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A1774

Sigma-Aldrich

Amikacin disulfate salt

potency: 674-786 μg per mg (as amikacin base)

Synonym(s):

(2S)-4-amino-N-[(1R,2S,3S,4R,5S)-5-amino-2-(3-amino-3-deoxy-alpha-D-glucopyranosyloxy)-4-(6-amino-6-deoxy-alpha-D-glucopyranosyloxy)-3-hydroxycyclohexyl]-2-hydroxybutanamide disulfate, Antibiotic BB-K8 sulfate

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About This Item

Empirical Formula (Hill Notation):
C22H43N5O13 · 2H2SO4
CAS Number:
39831-55-5
Molecular Weight:
781.76
Beilstein/REAXYS Number:
6172633
EC Number:
254-648-6
MDL number:
MFCD00167475
UNSPSC Code:
51101500
PubChem Substance ID:
24890586
NACRES:
NA.85

biological source

synthetic

Quality Level

200

form

powder or crystals

potency

674-786 μg per mg (as amikacin base)

color

white to off-white

antibiotic activity spectrum

Gram-negative bacteria
mycobacteria

mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

OS(O)(=O)=O.OS(O)(=O)=O.NCC[C@H](O)C(=O)N[C@@H]1C[C@H](N)[C@@H](O[C@H]2O[C@H](CN)[C@@H](O)[C@H](O)[C@H]2O)[C@H](O)[C@H]1O[C@H]3O[C@H](CO)[C@@H](O)[C@H](N)[C@H]3O

InChI

1S/C22H43N5O13.2H2O4S/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;2*1-5(2,3)4/h6-19,21-22,28-35H,1-5,23-26H2,(H,27,36);2*(H2,1,2,3,4)/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+;;/m0../s1

InChI key

FXKSEJFHKVNEFI-GCZBSULCSA-N

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General description

Chemical structure: aminoglycoside

Application

Amikacin is an aminoglycoside antibiotic commonly used in the treatment of drug-resistant mycobacteria . It is used to study organism-directed delivery of antibiotics as well as drug resistance .

Biochem/physiol Actions

Amikacin prevents bacterial protein synthesis by binding to the 30S ribosome subunit and inducing mRNA misreading.

Packaging

Bottomless glass bottle. Contents are inside inserted fused cone.

Other Notes

Keep container tightly closed in a dry and well-ventilated place.

pictograms

Exclamation markHealth hazard
GHS07,GHS08

signalword

Warning

Hazard Classifications

Repr. 2 - Skin Sens. 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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Targeted Delivery of Amikacin into Granuloma.
Ana Montes-Worboys, et al.
American Journal of Respiratory Cell and Molecular Biology, 182, 1546-1553 (2010)
A M Lovering et al.
The Journal of antimicrobial chemotherapy, 43(5), 719-721 (1999-06-26)
Antibiotic-free human serum was spiked with known concentrations of liposomal amikacin and assayed on the Abbott TDx System, using polarization fluoroimmuno assay (PFIA) kits from Abbott Laboratories, Oxis and Sigma. Although all three kits gave a linear response, the Abbott
Kathryn Y Burge et al.
Journal of human lactation : official journal of International Lactation Consultant Association, 35(3), 538-549 (2019-05-06)
Human milk is known to be protective against necrotizing enterocolitis, a devastating intestinal inflammatory disease affecting the preterm population. Although the pathogenesis of necrotizing enterocolitis is yet to be solidified, intestinal integrity dysfunction, bacterial invasion and/or translocation, and inflammation may
Irina Debnath et al.
Infection and immunity, 81(5), 1450-1459 (2013-02-23)
Strains of uropathogenic Escherichia coli (UPEC) are the primary cause of urinary tract infections, representing one of the most widespread and successful groups of pathogens on the planet. To colonize and persist within the urinary tract, UPEC must be able
Adi V Gundlapalli et al.
Diagnostic microbiology and infectious disease, 75(3), 256-259 (2013-01-12)
Antimicrobial shortages have made treating certain infections more difficult. A web-based survey asking about experience with antimicrobial drug shortages was distributed in 2011 to 1328 infectious diseases physician members of the Emerging Infectious Diseases Network of the Infectious Diseases Society
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