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A2024

Sigma-Aldrich

Apramycin sulfate salt

Synonym(s):

Nebramycin II

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About This Item

Empirical Formula (Hill Notation):
C21H41N5O11 · xH2SO4
CAS Number:
65710-07-8
Molecular Weight:
539.58 (free base basis)
EC Number:
265-890-7
MDL number:
MFCD06200257
UNSPSC Code:
51281633
PubChem Substance ID:
329770728
NACRES:
NA.85

biological source

Streptomyces tenebrarius

form

powder

color

white to brown

antibiotic activity spectrum

Gram-negative bacteria

Mode of action

protein synthesis | interferes

storage temp.

2-8°C

SMILES string

OS(O)(=O)=O.CN[C@H]1[C@@H](O)[C@H]2O[C@H](O[C@@H]3[C@@H](N)C[C@@H](N)[C@H](O)[C@H]3O)[C@H](N)C[C@@H]2O[C@@H]1O[C@H]4O[C@H](CO)[C@@H](N)[C@H](O)[C@H]4O

InChI

1S/C21H41N5O11.H2O4S/c1-26-11-14(30)18-8(33-20(11)37-21-16(32)13(29)10(25)9(4-27)34-21)3-7(24)19(36-18)35-17-6(23)2-5(22)12(28)15(17)31;1-5(2,3)4/h5-21,26-32H,2-4,22-25H2,1H3;(H2,1,2,3,4)/t5-,6+,7-,8+,9-,10-,11+,12+,13+,14-,15-,16-,17-,18+,19+,20-,21-;/m1./s1

InChI key

WGLYHYWDYPSNPF-RQFIXDHTSA-N

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General description

Chemical structure: aminoglycoside

Application

Apramycin is used to study antibiotic resistance as well as protein synthesis translocation-step inhibition in bacteria and prokaryotes.

Biochem/physiol Actions

Apramycin inhibits protein synthesis by blocking translocation. It is also able to bind to the eukaryotic decoding site. At low concentrations it inhibits elongation and induces misreading of mRNA during protein synthesis.

Packaging

1G, 5G

Other Notes

Keep container tightly closed in a dry and well-ventilated place. Keep in a dry place.Storage class (TRGS 510): Non-combustible, acute toxic Cat.3 / toxic hazardous materials or hazardous materials causing chronic effects.

Pictograms

Health hazard
GHS08

Signal Word

Danger

Hazard Statements

H360FD

Hazard Classifications

Repr. 1B

Storage Class Code

6.1C - Combustible acute toxic Cat.3 / toxic compounds or compounds which causing chronic effects

WGK

WGK 3

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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G J Gunn et al.
Veterinary journal (London, England : 1997), 175(3), 416-418 (2007-04-24)
A random survey of farms in the Highlands and Islands of Scotland provides estimated of the prevalence of calves, finishers and cows carrying ampicillin, apramycin and/or nalidixic acid resistant Escherichia coli. While the survey provides information on the geographical variation
Paulo Martins da Costa et al.
Veterinary microbiology, 139(3-4), 284-292 (2009-07-08)
The present study investigates, under field conditions, the influence of antimicrobial administration on prevalence and patterns of antimicrobial resistance among Escherichia coli and Enterococcus spp. isolated from growing broilers. For this purpose, a group of 16,000 commercial broiler chickens was
C M Yates et al.
Biology letters, 2(3), 463-465 (2006-12-07)
The study of antibiotic resistance has in the past focused on organisms that are pathogenic to humans or animals. However, the development of resistance in commensal organisms is of concern because of possible transfer of resistance genes to zoonotic pathogens.
D Balenci et al.
Dalton transactions (Cambridge, England : 2003), (7)(7), 1123-1130 (2009-03-27)
The interaction of apramycin with copper at different pH values was investigated by potentiometric titrations and EPR, UV-vis and CD spectroscopic techniques. The Cu(II)-apramycin complex prevailing at pH 6.5 was further characterized by NMR spectroscopy. Metal-proton distances derived from paramagnetic
Min-Jung Choi et al.
Foodborne pathogens and disease, 8(1), 119-123 (2011-01-11)
A total of 1921 Escherichia coli isolated from healthy animals (501 from cattle, 832 from pigs, and 588 from chickens) and 237 isolates from diseased pigs were tested to determine the prevalence of apramycin and gentamicin resistance in Korea during
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