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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:
6172633
EC Number:
254-648-6
MDL number:
MFCD00167475
UNSPSC Code:
51281632
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

Health hazardExclamation mark
GHS08,GHS07

Signal Word

Warning

Hazard Statements

H317,H361fd

Hazard Classifications

Repr. 2 - Skin Sens. 1

Storage Class Code

11 - Combustible Solids

WGK

WGK 2

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Personal Protective Equipment

dust mask type N95 (US), Eyeshields, Gloves

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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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
Targeted Delivery of Amikacin into Granuloma.
Ana Montes-Worboys, et al.
American Journal of Respiratory Cell and Molecular Biology, 182, 1546-1553 (2010)
Sabine Ladrech et al.
The European journal of neuroscience, 38(6), 2962-2972 (2013-07-10)
To examine whether an inflammatory process occurs in the amikacin-poisoned cochlea, we investigated the presence of the cytokines tumour necrosis factor-α (TNF-α), interleukin (IL)-1β, and IL-10. No TNF-α, IL-1β or IL-10 was detected in the cochlear perilymph after the loss
Kenneth S Chen et al.
Pediatric blood & cancer, 60(11), 1772-1777 (2013-06-22)
Children undergoing cancer therapy often receive aminoglycosides to treat febrile neutropenia or gram-negative infections. The magnitude of the risk of developing aminoglycoside-induced ototoxicity and the dose threshold at which that risk significantly increases are unknown. Eligible cancer patients received the
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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