Neomycin sulfate

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Neomycin sulfate
Category Antibiotics
Catalog number BBF-05845
CAS 1405-10-3
Molecular Weight 712.72
Molecular Formula C23H46N6O13.H2SO4
Purity >98%

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Description

Neomycin sulfate is an aminoglycoside antibiotic. It can be used to prevent and treat gastrointestinal infections caused by gram-negative bacteria such as Salmonella and Escherichia coli, such as Salmonella infection in pigs and chickens, E. coli disease, chicken paratyphoid, staphylococcal disease, necrotizing enteritis, fowl cholera, etc.

Specification

Related CAS 1404-04-2 (free base) 879480-48-5 (trisulfate)
Synonyms Framycetin Sulfate; Neomycin B Sulfate
Storage Store at 2-8°C
IUPAC Name (2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-[(1R,2R,3S,4R,6S)-4,6-diamino-2-[(2S,3R,4S,5R)-4-[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol;sulfuric acid
Canonical SMILES C1C(C(C(C(C1N)OC2C(C(C(C(O2)CN)O)O)N)OC3C(C(C(O3)CO)OC4C(C(C(C(O4)CN)O)O)N)O)O)N.OS(=O)(=O)O
InChI InChI=1S/C23H46N6O13.H2O4S/c24-2-7-13(32)15(34)10(28)21(37-7)40-18-6(27)1-5(26)12(31)20(18)42-23-17(36)19(9(4-30)39-23)41-22-11(29)16(35)14(33)8(3-25)38-22;1-5(2,3)4/h5-23,30-36H,1-4,24-29H2;(H2,1,2,3,4)/t5-,6+,7-,8+,9-,10-,11-,12+,13+,14+,15-,16-,17-,18-,19+,20+,21-,22?,23+;/m1./s1
InChI Key OIXVKQDWLFHVGR-VTSVPHRWSA-N

Properties

Appearance Yellowish Brown Powder
Application Anti-Bacterial Agents
Antibiotic Activity Spectrum Gram-negative bacteria
Boiling Point 1046.1°C at 760 mmHg
Melting Point >187°C (dec.)
Solubility Soluble in Water

Reference Reading

1.Comparison of 3 Topical Treatments against Ulcerative Dermatitis in Mice with a C57BL/6 Background.
Michaud CR1, Qin J2, Elkins WR1, Gozalo AS3. Comp Med. 2016;66(2):100-4.
Ulcerative dermatitis (UD) is a common condition in C57BL/6 mice and strains with this background. The etiology of UD is unclear but appears to have a genetic component associated with the C57BL/6 strain and has been reported as secondary to a variety of conditions. Treatment is unrewarding, resulting in euthanasia in many cases. In the present study we compared 3 topical treatments against spontaneous UD in mice with a C57BL/6 background. In total, 301 mice of both sexes were included in this study, and the tested treatments comprised bacitracin-neomycin sulfate-polymixin B sulfate ointment twice daily, 10% povidone-iodine ointment plus 1% silver sulfadiazine cream once daily, and 0.005% sodium hypochlorite once daily. Lesion healing was defined as complete skin reepithelialization with or without hair regrowth. Sex, age, lesion location, and type and length of treatment were analyzed by using univariate and multivariate logistic regression.
2.Structural basis for inhibition of the deadenylase activity of human CNOT6L.
Zhang Q1, Yan D1,2, Guo E1,2, Ding B1, Yang W1, Liu R1, Yamamoto T3, Bartlam M1,2. FEBS Lett. 2016 Mar 25. doi: 10.1002/1873-3468.12160. [Epub ahead of print]
Human CNOT6L/CCR4, a member of the endonuclease-exonuclease-phosphatase (EEP) family enzymes, is one of the two deadenylase enzymes in the conserved CCR4-NOT complex. Here we report inhibitor-bound crystal structures of the human CNOT6L nuclease domain in complex with the nucleotide cytidine-5'-monophosphate (CMP) and the aminoglycoside neomycin. Deadenylase activity assays show that nucleotides are effective inhibitors of both CNOT6L and CNOT7, with adenine-5'-monophosphate (AMP) more effective than other nucleotides, and that neomycin is a weak deadenylase inhibitor. Structural analysis shows that all inhibitors occupy the substrate and magnesium binding sites of CNOT6L, suggesting that inhibitors compete with both substrate and divalent magnesium ions for overlapping binding sites. This article is protected by copyright. All rights reserved.
3.Presence of antimicrobial resistance in coliform bacteria from hatching broiler eggs with emphasis on ESBL/AmpC-producing bacteria.
Mezhoud H1, Chantziaras I2,3, Iguer-Ouada M4, Moula N5,6, Garmyn A3, Martel A3, Touati A1, Smet A3, Haesebrouck F3, Boyen F3. Avian Pathol. 2016 Mar 24:1-30. [Epub ahead of print]
Antimicrobial resistance is recognized as one of the most important global health challenges. Broilers are an important reservoir of antimicrobial resistant bacteria in general and, more particularly, ESBL/AmpC-producing Enterobacteriaceae. Since contamination of 1-day-old chicks is a potential risk factor for the introduction of antimicrobial resistant Enterobacteriaceae in the broiler production chain, the presence of antimicrobial resistant coliform bacteria in broiler hatching eggs was explored in the present study. Samples from 186 hatching eggs, collected from eleven broiler breeder farms, were inoculated on MacConkey agar with or without ceftiofur and investigated for the presence of antimicrobial resistant lactose positive Enterobacteriaceae, particularly, ESBL/AmpC-producers. Escherichia coli and Enterobacter cloacae were obtained from the eggshells in ten out of eleven (10/11) sampled farms. The majority of the isolates were recovered from crushed eggshells after external decontamination suggesting that these bacteria are concealed from the disinfectants in the egg shell pores.
4.Improvement in adiposity with oligofructose is modified by antibiotics in obese rats.
Bomhof MR1, Paul HA2, Geuking MB3, Eller LK1, Reimer RA4. FASEB J. 2016 Apr 8. pii: fj.201600151R. [Epub ahead of print]
Given the intimate link between gut microbiota and host physiology, there is growing interest in understanding the mechanisms by which diet influences gut microbiota and affects human metabolic health. Using antibiotics and the prebiotic oligofructose, which has been shown to counteract excess fat mass, we explored the gut microbiota-dependent effects of oligofructose on body composition and host metabolism. Diet-induced obese male Sprague Dawley rats, fed a background high-fat/sucrose diet, were randomized to one of the following diets for 6 wk:1) high-energy control;2) 10% oligofructose;3) ampicillin;4) ampicillin + 10% oligofructose;5) ampicillin/neomycin; or6) ampicillin/neomycin + 10% oligofructose. Combining oligofructose with ampicillin treatment blunted the decrease in adiposity seen with oligofructose. Although ampicillin did not affect total bacteria, ampicillin impeded oligofructose-induced increases inBifidobacteriumandLactobacillus In contrast, the combination of ampicillin and neomycin reduced total bacteria but did not abrogate the oligofructose-induced decrease in adiposity.

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