Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H22N6O5S |
Molecular Weight | 398.437 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
C[S@@+](CC[C@H](N)C([O-])=O)C[C@H]1O[C@H]([C@H](O)[C@@H]1O)N2C=NC3=C2N=CN=C3N
InChI
InChIKey=MEFKEPWMEQBLKI-FCKMPRQPSA-N
InChI=1S/C15H22N6O5S/c1-27(3-2-7(16)15(24)25)4-8-10(22)11(23)14(26-8)21-6-20-9-12(17)18-5-19-13(9)21/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25)/t7-,8+,10+,11+,14+,27-/m0/s1
Molecular Formula | C15H22N6O5S |
Molecular Weight | 398.437 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
DescriptionCurator's Comment: description was created based on several sources, including
http://depressionet.com.au/articles/same.pdf
http://umm.edu/health/medical/altmed/supplement/sadenosylmethionine
https://www.ncbi.nlm.nih.gov/pubmed/?term=22659519
Curator's Comment: description was created based on several sources, including
http://depressionet.com.au/articles/same.pdf
http://umm.edu/health/medical/altmed/supplement/sadenosylmethionine
https://www.ncbi.nlm.nih.gov/pubmed/?term=22659519
S-Adenosylmethionine (often referred to as SAMe) is a methyl donor and a cofactor for enzyme-catalyzed methylations, including catechol O-methyltransferase (COMT) and DNA methyltransferases (DNMT). Although present in all cells, it is concentrated in liver where 85% of all methylation reactions occur. SAM is anti-apoptotic in normal hepatocytes and normal colon epithelial cells but pro-apoptotic in liver human hepatocellular carcinoma (HCC), HepG2 cells and colon cancer cells. Because of structural instability, stable salt forms of SAM are required for its use as an oral drug. The commonly used salts: tosylate, butanedisulfonate, disulfate tosylate, disulfate ditosylate, and disulfate monotosylate. SAMe has been marketed in some European countries since the mid-1980s for the treatment of depression and for other medical conditions such as osteoarthritis (joint disease that causes joint pain and stiffness), fibromyalgia (widespread pain and stiffness). In addition, it is used to treat liver disease and migraine headaches. However, it is not formally approved in the UK for the treatment of depression, and in the USA, it is classified only as a dietary supplement. Some research suggests that it is more effective than placebo in treating mild-to-moderate depression and is just as effective as antidepressant medications without the side effects (headaches, sleeplessness, and sexual dysfunction). In addition, antidepressants tend to take 6 to 8 weeks to begin working, while It seems to begin more quickly. Researchers are not sure how SAMe works to relieve depression. But they speculate it might increase the amount of serotonin in the brain just as some antidepressants do. Many studies have examined injectable forms of SAMe, not oral supplements.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL3313835 Sources: https://www.ncbi.nlm.nih.gov/pubmed/12660248 |
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Target ID: CHEMBL2023 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18486144 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
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Palliative | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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Tremor induced by S-adenosyl-L-methionine: possible relation to L-dopa effects. | 1978 Dec |
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Ethynylestradiol-induced impairment of bile secretion in the rat: protective effects of S-adenosyl-L-methionine and its implication in estrogen metabolism. | 1981 Jan |
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Open trial of S-adenosylmethionine for treatment of depression. | 1984 Mar |
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S-adenosylmethionine: studies on chemical and enzymatic synthesis. | 1987 Feb |
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Reversal of extrahepatic membrane cholesterol deposition in patients with chronic liver diseases by S-adenosyl-L-methionine. | 1992 Sep |
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S-adenosyl-L-methionine decreases motor activity in the rat: similarity to Parkinson's disease-like symptoms. | 1993 May |
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Differential kinetic properties of L-2-amino-4-methylthio-cis-but-3-enoic acid, a methionine analog inhibitor of S-adenosylmethionine synthetase. | 1993 Sep 3 |
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The clinical potential of ademetionine (S-adenosylmethionine) in neurological disorders. | 1994 Aug |
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Effects of some thiol chelators on enzymatic activities in blood, liver and kidneys of acute arsenic (III) exposed mice. | 1998 Mar |
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Farnesyl-L-cysteine analogs block SAM-induced Parkinson's disease-like symptoms in rats. | 2000 Aug |
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Effect of tauroursodeoxycholate and S-adenosyl-L-methionine on 17beta-estradiol glucuronide-induced cholestasis. | 2001 Feb |
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Decrease of methionine and S-adenosylmethionine and increase of homocysteine in treated patients with Parkinson's disease. | 2001 Jul 27 |
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Spontaneous oxidative stress and liver tumors in mice lacking methionine adenosyltransferase 1A. | 2002 Aug |
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Identification of protein arginine methyltransferase 2 as a coactivator for estrogen receptor alpha. | 2002 Aug 9 |
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Inhibition mechanism of S-adenosylmethionine-induced movement deficits by prenylcysteine analogs. | 2003 Dec |
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Detecting selection using a single genome sequence of M. tuberculosis and P. falciparum. | 2004 Apr 29 |
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Heterodimeric interactions among the 1-amino-cyclopropane-1-carboxylate synthase polypeptides encoded by the Arabidopsis gene family. | 2004 Feb 24 |
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Inhibition of CYP2E1 catalytic activity in vitro by S-adenosyl-L-methionine. | 2005 Apr 1 |
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Folate transport gene inactivation in mice increases sensitivity to colon carcinogenesis. | 2005 Feb 1 |
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S-adenosylmethionine blocks collagen I production by preventing transforming growth factor-beta induction of the COL1A2 promoter. | 2005 Sep 2 |
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Metabolic endophenotype and related genotypes are associated with oxidative stress in children with autism. | 2006 Dec 5 |
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Tolcapone decreases plasma levels of S-adenosyl-L-homocysteine and homocysteine in treated Parkinson's disease patients. | 2006 Jun |
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Betaine-homocysteine S-methyltransferase-2 is an S-methylmethionine-homocysteine methyltransferase. | 2008 Apr 4 |
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Ethanol inhibits methionine adenosyltransferase II activity and S-adenosylmethionine biosynthesis and enhances caspase-3-dependent cell death in T lymphocytes: relevance to alcohol-induced immunosuppression. | 2008 Jun |
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Mthfd1 is an essential gene in mice and alters biomarkers of impaired one-carbon metabolism. | 2009 Jan 16 |
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Induction of avian musculoaponeurotic fibrosarcoma proteins by toxic bile acid inhibits expression of glutathione synthetic enzymes and contributes to cholestatic liver injury in mice. | 2010 Apr |
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Effects of salvianolic acids on oxidative stress and hepatic fibrosis in rats. | 2010 Jan 15 |
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Methotrexate-induced myelopathy responsive to substitution of multiple folate metabolites. | 2010 May |
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S-adenosylmethionine decreases lipopolysaccharide-induced phosphodiesterase 4B2 and attenuates tumor necrosis factor expression via cAMP/protein kinase A pathway. | 2011 May |
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Wilson's disease: changes in methionine metabolism and inflammation affect global DNA methylation in early liver disease. | 2013 Feb |
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Alterations in hepatic metabolism of sulfur amino acids in non-obese type-2 diabetic Goto-Kakizaki rats. | 2013 Jul 5 |
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/19302903
SAMe tosylate disulfate (STD) 1000 mg for 5 days, either in enteric-coated tablet formulation or as a 250-mL IV infusion
Route of Administration:
Other
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/?term=22659519
Curator's Comment: Effect of S-adenosyl-L-methionine disulfate tosylate salt (SAMe-ST) and L-methionine (L-Met) on primary cultured rat hepatocytes were studied. In cultured hepatocytes treated with CCl4, SAMe-ST and L-Met suppressed the decrease in urea-nitrogen secretion as well as the leakages of GOT and GPT. The membrane-protective action of these two compounds was verified by the histological data. Failure of SAMe-ST to counteract CCl4-induced reduction of radioactive leucine incorporation into the trichloroacetic acid-insoluble materials in hepatocytes indicates that the observed effects of SAMe-ST or L-Met do not involve acceleration of protein synthesis. The present results indicate that SAMe-ST remarkably protects hepatocytes from CCl4-induced hepatotoxicity, probably by either changing the structure or compositions of membrane phospholipids or by modifying the interaction of CCl4 with the intracellular drug-metabolizing enzyme systems.
Unknown
Substance Class |
Chemical
Created
by
admin
on
Edited
Sat Dec 16 10:51:19 UTC 2023
by
admin
on
Sat Dec 16 10:51:19 UTC 2023
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Record UNII |
6EZ5466ZUX
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Record Status |
Validated (UNII)
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Record Version |
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-
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78548-84-2
Created by
admin on Sat Dec 16 10:51:19 UTC 2023 , Edited by admin on Sat Dec 16 10:51:19 UTC 2023
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6EZ5466ZUX
Created by
admin on Sat Dec 16 10:51:19 UTC 2023 , Edited by admin on Sat Dec 16 10:51:19 UTC 2023
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RACEMATE -> ENANTIOMER |
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ENANTIOMER -> ENANTIOMER |
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