Streptomycin

(CC) Image: David E. Volk
streptomycin
IUPAC name: see chemistry section Synonyms: Kantrex® Formula: C21H39N7O12
Uses:	antibiotic drug
Properties:	aminoglycoside
Hazards:	see drug interactions
Mass (g/mol): CAS #: 581.5741 57-92-1

Streptomycin is an aminoglycoside antibiotic produced by the soil actinomycete Streptomyces griseus used to treat Gram-negative aerobic bacteria such as Acinetobacter, Enterobacter and Pseudomonas and some mycobacteria, including those that cause tuberculosis. Aminoglycoside antibiotics are mostly ineffective against anearobic bacteria, fungi and viruses, but can be used from Gram-positive bacteria, although better antibiotic treatment options exist for them.

Mechanism of action

Aminoglycosides bind to four specific nucleotides in the 16S rRNA around nucletide 1400 and one amino acid in the S12 protein of the 30S ribosomal subunit. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This interferes with the formation of an initiation complex and leads to misreading of mRNA and incorporation of incorrect amino acids into the polypeptide, which in turns leads to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes.

Chemistry

Its IUPAC chemical name is 2-[(1S,2R,3R,4S,5R,6R)-5-(diaminomethylideneamino)-2-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R, 6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-methylaminooxan-2-yl]oxy-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy-3,4,6-trihydroxycyclohexyl]guanidine and it has chemical formula C₂₁H₃₉N₇O₁₂, giving it a molecular mass of 581.5741 g/mol.

External links

• Streptomycin - FDA approved drug information (drug label) from DailyMed (U.S. National Library of Medicine).
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