Dihydrostreptomycin

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Dihydrostreptomycin
QJ51GA90 (WHO
)
Identifiers
  • 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-hydroxy-4-(hydroxymethyl)- 5-methyloxolan-2-yl]oxy-3,4,6-trihydroxycyclohexyl]guanidine
JSmol)
  • C[C@H]1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)NC(=N)N)O)NC(=N)N)O[C@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)NC)(CO)O
  • InChI=1S/C21H41N7O12/c1-5-21(36,4-30)16(40-17-9(26-2)13(34)10(31)6(3-29)38-17)18(37-5)39-15-8(28-20(24)25)11(32)7(27-19(22)23)12(33)14(15)35/h5-18,26,29-36H,3-4H2,1-2H3,(H4,22,23,27)(H4,24,25,28)/t5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+/m0/s1
  • Key:ASXBYYWOLISCLQ-HZYVHMACSA-N
  (verify)

Dihydrostreptomycin is a derivative of

semisynthetic aminoglycoside antibiotic used in the treatment of tuberculosis.[2]

It acts by irreversibly binding the S12 protein in the bacterial

mRNA and the bacterial ribosome. This leads to the synthesis of defective, nonfunctional proteins, which results in the bacterial cell's death.[1]

It causes ototoxicity,[3] which is why it is no longer used in humans.[citation needed]

See also

References

  1. ^ a b "Dihydrostreptomycin (Code C61724) - NCI Thesaurus". Retrieved July 7, 2016.
  2. ^ "Dihydrostreptomycin Sulfate - MeSH - NCBI". Retrieved July 7, 2016.
  3. PMID 13186082
    .

External links
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