D5155

Sigma-Aldrich

Dihydrostreptomycin sesquisulfate

BioReagent, suitable for cell culture, ≥95.0% (HPLC)

Linear Formula:
C21H41N7O12 · 3/2H2SO4
CAS Number:
Molecular Weight:
730.71
Beilstein/REAXYS Number:
3894221
EC Number:
MDL number:
PubChem Substance ID:
NACRES:
NA.76

Quality Level

product line

BioReagent

assay

≥95.0% (HPLC)

form

powder

application(s)

cell culture | mammalian: suitable

color

white to off-white

Mode of action

protein synthesis | interferes

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycobacteria

storage temp.

2-8°C

SMILES string

OS(O)(=O)=O.OS(O)(=O)=O.OS(O)(=O)=O.CN[C@H]1[C@H](O)[C@@H](O)[C@H](CO)O[C@H]1O[C@H]2[C@@H](O[C@@H](C)[C@]2(O)CO)O[C@@H]3[C@@H](O)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]3NC(N)=N.CN[C@H]4[C@H](O)[C@@H](O)[C@H](CO)O[C@H]4O[C@H]5[C@@H](O[C@@H](C)[C@]5(O)CO)O[C@@H]6[C@@H](O)[C@H](O)[C@@H](NC(N)=N)[C@H](O)[C@H]6NC(N)=N

InChI

1S/2C21H41N7O12.3H2O4S/c2*1-5-21(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;3*1-5(2,3)4/h2*5-18,26,29-36H,3-4H2,1-2H3,(H4,22,23,27)(H4,24,25,28);3*(H2,1,2,3,4)/t2*5-,6-,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,21+;;;/m00.../s1

InChI key

CZWJCQXZZJHHRH-YZTFXSNBSA-N

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Related Categories

General description

Chemical structure: aminoglycoside

Application

Dihydrostreptomycin sesquisulfate is a derivative of streptomycin used in aminoglyside uptake studies. Other studies have also used it as an electrode for a cochlear amplifier in the hair-cell bundle of lizards.

Biochem/physiol Actions

Mode of Action: Dihydrostreptomycin sesquisulfate inhibits protein synthesis at the level o the 30S ribosomal subunit and the 16s rRNA.

Pictograms

Exclamation markHealth hazard

Signal Word

Warning

Hazard Statements

Personal Protective Equipment

dust mask type N95 (US),Eyeshields,Gloves

RIDADR

NONH for all modes of transport

WGK Germany

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificate of Analysis
Certificate of Origin
S McDougall et al.
New Zealand veterinary journal, 55(4), 161-170 (2007-08-07)
To compare the proportions of clinical and bacteriological cure of glands of dairy cows diagnosed with clinical mastitis, following treatment with one of three different intramammary antibiotic preparations. Cows from dairy cow herds (n=28) across New Zealand which were diagnosed...
Marc Cherlet et al.
Journal of mass spectrometry : JMS, 42(5), 647-656 (2007-04-19)
Dihydrostreptomycin (DHS) is an aminoglycoside antibiotic used in veterinary medicine in combination with benzylpenicillin for the treatment of bacterial infections in cattle, pigs and sheep. A method to determine its residues in edible tissues of cattle, as well as in...
Katy Jeannot et al.
Journal of bacteriology, 187(15), 5341-5346 (2005-07-21)
MexXY is an inducible efflux system that contributes to the natural resistance of Pseudomonas aeruginosa to antibiotics. Experiments involving real-time PCR after reverse transcription in reference strain PAO1 showed concentration-dependent induction of gene mexY by various ribosome inhibitors (e.g., chloramphenicol...
Shin-ichi Kawano
Rapid communications in mass spectrometry : RCM, 23(6), 907-914 (2009-02-19)
Impurities in streptomycin (STR) and dihydrostreptomycin (DHS) were investigated by hydrophilic interaction chromatography/electrospray ionization quadrupole ion trap/time-of-flight mass spectrometry (HILIC/ESI-QIT/TOFMS). Samples were separated on a fused-core silica column (100 mmx2.1 mm i.d., particle size: 2.7 microm) with isocratic elution using...
A C Whist et al.
Journal of dairy science, 89(12), 4649-4659 (2006-11-16)
The objective of this study was to see if introduction of a 2-yr combined selective dry-cow therapy and teat-dipping trial would reduce clinical mastitis (CM) events in 164 Norwegian dairy herds. Three different penicillin or penicillin/dihydrostreptomycin-based dry-cow treatments, and 3...

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