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
The viral transmembrane superfamily: possible divergence of Arenavirus and Filovirus glycoproteins from a common RNA virus ancestor.
2001
1.9 A x-ray study shows closed flap conformation in crystals of tethered HIV-1 PR.
2001 Apr 1
Saccharomyces cerevisiae is capable of de Novo pantothenic acid biosynthesis involving a novel pathway of beta-alanine production from spermine.
2001 Apr 6
Bus, a bushy Arabidopsis CYP79F1 knockout mutant with abolished synthesis of short-chain aliphatic glucosinolates.
2001 Feb
Measurement of the synthesis, turnover, and assembly of alpha- and beta-erythroid and nonerythroid spectrins in cultured rat hippocampal neurons.
2001 Feb
Intestinal uptake of betaine in vitro and the distribution of methyl groups from betaine, choline, and methionine in the body of broiler chicks.
2001 Feb
A bifunctional dihydrofolate synthetase--folylpolyglutamate synthetase in Plasmodium falciparum identified by functional complementation in yeast and bacteria.
2001 Feb
The amino acid profiles of the whole plant and of four plant residues from temperate and tropical forages.
2001 Feb
[Inhibition effect of Amaryllidaceae alkaloids, lycorine and lycoricidinol on macrophage TNF-alpha production].
2001 Feb
Similarity between condensed phase and gas phase chemistry: fragmentation of peptides containing oxidized cysteine residues and its implications for proteomics.
2001 Feb
Vibrational spectroscopic study of DL-methionine dihydrogen phosphate.
2001 Feb
Lowered weight gain during pregnancy and risk of neural tube defects among offspring.
2001 Feb
The folate cycle and disease in humans.
2001 Feb
Rapid acquisition of entire DNA polymerase gene of a novel herpesvirus from green turtle fibropapilloma by a genomic walking technique.
2001 Feb
Evaluation of liver regeneration using the L-[1-13C]methionine breath test.
2001 Feb
Contrasting responses by basal ganglia met-enkephalin systems to low and high doses of methamphetamine in a rat model.
2001 Feb
Two functional copies of the DGCR6 gene are present on human chromosome 22q11 due to a duplication of an ancestral locus.
2001 Feb
Evaluation of pleomorphic xanthoastrocytoma by use of positron emission tomography with.
2001 Feb
Therapeutic targets in radiotherapy.
2001 Feb 1
In situ kinetic characterization of methylthioadenosine transport by the adenosine transporter (P2) of the African Trypanosoma brucei brucei and Trypanosoma brucei rhodesiense.
2001 Feb 15
A mutation in alpha-tropomyosin(slow) affects muscle strength, maturation and hypertrophy in a mouse model for nemaline myopathy.
2001 Feb 15
Extracellular amino acid profiles in the paraventricular nucleus of the rat hypothalamus are influenced by diet composition.
2001 Feb 23
Steroidogenic acute regulatory protein expression is dependent upon post-translational effects of cAMP-dependent protein kinase A.
2001 Feb 28
Orientations of Tyr 21 and Tyr 24 in the capsid of filamentous virus Ff determined by polarized Raman spectroscopy.
2001 Feb 6
[Homocysteine, endothelial dysfunction and cardiovascular risk: pathomechanisms and therapeutic options].
2001 Jan
The influence of drinking water containing sodium chloride on performance and eggshell quality of a modern, colored layer strain.
2001 Jan
Intestinal disappearance and mesenteric and portal appearance of amino acids in dairy cows fed ruminally protected methionine.
2001 Jan
Effects of alimet on nutrient digestibility, bacterial protein synthesis, and ruminal disappearance during continuous culture.
2001 Jan
Effects of methionine loading on plasma and erythrocyte sulphur amino acids and sulph-hydryls before and after co-factor supplementation in haemodialysis patients.
2001 Jan
Retarded myelination in the lumbar spinal cord of piglets born with spread-leg syndrome.
2001 Jan
Impaired response to interferon-gamma in activated macrophages due to tyrosine nitration of STAT1 by endogenous nitric oxide.
2001 Jan
Sec63p and Kar2p are required for the translocation of SRP-dependent precursors into the yeast endoplasmic reticulum in vivo.
2001 Jan 15
Thromboangiitis obliterans (Buerger's disease).
2001 Jan 18
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 Jan 20
Evaluation of lysine and methionine production in some Lactobacilli and yeasts from ogi.
2001 Jan 22
The effects of processing methods on the levels of lysine, methionine and the general acceptability of ogi processed using starter cultures.
2001 Jan 22
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 Jan 23
Mapping the energy surface for the folding reaction of the coiled-coil peptide GCN4-p1.
2001 Jan 23
The additional methionine residue at the N-terminus of bacterially expressed human interleukin-2 affects the interaction between the N- and C-termini.
2001 Jan 30
Eukaryotic translation initiation factor 5 (eIF5) acts as a classical GTPase-activator protein.
2001 Jan 9
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
Synthesis of active high mannose-type lipoprotein lipase in human adipose tissues.
2001 Mar
Inhibitory effect of reactive oxygen species on angiotensin I-converting enzyme (kininase II).
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
COMT-dependent protection of dopaminergic neurons by methionine, dimethionine and S-adenosylmethionine (SAM) against L-dopa toxicity in vitro.
2001 Mar 2
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 Mar 2
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 Wed Jul 05 23:31:29 UTC 2023
Edited
by admin
on Wed Jul 05 23:31:29 UTC 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 63380-0
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LOINC 56957-4
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LOINC 53397-6
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LOINC 53156-6
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LOINC 26963-9
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LOINC 17264-3
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DSLD 171 (Number of products:32)
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LOINC 25959-8
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LOINC 47702-6
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LOINC 47701-8
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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 44338-2
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LOINC 2624-5
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LOINC 47703-4
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LOINC 15130-8
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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 25956-4
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LOINC 47704-2
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LOINC 22681-1
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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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LOINC 13772-9
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LOINC 47705-9
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LOINC 53161-6
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LOINC 2621-1
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LOINC 55943-5
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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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LOINC 30063-2
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LOINC 13376-9
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LOINC 22716-5
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LOINC 27953-9
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LOINC 2623-7
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LOINC 25476-3
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LOINC 2620-3
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LOINC 32257-8
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LOINC 22648-0
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Code System Code Type Description
NSC
22946
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
CHEBI
49038
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
DAILYMED
AE28F7PNPL
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
CHEBI
64558
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
DRUG BANK
DB00134
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
EVMPD
SUB21984
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
INN
452
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
MESH
D008715
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
CHEBI
49037
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
RXCUI
6837
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY RxNorm
RS_ITEM_NUM
1411504
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
CHEBI
16044
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
CHEBI
16811
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
EVMPD
SUB08850MIG
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
MERCK INDEX
M7317
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY Merck Index
CAS
63-68-3
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
NCI_THESAURUS
C29600
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
DRUG CENTRAL
3347
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
ChEMBL
CHEMBL42336
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
ECHA (EC/EINECS)
200-562-9
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
HSDB
4317
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
CHEBI
57844
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
ChEMBL
CHEMBL274119
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
FDA UNII
AE28F7PNPL
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
EPA CompTox
DTXSID5040548
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
SMS_ID
100000092414
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
WIKIPEDIA
METHIONINE
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
PUBCHEM
6137
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
CHEBI
16643
Created by admin on Wed Jul 05 23:31:29 UTC 2023 , Edited by admin on Wed Jul 05 23:31:29 UTC 2023
PRIMARY
Related Record Type Details
SALT/SOLVATE -> PARENT
LABELED -> NON-LABELED
SALT/SOLVATE -> PARENT
Related Record Type Details
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
Related Record Type Details
ACTIVE MOIETY