Substance
ID:449617
Names and Identifiers
IUPAC name
1-[(1R,2R,3S,4R,5R,6S)-3-carbamimidamido-4-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,5,6-trihydroxycyclohexyl]guanidine
IUPAC Traditional name
1-[(1R,2R,3S,4R,5R,6S)-3-carbamimidamido-4-{[(2R,3R,4R,5S)-3-{[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy}-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy}-2,5,6-trihydroxycyclohexyl]guanidine
Synonyms
MerstepStreptomycinEstreptomicinaStreptomisinAgreptAgrimycin
Registration numbers
CAS Number
Properties
Pharmacology Properties
Mechanism of Action
Activity increased in alkaline medium binds irreversibly to the bacterial ribosomal 30S subunit
Blocks the recognition step in protein-synthesis
Protein synthesis inhibitor
Causes ribosomal dissociation from messenger RNA
Causes misreading of the genetic code
Apoptosis-inducer
Product Information
Biological Source
Isol. from Streptomyces griseus
Application(s)
Clinically used broad spectrum antibacterial (tuberculostatic) agent
Aminoglycoside antibiotic
Molecule Details
No Data Available
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Molecular Spectra
No Data Available
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References
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• Aminoglycosides, (Ed. Whelton, A. et al), M. Dekker, 1982, (book)
• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 8762, (synonyms)
• Neidle, S. et al., Tet. Lett., 1968, 4725, (cryst struct)
• Umezawa, S. et al., J. Antibiot., 1974, 27, 997, (synth)
• Agrochemicals Handbook, 3rd edn., Royal Society of Chemistry, 1992, A481
• Martindale, The Extra Pharmacopoeia, 30th edn., Pharmaceutical Press, 1993, 203
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, SLW500; SLY500
• Umezawa, S., J. Antibiot., 1979, 32, S60, (rev, synth)
• Mossa, J.S. et al., Anal. Profiles Drug Subst., 1987, 16, 507, (rev, synth, anal)
• Pesticide Manual, 9th edn., 1991, No. 10970
• Bock, K. et al., J. Antibiot., 1974, 27, 139, (cmr)
• Emery, W.B., Chem. Ind. (London), 1952, 254, (rev)
• Munro, M.H.G. et al., J.A.C.S., 1975, 97, 4782, (biosynth)
• Wallace, B.J. et al., Antibiotics (N.Y.), 1979, 5, 272, (rev, props)
• Pennington, F.C. et al., J.A.C.S., 1953, 75, 2261, (synth)
• Munro, M.H.G. et al., J. Antibiot., 1982, 35, 1331, (cmr)
• Textbook of Adverse Drug Reactions, 4th edn., (ed. Davies, D.M.), Oxford University Press, 1991