netilmicin

Also known as 1-N-ethylsisomicin, netilmycin

Netilmicin ('1-N-ethylsisomicin') is a semisynthetic aminoglycoside antibiotic, and a derivative of sisomicin, produced by Micromonospora inyoensis. Aminoglycoside antibiotics have the ability to kill a wide variety of bacteria. Netilmicin is not absorbed from the gut and is therefore only given by injection or infusion. It is only used in the treatment of serious infections particularly those resistant to gentamicin.

Chemical data

Formula: C21H41N5O7
Molecular weight: 475.6 g/mol
IUPAC name: (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-(methylamino)oxane-3,5-diol
SMILES: CCN[C@@H]1C[C@@H]([C@H]([C@@H]([C@H]1O[C@@H]2[C@@H]([C@H]([C@@](CO2)(C)O)NC)O)O)O[C@@H]3[C@@H](CC=C(O3)CN)N)N
InChIKey: CIDUJQMULVCIBT-MQDUPKMGSA-N
XLogP: -4.2
Polar surface area: 200 Å²
H-bond donors: 8
H-bond acceptors: 12
Formal charge: 0

via PubChem

Research

2,041 papers

Netilmicin reassessed.Drug and therapeutics bulletin · 1989
Netilmicin (Netromycin, Schering-Plough).Drug intelligence & clinical pharmacy · 1983
[Netilmicin].Antibiotiki i khimioterapiia = Antibiotics and chemoterapy [sic] · 1993
[Netilmicin preparation].The Japanese journal of antibiotics · 1982
Netilmicin: a review of toxicity in laboratory animals.The Journal of international medical research · 1978

via PubMed

Wikidata facts

Mass: 475.3005986519999

Show 4 more facts

chemical formula: C₂₁H₄₁N₅O₇
canonical SMILES: CCNC1CC(C(C(C1OC2C(C(C(CO2)(C)O)NC)O)O)OC3C(CC=C(O3)CN)N)N
isomeric SMILES: CCN[C@@H]1C[C@H](N)[C@@H](O[C@H]2OC(CN)=CC[C@H]2N)[C@H](O)[C@H]1O[C@H]3OC[C@](C)(O)[C@H](NC)[C@H]3O
NCI Thesaurus ID: C66236

Sources (4)

via Wikidata · CC0

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Article

3 sections

Contents

Comparison with drugs
References
Further reading

{{Drugbox | Verifiedfields = changed | verifiedrevid = 462259703 | IUPAC_name = (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-(methylamino)oxane-3,5-diol | image = Netilmicin structure.svg | image_class = skin-invert-image