Streptomycin

• Catalog No.: Bio-0644
• CAS Number: 57-92-1
• M. F.: C21H39N7O12
• M. W.: 581.57406

SYNONYMS

• 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: Agrept; Merstep; Agrimycin; Streptomisin; Estreptomicina

DATABASE IDS

• CAS Number: 57-92-1

PROPERTIES

• Application(s): Aminoglycoside antibiotic
• Application(s): Clinically used broad spectrum antibacterial (tuberculostatic) agent
• Biological Source: Isol. from Streptomyces griseus
• Mechanism of Action: Protein synthesis inhibitor
• Mechanism of Action: Activity increased in alkaline medium binds irreversibly to the bacterial ribosomal 30S subunit
• Mechanism of Action: Blocks the recognition step in protein-synthesis
• Mechanism of Action: Causes misreading of the genetic code
• Mechanism of Action: Causes ribosomal dissociation from messenger RNA
• Mechanism of Action: Apoptosis-inducer

REFERENCES

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• Pennington, F.C. et al., J.A.C.S., 1953, 75, 2261, (synth)
• Neidle, S. et al., Tet. Lett., 1968, 4725, (cryst struct)
• Bock, K. et al., J. Antibiot., 1974, 27, 139, (cmr)
• Umezawa, S. et al., J. Antibiot., 1974, 27, 997, (synth)
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• Aminoglycosides, (Ed. Whelton, A. et al), M. Dekker, 1982, (book)
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• Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994, 8762, (synonyms)
• Lewis, R.J., Sax's Dangerous Properties of Industrial Materials, 8th edn., Van Nostrand Reinhold, 1992, SLW500; SLY500