U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ABSOLUTE
Molecular Formula C5H11NO2S
Molecular Weight 149.211
Optical Activity UNSPECIFIED
Defined Stereocenters 1 / 1
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of METHIONINE

SMILES

CSCC[C@H](N)C(O)=O

InChI

InChIKey=FFEARJCKVFRZRR-BYPYZUCNSA-N
InChI=1S/C5H11NO2S/c1-9-3-2-4(6)5(7)8/h4H,2-3,6H2,1H3,(H,7,8)/t4-/m0/s1

HIDE SMILES / InChI

Molecular Formula C5H11NO2S
Molecular Weight 149.211
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

Description
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.

Originator

Sources: Journal of Biological Chemistry, Volume92, Pages 449-52, Journal, 1931

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
MEONINE

Approved Use

It 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 Use

Unknown
Primary
Unknown

Approved Use

Unknown
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
2.1 μg/mL
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

AUC

ValueDoseCo-administeredAnalytePopulation
17.81 μg × h/mL
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

T1/2

ValueDoseCo-administeredAnalytePopulation
3.36 h
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

Doses

DosePopulationAdverse 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: Page: p.267
unhealthy, 31-62
n = 12
Health Status: unhealthy
Condition: AIDS-associated myelopathy
Age Group: 31-62
Sex: M+F
Population Size: 12
Sources: Page: p.267
Disc. AE: Gastrointestinal symptom NOS...
AEs leading to
discontinuation/dose reduction:
Gastrointestinal symptom NOS (8.3%)
Sources: Page: p.267
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: Page: p.1273
unhealthy, 42.5
n = 28
Health Status: unhealthy
Condition: AIDS-associated myelopathy
Age Group: 42.5
Sex: M+F
Population Size: 28
Sources: Page: p.1273
AEs

AEs

AESignificanceDosePopulation
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: Page: p.267
unhealthy, 31-62
n = 12
Health Status: unhealthy
Condition: AIDS-associated myelopathy
Age Group: 31-62
Sex: M+F
Population Size: 12
Sources: Page: p.267
PubMed

PubMed

TitleDatePubMed
Palladium(II) and platinum(II) complexes as synthetic peptidases.
2001
1.9 A x-ray study shows closed flap conformation in crystals of tethered HIV-1 PR.
2001 Apr 1
Cytochrome p450 CYP79F1 from arabidopsis catalyzes the conversion of dihomomethionine and trihomomethionine to the corresponding aldoximes in the biosynthesis of aliphatic glucosinolates.
2001 Apr 6
Transepithelially transported pro-phenoloxidase in the cuticle of the silkworm, Bombyx mori. Identification of its methionyl residues oxidized to methionine sulfoxides.
2001 Apr 6
Measurement of the synthesis, turnover, and assembly of alpha- and beta-erythroid and nonerythroid spectrins in cultured rat hippocampal neurons.
2001 Feb
The amino acid profiles of the whole plant and of four plant residues from temperate and tropical forages.
2001 Feb
Vibrational spectroscopic study of DL-methionine dihydrogen phosphate.
2001 Feb
Elevation of asymmetrical dimethylarginine may mediate endothelial dysfunction during experimental hyperhomocyst(e)inaemia in humans.
2001 Feb
Effects of acute methionine loading and vitamin C on endogenous fibrinolysis, endothelium-dependent vasomotion and platelet aggregation.
2001 Feb
Evaluation of liver regeneration using the L-[1-13C]methionine breath test.
2001 Feb
Nuclear forms of parathyroid hormone-related peptide are translated from non-AUG start sites downstream from the initiator methionine.
2001 Feb
Evaluation of pleomorphic xanthoastrocytoma by use of positron emission tomography with.
2001 Feb
Trp 346 and Leu 352 residues in protective antigen are required for the expression of anthrax lethal toxin activity.
2001 Feb 16
Importance of the anticodon sequence in the aminoacylation of tRNAs by methionyl-tRNA synthetase and by valyl-tRNA synthetase in an Archaebacterium.
2001 Feb 2
Extracellular amino acid profiles in the paraventricular nucleus of the rat hypothalamus are influenced by diet composition.
2001 Feb 23
A 7-kDa prion protein (PrP) fragment, an integral component of the PrP region required for infectivity, is the major amyloid protein in Gerstmann-Sträussler-Scheinker disease A117V.
2001 Feb 23
Chronic maternal smoking and cord blood amino acid and enzyme levels at term.
2001 Jan
Direct actions of cannabinoids on synaptic transmission in the nucleus accumbens: a comparison with opioids.
2001 Jan
Intestinal aminooligopeptidase in diabetic BioBreed rat: altered posttranslational processing and trafficking.
2001 Jan
The coenzyme b12 analog 5'-deoxyadenosylcobinamide-gdp supports catalysis by methylmalonyl-coa mutase in the absence of trans-ligand coordination.
2001 Jan 12
Selective degradation of oxidized calmodulin by the 20 S proteasome.
2001 Jan 12
Subtle alterations in growth medium composition can dramatically alter the percentage of unsaturated fatty acids in the yeast Saccharomyces cerevisiae.
2001 Jan 15
Evaluation of lysine and methionine production in some Lactobacilli and yeasts from ogi.
2001 Jan 22
Crystallization and preliminary X-ray crystallographic studies of recombinant human betaine-homocysteine S-methyltransferase.
2001 Mar
Structure of the M148Q mutant of rusticyanin at 1.5 A: a model for the copper site of stellacyanin.
2001 Mar
Evidence against oxidative stress as mechanism of endothelial dysfunction in methionine loading model.
2001 Mar
Kinetics of the reactions of hypochlorous acid and amino acid chloramines with thiols, methionine, and ascorbate.
2001 Mar 1
Thermodynamics of the helix-coil transition: Binding of S15 and a hybrid sequence, disulfide stabilized peptide to the S-protein.
2001 Mar 1
Residue Met(156) contributes to the labile enzyme conformation of coagulation factor VIIa.
2001 Mar 2
Impaired ATP synthase assembly associated with a mutation in the human ATP synthase subunit 6 gene.
2001 Mar 2
Signalling pathways regulating the dephosphorylation of Ser729 in the hydrophobic domain of protein kinase Cepsilon upon cell passage.
2001 Mar 30
Sequence requirements for the N-methyl-D-aspartate receptor antagonist activity of conantokin-R.
2001 Mar 9
Uptake of tritiated thymidine, deoxyglucose and methionine in three lung cancer cell lines: deoxyglucose uptake mirrors tritiated thymidine uptake.
2001 Mar-Apr
Patents

Sample Use Guides

In Vivo Use Guide
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
by admin
on Fri Dec 15 16:03:30 GMT 2023
Edited
by admin
on Fri Dec 15 16:03:30 GMT 2023
Record UNII
AE28F7PNPL
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
METHIONINE
EP   HSDB   II   INCI   INN   MART.   MI   USAN   USP   VANDF   WHO-DD  
USAN   INN   INCI  
Official Name English
L-METHIONINE [FCC]
Common Name English
METHIONINE [HSDB]
Common Name English
METHIONINE [INCI]
Common Name English
L-METHIONINE [JAN]
Common Name English
METHIONINE [EP MONOGRAPH]
Common Name English
Methionine [WHO-DD]
Common Name English
(2S)-2-AMINO-4-(METHYLSULFANYL)BUTANOIC ACID
Systematic Name English
METHIONINE [USAN]
Common Name English
NSC-22946
Code English
METHIONINE [II]
Common Name English
L-METHIONINE
FCC   USP-RS  
Systematic Name English
METHIONINE [MI]
Common Name English
METHIONINE [MART.]
Common Name English
methionine [INN]
Common Name English
LEUCINE IMPURITY B [EP IMPURITY]
Common Name English
L-METHIONINE [USP-RS]
Common Name English
METHIONINE [USP MONOGRAPH]
Common Name English
METHIONINE [VANDF]
Common Name English
Classification Tree Code System Code
LOINC 47706-7
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LOINC 17264-3
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DSLD 171 (Number of products:32)
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DSLD 1779 (Number of products:2)
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WHO-ATC V03AB26
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DSLD 2065 (Number of products:1257)
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LOINC 27098-3
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WHO-VATC QG04BA90
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LOINC 26844-1
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FDA ORPHAN DRUG 91795
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LOINC 47700-0
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LOINC 15145-6
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NCI_THESAURUS C68442
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LOINC 2622-9
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LOINC 13405-6
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WHO-VATC QV03AB26
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LOINC 20651-6
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CFR 21 CFR 172.320
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WHO-VATC QA05BA90
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LOINC 32258-6
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Code System Code Type Description
NSC
22946
Created by admin on Fri Dec 15 16:03:30 GMT 2023 , Edited by admin on Fri Dec 15 16:03:30 GMT 2023
PRIMARY
CHEBI
49038
Created by admin on Fri Dec 15 16:03:30 GMT 2023 , Edited by admin on Fri Dec 15 16:03:30 GMT 2023
PRIMARY
DAILYMED
AE28F7PNPL
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PRIMARY
CHEBI
64558
Created by admin on Fri Dec 15 16:03:30 GMT 2023 , Edited by admin on Fri Dec 15 16:03:30 GMT 2023
PRIMARY
DRUG BANK
DB00134
Created by admin on Fri Dec 15 16:03:30 GMT 2023 , Edited by admin on Fri Dec 15 16:03:30 GMT 2023
PRIMARY
EVMPD
SUB21984
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PRIMARY
INN
452
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PRIMARY
MESH
D008715
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PRIMARY
CHEBI
49037
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PRIMARY
RXCUI
6837
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PRIMARY RxNorm
RS_ITEM_NUM
1411504
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PRIMARY
CHEBI
16044
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PRIMARY
CHEBI
16811
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PRIMARY
EVMPD
SUB08850MIG
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PRIMARY
MERCK INDEX
m7317
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PRIMARY Merck Index
CAS
63-68-3
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PRIMARY
NCI_THESAURUS
C29600
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PRIMARY
DRUG CENTRAL
3347
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PRIMARY
ChEMBL
CHEMBL42336
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PRIMARY
ECHA (EC/EINECS)
200-562-9
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PRIMARY
HSDB
4317
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PRIMARY
CHEBI
57844
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PRIMARY
ChEMBL
CHEMBL274119
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PRIMARY
FDA UNII
AE28F7PNPL
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PRIMARY
EPA CompTox
DTXSID5040548
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PRIMARY
SMS_ID
100000092414
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PRIMARY
WIKIPEDIA
METHIONINE
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PRIMARY
PUBCHEM
6137
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PRIMARY
CHEBI
16643
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PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
LABELED -> NON-LABELED
SALT/SOLVATE -> PARENT
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IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
EP
IMPURITY -> PARENT
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
PARENT -> IMPURITY
CHROMATOGRAPHIC PURITY (TLC)
EP
IMPURITY -> PARENT
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
EP
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ACTIVE MOIETY