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D7253

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
UNSPSC Code:
51102829
NACRES:
NA.85
PubChem Substance ID:
24894093
EC Number:
226-823-7
Beilstein/REAXYS Number:
3894221
MDL number:
MFCD00070252

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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

200

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Show Differences

1 of 4

This Item
1203008D5155D1954000
Dihydrostreptomycin sesquisulfate

Sigma-Aldrich

D7253

Dihydrostreptomycin sesquisulfate

Dihydrostreptomycin sulfate United States Pharmacopeia (USP) Reference Standard

USP

1203008

Dihydrostreptomycin sulfate

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

Sigma-Aldrich

D5155

Dihydrostreptomycin sesquisulfate

Dihydrostreptomycin sulfate European Pharmacopoeia (EP) Reference Standard

D1954000

Dihydrostreptomycin sulfate

antibiotic activity spectrum

Gram-negative bacteria, mycobacteria, Gram-positive bacteria

antibiotic activity spectrum

-

antibiotic activity spectrum

Gram-negative bacteria, Gram-positive bacteria, mycobacteria

antibiotic activity spectrum

-

mode of action

protein synthesis | interferes

mode of action

-

mode of action

protein synthesis | interferes

mode of action

-

Quality Level

200

Quality Level

-

Quality Level

200

Quality Level

-

form

powder

form

-

form

powder

form

-

biological source

microbial

biological source

-

biological source

-

biological source

-

storage temp.

2-8°C

storage temp.

-

storage temp.

2-8°C

storage temp.

-

Application

Dihydrostreptomycin sesquisulfate is a derivative of streptomycin used in aminoglycoside uptake studies[1][2]. It has also been used as an electrode for a cochlear amplifier in the hair-cell bundle of lizards[3].

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
GHS08,GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Repr. 2

Storage Class

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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Certificates of Analysis (COA)

Lot/Batch Number
0000511784
0000504474
0000504474
0000488320
0000471169

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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
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
Murali Pendela et al.
Rapid communications in mass spectrometry : RCM, 23(12), 1856-1862 (2009-05-19)
Dihydrostreptomycin sulphate (DHS) is a water-soluble, broad-spectrum aminoglycoside antibiotic. For quantitative analysis, the European Pharmacopoeia (Ph. Eur.) prescribes an ion-pairing liquid chromatography/ultraviolet (LC/UV) method using a C18 stationary phase. Several unknown compounds were detected in commercial samples. Hence, for characterization
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
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