Dihydrostreptomycin

Dihydrostreptomycin
Clinical data
AHFS/Drugs.comInternational Drug Names
ATC code
Identifiers
IUPAC name
  • 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
CAS Number
PubChem CID
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.004.445 Edit this at Wikidata
Chemical and physical data
FormulaC21H41N7O12
Molar mass583.596 g·mol−1
3D model (JSmol)
SMILES
  • 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
  • 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 streptomycin that has a bactericidal properties.[1] It is a semisynthetic aminoglycoside antibiotic used in the treatment of tuberculosis.[2]

It acts by irreversibly binding the S12 protein in the bacterial 30S ribosomal subunit, after being actively transported across the cell membrane, which interferes with the initiation complex between the 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.

See also

  • Translation (biology)

References

  1. 1 2 "Dihydrostreptomycin (Code C61724) - NCI Thesaurus". Retrieved July 7, 2016.
  2. ↑ "Dihydrostreptomycin Sulfate - MeSH - NCBI". Retrieved July 7, 2016.
  3. ↑ Harrison WH (1954). "Ototoxicity of dihydrostreptomycin". Quarterly Bulletin. Northwestern University. 28 (3): 271–3. PMC 3803976. PMID 13186082.
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