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Streptomycin

Cat No.:V6367 Purity: ≥98%
Streptomycin sulfate is an aminoglycoside antibiotic that can inhibit protein synthesis.
Streptomycin
Streptomycin Chemical Structure CAS No.: 3810-74-0
Product category: New1
This product is for research use only, not for human use. We do not sell to patients.
Size Price Stock Qty
10g
50g
Other Sizes

Other Forms of Streptomycin:

  • Streptomycin/OVA
  • Streptomycin/BSA
  • Streptomycin
Official Supplier of:
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Top Publications Citing lnvivochem Products
Product Description
Streptomycin sulfate is an aminoglycoside antibiotic that can inhibit protein synthesis.
Biological Activity I Assay Protocols (From Reference)
ln Vitro
As the concentration of CV in the growing medium grew, so did strain RB1's sensitivity to streptomycin. Cytochrome aa3 levels and streptomycin sensitivity both rise with increasing CV concentration in the growing medium. B. subtilis cannot accumulate streptomycin without cytochrome aa3 [1]. Streptomycin has an impact on tRNA selection. Mutations causing streptomycin resistance often localize to protein S12, and the majority of these variations show increased discrimination during tRNA selection [2].
Toxicity/Toxicokinetics
Effects During Pregnancy and Lactation
◉ Summary of Use during Lactation
Similar to other aminoglycoside antibiotics, streptomycin is poorly excreted into breastmilk. Newborn infants apparently absorb small amounts of aminoglycosides, but serum levels are far below those attained when treating newborn infections and systemic effects of streptomycin are unlikely. Older infants would be expected to absorb even less streptomycin Monitor the infant for possible effects on the gastrointestinal flora, such as diarrhea, candidiasis (e.g., thrush, diaper rash) or rarely, blood in the stool indicating possible antibiotic-associated colitis.
◉ Effects in Breastfed Infants
Relevant published information was not found as of the revision date.
◉ Effects on Lactation and Breastmilk
One observational study found no inhibition of lactation by streptomycin.
References

[1]. Correlation between cytochrome aa3 concentrations and streptomycin accumulation in Bacillus subtilis. Antimicrob Agents Chemother. 1984 Oct;26(4):507-12.

[2]. Mutational analysis of S12 protein and implications for the accuracy of decoding by the ribosome. J Mol Biol, 2007. 374(4): p. 1065-76.

Additional Infomation
Streptomycin Sulfate can cause developmental toxicity according to state or federal government labeling requirements.
Streptomycin sulfate (2:3) (salt) appears as an antibacterial. White to light gray or pale buff powder with faint amine-like odor.
Streptomycin sulfate is an aminoglycoside sulfate salt. It is functionally related to a streptomycin.
Streptomycin Sulfate is the sulfate salt form of streptomycin, an aminoglycoside antibiotic derived from Streptomyces griseus with antibacterial property. Streptomycin sulfate binds to the S12 protein of the bacterial 30S ribosomal subunit, thereby inhibiting peptide elongation and protein synthesis, consequently leading to bacterial cell death.
An antibiotic produced by the soil actinomycete Streptomyces griseus. It acts by inhibiting the initiation and elongation processes during protein synthesis.
See also: Streptomycin (has active moiety) ... View More ...
These protocols are for reference only. InvivoChem does not independently validate these methods.
Physicochemical Properties
Exact Mass
1456.433
CAS #
3810-74-0
Related CAS #
Streptomycin;57-92-1
PubChem CID
19648
Appearance
White to off-white solid powder
Boiling Point
948.2ºC at 760 mmHg
Flash Point
527.3ºC
Index of Refraction
-85 ° (C=1, H2O)
Hydrogen Bond Donor Count
30
Hydrogen Bond Acceptor Count
42
Rotatable Bond Count
18
Heavy Atom Count
95
Complexity
1020
Defined Atom Stereocenter Count
30
SMILES
S(=O)(=O)(O[H])O[H].S(=O)(=O)(O[H])O[H].S(=O)(=O)(O[H])O[H].O([C@@]1([H])[C@@]([H])([C@@](C([H])=O)([C@]([H])(C([H])([H])[H])O1)O[H])O[C@@]1([H])[C@]([H])([C@@]([H])([C@]([H])([C@]([H])(C([H])([H])O[H])O1)O[H])O[H])N([H])C([H])([H])[H])[C@@]1([H])[C@@]([H])([C@]([H])([C@@]([H])([C@]([H])([C@]1([H])/N=C(\N([H])[H])/N([H])[H])O[H])/N=C(\N([H])[H])/N([H])[H])O[H])O[H].O([C@@]1([H])[C@@]([H])([C@@](C([H])=O)([C@]([H])(C([H])([H])[H])O1)O[H])O[C@@]1([H])[C@]([H])([C@@]([H])([C@]([H])([C@]([H])(C([H])([H])O[H])O1)O[H])O[H])N([H])C([H])([H])[H])[C@@]1([H])[C@@]([H])([C@]([H])([C@@]([H])([C@]([H])([C@]1([H])/N=C(\N([H])[H])/N([H])[H])O[H])/N=C(\N([H])[H])/N([H])[H])O[H])O[H]
InChi Key
QTENRWWVYAAPBI-YCRXJPFRSA-N
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-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+;;;/m00.../s1
Chemical Name
2-[(1R,2R,3S,4R,5R,6S)-3-(diaminomethylideneamino)-4-[(2R,3R,4R,5S)-3-[(2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)oxan-2-yl]oxy-4-formyl-4-hydroxy-5-methyloxolan-2-yl]oxy-2,5,6-trihydroxycyclohexyl]guanidine;sulfuric acid
HS Tariff Code
2934.99.9001
Storage

Powder      -20°C    3 years

                     4°C     2 years

In solvent   -80°C    6 months

                  -20°C    1 month

Note: Please store this product in a sealed and protected environment (e.g. under nitrogen), avoid exposure to moisture and light.
Shipping Condition
Room temperature (This product is stable at ambient temperature for a few days during ordinary shipping and time spent in Customs)
Solubility Data
Solubility (In Vitro)
H2O : ≥ 100 mg/mL (~137.23 mM)
DMSO :< 1 mg/mL
Solubility (In Vivo)
Solubility in Formulation 1: 100 mg/mL (137.23 mM) in PBS (add these co-solvents sequentially from left to right, and one by one), clear solution; with sonication.

 (Please use freshly prepared in vivo formulations for optimal results.)
Calculator

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Note: Chemical formula is case sensitive: C12H18N3O4  c12h18n3o4
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In vivo Formulation Calculator (Clear solution)
Step 1: Enter information below (Recommended: An additional animal to make allowance for loss during the experiment)
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Calculation results

Working concentration mg/mL;

Method for preparing DMSO stock solution mg drug pre-dissolved in μL DMSO (stock solution concentration mg/mL). Please contact us first if the concentration exceeds the DMSO solubility of the batch of drug.

Method for preparing in vivo formulation:Take μL DMSO stock solution, next add μL PEG300, mix and clarify, next addμL Tween 80, mix and clarify, next add μL ddH2O,mix and clarify.

(1) Please be sure that the solution is clear before the addition of next solvent. Dissolution methods like vortex, ultrasound or warming and heat may be used to aid dissolving.
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Clinical Trial Information
NCT Number Recruitment interventions Conditions Sponsor/Collaborators Start Date Phases
NCT00004444 COMPLETED Drug: paromomycin
Drug: streptomycin
Tuberculosis, Pulmonary FDA Office of Orphan Products Development 1994-11 Not Applicable
NCT00128466 COMPLETED Drug: gentamicin
Drug: streptomycin
Plague Centers for Disease Control and Prevention 2004-08 Phase 2
Phase 3
NCT01432925 COMPLETED Procedure: surgical intervention on Buruli ulcer Buruli Ulcer
Mycobacterium Ulcerans Disease
University Medical Center Groningen 2011-09 Not Applicable
NCT04110340 RECRUITING Drug: Ciprofloxacin
Drug: Streptomycin
Drug: Gentamicin
Plague, Bubonic
Plague, Pneumonic
University of Oxford 2020-02-15 Phase 3
NCT02604849 COMPLETED Drug: Neomycin
Drug: Streptomycin
Drug: Gentamicins
Patients Colonized by Klebsiella
Pneumoniae
Maimónides Biomedical Research Institute of Córdoba 2012-07
Biological Data
  • In vivo growth of chromosomal S12 knockout strain and S12 variant strains. (a) Chromosomal S12 knockout strain is viable only when S12 protein is expressed from the plasmid in the presence of IPTG. (b) Part of sequence alignment of S12 protein from bacteria, archaea and metazoans. The residues in dark and light blue show 100% and 80-90% conservation respectively. Arrowheads mark the sites chosen for alanine substitution mutations. The conserved PNSA and PGVR loops are enclosed in boxes. Ec, E. coli; Tt, T. thermophilus; Bs, B. subtilis; Hm, H. marismortui; Sp, S. pombe; Rn, R. norvegicus; Ms, M. musculus; Hs, H. sapiens; At, A. thaliana; Eg, E. gracilis. (c) The S12 residues mutated to alanine (shown as blue sticks) in the present study cluster near the decoding site (left panel). The right panel shows the S12 residues P44 and S46 (shown in blue) interacting with the decoding region upon binding of cognate anticodon-stem-loop (ASL). S12 protein is shown in light blue, neighboring helices (h27 in yellow and h44 including A1492 and A1493 in magenta), A-site codon in orange and ASL in green. (d) The dominant growth phenotype of wild type (WT) or mutant (K42A, P44A, N45A, S46A, R53A, R85A, D88A, L89A, P90A, G91A or R93A) S12. S12 protein was expressed from plasmid carrying a carbenicillin (Carb) resistance marker using IPTG in cells carrying an intact chromosomal copy of the S12 gene. For control cells were plated in the absence of IPTG. (e) The recessive growth phenotype of WT and variant S12 expressed from plasmid with Carb resistance gene. Cells with chromosomal S12 gene replaced with a kanamycin (Kan) resistance marker grow only when expression of the WT or a viable S12 mutant (K42A, N45A, S46A, R53A, R85A, L89A, P90A, G91A or R93A) is induced from the plasmid. Streptomycin (Strep) resistance was assessed by plating in the presence of the antibiotic.[2]. Sharma, D., et al., Mutational analysis of S12 protein and implications for the accuracy of decoding by the ribosome. J Mol Biol, 2007. 374(4): p. 1065-76.
  • Modulation of the decoding properties of wild type and S12 variant ribosomes by miscoding antibiotics. (a) The endpoint of dipeptide (fMet-Phe) formation with a near-cognate (AUC) codon in the A site of wild type (WT) or S12 variant ribosomes (K42A, N45A, S46A, R53A, P90A, R93A), in the absence or presence of streptomycin (Strep) and paromomycin (Paromo). A similar endpoint analysis was carried out with varying concentrations of paromomycin (0-2 mM). The fraction TC converted to fMet-Phe was plotted as a function of paromomycin concentration and fit to single (a - WT, K42A, R53A) or double (c - N45A, S46A, P90A, R93A) hyperbolic equations. The inset in (c) shows the data points from 0 to 20 μM paromomycin, fit to a single hyperbolic equation.[2]. Sharma, D., et al., Mutational analysis of S12 protein and implications for the accuracy of decoding by the ribosome. J Mol Biol, 2007. 374(4): p. 1065-76.
  • Structural implications for the modulation of decoding by S12 and paromomycin. (a) Structural view of S12 protein (light blue) contacting helix 44 (h44, magenta) and helix 27 (h27, yellow) (PDB accession no. 1FJG) 19. The sites of lethal mutations in S12 (P44 and D88) are shown in black. S12 residues K42 and R53 (dark blue) make hydrogen bonds with the backbone of A1412 (h44) and A913 (h27) respectively to facilitate domain closure as induced either by the miscoding antibiotics or the cognate ASL. The miscoding antibiotics streptomycin (Strep, red) and paromomycin (Par, green) bind near the decoding region at distinct sites. (b) The interface surface of small ribosomal subunit (PDB accession no. 1N32) 9. The boxed region in the left panel is depicted as a cartoon in the right panel. The color coding is essentially as above, except that helix 18 (h18, dark pink), A site codon (orange) and anticodon-stem-loop (ASL, green) are also shown. Streptomycin forms contacts with h27/h44 in the platform domain and h18/S12 (K42) in the shoulder domain of the small subunit. Paromomycin binding to the canonical binding site in h44 (Par1) results in the flipping out of A1492 and A1493 that facilitates binding of near-cognate ASL and domain closure. [2]. Sharma, D., et al., Mutational analysis of S12 protein and implications for the accuracy of decoding by the ribosome. J Mol Biol, 2007. 374(4): p. 1065-76.
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