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 System

Netilmicin 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

• Language:English Provider:SigmaAldrich

Netilmicin sulfate Usage And Synthesis

Description

Netilmicin 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 Properties

Off-White to Pale Beige Solid

Uses

Netilmicin 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.

Definition

ChEBI: Netilmicin sulfate is an aminoglycoside sulfate salt. It is functionally related to a netilmycin.

Application

Netilmicin was synthesized by ScheringPlough Co. in 1976. The ethyl moiety was introduced at the 1-amino group of sisomicin. Its design was based on an understanding of the biochemical mechanisms of bacterial resistance to the gentamicin – sisomicin antibiotic group. The modification at the 1-amino group is known to prevent adenylation at the 2- hydroxyl group and acetylation at the 3-amino group, and to deter acetylation at the 6 -amino residue. Netilmicin shows almost the same activity against a variety of gram-positive and gram-negative bacteria as sisomicin and strong activity against gentamicin – sisomicin-resistant bacteria. It is now under study for evaluation of its clinical efficacy and safety.

Clinical Use

Netilmicin 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 (56391-57-2)Related Product Information

• Copper(II) sulfate
• Sisomicin
• Aluminum sulfate
• 3-Aminophenol
• Glycine
• Barium sulfate
• Sodium thiosulfate
• Zinc sulfate heptahydrate
• ALTRENOGEST
• Ammonium sulfate
• Tris(hydroxymethyl)aminomethane
• Ferrous sulfate heptahydrate
• Vanadyl sulfate
• NETILMICIN
• 6-Aminocaproic acid
• Magnesium sulfate heptahydrate
• Sodium sulfate
• sulfate