s-methionine
DL-Methionine is a racemic form of the respective sulfur aminoacid. DL-Methionine participates in synthesis of tissue proteins, vitamins, enzymes and hormones taking part in nitrogen, carbohydrate and fat metabolisms, and it is the important source of methyl groups for synthesis of all nucleic acids, as well as the sulfur source for sulfonic compounds. Methionine is used to prevent liver damage in acetaminophen (Tylenol) poisoning. It is also used for increasing the acidity of urine, treating liver disorders, and improving wound healing. Other uses include treating depression, alcoholism, allergies, asthma, copper poisoning, radiation side effects, schizophrenia, drug withdrawal, and Parkinson's disease. It is also used as a food additive in livestock to boost performance. DL-Methionin is the first limiting amino acid in poultry, and probably also in high-yielding cows, and is the second or third limiting amino acid in pigs fed conventional diets. — NCATS
Clinical trial activity
17 trials · 21 clinical orgs · 0 marketing orgs
Earliest trial started Mar 28, 2002 (NCT00032695)
Timeline
Indications
Approved for
Studied for
- Acquired Immunodeficiency Syndrome · Phase 3
- Carcinoma, Squamous Cell · Phase 1
- Craniopharyngioma · Phase 2
- Depressive Disorder · Phase 4
- Ependymoma · Phase 2
- Glioma · Phase 2
- Head and Neck Neoplasms · Phase 1
- Hearing Loss, Noise-Induced · Phase 3
- Hodgkin Disease · Phase 2
- Hyperparathyroidism, Primary · Phase 2
- Liver Diseases · Phase 4
- Lymphoma, Non-Hodgkin · Phase 2
- Medulloblastoma · Phase 2
- Mucositis · Phase 1
- Neoplasms · Phase 2
- Neuroblastoma · Phase 2
- Osteosarcoma · Phase 2
- Rhabdomyosarcoma · Phase 2
- Sarcoidosis, Pulmonary · Phase 2/Phase 3
- Sarcoma, Ewing · Phase 2
- Spinal Cord Diseases · Phase 3
- Squamous Cell Carcinoma of Head and Neck · Phase 1
- Vitamin B 6 Deficiency · Phase 2/Phase 3
Mechanism of action
Chemistry & pharmacology
SMILES
CSCCC(N)C(O)=O- Mol. weight
- 149.211 g/mol
- Lipinski Ro5
- Pass
- Rule of 3
- No
- Chirality
- Single Stereoisomer
- Inorganic
- No
- Polymer
- No
Oral
No
Parenteral
No
Topical
No
Sources
- NCATS73JWT2K6T3 ↗
- ChEMBLCHEMBL42336 ↗
- NCATSAE28F7PNPL ↗
Also known as
- (2s)-2-amino-4-(methylsulfanyl)butanoic acid
- (2s)-2-amino-4-(methylsulfanyl)butanoic acid
- d-methionine
- d-methionine
- d-methionine
- l-a-amino-g-methylthiobutyric acid
- l-a-amino-g-methylthiobutyric acid
- l-alpha-amino-gamma-methylmercaptobutyric acid
- l-alpha-amino-gamma-methylmercaptobutyric acid
- l-methionin
- l-methionin
- l-methionine
- l-methionine
- l-methionine
- l-methionine
- l-methionine
- l-(-)-methionine
- l-(-)-methionine
- l-α-amino-γ-methylmercaptobutyric acid
- l-α-amino-γ-methylmercaptobutyric acid
- m
- m
- met
- met
- methionine
- methionine
- methionine
- methionine
- methionine
- methionine
- methionine
- methionine
- methionine
- racemethionine
- racemethionine
- (s)-2-amino-4-(methylthio)butanoic acid
- (s)-2-amino-4-(methylthio)butanoic acid
- (s)-2-amino-4-(methylthio)butyric acid
- (s)-2-amino-4-(methylthio)butyric acid
- (s)-methionine
- (s)-methionine
- s-methionine
Clinical trials
| NCT ID | Phase | Start date | Sponsor(s) |
|---|---|---|---|
| NCT02824419 | Phase 2/Phase 3 (Phase 3) | May 1, 2016 | University of Turku |
| NCT02566434 | N/A | Jul 1, 2015 | International Council on Amino Acid Science, Texas A&M University |
| NCT02216253 | N/A | Oct 1, 2014 | Vita-Salute University of Milano. Italy |
| NCT01783002 | Phase 2 | May 1, 2014 | British Columbia Cancer Agency, University of British Columbia |
| NCT01871766 | Phase 2 | Dec 4, 2013 | St. Jude Children's Hospital |
| NCT01345474 | Phase 3 | Sep 1, 2013 | Department of Defense, MetArmor, Southern Illinois University, United States Army |
| NCT02903355 | Phase 3 | Sep 1, 2013 | MetArmor, Southern Illinois University, United States Army |
| NCT01650181 | Phase 4 | Nov 1, 2011 | Instituto Nacional de Ciencias Medicas y Nutricion Salvador Zubiran |
| NCT01128244 | Phase 2/Phase 3 (Phase 3) | Apr 1, 2010 | University of Florida |
| NCT00840047 | Phase 2 | Jul 20, 2009 | St. Jude Children's Hospital |
| NCT00877812 | N/A | Jan 1, 2008 | National Institutes of Health (NIH), University of Florida |
| NCT00427102 | Phase 1 | Jan 1, 2007 | Johns Hopkins University |
| NCT00253773 | N/A | Jan 1, 2005 | Emory University, National Institute of Diabetes and Digestive and Kidney Diseases (NIDDK) |
| NCT00226356 | Phase 4 | Dec 1, 2004 | Brain & Behavior Research Foundation, Harvard University |
| NCT00253760 | N/A | Feb 1, 2004 | Emory University, National Institute of Diabetes and Digestive and Kidney Diseases (NIDDK) |
| NCT00597246 | N/A | May 13, 2003 | Cornell University |
| NCT00032695 | Phase 3 | Mar 28, 2002 | National Institute of Neurological Disorders and Stroke (NINDS) |