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D7253

Sigma-Aldrich

Dihydrostreptomycin sesquisulfate

Synonym(s):

Didromycin, Dihydrostreptomycin 3/2 sulfate, Dihydrostreptomycin sulfate

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About This Item

Linear Formula:
C21H41N7O12 · 3/2H2SO4
CAS Number:
5490-27-7
Molecular Weight:
730.71
Beilstein:
3894221
EC Number:
226-823-7
MDL number:
MFCD00070252
UNSPSC Code:
51102829
PubChem Substance ID:
24894093
NACRES:
NA.85

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

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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General description

Chemical structure: aminoglycoside

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.

Pictograms

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H302,H361fd

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

Certificates of Analysis (COA)

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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
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
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
G Martins et al.
Veterinary journal (London, England : 1997), 193(2), 600-601 (2012-03-01)
This study presents a Brazilian goat herd with reproductive failure over 2009-2010, in which there were abortions (22/50; 44%), embryonic resorption (6/50; 12%) and neonatal deaths (2/50; 4%). A diagnosis of leptospirosis was made, based on serology (microscopic agglutination test
Walter Marcotti et al.
The Journal of physiology, 567(Pt 2), 505-521 (2005-07-05)
The most serious side-effect of the widely used aminoglycoside antibiotics is irreversible intracellular damage to the auditory and vestibular hair cells of the inner ear. The mechanism of entry into the hair cells has not been unequivocally resolved. Here we
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