6'''-Deamino-6'''-hydroxyneomycin B dihydrate

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Category Antibiotics
Catalog number BBF-02007
CAS 78524-73-9
Molecular Weight 615.63
Molecular Formula C23H45N5O14

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Description

6'''-Deamino-6'''-hydroxyneomycin B dihydrate is an aminoglycoside antibiotic produced by Streptomyces fradiae UC 75. It has anti-gram-positive and negative bacteria activity.

Specification

Synonyms 6'''-Deamino-6'''-hydroxyneomycin B; D-Streptamine, O-2-amino-2-deoxy-beta-L-idopyranosyl-(1-3)-O-beta-D-ribofuranosyl-(1-5)-O-(2,6-diamino-2,6-dideoxy-alpha-D-glucopyranosyl-(1-4))-2-deoxy-, (R-(E))-; D-Streptamine, O-2-amino-2-deoxy-beta-L-idopyranosyl-(1-3)-O-beta-D-ribofuranosyl-(1-5)-O-(2,6-diamino-2,6-dideoxy-alpha-D-glucopyranosyl-(1-4)-2-deoxy-, dihydrate
Storage Store at -20°C
IUPAC Name 5-amino-2-(aminomethyl)-6-[4,6-diamino-2-[4-[3-amino-4,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy-3-hydroxycyclohexyl]oxyoxane-3,4-diol
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)CO)O)O)N)O)O)N
InChI InChI=1S/C23H45N5O14/c24-2-7-13(32)15(34)10(27)21(37-7)40-18-6(26)1-5(25)12(31)20(18)42-23-17(36)19(9(4-30)39-23)41-22-11(28)16(35)14(33)8(3-29)38-22/h5-23,29-36H,1-4,24-28H2
InChI Key LJQMKWFPBUGQOO-UHFFFAOYSA-N

Properties

Appearance White Powder
Antibiotic Activity Spectrum Gram-positive bacteria; Gram-negative bacteria
Boiling Point 939.8±65.0°C at 760 mmHg
Density 1.6±0.1 g/cm3
Solubility Soluble in Water

Reference Reading

1. Evaluation of the impact of tromethamine edetate disodium dihydrate on antimicrobial susceptibility of Pseudomonas aeruginosa in biofilm in vitro
Charlotte C Pye, Ameet Singh, J Scott Weese Vet Dermatol. 2014 Apr;25(2):120-3, e33-4. doi: 10.1111/vde.12115. Epub 2014 Mar 3.
Background: Biofilm formation by Pseudomonas aeruginosa has been documented in canine otic isolates. An increase in minimal inhibitory concentration (MIC) for specific antibiotics has been noted for biofilm-embedded bacteria. Tromethamine edetate disodium dihydrate buffered to pH 8 with tromethamine hydrochloride and deionized water (Triz-EDTA(®)) has been documented to potentiate bactericidal activity when used in combination with topical antibiotics, but the impact on biofilm-embedded bacteria is unknown. Hypothesis/objectives: The objective of this study was to evaluate the impact of Triz-EDTA(®) use on in vitro antimicrobial susceptibility of biofilm-embedded P. aeruginosa. Methods: Biofilm formation was documented using a microtitre plate assay. Broth microdilution was used to assess the MIC of neomycin, polymyxin B, enrofloxacin and gentamicin for the biofilm-embedded bacteria. The microtitre plate assay was again used to assess the MIC of neomycin, polymyxin B, enrofloxacin and gentamicin for biofilm-embedded bacteria with added Triz-EDTA(®). Results: Thirty-one isolates from dogs with otitis were tested. Addition of Triz-EDTA(®) significantly reduced MICs for neomycin (P < 0.003) and gentamicin (P < 0.02) but not for polymyxin B (P = 0.3). Enrofloxacin MICs increased in the presence of Triz-EDTA (P < 0.036). Conclusions and clinical importance: Triz-EDTA(®) may be a useful adjunctive treatment for chronic cases of Pseudomonas otitis where biofilms may have developed, if gentamicin or neomycin is to be used as a topical treatment. In vivo study is required to confirm this effect.

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