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Merck

D7253

Dihydrostreptomycin sesquisulfate

Sinónimos:

Didromycin, Dihydrostreptomycin 3/2 sulfate, Dihydrostreptomycin sulfate

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About This Item

Fórmula lineal:
C21H41N7O12 · 3/2H2SO4
Número CAS:
Peso molecular:
730.71
UNSPSC Code:
51102829
NACRES:
NA.85
PubChem Substance ID:
EC Number:
226-823-7
Beilstein/REAXYS Number:
3894221
MDL number:

InChI key

CZWJCQXZZJHHRH-YZTFXSNBSA-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

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

biological source

microbial

form

powder

color

white to off-white

antibiotic activity spectrum

Gram-negative bacteria
Gram-positive bacteria
mycobacteria

mode of action

protein synthesis | interferes

storage temp.

2-8°C

Quality Level

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Application

Dihydrostreptomycin sesquisulfate is a derivative of streptomycin used in aminoglycoside uptake studies. It has also been used 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 of the 30s ribosomal subunit and the 16s rRNA.

General description

Chemical structure: aminoglycoside

pictograms

Health hazardExclamation mark

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)


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J M Zenilman et al.
Antimicrobial agents and chemotherapy, 30(6), 877-882 (1986-12-01)
We studied the effects of various concentrations of oxacillin on streptomycin uptake and killing for several strains of Staphylococcus aureus. When streptomycin was present in concentrations below the MIC, addition of oxacillin at concentrations greater than or equal to the
L J Mandel et al.
Antimicrobial agents and chemotherapy, 26(4), 563-569 (1984-10-01)
[3H]gentamicin uptake and killing were studied in three strains of gentamicin-resistant Staphylococcus aureus possessing plasmid-encoded, gentamicin-modifying enzymes and in three isogenic, enzyme-free, gentamicin-susceptible derivatives. At low (less than or equal to 2.0 micrograms/ml) concentrations of gentamicin, uptake by resistant organisms
G A Manley et al.
Proceedings of the National Academy of Sciences of the United States of America, 98(5), 2826-2831 (2001-02-28)
Vertebrate sensory hair cells achieve high sensitivity and frequency selectivity by adding self-generated mechanical energy to low-level signals. This allows them to detect signals that are smaller than thermal molecular motion and to achieve significant resonance amplitudes and frequency selectivity
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
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

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