Dihydrostreptomycin

From Wikipedia, the free encyclopedia
Jump to: navigation, search
Dihydrostreptomycin
Dihydrostreptomycin.svg
Systematic (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
Clinical data
AHFS/Drugs.com International Drug Names
Identifiers
CAS Number 128-46-1
ATC code S01AA15 (WHO) QA07AA90 (WHO) QJ01GA90 (WHO) QJ51GA90 (WHO)
PubChem CID 439369
ChemSpider 388489
UNII P2I6R8W6UA YesY
ChEMBL CHEMBL1950576
Chemical data
Formula C21H41N7O12
Molar mass 583.59 g/mol
  (verify)

Dihydrostreptomycin is a derivative of streptomycin that has a bactericidal property.[1] It's 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 non-functional 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[edit]

References[edit]

  1. ^ a b "Dihydrostreptomycin (Code C61724) - NCI Thesaurus". Retrieved July 7, 2016. 
  2. ^ "Dihydrostreptomycin Sulfate - MeSH - NCBI". Retrieved July 7, 2016. 
  3. ^ Harrison, Wiley H. (1954). "Ototoxicity of dihydrostreptomycin.". Quarterly bulletin. Northwestern University (Evanston, Ill.). Medical School. 28 (3): 271–3. PMC 3803976free to read. PMID 13186082. 

External links[edit]