Dihydrostreptomycin | Antibiotic | CAS# 128-46-1

MedKoo Cat#: 571376 | Name: Dihydrostreptomycin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Dihydrostreptomycin is an antibiotic.

Chemical Structure

Dihydrostreptomycin

CAS#128-46-1 (free base)

Theoretical Analysis

MedKoo Cat#: 571376

Name: Dihydrostreptomycin

CAS#: 128-46-1 (free base)

Chemical Formula: C21H41N7O12

Exact Mass: 583.2813

Molecular Weight: 583.60

Elemental Analysis: C, 43.22; H, 7.08; N, 16.80; O, 32.90

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

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Related CAS #

128-46-1 (free base) 5490-27-7 (sulfate)

Synonym

Dihydrostreptomycin; Abiocine; Vibriomycin; Dihydrostreptomycine

IUPAC/Chemical Name

1,1'-((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

InChi Key

ASXBYYWOLISCLQ-HZYVHMACSA-N

InChi Code

InChI=1S/C21H41N7O12/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/h5-18,26,29-36H,3-4H2,1-2H3,(H4,22,23,27)(H4,24,25,28)/t5-,6-,7+,8-,9-,10-,11+,12-,13-,14+,15+,16-,17-,18-,21+/m0/s1

SMILES Code

CN[C@H]1[C@@H]([C@H]([C@@H](O[C@H]1O[C@H]2[C@@H](O[C@H]([C@@]2(CO)O)C)O[C@H]3[C@@H]([C@H]([C@@H]([C@H]([C@@H]3NC(N)=N)O)NC(N)=N)O)O)CO)O)O

Appearance

Solid powder

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

>2 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

2934.99.9001

More Info

Instruction

View handling instruction

Preparing Stock Solutions

The following data is based on the product molecular weight 583.60 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

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. eCollection 2016 Jun. PubMed PMID: 27280286; PubMed Central PMCID: PMC4900634. 2: Rautmann G, Daas A, Buchheit KH. Collaborative study for the establishment of the 3rd international standard for dihydrostreptomycin. Pharmeur Bio Sci Notes. 2012 Apr;2012:16-38. PubMed PMID: 23327890. 3: Bohm DA, Stachel CS, Gowik P. Confirmatory method for the determination of streptomycin and dihydrostreptomycin in honey by LC-MS/MS. Food Addit Contam Part A Chem Anal Control Expo Risk Assess. 2012;29(2):189-96. doi: 10.1080/19440049.2011.635347. Epub 2011 Dec 6. PubMed PMID: 22145906. 4: Iscla I, Wray R, Wei S, Posner B, Blount P. Streptomycin potency is dependent on MscL channel expression. Nat Commun. 2014 Sep 10;5:4891. doi: 10.1038/ncomms5891. PubMed PMID: 25205267; PubMed Central PMCID: PMC4161981. 5: 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. 6: 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. 7: Groen K, Pereboom-De Fauw DP, Van Veen-Rutgers A, Vulto AG, De Neeling AJ. Bioavailability in the rabbit of penicillin and dihydrostreptomycin from three commercial penicillin/aminoglycoside fixed combination products for intramuscular injection. J Vet Pharmacol Ther. 1996 Oct;19(5):364-9. PubMed PMID: 8905570. 8: Maier S, Grisebach H. Biosynthesis of streptomycin. Enzymic oxidation of dihydrostreptomycin (6-phosphate) to streptomycin (6-phosphate) with a particulate fraction of Streptomyces griseus. Biochim Biophys Acta. 1979 Aug 22;586(2):231-41. PubMed PMID: 89869. 9: Lightbown JW, Kogut M, Uemura K, Grab B. The second International Standard for Dihydrostreptomycin. Bull World Health Organ. 1966;34(3):429-35. PubMed PMID: 4161602; PubMed Central PMCID: PMC2475972. 10: Breson K, Petersen BN, Rasmussen F. Ototoxicity in 626 patients with pulmonary tuberculosis treated with dihydrostreptomycin, streptomycin sulphate, or a combination of both. Scand J Respir Dis. 1972;53(1):44-50. PubMed PMID: 4115290. 11: Manners JG, Stewart R. Presence of dihydrostreptomycin and penicillin in cows' milk following intrauterine administration. Aust Vet J. 1982 May;58(5):203-4. PubMed PMID: 6182871. 12: 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. 13: HUMPHREY JH, LIGHTBOWN JW, MUSSETT MV, PERRY WL. The international standard for dihydrostreptomycin. Bull World Health Organ. 1954;10(6):901-9. PubMed PMID: 13199653; PubMed Central PMCID: PMC2542184. 14: 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. Epub 2005 Jun 30. PubMed PMID: 15994187; PubMed Central PMCID: PMC1474200. 15: Gremilogianni AM, Megoulas NC, Koupparis MA. Hydrophilic interaction vs ion pair liquid chromatography for the determination of streptomycin and dihydrostreptomycin residues in milk based on mass spectrometric detection. J Chromatogr A. 2010 Oct 22;1217(43):6646-51. doi: 10.1016/j.chroma.2010.04.059. Epub 2010 Apr 28. PubMed PMID: 20546761. 16: 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. 17: Groen K, Mevius DJ, Pereboom-De-Fauw DP, DeNeeling AJ, Vulto AG. Bioequivalence study in calves of three commercial penicillin/dihydrostreptomycin fixed combination products for intramuscular injection. J Vet Pharmacol Ther. 1996 Oct;19(5):370-5. PubMed PMID: 8905571. 18: Kawano S. Analysis of impurities in streptomycin and dihydrostreptomycin by hydrophilic interaction chromatography/electrospray ionization quadrupole ion trap/time-of-flight mass spectrometry. Rapid Commun Mass Spectrom. 2009 Mar;23(6):907-14. doi: 10.1002/rcm.3936. PubMed PMID: 19224534. 19: Kondo S, Ikeda Y, Ikeda T, Gomi S, Naganawa H, Hamada M, Umezawa H. 5'-Hydroxy-2"-N-demethyl-dihydrostreptomycin produced by a Streptomyces. J Antibiot (Tokyo). 1985 Mar;38(3):433-5. PubMed PMID: 2409065. 20: Nichols WW, Young SN. Respiration-dependent uptake of dihydrostreptomycin by Escherichia coli. Its irreversible nature and lack of evidence for a uniport process. Biochem J. 1985 Jun 1;228(2):505-12. PubMed PMID: 2409962; PubMed Central PMCID: PMC1145009.