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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:
51101500
PubChem Substance ID:
24890796
NACRES:
NA.85

biological source

synthetic

Quality Level

200

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

Related Categories

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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Amikacin impurity I European Pharmacopoeia (EP) Reference Standard

Y0001467

Amikacin impurity I

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
M P Goren et al.
The Pediatric infectious disease journal, 8(5), 278-282 (1989-05-01)
A three-drug antibiotic regimen including vancomycin and amikacin has been recommended as effective treatment in clinical settings in which Gram-positive bacteremias are a serious problem. To determine if vancomycin potentiates the tubular proteinuria associated with amikacin therapy, we studied febrile
P Van der Auwera
The Journal of antimicrobial chemotherapy, 27 Suppl C, 63-71 (1991-05-01)
The pharmacokinetic parameters of amikacin given once daily were compared to those of amikacin given bd at different daily dosages. In adult patients, 'peak' serum concentrations (30 min after 30 min infusion) were linearly proportional to the dose given with
Amikacin.
R D Meyer
Annals of internal medicine, 95(3), 328-332 (1981-09-01)
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