Kanamycin B
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Hodoodo CAT#: H540254

CAS#: 4696-76-8

Description: Kanamycin B is an inhibitor of protein translation and mammalian RNA splicing. It inhibits growth of gram negative bacteria, prevents formulation of the initiation complex, and decreases action potential amplitude in cardiac pacemaker cells.


Chemical Structure

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Kanamycin B
CAS# 4696-76-8

Theoretical Analysis

Hodoodo Cat#: H540254
Name: Kanamycin B
CAS#: 4696-76-8
Chemical Formula: C18H37N5O10
Exact Mass: 483.25
Molecular Weight: 483.510
Elemental Analysis: C, 44.71; H, 7.71; N, 14.48; O, 33.09

Price and Availability

Size Price Availability Quantity
100mg USD 250 2 Weeks
1g USD 650 2 Weeks
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Synonym: Bekanamycin; NK-1006; NK1006; NK 1006; Nebramycin V

IUPAC/Chemical Name: (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-(((1R,2S,3S,4R,6S)-4,6-diamino-3-(((2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-2-hydroxycyclohexyl)oxy)tetrahydro-2H-pyran-3,4-diol

InChi Key: SKKLOUVUUNMCJE-FQSMHNGLSA-N

InChi Code: InChI=1S/C18H37N5O10/c19-2-6-11(26)12(27)9(23)17(30-6)32-15-4(20)1-5(21)16(14(15)29)33-18-13(28)8(22)10(25)7(3-24)31-18/h4-18,24-29H,1-3,19-23H2/t4-,5+,6+,7+,8-,9+,10+,11+,12+,13+,14-,15+,16-,17+,18+/m0/s1

SMILES Code: NC[C@H]1O[C@@H]([C@@H]([C@H]([C@@H]1O)O)N)O[C@@H]2[C@H](C[C@H]([C@@H]([C@H]2O)O[C@H]3O[C@@H]([C@H]([C@@H]([C@H]3O)N)O)CO)N)N

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:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 483.51 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.

Recalculate based on batch purity %
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:
In vitro protocol:
In vivo protocol:

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1: Zhang Y, He HM, Zhang J, Liu FJ, Li C, Wang BW, Qiao RZ. HPLC-ELSD determination of kanamycin B in the presence of kanamycin A in fermentation broth. Biomed Chromatogr. 2015 Mar;29(3):396-401. doi: 10.1002/bmc.3289. Epub 2014 Jul 17. PubMed PMID: 25042110.

2: Fosso MY, Shrestha SK, Green KD, Garneau-Tsodikova S. Synthesis and Bioactivities of Kanamycin B-Derived Cationic Amphiphiles. J Med Chem. 2015 Dec 10;58(23):9124-32. doi: 10.1021/acs.jmedchem.5b01375. Epub 2015 Dec 1. PubMed PMID: 26592740; PubMed Central PMCID: PMC5154386.

3: Truitt AR, Choi BE, Li J, Soto AM. Effect of Mutations on the Binding of Kanamycin-B to RNA Hairpins Derived from the Mycobacterium tuberculosis Ribosomal A-Site. Biochemistry. 2015 Dec 29;54(51):7425-37. doi: 10.1021/acs.biochem.5b00710. Epub 2015 Dec 17. PubMed PMID: 26560864.

4: Ni X, Li D, Yang L, Huang T, Li H, Xia H. Construction of kanamycin B overproducing strain by genetic engineering of Streptomyces tenebrarius. Appl Microbiol Biotechnol. 2011 Feb;89(3):723-31. doi: 10.1007/s00253-010-2908-5. Epub 2010 Oct 9. PubMed PMID: 20936279.

5: Fosso M, AlFindee MN, Zhang Q, Nziko Vde P, Kawasaki Y, Shrestha SK, Bearss J, Gregory R, Takemoto JY, Chang CW. Structure-activity relationships for antibacterial to antifungal conversion of kanamycin to amphiphilic analogues. J Org Chem. 2015 May 1;80(9):4398-411. doi: 10.1021/acs.joc.5b00248. Epub 2015 Apr 13. PubMed PMID: 25826012.

6: Yamasaki T, Narita Y, Hoshi H, Aburaki S, Kamei H, Naito T, Kawaguchi H. Synthesis and biological activity of 1-N-[4-(substituted)amidino and guanidino-2-hydroxybutyryl]kanamycins A and B. J Antibiot (Tokyo). 1991 Jun;44(6):646-58. PubMed PMID: 2071490.

7: Yung MW. Comparative ototoxicity of kanamycin A and kanamycin B in the guinea pig. Acta Otolaryngol. 1987 Jan-Feb;103(1-2):73-80. PubMed PMID: 3564930.

8: Carrier D, Chartrand N, Matar W. Comparison of the effects of amikacin and kanamycins A and B on dimyristoylphosphatidylglycerol bilayers. An infrared spectroscopic investigation. Biochem Pharmacol. 1997 Feb 7;53(3):401-8. PubMed PMID: 9065744.

9: Gao W, Wu Z, Sun J, Ni X, Xia H. Modulation of kanamycin B and kanamycin A biosynthesis in Streptomyces kanamyceticus via metabolic engineering. PLoS One. 2017 Jul 28;12(7):e0181971. doi: 10.1371/journal.pone.0181971. eCollection 2017. PubMed PMID: 28753625; PubMed Central PMCID: PMC5533434.

10: Mingeot-Leclercq MP, Van Schepdael A, Brasseur R, Busson R, Vanderhaeghe HJ, Claes PJ, Tulkens PM. New derivatives of kanamycin B obtained by modifications and substitutions in position 6''. 2. In vitro and computer-aided toxicological evaluation with respect to interactions with phosphatidylinositol. J Med Chem. 1991 Apr;34(4):1476-82. PubMed PMID: 2016725.

11: Song KM, Cho M, Jo H, Min K, Jeon SH, Kim T, Han MS, Ku JK, Ban C. Gold nanoparticle-based colorimetric detection of kanamycin using a DNA aptamer. Anal Biochem. 2011 Aug 15;415(2):175-81. doi: 10.1016/j.ab.2011.04.007. Epub 2011 Apr 15. PubMed PMID: 21530479.

12: Yung MW, Green C. Interaction of kanamycin A and kanamycin B with phospholipids. J Antibiot (Tokyo). 1987 Jun;40(6):862-7. PubMed PMID: 3610836.

13: Kato T, Yang G, Teo Y, Juskeviciene R, Perez-Fernandez D, Shinde HM, Salian S, Bernet B, Vasella A, Böttger EC, Crich D. Synthesis and Antiribosomal Activities of 4'-O-, 6'-O-, 4″-O-, 4',6'-O- and 4″,6″-O-Derivatives in the Kanamycin Series Indicate Differing Target Selectivity Patterns between the 4,5- and 4,6-Series of Disubstituted 2-Deoxystreptamine Aminoglycoside Antibiotics. ACS Infect Dis. 2015 Oct 9;1(10):479-86. doi: 10.1021/acsinfecdis.5b00069. Epub 2015 Aug 6. PubMed PMID: 27623314.

14: Portnoĭ IuA, Kartseva VD, Nikolaev GM, Chizhova NV. [Determination of the kanamycin B content of kanamycin preparations by column chromatography]. Antibiot Med Biotekhnol. 1987 Aug;32(8):583-5. Russian. PubMed PMID: 2823693.

15: Kumar V, Jones GS Jr, Blacksberg I, Remers WA, Misiek M, Pursiano TA. Aminoglycoside antibiotics. 3. Epimino derivatives of neamine, ribostamycin, and kanamycin B. J Med Chem. 1980 Jan;23(1):42-9. PubMed PMID: 6244410.

16: Van Schepdael A, Busson R, Vanderhaeghe HJ, Claes PJ, Verbist L, Mingeot-Leclercq MP, Brasseur R, Tulkens PM. New derivatives of kanamycin B obtained by combined modifications in positions 1 and 6". Synthesis, microbiological properties, and in vitro and computer-aided toxicological evaluation. J Med Chem. 1991 Apr;34(4):1483-92. PubMed PMID: 2016726.

17: Kwon M, Chun SM, Jeong S, Yu J. In vitro selection of RNA against kanamycin B. Mol Cells. 2001 Jun 30;11(3):303-11. PubMed PMID: 11459219.

18: Tebiakina AE, Shneerson AN, Braginskaia PS, Sinitsyna ZT, Korchagin VB, Korobitskaia AA. [Quantitative determination of the kanamycin B content in kanamycin preparations]. Antibiotiki. 1969 Aug;14(8):709-12. Russian. PubMed PMID: 4985086.

19: Dubost M, Pascal C, Terlain B, Thomas JP. [Detection of kanamycin B in kanamycin by thin layer chromatography]. J Chromatogr. 1973 Nov 7;86(1):274-8. French. PubMed PMID: 4765317.

20: Toda S, Nakagawa S, Naito T. Aminoglycoside antibiotics. X. chemical conversion of kanamycin B to kanamycin C and 6'-deoxy-kanamycin C. J Antibiot (Tokyo). 1977 Nov;30(11):1002-3. PubMed PMID: 591453.