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
Palladium(II) and platinum(II) complexes as synthetic peptidases.	2001	11219007
Novel mutations in the GALK1 gene in patients with galactokinase deficiency.	2001	11139256
Different usage of the glycosaminoglycan attachment sites of biglycan.	2001 Apr 20	11145959
Saccharomyces cerevisiae is capable of de Novo pantothenic acid biosynthesis involving a novel pathway of beta-alanine production from spermine.	2001 Apr 6	11154694
Bus, a bushy Arabidopsis CYP79F1 knockout mutant with abolished synthesis of short-chain aliphatic glucosinolates.	2001 Feb	11226190
The folate cycle and disease in humans.	2001 Feb	11169015
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	11226379
Regulation of cell function by methionine oxidation and reduction.	2001 Feb 15	11179387
Trp 346 and Leu 352 residues in protective antigen are required for the expression of anthrax lethal toxin activity.	2001 Feb 16	11178978
Extracellular amino acid profiles in the paraventricular nucleus of the rat hypothalamus are influenced by diet composition.	2001 Feb 23	11172779
Orientations of Tyr 21 and Tyr 24 in the capsid of filamentous virus Ff determined by polarized Raman spectroscopy.	2001 Feb 6	11170449
Intestinal disappearance and mesenteric and portal appearance of amino acids in dairy cows fed ruminally protected methionine.	2001 Jan	11210033
Intestinal apical amino acid absorption during development of the pig.	2001 Jan	11124157
Intestinal aminooligopeptidase in diabetic BioBreed rat: altered posttranslational processing and trafficking.	2001 Jan	11123203
Characterization of promoter region and genomic structure of the murine and human genes encoding Src like adapter protein.	2001 Jan 10	11179692
Cloning and functional analysis of the Sry-related HMG box gene, Sox18.	2001 Jan 10	11179689
Analysis of the subsite specificity of rat insulysin using fluorogenic peptide substrates.	2001 Jan 12	11042190
Selective degradation of oxidized calmodulin by the 20 S proteasome.	2001 Jan 12	11010965
Sec63p and Kar2p are required for the translocation of SRP-dependent precursors into the yeast endoplasmic reticulum in vivo.	2001 Jan 15	11226176
Haem-linked interactions in horseradish peroxidase revealed by spectroscopic analysis of the Phe-221-->Met mutant.	2001 Jan 15	11139379
Thromboangiitis obliterans (Buerger's disease).	2001 Jan 18	11188842
Diet-induced hyperhomocysteinemia exacerbates neointima formation in rat carotid arteries after balloon injury.	2001 Jan 2	11136698
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	11177396
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	11170402
Mapping the energy surface for the folding reaction of the coiled-coil peptide GCN4-p1.	2001 Jan 23	11170389
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	11170412
Crystallization and preliminary X-ray crystallographic studies of recombinant human betaine-homocysteine S-methyltransferase.	2001 Mar	11223523
The effects of oral methionine and homocysteine on endothelial function.	2001 Mar	11179277
Evidence against oxidative stress as mechanism of endothelial dysfunction in methionine loading model.	2001 Mar	11179081
Relative reactivities of N-chloramines and hypochlorous acid with human plasma constituents.	2001 Mar 1	11182523
COMT-dependent protection of dopaminergic neurons by methionine, dimethionine and S-adenosylmethionine (SAM) against L-dopa toxicity in vitro.	2001 Mar 2	11223018
Impaired ATP synthase assembly associated with a mutation in the human ATP synthase subunit 6 gene.	2001 Mar 2	11076946
Transporters on demand: intrahepatic pools of canalicular ATP binding cassette transporters in rat liver.	2001 Mar 9	11113123
Sequence requirements for the N-methyl-D-aspartate receptor antagonist activity of conantokin-R.	2001 Mar 9	11096077
Uptake of tritiated thymidine, deoxyglucose and methionine in three lung cancer cell lines: deoxyglucose uptake mirrors tritiated thymidine uptake.	2001 Mar-Apr	11125281

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