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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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R Doug Wagner et al.
Antimicrobial agents and chemotherapy, 52(4), 1230-1237 (2008-01-30)
A bioassay was developed to measure the minimum concentration of an antimicrobial drug that disrupts the colonization resistance mediated by model human intestinal microbiota against Salmonella invasion of Caco-2 intestinal cells. The bioassay was used to measure the minimum disruptive
Vibeke F Jensen et al.
The Journal of antimicrobial chemotherapy, 58(1), 101-107 (2006-05-20)
Resistance towards the veterinary drug apramycin can be caused by the aac(3)-IV gene, which also confers resistance towards the important human antibiotic gentamicin. The objectives of this study were to investigate the temporal occurrence and the genetic background of apramycin
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
T-W Hahn et al.
Journal of animal science, 84(6), 1422-1428 (2006-05-16)
Two experiments were conducted to evaluate the efficacy of beta-glucan on growth performance, nutrient digestibility, and immunity in weanling pigs. In Exp. 1, 210 weanling pigs (6.38 +/- 0.92 kg of BW) were fed dietary beta-glucan (0, 0.01, 0.02, 0.03
C M Yates et al.
The Journal of antimicrobial chemotherapy, 54(2), 534-537 (2004-07-03)
The aminoglycoside apramycin has been used extensively in animal husbandry in the UK since 1978. This study aimed to determine both whether calves that had never been treated with aminoglycoside antibiotics harboured apramycin-resistant (apr(R)) commensal Escherichia coli, and the mode
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