Nebramycin

Base Information

• Chemical Name: Nebramycin
• CAS No.: 32986-56-4
• Molecular Formula: C18H37N5O9
• Molecular Weight: 467.52
• Hs Code.: 2941.90
• NSC Number: 180514
• DSSTox Substance ID: DTXSID90860478
• Nikkaji Number: J27.404F
• NCI Thesaurus Code: C174761
• ChEMBL ID: CHEMBL14440
• Mol file: 32986-56-4.mol

Synonyms:Nebramycin

Chemical Property of Nebramycin

Chemical Property:

• Appearance/Colour: White powder
• Vapor Pressure: 2.18E-25mmHg at 25°C
• Melting Point: 178 °C
• Refractive Index: 143 ° (C=4, H2O)
• Boiling Point: 775.436 °C at 760 mmHg
• PKA: pKa 6.7 (Uncertain);8.3 (Uncertain);9.9 (Uncertain)
• Flash Point: 422.8 °C
• PSA: 268.17000
• Density: 1.52 g/cm³
• LogP: -2.79430
• Storage Temp.: 2-8°C
• Solubility.: H2O: 50 mg/mL, clear, faintly yellow
• Water Solubility.: Soluble in water
• XLogP3: -6.2
• Hydrogen Bond Donor Count: 10
• Hydrogen Bond Acceptor Count: 14
• Rotatable Bond Count: 6
• Exact Mass: 467.25912777
• Heavy Atom Count: 32
• Complexity: 609

Purity/Quality:

99%min ^*data from raw suppliers

Tobramycin ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/37/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(C(C(C(C1N)OC2C(C(C(C(O2)CO)O)N)O)O)OC3C(CC(C(O3)CN)O)N)N
• Description: Tobramycin is one component (factor 6) of a mixture produced by fermentation of Streptomyces tenebrari us. Lacking the C-3′ hydroxyl group, it is not a substrate for APH(3′)-1 and APH(3′)-II and so has an intrinsically broader spectrum than kanamycin. It is a substrate, however, for adenylation at C-2′ by ANT (2′) and acetylation at C-3 by AAC(3)-I and AAC(3)-II and at C-2′ by AAC(2′).
• Uses: Single factor antibiotic comprising about 10% of nebramycin, the aminoglycosidic antibiotic complex produced by Streptomyces tenebrarius. Antibacterial Antihypertensive Tobramycin is an aminoglycoside antibiotic.
• Indications: Tobramycin is highly active with respect to Gram-negative microorganisms (blue-pus bacillus and gastric bacilli, rabbit fever, serratia, providencia, enterobacteria, proteus, salmonella, shigella), as well as Gram-positive microorganisms (staphylococci, including those resistant to penicillin and some cephalosporins), and a few strains of streptococci.It is used for severe bacterial infections: peritonitis, sepsis, meningitis, osteomyelitis, endocarditis, pneumonia, pleural empyema, pulmonary abscess, purulent skin infections and soft tissue infections, and infections of the urinary tract caused by microorganisms that are sensitive to the drug. Synonyms of this drug are nebicine, obracine, and others.
• Therapeutic Function: Antibiotic
• Clinical Use: Severe infections caused by susceptible micro-organisms Ps. aeruginosa infections, including chronic pulmonary infections in cystic fibrosis (administration by injection or nebulizer) For practical purposes use is identical to that of gentamicin, except possibly for Pseudomonas infection, where it has somewhat greater activity against gentamicin-susceptible and some gentamicin-resistant strains. Its value as a substitute for gentamicin in the speculative treatment of severe undiagnosed infection is offset by its lower activity against other organisms that may be implicated. It has been used extensively to treat Ps. aeruginosa infections in patients with cystic fibrosis.
• Drug interactions: Potentially hazardous interactions with other drugs Antibacterials: increased risk of nephrotoxicity with colistimethate or polymyxins and possibly cephalosporins; increased risk of ototoxicity and nephrotoxicity with capreomycin or vancomycin. Ciclosporin: increased risk of nephrotoxicity. Cytotoxics: increased risk of nephrotoxicity and possibly of ototoxicity with platinum compounds. Diuretics: increased risk of ototoxicity with loop diuretics. Muscle relaxants: enhanced effect of nondepolarising muscle relaxants and suxamethonium. Parasympathomimetics: antagonism of effect of neostigmine and pyridostigmine. Tacrolimus: increased risk of nephrotoxicity.

Technology Process of Nebramycin

There total 3 articles about Nebramycin which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

fosfomycin (23155-02-4) → tobramycin (32986-56-4)

Guidance literature:

Reference yield:

tobramycin sulfate → tobramycin (32986-56-4)

Guidance literature:

tobramycin sulfate;

With trifluoroacetic acid; In water;

DOI:10.1002/cmdc.201200150

Reference yield:

→ tobramycin (32986-56-4)

Guidance literature:

DOI:10.1246/bcsj.49.3649 DOI:10.7164/antibiotics.26.403

upstream raw materials:

fosfomycin

Downstream raw materials:

di-tert-butyl ((1S,3R,4S,5S,6R)-4-(((2S,3R,4S,5S,6R)-4-((tert-butoxycarbonyl)amino)-3,5-dihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)oxy)-6-(((2R,3R,5S,6R)-3-((tert-butoxycarbonyl)amino)-6-(((tert-butoxycarbonyl)methyl)-5-hydroxytetrahydro-2H-pyran-2-yl)oxy)-5-hydroxycyclohexane-1,3-diyl)dicarbamate)

1,3,2',6',3''-pentakis(N-benzyloxycarbonyl)-3'-deoxykanamycin B

O-3-azido-3-deoxy-α-D-glucopyranosyl-(1→6)-O-[2,6-diazido-2,3,6-trideoxy-α-D-ribo-hexopyranosyl-(1→4)]-1,3-diazido-1,2,3-trideoxy-D-myo-inositol

C₅₀H₈₃N₁₁O₁₉

Refernces

• 1、 Fair, Richard J.,Hensler, Mary E.,Thienphrapa, Wdee,Dam, Quang N.,Nizet, Victor,Tor, Yitzhak. "Selectively Guanidinylated Aminoglycosides as Antibiotics". experimental part. p. 1237 - 1244. Retrieved 2012/08/29.
• 2、 -. "Site-specific aminoglycoside derivatives and their use in immunodiagnostic assays". . . Retrieved 2008/06/13.