An aminoglycoside antibiotic
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Streptomycin (sulfate)

Item No. 21211

Technical Information
Formal Name
O-2-deoxy-2-(methylamino)-α-L-glucopyranosyl-(1→2)-O-5-deoxy-3-C-formyl-α-L-lyxofuranosyl-(1→4)-N1,N3-bis(aminoiminomethyl)-D-streptamine
CAS Number
3810-74-0
Molecular Formula
C21H39N7O12 • 1.5H2SO4
Formula Weight
Purity
≥95%
A crystalline solid
DMF: 13 mg/mlDMSO: 2 mg/mlPBS (pH 7.2): 10 mg/ml
λmax
231 nm
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@](C=O)(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/2C21H39N7O12.3H2O4S/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*4-18,26,29,31-36H,3H2,1-2H3,(H4,22,23,27)(H4,24,25,28);3*(H2,1,2,3,4)/t2*5-,6-,7+,8-
InChi Key
QTENRWWVYAAPBI-YCRXJPFRSA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Product Description

    Streptomycin is an aminoglycoside antibiotic that inhibits growth of both Gram-negative (MICs = 1 and 16 μg/mL for K. pneumoniae and S. marcescens, respectively) and Gram-positive bacteria (MIC = 0.25 μg/mL for S. pneumoniae).1 It inhibits growth of M. tuberculosis H37Rv (MIC = 5 μg/mL) and of susceptible strains from clinical isolates (MICs = ≤0.125-1 μg/mL).2,3 Streptomycin (150 mg/kg), in combination with isoniazid (Item No. 20378), rifapentine (Item No. 20307), and moxifloxacin (Item No. 14830), administered once per week over 6 months to M. tuberculosis-inoculated mice results in clearance of the pathogen from the lungs of the majority of treated mice.4 However, after 3 months without treatment, 58% of treated mice produce a positive lung culture. Streptomycin acts by inhibiting protein synthesis in prokaryotes by binding to the 30S ribosomal subunit.5,6,7,8 It has been used, in combination with penicillin G (Item No. 21615), in antibiotic cocktails to prevent bacterial growth in cell culture.9 Formulations containing streptomycin in combination with other antibiotics have been used to treat tuberculosis.

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Syed, H.C., and Ravaoarinoro, M. LiF reduces MICs of antibiotics against clinical isolates of gram-positive and gram-negative bacteria. Int. J. Microbiol. 454065 (2012).

    2. Jhamb, S.S., Goyal, A., and Singh, P.P. Determination of the activity of standard anti-tuberculosis drugs against intramacrophage Mycobacterium tuberculosis, in vitro: MGIT 960 as a viable alternative for BACTEC 460. Braz. J. Infect. Dis. 18(3), 336-340 (2014).

    3. Franzblau, S.G., Witzig, R.S., McLaughlin, J.C., et alRapid, low-technology MIC determination with clinical Mycobacterium tuberculosis isolates by using the microplate Alamar Blue assay. J. Clin. Microbiol. 36(2), 362-366 (1998).

    4. Lounis, N., Bentoucha, A., Truffot-Pernot, C., et alEffectiveness of once-weekly rifapentine and moxifloxacin regimens against Mycobacterium tuberculosis in mice. Antimicrob. Agents Chemother. 45(12), 3482-3486 (2001).

    5. Luzzatto, L., Apirion, D., and Schlessinger, D. Mechanism of action of streptomycin in E. coli: Interruption of the ribosome cycle at the initiation of protein synthesis. Proc. Natl. Acad. Sci. USA 60(3), 873-880 (1968).

    6. Moazed, D., and Noller, H.F. Interaction of antibiotics with functional sites in 16S ribosomal RNA. Nature 327(6121), 389-394 (1987).

    7. Carter, A.P., Clemons, W.M., Brodersen, D.E., et alFunctional insights from the structure of the 30S ribosomal subunit and its interactions with antibiotics. Nature 407(6802), 340-348 (2000).

    8. Sharma, D., Cukras, A.R., Rogers, E.J., et alMutational analysis of S12 protein and implications for the accuracy of decoding by the ribosome. J. Mol. Biol. 374(4), 1065-1076 (2007).

    9. Varghese, D.S., Parween, S., Ardah, M.T., et alEffects of aminoglycoside antibiotics on human embryonic stem cell viability during differentiation in vitro. Stem Cells Int. 2017, 2451927 (2017).