An aminoglycoside antibiotic
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Amikacin

Item No. 15405

Product Insert (PDF)Safety Data Sheet (SDS) (PDF)
Technical Information
Formal Name
O-3-amino-3-deoxy-α-D-glucopyranosyl-(1→6)-O-[6-amino-6-deoxy-α-D-glucopyranosyl-(1→4)]-N1-[(2S)-4-amino-2-hydroxy-1-oxobutyl]-2-deoxy-D-streptamine
CAS Number
37517-28-5
Synonyms
  • Antibiotic BB-K 8
  • BAY 41-6551
  • BB-K 8
  • Lukadin
  • Potentox
Molecular Formula
C22H43N5O13
Formula Weight
585.6
Purity
≥98%
Formulation (Request formulation change)
A crystalline solid
Solubility(Learn about Variance in Solubility)
PBS (pH 7.2): 5 mg/ml
SMILES
NC[C@@H](O1)[C@@H](O)[C@H](O)[C@@H](O)[C@@]1([H])O[C@@H]2[C@@H](N)C[C@@H](NC([C@@H](O)CCN)=O)[C@H](O[C@@]3([H])O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O)[C@H]2O
InChi Code
InChI=1S/C22H43N5O13/c23-2-1-8(29)20(36)27-7-3-6(25)18(39-22-16(34)15(33)13(31)9(4-24)37-22)17(35)19(7)40-21-14(32)11(26)12(30)10(5-28)38-21/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+/m0/s1
InChi Key
LKCWBDHBTVXHDL-RMDFUYIESA-N
Shipping & Storage Information
Storage
-20°C
Shipping
Room temperature in continental US; may vary elsewhere
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    Cayman Chemical
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    Product Description

    Amikacin is an aminoglycoside antibiotic derived from kanamycin A. Like other aminoglycosides, amikacin binds to bacterial ribosomes and disrupts translation.1 However, the specific binding sites differ between different aminoglycoside antibiotics, as do the mechanisms of resistance.1,2,3,4 Amikacin is effective against Gram-negative and Gram-positive bacteria.2

    WARNING This product is not for human or veterinary use.

    References & Product Citations
    Product Description References

    1. Le Goffic, F., Capmau, M.L., Tangy, F., et al. Have deoxystreptamine aminoglycoside antibiotics the same binding site on bacterial ribosomes? J. Antibiot. (Tokyo) 33(8), 895-899 (1980).

    2. Price, K.E., Purisano, T.A., DeFuria, M.D., et al. Activity of BB-K8 (amikacin) against clinical isolates resistant to one or more aminoglycoside antibiotics. Antimicrob. Agents Chemother. 5(2), 143-152 (2014).

    3. Georghiou, S.B., Magana, M., Garfein, R.S., et al. Evaluation of genetic mutations associated with Mycobacterium tuberculosis resistance to amikacin, kanamycin and capreomycin: A systematic review. PLoS One 7(3), e33275 (2012).

    4. Davis, M.A., Baker, K.N.K., Orfe, L.H., et al. Discovery of a gene conferring multiple-aminoglycoside resistance in Escherichia coli. Antimicrob. Agents Chemother. 54(6), 2666-2669 (2010).