METHIONINE

US Previously Marketed

First approved in 1945

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 Search

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
Sources: https://www.drugs.com/cdi/me-500.html
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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
S-adenosylmethionine synthetase (MAT 1 and MAT 2) 3 Target ID: CHEMBL2111450 Sources: https://www.ncbi.nlm.nih.gov/pubmed/3755757	Substrate 661

Conditions

Condition	Modality	Highest Phase	Product
Alkaline urine 3 Sources: https://www.ndrugs.com/?s=meonine	Primary	Approved 8583	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.
Skin irritation in incontinent adults and diaper rash in infants 3 Sources: https://www.drugs.com/cons/me-500.html	Primary	Not Provided 511	Me-500 Approved Use Unknown
AIDS vacuolar myelopathy 3 Sources: https://clinicaltrials.gov/ct2/show/NCT00032695	Primary	Phase III 665	Unknown Approved Use Unknown

C_max

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

T_1/2

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: https://pubmed.ncbi.nlm.nih.gov/9674817	unhealthy, 31-62 Health Status: unhealthy Age Group: 31-62 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/9674817	Disc. AE: Gastrointestinal symptom NOS... AEs leading to discontinuation/dose reduction: Gastrointestinal symptom NOS (8.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/9674817
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: https://pubmed.ncbi.nlm.nih.gov/15477550	unhealthy, 42.5 Health Status: unhealthy Age Group: 42.5 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/15477550	Sources: https://pubmed.ncbi.nlm.nih.gov/15477550

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: https://pubmed.ncbi.nlm.nih.gov/9674817	unhealthy, 31-62 Health Status: unhealthy Age Group: 31-62 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/9674817

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:16811	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:16811
ChemicalBook	CB6208758	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6208758
ChemicalBook	CB9208759	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB9208759
eMolecules	495925	https://www.emolecules.com/cgi-bin/more?vid=495925
MolPort	MolPort-000-928-154	https://www.molport.com/shop/molecule-link/MolPort-000-928-154

PubMed

Title	Date	PubMed
1.9 A x-ray study shows closed flap conformation in crystals of tethered HIV-1 PR.	2001-04-01	11170214
COMT-dependent protection of dopaminergic neurons by methionine, dimethionine and S-adenosylmethionine (SAM) against L-dopa toxicity in vitro.	2001-03-02	11223018
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	11222987
Kinetics of the reactions of hypochlorous acid and amino acid chloramines with thiols, methionine, and ascorbate.	2001-03-01	11182528
Relative reactivities of N-chloramines and hypochlorous acid with human plasma constituents.	2001-03-01	11182523
Thermodynamics of the helix-coil transition: Binding of S15 and a hybrid sequence, disulfide stabilized peptide to the S-protein.	2001-03-01	11170206
Crystallization and preliminary X-ray crystallographic studies of recombinant human betaine-homocysteine S-methyltransferase.	2001-03	11223523
Structure of the M148Q mutant of rusticyanin at 1.5 A: a model for the copper site of stellacyanin.	2001-03	11223511
Synthesis of active high mannose-type lipoprotein lipase in human adipose tissues.	2001-03	11223423
Inhibitory effect of reactive oxygen species on angiotensin I-converting enzyme (kininase II).	2001-03	11207678
The effects of oral methionine and homocysteine on endothelial function.	2001-03	11179277
Evidence against oxidative stress as mechanism of endothelial dysfunction in methionine loading model.	2001-03	11179081
Steroidogenic acute regulatory protein expression is dependent upon post-translational effects of cAMP-dependent protein kinase A.	2001-02-28	11223189
Extracellular amino acid profiles in the paraventricular nucleus of the rat hypothalamus are influenced by diet composition.	2001-02-23	11172779
Trp 346 and Leu 352 residues in protective antigen are required for the expression of anthrax lethal toxin activity.	2001-02-16	11178978
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	11226379
Regulation of cell function by methionine oxidation and reduction.	2001-02-15	11179387
Orientations of Tyr 21 and Tyr 24 in the capsid of filamentous virus Ff determined by polarized Raman spectroscopy.	2001-02-06	11170449
Therapeutic targets in radiotherapy.	2001-02-01	11173124
Bus, a bushy Arabidopsis CYP79F1 knockout mutant with abolished synthesis of short-chain aliphatic glucosinolates.	2001-02	11226190
Measurement of the synthesis, turnover, and assembly of alpha- and beta-erythroid and nonerythroid spectrins in cultured rat hippocampal neurons.	2001-02	11223413
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	11223388
A bifunctional dihydrofolate synthetase--folylpolyglutamate synthetase in Plasmodium falciparum identified by functional complementation in yeast and bacteria.	2001-02	11223131
The amino acid profiles of the whole plant and of four plant residues from temperate and tropical forages.	2001-02	11219464
[Inhibition effect of Amaryllidaceae alkaloids, lycorine and lycoricidinol on macrophage TNF-alpha production].	2001-02	11218731
Similarity between condensed phase and gas phase chemistry: fragmentation of peptides containing oxidized cysteine residues and its implications for proteomics.	2001-02	11212008
Vibrational spectroscopic study of DL-methionine dihydrogen phosphate.	2001-02	11206558
Lowered weight gain during pregnancy and risk of neural tube defects among offspring.	2001-02	11171858
Elevation of asymmetrical dimethylarginine may mediate endothelial dysfunction during experimental hyperhomocyst(e)inaemia in humans.	2001-02	11171285
Effects of acute methionine loading and vitamin C on endogenous fibrinolysis, endothelium-dependent vasomotion and platelet aggregation.	2001-02	11171280
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	11170412
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	11170402
Mapping the energy surface for the folding reaction of the coiled-coil peptide GCN4-p1.	2001-01-23	11170389
Evaluation of lysine and methionine production in some Lactobacilli and yeasts from ogi.	2001-01-22	11205947
The effects of processing methods on the levels of lysine, methionine and the general acceptability of ogi processed using starter cultures.	2001-01-22	11205940
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	11177396
Thromboangiitis obliterans (Buerger's disease).	2001-01-18	11188842
Sec63p and Kar2p are required for the translocation of SRP-dependent precursors into the yeast endoplasmic reticulum in vivo.	2001-01-15	11226176
Characterization of promoter region and genomic structure of the murine and human genes encoding Src like adapter protein.	2001-01-10	11179692
Cloning and functional analysis of the Sry-related HMG box gene, Sox18.	2001-01-10	11179689
[Homocysteine, endothelial dysfunction and cardiovascular risk: pathomechanisms and therapeutic options].	2001-01	11220081
The influence of drinking water containing sodium chloride on performance and eggshell quality of a modern, colored layer strain.	2001-01	11214342
Intestinal disappearance and mesenteric and portal appearance of amino acids in dairy cows fed ruminally protected methionine.	2001-01	11210033
Effects of alimet on nutrient digestibility, bacterial protein synthesis, and ruminal disappearance during continuous culture.	2001-01	11210029
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	11209001
Retarded myelination in the lumbar spinal cord of piglets born with spread-leg syndrome.	2001-01	11195089
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	11170560
Lack of association between the Met196Arg polymorphism in the TNFR2 gene and autoimmune diseases accompanied by vasculitis including SLE in Japanese.	2001-01	11169260
Palladium(II) and platinum(II) complexes as synthetic peptidases.	2001	11219007
The viral transmembrane superfamily: possible divergence of Arenavirus and Filovirus glycoproteins from a common RNA virus ancestor.	2001	11208257

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

In Vitro Use Guide

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 `Mon Mar 31 18:17:41 GMT 2025` Edited by `admin` on `Mon Mar 31 18:17:41 GMT 2025`
Record UNII	AE28F7PNPL
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

METHIONINE

Official Name

English

L-METHIONINE

Preferred Name

English

L-METHIONINE [FCC]

Common Name

English

METHIONINE [HSDB]

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

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