Netilmicin sulfate

Netilmicin sulfate
  • CAS No.:56391-57-2
Other grades of this product :
Netilmicin sulfate Basic information
Product Name:Netilmicin sulfate
Synonyms:D-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-β-L-arabinopyranosyl-(1→6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-α-D-glycero-hex-4-enopyranosyl-(1→4)]-2-deoxy-N1-ethyl-, sulfate (2:5);Netilmicin sulfhate;Netilmicin sulfate(2:5);Netilmicin sulphate, 1-N-Ethylsisomicin;6-diamino-2,3,4,6-tetradeoxy-alpha-d-glycero-hex-4-enopyranosyl-(1-4)-6)-o-(;netromycin;sulfate(2:5)(salt);Sulfate NetilMicin
CAS:56391-57-2
MF:C42H92N10O34S5
MW:1441.55
EINECS:260-147-3
Product Categories:Active Pharmaceutical Ingredients;Intermediates & Fine Chemicals;Pharmaceuticals
Mol File:56391-57-2.mol
Netilmicin sulfate Chemical Properties
Melting point >194°C (dec.)
Boiling point 868℃
storage temp. Inert atmosphere,2-8°C
solubility H2O: soluble10mg/mL
form Solid
color white to faint yellow
Water Solubility Soluble in water
Sensitive Light Sensitive & Hygroscopic
Stability:Hygroscopic
EPA Substance Registry SystemNetilmicin sulfate (56391-57-2)
Safety Information
Hazard Codes T,Xi
Risk Statements 61-20/21/22-60
Safety Statements 53-36/37/39-45-37/39-36-26
WGK Germany 3
RTECS WK2286000
HS Code 2941906000
MSDS Information
ProviderLanguage
SigmaAldrich English
Netilmicin sulfate Usage And Synthesis
DescriptionNetilmicin Sulfate is the sulfate salt form of netilimicin, a member of the aminoglycoside family of antibiotics. Netilmicin is derived from sisomicin, a naturally occurring aminoglycoside antibiotic produced by the fermentation of Micromonospora inyoensis. It is an active aminoglycoside antibiotic against most Gram-negative and some Gram-positive bacteria, including certain strains resistant to gentamicin.
Chemical PropertiesOff-White to Pale Beige Solid
UsesNetilmicin sulfate is used as a broad spectrum antibiotic active against most Gram-negative and some Gram-positive bacteria. It is a semisynthetic 1-N-ethyl derivative of sisomycin, an aminoglycoside antibiotic with action similar to gentamicin, but has less ear and kidney toxicity. It is used to treat gram-negative bacterial infections, gonorrhea, skin infections, and other infectious diseases. Since netilmicin sulfate cannot be absorbed from the gut, it can only be administered by injection.
Clinical UseNetilmicin sulfate, 1-N-ethylsisomicin (Netromycin), is asemisynthetic derivative prepared by reductive ethylation138of sisomicin, an aminoglycoside antibiotic obtained fromMicromonospora inyoensis. Structurally, sisomicin andnetilmicin resemble gentamicin Cla, a component of the gentamicincomplex.Against most strains of Enterobacteriaceae, P. aeruginosa,and S. aureus, sisomicin and netilmicin are comparableto gentamicin in potency. Netilmicin is active, however,against many gentamicin-resistant strains, in particularamong E. coli, Enterobacter, Klebsiella, and Citrobacterspp. A few strains of gentamicin-resistant P. aeruginosa, S.marcescens, and indole-positive Proteus spp. are also sensitiveto netilmicin. Very few gentamicin-resistant bacterialstrains are sensitive to sisomicin, however. The potency ofnetilmicin against certain gentamicin-resistant bacteria is attributedto its resistance to inactivation by bacterial enzymesthat adenylylate or phosphorylate gentamicin and sisomicin.Evidently, the introduction of a 1-ethyl group in sisomicinmarkedly decreases the affinity of these enzymes forthe molecule in a manner similar to that observed in the1-N-ε-amino-α-hydroxybutyryl amide of kanamycin A(amikacin). Netilmicin, however, is inactivated by most of the bacterial enzymes that acetylate aminoglycosides,whereas amikacin is resistant to most of these enzymes.The pharmacokinetic and toxicological properties ofnetilmicin and gentamicin appear to be similar clinically,though animal studies have indicated greater nephrotoxicityfor gentamicin.
Netilmicin sulfate Preparation Products And Raw materials
Raw materialsEthanol-->Ammonium hydroxide-->Cupric acetate monohydrate-->Copper(II) acetate

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