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EntityQ3707637· pop 15· linked from 139 articles

dihydrostreptomycin

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Also known as N,N'''-[(1R,2R,3S,4R,5R,6S)-4-({5-deoxy-2-O-[2-deoxy-2-(methylamino)-alpha-L-glucopyranosyl]-3-C-(hydroxymethyl)-alpha-L-lyxofuranosyl}oxy)-2,5,6-trihydroxycyclohexane-1,3-diyl]diguanidine, DHMS, DST

Dihydrostreptomycin is semisynthetic aminoglycoside antibiotic with bactericidal properties. It is the dihydro derivative of streptomycin, and was formerly used in the treatment of tuberculosis.

Wikidata facts

Mass
583.281
Show 4 more facts
chemical formula
C₂₁H₄₁N₇O₁₂
canonical SMILES
CC1C(C(C(O1)OC2C(C(C(C(C2O)O)N=C(N)N)O)N=C(N)N)OC3C(C(C(C(O3)CO)O)O)NC)(CO)O
isomeric 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)N=C(N)N)O)N=C(N)N)O[C@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)NC)(CO)O
found in taxon
Streptomyces
Sources (3)

via Wikidata · CC0

~1 min read

Encyclopedic overview

1 sections
Contents
  • References

Dihydrostreptomycin is semisynthetic aminoglycoside antibiotic with bactericidal properties. It is the dihydro derivative of streptomycin, and was formerly used in the treatment of tuberculosis.

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.

Excerpted from Wikipedia’s “dihydrostreptomycin” article, available under the CC BY-SA 4.0 licence.

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