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| | 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 System | Netilmicin sulfate (56391-57-2) |
| | 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. | | 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 Preparation Products And Raw materials |
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