are influenced by diet composition. | 2001-02-23 |
|
| Trp 346 and Leu 352 residues in protective antigen are required for the expression of anthrax lethal toxin activity. | 2001-02-16 |
|
| In situ kinetic characterization of methylthioadenosine transport by the adenosine transporter (P2) of the African Trypanosoma brucei brucei and Trypanosoma brucei rhodesiense. | 2001-02-15 |
|
| Regulation of cell function by methionine oxidation and reduction. | 2001-02-15 |
|
| Orientations of Tyr 21 and Tyr 24 in the capsid of filamentous virus Ff determined by polarized Raman spectroscopy. | 2001-02-06 |
|
| Therapeutic targets in radiotherapy. | 2001-02-01 |
|
| Bus, a bushy Arabidopsis CYP79F1 knockout mutant with abolished synthesis of short-chain aliphatic glucosinolates. | 2001-02 |
|
| Measurement of the synthesis, turnover, and assembly of alpha- and beta-erythroid and nonerythroid spectrins in cultured rat hippocampal neurons. | 2001-02 |
|
| Intestinal uptake of betaine in vitro and the distribution of methyl groups from betaine, choline, and methionine in the body of broiler chicks. | 2001-02 |
|
| A bifunctional dihydrofolate synthetase--folylpolyglutamate synthetase in Plasmodium falciparum identified by functional complementation in yeast and bacteria. | 2001-02 |
|
| The amino acid profiles of the whole plant and of four plant residues from temperate and tropical forages. | 2001-02 |
|
| [Inhibition effect of Amaryllidaceae alkaloids, lycorine and lycoricidinol on macrophage TNF-alpha production]. | 2001-02 |
|
| Similarity between condensed phase and gas phase chemistry: fragmentation of peptides containing oxidized cysteine residues and its implications for proteomics. | 2001-02 |
|
| Vibrational spectroscopic study of DL-methionine dihydrogen phosphate. | 2001-02 |
|
| Lowered weight gain during pregnancy and risk of neural tube defects among offspring. | 2001-02 |
|
| Elevation of asymmetrical dimethylarginine may mediate endothelial dysfunction during experimental hyperhomocyst(e)inaemia in humans. | 2001-02 |
|
| Effects of acute methionine loading and vitamin C on endogenous fibrinolysis, endothelium-dependent vasomotion and platelet aggregation. | 2001-02 |
|
| The additional methionine residue at the N-terminus of bacterially expressed human interleukin-2 affects the interaction between the N- and C-termini. | 2001-01-30 |
|
| Electronic characterization of the oxidized state of the blue copper protein rusticyanin by 1H NMR: is the axial methionine the dominant influence for the high redox potential? | 2001-01-23 |
|
| Mapping the energy surface for the folding reaction of the coiled-coil peptide GCN4-p1. | 2001-01-23 |
|
| Evaluation of lysine and methionine production in some Lactobacilli and yeasts from ogi. | 2001-01-22 |
|
| The effects of processing methods on the levels of lysine, methionine and the general acceptability of ogi processed using starter cultures. | 2001-01-22 |
|
| Comparison of Vif sequences from diverse geographical isolates of HIV type 1 and SIV(cpz) identifies substitutions common to subtype C isolates and extensive variation in a proposed nuclear transport inhibition signal. | 2001-01-20 |
|
| Thromboangiitis obliterans (Buerger's disease). | 2001-01-18 |
|
| Sec63p and Kar2p are required for the translocation of SRP-dependent precursors into the yeast endoplasmic reticulum in vivo. | 2001-01-15 |
|
| Characterization of promoter region and genomic structure of the murine and human genes encoding Src like adapter protein. | 2001-01-10 |
|
| Cloning and functional analysis of the Sry-related HMG box gene, Sox18. | 2001-01-10 |
|
| [Homocysteine, endothelial dysfunction and cardiovascular risk: pathomechanisms and therapeutic options]. | 2001-01 |
|
| The influence of drinking water containing sodium chloride on performance and eggshell quality of a modern, colored layer strain. | 2001-01 |
|
| Intestinal disappearance and mesenteric and portal appearance of amino acids in dairy cows fed ruminally protected methionine. | 2001-01 |
|
| Effects of alimet on nutrient digestibility, bacterial protein synthesis, and ruminal disappearance during continuous culture. | 2001-01 |
|
| Effects of methionine loading on plasma and erythrocyte sulphur amino acids and sulph-hydryls before and after co-factor supplementation in haemodialysis patients. | 2001-01 |
|
| Retarded myelination in the lumbar spinal cord of piglets born with spread-leg syndrome. | 2001-01 |
|
| Near-infrared reflectance spectroscopy enables the fast and accurate prediction of the essential amino acid contents in soy, rapeseed meal, sunflower meal, peas, fishmeal, meat meal products, and poultry meal. | 2001-01 |
|
| Lack of association between the Met196Arg polymorphism in the TNFR2 gene and autoimmune diseases accompanied by vasculitis including SLE in Japanese. | 2001-01 |
|
| Palladium(II) and platinum(II) complexes as synthetic peptidases. | 2001 |
|
| The viral transmembrane superfamily: possible divergence of Arenavirus and Filovirus glycoproteins from a common RNA virus ancestor. | 2001 |
Patents
Sample Use Guides
Adults and teenagers—The usual dose is 200 milligrams (mg) three or four times a day.
Children—The usual dose is the contents of 1 capsule (200 mg) added to a warm bottle of milk or formula in the evening, or added to a glass of juice or water.
Route of Administration:
Oral
MCF-7 cells were obtained from American Type Culture Collection (Manassas, VA). Cells were cultured in a 5% CO~-humidified atmosphere at 37 OC in control medium, which consisted of Dulbecco's modified Eagle medium-F12 medium (1:1) supplemented with 5% bovine serum and 10 txg/ml insulin. Various concentrations (0.02, 0.2, 2, 5, and 10 g of methionine/L) were tested to determine the optimal level of methionine supplementation that causes the maximum inhibition of breast cancer cells. Cells were seeded in 96-well plates at a density of 1 • 10 a cells/well and grown in control medium for 24 h. The medium was then replaced with either control or methionine-supplemented treatment media as described above. Cell growth was assessed daily by the CellTiter 96 Aqueous One-Solution Cell Proliferation Assay reagent (Promega, Madison, WI). We found that cell growth was significantly suppressed by 5 to 10 g/L methionine on day 1, and no more growth was detected after 3 d of treatment.
| Substance Class |
Chemical
Created
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| Record UNII |
2YR4SPE61X
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| Record Status |
Validated (UNII)
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| Record Version |
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