| Identification | Back Directory | [Name]
Netilmicin sulfate | [CAS]
56391-57-2 | [Synonyms]
Netililn
Zetamicin
netromycin
Netromicine
sulfate(2:5)(salt)
1-N-ETHYLSISOMICIN
NETILMICIN SULFATE
NETILMYCIN SULFATE
Netromycin sulfate
Sulfate NetilMicin
Netilmicin sulfhate
NETILMYCIN SULPHATE
Netilmicin Sulfate Usp
NETILMICIN SULFATE SALT
Netilmicin sulfate(2:5)
NETILMICIN SULFATE USP EP
1-N-ETHYLSISOMICIN SULFATE
Netilmicin Sulfate (500 mg)
Netilmicin sulphate, 1-N-Ethylsisomicin
Netilmicin sulfate salt,1-N-Ethylsisomicin
6-diamino-2,3,4,6-tetradeoxy-alpha-d-glycero-hex-4-enopyranosyl-(1-4)-6)-o-(
O-3-Deoxy-4-C-methyl-3-(methylamino)-b-l-arabinopyranosyl-(1-6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-a-D-glycero-hex-4-enopyranosyl-(1-4)]-2-deoxy-Nethyl-D-streptamine
O-3-Deoxy-4-C-methyl-3-(methylamino)--l-arabinopyranosyl-(1-6)-O-[2,6-diamino-2,3,4,6-tetradeoxy-a-D-glycero-hex-4-enopyranosyl-(1-4)]-2-deoxy-N’-ethyl-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-N'-ethyl-D-streptaMine
4-O-[[3α-Amino-6-(aminomethyl)-3,4-dihydro-2H-pyran]-2α-yl]-6-O-[4-C-methyl-3-(methylamino)-3-deoxy-β-L-arabinopyranosyl]-N1-ethyl-2-deoxy-D-streptamine·2.5sulfuric acid
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)
O-3-Deoxy-4-C-methyl-3-methylamino-ss-L-arabinopyranosyl-(1->6)-O-[2, 6-diamino-4,5-dehydro-2,3,4,6-tetradeoxy-a-D-glycero-hexopyranosyl-(1->4)]-2-deoxy-1-N-ethyl-D-streptamine hemiheptasulfate
D-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-b-L-arabinopyranosyl-(16)-O-[2,6-diamino-2,3,4,6-tetradeoxy-a-D-glycero-hex-4-enopyranosyl-(14)]-2-deoxy-N1-ethyl-, sulfate (2:5) (salt) (9CI)
O-3-DEOXY-4-C-METHYL-3-METHYLAMINO-BETA-L-ARABINOPYRANOSYL-(1->6)-O-[2, 6-DIAMINO-4,5-DEHYDRO-2,3,4,6-TETRADEOXY-A-D-GLYCERO-HEXOPYRANOSYL-(1->4)]-2-DEOXY-1-N-ETHYL-D-STREPTAMINE HEMIHEPTASULFATE
(2r,3r,4r,5r)-2-[(1s,2s,3r,4s,6r)-4-amino-3-[[(2s,3r)-3-amino-6-(aminomethyl)-3,4-dihydro-2h-pyran-2-yl]oxy]-6-ethylamino-2-hydroxycyclohexyl]oxy-5-methyl-4-methylaminooxane-3,5-diol sulfate (2:5)
Netilmicin sulfate (2R,3R,4R,5R)-2-[(1S,2S,3R,4S,6R)-4-Amino-3-[[(2S,3R)-3-amino-6-(aminomethyl)-3,4-dihydro-2H-pyran-2-yl]oxy]-6-ethylamino-2-hydroxycyclohexyl]oxy-5-methyl-4-methylaminooxane-3,5-diol sulfate (2:5) | [EINECS(EC#)]
260-147-3 | [Molecular Formula]
C42H92N10O34S5 | [MDL Number]
MFCD01311715 | [MOL File]
56391-57-2.mol | [Molecular Weight]
1441.55 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-White to Pale Beige Solid | [Uses]
antibiotics | [Uses]
Semisynthetic aminoglycoside antibiotic, related to sisomicin. Antibacterial. | [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. | [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. |
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