Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H22N6O5S.C7H8O3S.2H2O4S |
Molecular Weight | 766.796 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 6 / 6 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OS(O)(=O)=O.OS(O)(=O)=O.CC1=CC=C(C=C1)S(O)(=O)=O.C[S@+](CC[C@H](N)C([O-])=O)C[C@H]2O[C@H]([C@H](O)[C@@H]2O)N3C=NC4=C3N=CN=C4N
InChI
InChIKey=XDCFCHNAIMYBAZ-OMVLBNCZSA-N
InChI=1S/C15H22N6O5S.C7H8O3S.2H2O4S/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;1-6-2-4-7(5-3-6)11(8,9)10;2*1-5(2,3)4/h5-8,10-11,14,22-23H,2-4,16H2,1H3,(H2-,17,18,19,24,25);2-5H,1H3,(H,8,9,10);2*(H2,1,2,3,4)/t7-,8+,10+,11+,14+,27+;;;/m0.../s1
Molecular Formula | C7H8O3S |
Molecular Weight | 172.202 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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 |
Molecular Formula | H2O4S |
Molecular Weight | 98.078 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Optical Activity | NONE |
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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Resolution of danazol-induced cholestasis with S-adenosylmethionine. | 1993 Mar |
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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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Heterodimeric interactions among the 1-amino-cyclopropane-1-carboxylate synthase polypeptides encoded by the Arabidopsis gene family. | 2004 Feb 24 |
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S-adenosylmethionine/homocysteine cycle alterations modify DNA methylation status with consequent deregulation of PS1 and BACE and beta-amyloid production. | 2005 Jan |
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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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Protein interactions in the human methionine synthase-methionine synthase reductase complex and implications for the mechanism of enzyme reactivation. | 2007 Jun 12 |
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Efficacy of methylcobalamin and folinic acid treatment on glutathione redox status in children with autism. | 2009 Jan |
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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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Novel protective mechanisms for S-adenosyl-L-methionine against acetaminophen hepatotoxicity: improvement of key antioxidant enzymatic function. | 2012 Aug 3 |
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Alterations in hepatic metabolism of sulfur amino acids in non-obese type-2 diabetic Goto-Kakizaki rats. | 2013 Jul 5 |
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Arsenic trioxide attenuates the invasion potential of human liver cancer cells through the demethylation-activated microRNA-491. | 2014 Jun 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 11:26:51 GMT 2023
by
admin
on
Sat Dec 16 11:26:51 GMT 2023
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Record UNII |
4G5PYL0DR1
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Record Status |
Validated (UNII)
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Record Version |
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375798-66-6
Created by
admin on Sat Dec 16 11:26:51 GMT 2023 , Edited by admin on Sat Dec 16 11:26:51 GMT 2023
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4G5PYL0DR1
Created by
admin on Sat Dec 16 11:26:51 GMT 2023 , Edited by admin on Sat Dec 16 11:26:51 GMT 2023
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Related Record | Type | Details | ||
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RACEMATE -> ENANTIOMER |