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Merck

A3650

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)
UNSPSC Code:
51281632
NACRES:
NA.85
PubChem Substance ID:
24890796
EC Number:
253-538-5
Beilstein/REAXYS Number:
1445422
MDL number:
MFCD11045969

Product Name

Amikacin hydrate, aminoglycoside antibiotic

InChI key

DTSOZYYWEZJFSS-XTHCGPPUSA-N

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

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

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

Quality Level

200

Related Categories

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.

General description

Chemical structure: aminoglycoside

Other Notes

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

Packaging

5G

Storage Class

11 - Combustible Solids

wgk

WGK 2

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

Eyeshields, Gloves, type N95 (US)

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Certificates of Analysis (COA)

Lot/Batch Number
0000502564
0000502564
0000501993
0000501992
0000501990

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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
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
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
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
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
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