Synonym
Dihydrostreptomycin Sulfate; Didromycin; Didromycine; Panstreptin; Dihydrostreptomycin sulphate; Dihydrostreptomyzinsulfat; NSC-756739; NSC756739; NSC 756739;
IUPAC/Chemical Name
bis(2,2'-((1R,2R,3S,4R,5R,6S)-4-(((2R,3R,4R,5S)-3-(((2S,3S,4S,5R,6S)-4,5-dihydroxy-6-(hydroxymethyl)-3-(methylamino)tetrahydro-2H-pyran-2-yl)oxy)-4-hydroxy-4-(hydroxymethyl)-5-methyltetrahydrofuran-2-yl)oxy)-2,5,6-trihydroxycyclohexane-1,3-diyl)diguanidine) tris(sulfate)
InChi Key
CZWJCQXZZJHHRH-SCXQCXSWSA-N
InChi Code
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 Code
C[C@H]1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)N=C(N)N)O)N=C(N)N)O[C@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)NC)(CO)O.C[C@H]1[C@@]([C@H]([C@@H](O1)O[C@@H]2[C@H]([C@@H]([C@H]([C@@H]([C@H]2O)O)N=C(N)N)O)N=C(N)N)O[C@H]3[C@H]([C@@H]([C@H]([C@@H](O3)CO)O)O)NC)(CO)O.OS(=O)(=O)O.OS(=O)(=O)O.OS(=O)(=O)O
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.03.00
Biological target:
Dihydrostreptomycin sulfate is an aminoglycoside antibiotic, used to treat bacterial diseases in cattle, pigs and sheep.
In vitro activity:
Thus, a modest but statistically significant DHS (dihydrostreptomycin)- and MscL-dependent glutamate flux can be measured in DHS-resistant cells independent of a decreased viability, strongly suggesting that DHS can influence MscL gating independent of DHS toxicity.
Reference: PLoS Biol. 2016 Jun 9;14(6):e1002473. https://pubmed.ncbi.nlm.nih.gov/27280286/
In vivo activity:
Here this study reports that extracellular dihydrostreptomycin not only blocks the mechano-electrical transducer channels of mouse outer mouse hair cells at negative membrane potentials, as previously shown, but also enters the cells through these channels, which are located in the cells' mechanosensory hair bundles. The results identify the open transducer channels as the main route for aminoglycoside entry. Intracellularly applied dihydrostreptomycin also blocks the transducer channels, but at positive membrane potentials.
Reference: J Physiol. 2005 Sep 1;567(Pt 2):505-21. https://pubmed.ncbi.nlm.nih.gov/15994187/
|
Solvent |
mg/mL |
mM |
comments |
| Solubility |
| Water |
100.0 |
68.43 |
|
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.
Preparing Stock Solutions
The following data is based on the
product
molecular weight
1,461.41
Batch specific molecular weights may vary
from batch to batch
due to the degree of hydration, which will
affect the solvent
volumes required to prepare stock solutions.
| Concentration / Solvent Volume / Mass |
1 mg |
5 mg |
10 mg |
| 1 mM |
1.15 mL |
5.76 mL |
11.51 mL |
| 5 mM |
0.23 mL |
1.15 mL |
2.3 mL |
| 10 mM |
0.12 mL |
0.58 mL |
1.15 mL |
| 50 mM |
0.02 mL |
0.12 mL |
0.23 mL |
Formulation protocol:
1. Wray R, Iscla I, Gao Y, Li H, Wang J, Blount P. Dihydrostreptomycin Directly Binds to, Modulates, and Passes through the MscL Channel Pore. PLoS Biol. 2016 Jun 9;14(6):e1002473. doi: 10.1371/journal.pbio.1002473. PMID: 27280286; PMCID: PMC4900634.
2. Marcotti W, van Netten SM, Kros CJ. The aminoglycoside antibiotic dihydrostreptomycin rapidly enters mouse outer hair cells through the mechano-electrical transducer channels. J Physiol. 2005 Sep 1;567(Pt 2):505-21. doi: 10.1113/jphysiol.2005.085951. Epub 2005 Jun 30. PMID: 15994187; PMCID: PMC1474200.
3. Corns LF, Johnson SL, Kros CJ, Marcotti W. Tmc1 Point Mutation Affects Ca2+ Sensitivity and Block by Dihydrostreptomycin of the Mechanoelectrical Transducer Current of Mouse Outer Hair Cells. J Neurosci. 2016 Jan 13;36(2):336-49. doi: 10.1523/JNEUROSCI.2439-15.2016. PMID: 26758827; PMCID: PMC4710764.
In vitro protocol:
1. Wray R, Iscla I, Gao Y, Li H, Wang J, Blount P. Dihydrostreptomycin Directly Binds to, Modulates, and Passes through the MscL Channel Pore. PLoS Biol. 2016 Jun 9;14(6):e1002473. doi: 10.1371/journal.pbio.1002473. PMID: 27280286; PMCID: PMC4900634.
In vivo protocol:
1. Marcotti W, van Netten SM, Kros CJ. The aminoglycoside antibiotic dihydrostreptomycin rapidly enters mouse outer hair cells through the mechano-electrical transducer channels. J Physiol. 2005 Sep 1;567(Pt 2):505-21. doi: 10.1113/jphysiol.2005.085951. Epub 2005 Jun 30. PMID: 15994187; PMCID: PMC1474200.
2. Corns LF, Johnson SL, Kros CJ, Marcotti W. Tmc1 Point Mutation Affects Ca2+ Sensitivity and Block by Dihydrostreptomycin of the Mechanoelectrical Transducer Current of Mouse Outer Hair Cells. J Neurosci. 2016 Jan 13;36(2):336-49. doi: 10.1523/JNEUROSCI.2439-15.2016. PMID: 26758827; PMCID: PMC4710764.
1: Adams E, Roets E, Hoogmartens J. Liquid chromatographic analysis of dihydrostreptomycin sulfate. J Pharm Biomed Anal. 1999 Dec;21(4):715-22. PubMed PMID: 10701936.
2: Yamashita H, Shimogori H, Sugahara K, Takahashi M. Cell proliferation in spiral ligament of mouse cochlea damaged by dihydrostreptomycin sulfate. Acta Otolaryngol. 1999;119(3):322-5. PubMed PMID: 10380736.
3: Mutlu OF. [The pharmacokinetics of dihydrostreptomycin sulfate in domestic pigeons (Columba livia Gmel., 1789 var. domestica)]. Tierarztl Prax. 1990 Aug;18(4):377-81. German. PubMed PMID: 1699297.
4: Perel'man EV, Temper RM, Tabachnik AL. [Immunological activity of dihydrostreptomycin sulfate--precipitated fractions from cell-free intestinal bacterial lysates]. Zh Mikrobiol Epidemiol Immunobiol. 1974 Jun;51(6):134-5. Russian. PubMed PMID: 4137421.
5: Likhoded VG, Tabachnik AL, Temper RM, Perel'man EV. [Isolation of protective complexes from disintegrated intestinal group bacteria by sedimentation with dihydrostreptomycin sulfate]. Zh Mikrobiol Epidemiol Immunobiol. 1973 Sep;50(9):95-8. Russian. PubMed PMID: 4133271.
6: Zheng JM, Chen HF, Chao JJ, Liang JH. [An electrolytic method for the preparation of dihydrostreptomycin sulfate]. Yao Xue Xue Bao. 1966 May;13(5):370. Chinese. PubMed PMID: 4161767.
7: GOMEZLUS R, SARRIACHUECA A. [ASSOCIATION OF DIHYDROSTREPTOMYCIN SULFATE AND SODIUM CITRATE IN THE TREATMENT OF INFANTILE DIARRHEA]. Clin Lab (Zaragoza). 1964 Dec;78:417-32. Spanish. PubMed PMID: 14253273.
8: CATTAN R, CARASSO R, CATTAN D, RUEFF B. [Use of dihydrostreptomycin sulfate by oral route in an adult gastroenterology department]. Presse Med. 1962 Jul 4-Aug 28;70:1683-4. French. PubMed PMID: 13877365.
9: TOSCANI T. [On the mechanism of the toxic action of massive doses of antibiotics: effects of dihydrostreptomycin sulfate]. Minerva Anestesiol. 1962 May;28:186-7. Italian. PubMed PMID: 13922079.
10: ADAMO F. [On the tolerance for a combination of dihydrostreptomycin pantothenate and dihydrostreptomycin sulfate in the therapy of tuberculosis with particular reference to the therapy of tuberculous meningitis]. Gazz Med Ital. 1960 Dec;119:519-22. Italian. PubMed PMID: 13681333.
11: HEWITT WL, GLORIG A, FINEGOLD S. Auditory nerve toxicity of dihydrostreptomycin sulfate and dihydrostreptomycin pantothenate. Antibiot Annu. 1957-1958;5:609-13. PubMed PMID: 13521866.
12: SHELTON DC, OLSON NO. Control of infectious synovitis. IX. The efficacy of dihydrostreptomycin sulfate as related to the time of experimental infection. Antibiot Annu. 1957-1958;5:272-8. PubMed PMID: 13521817.
13: KORTH W, SPEYER E. [Effect of streptomycin sulfate, dihydrostreptomycin sulfate, and penicillin, separate and combined]. Arzneimittelforschung. 1956 Aug;6(8):418-23. German. PubMed PMID: 13373634.
14: SCHMITTLE SC. Use of dibenzylethylenediamine dipenicillin G and dihydrostreptomycin sulfate in chronic respiratory disease of chickens. J Am Vet Med Assoc. 1954 Sep;125(930):221-3. PubMed PMID: 13183875.
15: SAVI C. [Velez sign in female genital tuberculosis during isoniazid and dihydrostreptomycin sulfate therapy]. Ann Ostet Ginecol. 1954 Aug;76(8):907-36. Italian. PubMed PMID: 13229153.
16: AGUIRRE MIQUEO D, VAZQUEZ LOPEZ F. [A new salt of dihydrostreptomycin: tri-2-(1-isonicotinoylhydrazono)-pyruvate of dihydrostreptomycin. II. Comparison of the toxicity of tri-2(1-isonicotinoylhydrazono)-pyruvate of dihydrostreptomycin with that of dihydrostreptomycin sulfate; effects of anion on dihydrostreptomycin toxicity]. Arch Inst Farmacol Exp (Madr). 1954;6(1):106-19. Spanish. PubMed PMID: 13239437.
17: BUCKWALTER FH, DUDA S. Stability studies of penicillin products. X. Procaine penicillin G and buffered potassium penicillin G with dihydrostreptomycin sulfate. Antibiot Chemother (Northfield). 1953 Nov;3(11):1113-6. PubMed PMID: 24542857.
18: ALLISON ST. Dihydrostreptomycin sulfate in pulmonary tuberculosis; report on neurotoxicity. Am Rev Tuberc. 1952 May;65(5):612-6. PubMed PMID: 14924181.
19: EASTERBROOKS HL, HELLER P, LIEBERMAN M, PLASTRIDGE WN, JUNGHERR EL. Fertility and bacterial content of diluted bull semen treated with various concentrations of dihydrostreptomycin sulfate. Am J Vet Res. 1951 Jul;12(44):191-3. PubMed PMID: 14847111.
20: Solomons IA, Regna PP. Crystalline Dihydrostreptomycin Sulfate. Science. 1949 May 20;109(2838):515. PubMed PMID: 17830001.
