119-04-0

Basic information

• Product Name: NEOMYCIN B
• Synonyms: NEOMYCIN STANDARD;NEOMYCIN B;actilin;actiline;antibiotique;enterfram;framycetin;framygen
• CAS NO: 119-04-0
• Molecular Formula: C₂₃H₄₆N₆O₁₃
• Molecular Weight: 614.64
• EINECS: 204-292-2
• Product Categories: L - ZAlphabetic;NA - NIMore...Close...;AminoglycosidesAntibiotics;Antibacterial;Antibiotics;Antibiotics A to;Antibiotics by Application;Antibiotics N-SAntibiotics;Antineoplastic and Immunosuppressive AntibioticsAntibiotics;Chemical Structure Class;Genetic Marker SelectionAntibiotics;Interferes with Protein SynthesisSpectrum of Activity;Mechanism of Action;N
• Mol File: 119-04-0.mol
• Article Data: 4

Chemical Properties

• Boiling Point: 658.4°C (rough estimate)
• Flash Point: 514.5 °C
• Appearance: /liquid
• Density: 1.3548 (rough estimate)
• Refractive Index: 1.6000 (estimate)
• Storage Temp.: 2-8°C
• Solubility: Aqueous Acid (Slightly), Water (Slightly)
• PKA: 12.93±0.70(Predicted)
• Stability: Hygroscopic
• Merck: 13,6482
• CAS DataBase Reference: NEOMYCIN B(CAS DataBase Reference)
• NIST Chemistry Reference: NEOMYCIN B(119-04-0)
• EPA Substance Registry System: NEOMYCIN B(119-04-0)

Safety Data

• Hazard Codes: Xn
• Statements: 42/43-63-36/37/38
• Safety Statements: 26-36/37/39-45-36/37-23
• WGK Germany: 2
• F: 8
• Hazardous Substances Data: 119-04-0(Hazardous Substances Data)

Usage

Uses

Neomycin C is an aminoglycoside antibiotic found in many topical medications. Neomycin has been used as a preventive measure for hepatic encephalopathy and hypercholesterolemia.

Definition

ChEBI: A tetracyclic antibacterial agent derived from neomycin, being a glycoside ester of neamine and neobiosamine B.

General Description

Chemical structure: aminoglycoside

Biochem/physiol Actions

Neomycin is an aminoglycoside antibiotic, produced by Streptomyces containing a minimum of 85% neomycin B. It acts as a selection agent for prokaryotic cells transformed using the neo selectable marker gene. Neomycin trisulfate is used to study the cytototoxic side effects of antibiotics, platelet-derived growth factor responses in certain fibroblasts and extraction of nuclear phosphatidylinositol 4,5-bisphosphate-interacting proteins. This product is recommended for use in cell culture applications at 5 mL/L.Mode of action: This product acts by binding to the 30S and 50S subunits, causing miscoding and inhibiting initiation and elongation during protein synthesis. Neomycin also blocks voltage-sensitive Ca2+ channels without affecting the Na+/Ca2+ antiporter in neurons.Antimicrobial spectrum: Neomycin acts against both gram-positive and gram-negative bacteria

InChI:InChI=1/C23H46N6O13/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/h5-23,30-36H,1-4,24-29H2/t5-,6+,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1

Upstream product

• 25389-98-4 neomycin B sulphate 
• 66-86-4 neomycin C 

Downstream Products

• 1064665-43-5 γ-L-Glu-[(S)-4-amino-2-hydroxybutyryl]-neomycin B 
• 1245566-44-2 C₂₆H₅₀N₆O₁₄ 
• 1245566-45-3 C₂₆H₅₀N₆O₁₄ 

Related news

Efficient synthesis of NEOMYCIN B (cas 119-04-0) related aminoglycosides09/03/2019

Aminoglycosides 6′-hydroxyl-ribostamycin and 5-(α-neobiosamine)-2-deoxystreptamine were chemically synthesized. These compounds will be used as standards to compare RNA binding affinity and specificity with neomycin B.detailed

Paromomycin and NEOMYCIN B (cas 119-04-0) derived cationic lipids: Synthesis and transfection studies08/31/2019

Cationic lipid-based nonviral gene delivery is an attractive approach for therapeutic gene transfer. Basically, gene transfection can be achieved by using synthetic vectors that compact DNA, forming cationic lipoplexes which can interact with the cell plasma membrane by electrostatic interaction...detailed

Synthesis and antibacterial activity of amphiphilic lysine-ligated NEOMYCIN B (cas 119-04-0) conjugates08/30/2019

Amphiphilic lysine-ligated neomycin B building blocks were prepared by reductive amination of a protected C5″-modified neomycin B-based aldehyde and side chain-unprotected lysine or lysine-containing peptides. It was demonstrated that a suitably protected lysine-ligated neomycin B conjugate (Ne...detailed

Relevant articles and documents

Characterization of a radical S-adenosyl-l-methionine epimerase, NeoN, in the last step of neomycin B biosynthesis

The last step of neomycin biosynthesis is the epimerization at C-5 of neomycin C to give neomycin B. A candidate enzyme responsible for the epimerization was a putative radical S-adenosyl-l-methionine (SAM) enzyme, NeoN, which is uniquely encoded in the n

TOTAL SYNTHESIS OF NEOMYCIN B

Total synthesis of neomycin B, a pseudo-tetrasaccharide aminoglycoside antibiotic, has been achieved through two key glycosylation reactions.Coupling of 3-O-acetyl-2,6-diazido-4-O-benzyl-2,6-dideoxy-L-idopyranosyl chloride with 5-O-benzoyl-1,2-O-isopropylidene-α-D-ribofuranose under modified Koenigs-Knorr conditions gave 70percent of the desired β-L disaccharide (3) and corresponding to neobiosamine in structure.After deisopropylidenation of 3 and acetylation, 1,2-di-O-acetyl-3-O-(3-O-acetyl-2,6-diazido-4-O-benzyl-2,6-dideoxy-β-L-idopyranosyl)-5-O-benzoyl-D-ribofuranose was coupled to HO-5 of 3,2',6'-tri-N-(benzyloxycarbonyl)-1-N:6-O-carbonyl-3',4'-di-O-(o-methoxybenzoyl)neamine, using trimethylsilyl trifluoromethanesulfonate, to give 60percent of the pseudo-tetrasaccharide 19 possessing the framework and masked functionality corresponding to neomycin B.Deblocking and reduction of the azido groups then gave neomycin B.