An aminoglycoside antibiotic
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Dihydrostreptomycin (sulfate)

Item No. 27879

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
O-2-deoxy-2-(methylamino)-α-L-glucopyranosyl-(1→2)-O-5-deoxy-3-C-(hydroxymethyl)-α-L-lyxofuranosyl-(1→4)-N1,N3-bis(aminoiminomethyl)-D-streptamine, sulfate (2:3)
CAS Number
5490-27-7
Molecular Formula
C21H41N7O12 • 1.5H2SO4
Formula Weight
730.7
Purity
≥95%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 10 mg/ml
SMILES
NC(N[C@@H]1[C@@H](O)[C@H](NC(N)=N)[C@](O[C@H]2[C@H](O[C@]3([H])O[C@@H](CO)[C@H](O)[C@@H](O)[C@@H]3NC)[C@](CO)(O)[C@H](C)O2)([H])[C@H](O)[C@H]1O)=N.OS(=O)(O)=O.OS(=O)(O)=O
InChi Code
InChI=1S/C21H41N7O12.2H2O4S/c1-5-21(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;2*1-5(2,3)4/h5-18,26,29-36H,3-4H2,1-2H3,(H4,22,23,27)(H4,24,25,28);2*(H2,1,2,3,4)/t5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+;;/m0../s1
InChi Key
SUGVNCGIHLAZCH-DEIZBOPUSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Dihydrostreptomycin is an aminoglycoside antibiotic and a derivative of streptomycin (Item No. 21211).1 It is active against B. subtilis, K. pneumoniae, S. marcescens, S. aureus, P. aeruginosa, and M. tuberculosis (MICs = 0.07, 0.08, 0.09, 0.06, 0.8, and 5.7 µg/ml, respectively). It interferes with bacterial protein synthesis by binding the 30S ribosomal subunit.2 Dihydrostreptomycin enhances phagocytosis and intracellular killing of E. coli by isolated mouse peritoneal macrophages.3 It improves survival in a mouse model of S. aureus infection.4 Formulations containing dihydrostreptomycin have been used in the prevention and treatment of bacterial infections in livestock.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Donovick, R., and Rake, G. Studies on some biological aspects of dihydrostreptomycin. J. Bacteriol. 53(2), 205-211 (1947).

    2. Kaji, H., and Tanaka, Y. Binding of dihydrostreptomycin to ribosomal subunits. J. Mol. Biol. 32(2), 221-230 (1968).

    3. Adam, D., Staber, F., Belohradsky, B.H., et al. Effect of dihydrostreptomycin on phagocytosis of mouse-peritoneal macrophages in vitro. Infect. Immun. 5(4), 537-541 (1972).

    4. Waksman, S.A., Frankel, J., and Graessle, O. The in vivo activity of neomycin. J. Bacteriol. 58(2), 229-237 (1949).