S-Adenosylmethionine
Title: S-Adenosylmethionine
CAS Registry Number: 29908-03-0
CAS Name: 5¢-[(3S)-(3-Amino-3-carboxypropyl)methylsulfonio]-5¢-deoxyadenosine inner salt
Additional Names: S-(5¢-desoxyadenosin-5¢-yl)-L-methionine; active methionine; ademetionine; AdoMet; SAMe
Molecular Formula: C15H22N6O5S
Molecular Weight: 398.44
Percent Composition: C 45.22%, H 5.57%, N 21.09%, O 20.08%, S 8.05%
Literature References: Physiological methyl donor involved in enzymatic transmethylation reactions; present in all living organisms. Enzymatic prepn: G. L. Cantoni, J. Am. Chem. Soc. 74, 2942 (1952). Synthesis of racemate: J. Baddiley, G. A. Jamieson, J. Chem. Soc. 1954, 4280; of optically active chloride: C. H. Shunk, J. W. Richter, US 2969353 (1961 to Merck & Co.). Review of enzymatic and microbial prepns: S. Shimizu, H. Yamada, Trends Biotechnol. 2, 137-141 (1984). Pharmacology and toxicity: G. Stramentinoli et al., Minerva Med. 66, 1541 (1975). Radioenzymatic determn in biological fluids: P. Giulidori, G. Stramentinoli, Anal. Biochem. 137, 217 (1984). Cytoprotective effects against bile-acid induced apoptosis: C. R. L. Webster et al., Vet. Ther. 3, 474 (2002). Clinical trial in arthritis: J. D. Bradley et al., J. Rheumatol. 21, 905 (1994); in depression: M. Fava et al., Psychiatry Res. 56, 295 (1995). Review of clinical efficacy in intrahepatic cholestasis: M. Coltorti et al., Methods Find. Exp. Clin. Pharmacol. 2, 69-78 (1990); in neurological disorders: T. Bottiglieri et al., Drugs 48, 137-152 (1994). Review of role in biological methylation: P. K. Chiang et al., FASEB J. 10, 471-480 (1996). Symposium on use in treatment of alcoholic liver disease: Alcohol 27, 149-198 (2002). Review of clinical use in canine hepatitis: A. Honeckman, Clin. Tech. Small Anim. Pract. 18, 239-244 (2003); in management of heptobiliary disorders: S. A. Center, Vet. Clin. Small Anim. 34, 67-172 (2004).
 
Derivative Type: 1,4-Butanedisulfonate
CAS Registry Number: 200393-05-1
Trademarks: Donamet (Abbott); Samyr (Boehringer, Ing.)
Molecular Formula: C15H22N6O5S.C4H10S2O6
Molecular Weight: 616.69
Percent Composition: C 37.00%, H 5.23%, N 13.63%, O 28.54%, S 15.60%
 
Derivative Type: Disulfate tosylate
CAS Registry Number: 55722-12-8
CAS Name: 5¢-[(3S)-(3-Amino-3-carboxypropyl)methylsulfonio]-5¢-deoxyadenosine sulfate (salt) 4-methylbenzenesulfonate (salt) sulfate (salt) (1:1:2:1)
Trademarks: Gumbaral (AWD); S-Amet (Europharma); Zentonil (V oquinol)
Molecular Formula: C15H23N6O5S.2C7H8O3S.H2SO4.HSO4
Molecular Weight: 939.00
Percent Composition: C 37.09%, H 4.51%, N 8.95%, O 32.37%, S 17.07%
 
Therap-Cat: Antidepressant; antirheumatic; hepatoprotectant.
Therap-Cat-Vet: Heptoprotectant.
Keywords: Anti-inflammatory (Nonsteroidal); Hepatoprotectant.

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