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A3650

Sigma-Aldrich

Amikacin hydrate

aminoglycoside antibiotic

Synonym(s):

N1-[(S)-4-Amino-2-hydroxybutyryl]kanamycin A

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About This Item

Empirical Formula (Hill Notation):
C22H43N5O13 · xH2O
CAS Number:
1257517-67-1
Molecular Weight:
585.60 (anhydrous basis)
Beilstein/REAXYS Number:
1445422
EC Number:
253-538-5
MDL number:
MFCD11045969
UNSPSC Code:
51281632
PubChem Substance ID:
24890796
NACRES:
NA.85

biological source

synthetic

form

powder

color

white to almost white

antibiotic activity spectrum

Gram-negative bacteria
mycobacteria

mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

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.H2O/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);1H2/t6-,7+,8-,9+,10+,11-,12+,13+,14+,15-,16+,17-,18+,19-,21+,22+;/m0./s1

InChI key

DTSOZYYWEZJFSS-XTHCGPPUSA-N

General description

Chemical structure: aminoglycoside

Application

Amikacin hydrate is used in antimicrobial susceptibility studies of organisms such as Mycobacterium tuberculosis and Ehrlichia phagocytophila.

Biochem/physiol Actions

Amikacin inhibits bacterial protein synthesis by binding to the 30S ribosome subunit and inducing mRNA misreading. It interferes with the translocation of tRNA from the A-site to the P-site.

Packaging

5G

Other Notes

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

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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H W Horowitz et al.
Antimicrobial agents and chemotherapy, 45(3), 786-788 (2001-02-22)
Human granulocytic ehrlichiosis is a recently described disease caused by an obligate intracellular gram-negative organism recently named Ehrlichia phagocytophila. To expand our knowledge of the susceptibility of E. phagocytophila, we tested six New York State isolates for susceptibility to 12
G J Alangaden et al.
Antimicrobial agents and chemotherapy, 42(5), 1295-1297 (1998-05-21)
An A1400G mutation of the rrs gene was identified in Mycobacterium tuberculosis (MTB) strain ATCC 35827 and in 13 MTB clinical isolates resistant to amikacin-kanamycin (MICs, >128 microg/ml). High-level cross-resistance may result from such a mutation since MTB has a
Meenu Sharma et al.
Journal of clinical microbiology, 49(12), 4112-4116 (2011-10-15)
The purpose of this study was to establish a standardized protocol for second-line antimicrobial susceptibility testing of Mycobacterium tuberculosis using the Bactec MGIT 960 system in Canadian laboratories. Four Canadian public health laboratories compared the susceptibility testing results of 9
Sophia B Georghiou et al.
PloS one, 7(3), e33275-e33275 (2012-04-06)
Rapid molecular diagnostics for detecting multidrug-resistant and extensively drug-resistant tuberculosis (M/XDR-TB) primarily identify mutations in Mycobacterium tuberculosis (Mtb) genes associated with drug resistance. Their accuracy, however, is dependent largely on the strength of the association between a specific mutation and
Hessel Van der Weide et al.
Antibiotics (Basel, Switzerland), 9(3) (2020-03-07)
Background: Recent scientific reports on the use of high dose tigecycline monotherapy as a "drug of last resort" warrant further research into the use of this regimen for the treatment of severe multidrug-resistant, Gram-negative bacterial infections. In the current study
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