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 8429	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 504	Me-500 Approved Use Unknown
AIDS vacuolar myelopathy 3 Sources: https://clinicaltrials.gov/ct2/show/NCT00032695	Primary	Phase III 656	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 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: https://pubmed.ncbi.nlm.nih.gov/9674817 Page: p.267	Disc. AE: Gastrointestinal symptom NOS... AEs leading to discontinuation/dose reduction: Gastrointestinal symptom NOS (8.3%) Sources: https://pubmed.ncbi.nlm.nih.gov/9674817 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: https://pubmed.ncbi.nlm.nih.gov/15477550 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: https://pubmed.ncbi.nlm.nih.gov/15477550 Page: p.1273	Sources: https://pubmed.ncbi.nlm.nih.gov/15477550 Page: p.1273

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 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: https://pubmed.ncbi.nlm.nih.gov/9674817 Page: p.267

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
MolPort	MolPort-000-928-154	https://www.molport.com/shop/molecule-link/MolPort-000-928-154
eMolecules	495925	https://www.emolecules.com/cgi-bin/more?vid=495925

PubMed

Title	Date	PubMed
Involvement of pro-enkephalin-derived peptides in immunity.	2001 Apr	11164883
Proteasome involvement in agonist-induced down-regulation of mu and delta opioid receptors.	2001 Apr 13	11152677
Different usage of the glycosaminoglycan attachment sites of biglycan.	2001 Apr 20	11145959
Further definition of the substance P (SP)/neurokinin-1 receptor complex. MET-174 is the site of photoinsertion p-benzoylphenylalanine4 SP.	2001 Apr 6	11116140
Measurement of the synthesis, turnover, and assembly of alpha- and beta-erythroid and nonerythroid spectrins in cultured rat hippocampal neurons.	2001 Feb	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 Feb	11223388
Lowered weight gain during pregnancy and risk of neural tube defects among offspring.	2001 Feb	11171858
The folate cycle and disease in humans.	2001 Feb	11169015
Nuclear forms of parathyroid hormone-related peptide are translated from non-AUG start sites downstream from the initiator methionine.	2001 Feb	11159841
Contrasting responses by basal ganglia met-enkephalin systems to low and high doses of methamphetamine in a rat model.	2001 Feb	11158242
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
A mutation in alpha-tropomyosin(slow) affects muscle strength, maturation and hypertrophy in a mouse model for nemaline myopathy.	2001 Feb 15	11157795
Trp 346 and Leu 352 residues in protective antigen are required for the expression of anthrax lethal toxin activity.	2001 Feb 16	11178978
Rate of intrachain contact formation in an unfolded protein: temperature and denaturant effects.	2001 Feb 2	11162121
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	11087738
Steroidogenic acute regulatory protein expression is dependent upon post-translational effects of cAMP-dependent protein kinase A.	2001 Feb 28	11223189
[Homocysteine, endothelial dysfunction and cardiovascular risk: pathomechanisms and therapeutic options].	2001 Jan	11220081
Intestinal disappearance and mesenteric and portal appearance of amino acids in dairy cows fed ruminally protected methionine.	2001 Jan	11210033
Impaired response to interferon-gamma in activated macrophages due to tyrosine nitration of STAT1 by endogenous nitric oxide.	2001 Jan	11159690
Laminin-8 (alpha4beta1gamma1) is synthesized by lymphoid cells, promotes lymphocyte migration and costimulates T cell proliferation.	2001 Jan	11148143
Maternal plasma homocysteine levels in women with preterm premature rupture of membranes.	2001 Jan	11133260
The V410M mutation associated with pyrethroid resistance in Heliothis virescens reduces the pyrethroid sensitivity of house fly sodium channels expressed in Xenopus oocytes.	2001 Jan	11102831
Characterization of promoter region and genomic structure of the murine and human genes encoding Src like adapter protein.	2001 Jan 10	11179692
Subtle alterations in growth medium composition can dramatically alter the percentage of unsaturated fatty acids in the yeast Saccharomyces cerevisiae.	2001 Jan 15	11124704
Thromboangiitis obliterans (Buerger's disease).	2001 Jan 18	11188842
Antisense modulation of 5,10-methylenetetrahydrofolate reductase expression produces neural tube defects in mouse embryos.	2001 Jan-Feb	11137375
Evidence against oxidative stress as mechanism of endothelial dysfunction in methionine loading model.	2001 Mar	11179081
Thermodynamics of the helix-coil transition: Binding of S15 and a hybrid sequence, disulfide stabilized peptide to the S-protein.	2001 Mar 1	11170206
Residue Met(156) contributes to the labile enzyme conformation of coagulation factor VIIa.	2001 Mar 2	11078728
Prostaglandin endoperoxide H synthase-1: the functions of cyclooxygenase active site residues in the binding, positioning, and oxygenation of arachidonic acid.	2001 Mar 30	11121412
Transporters on demand: intrahepatic pools of canalicular ATP binding cassette transporters in rat liver.	2001 Mar 9	11113123

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 `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

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Name

Type

Language

METHIONINE

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

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