Netilmicin

HCID 441306CAS 56391-56-1

기본 정보

표준 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]1OC[C@](C)(O)[C@H](NC)[C@H]1O
InChIKey
CIDUJQMULVCIBT-MQDUPKMGSA-N
분자식
C21H41N5O7
평균 분자량
475.6 g/mol
단동위원소 질량
475.30059865

개요

Netilmicin Sulfate can cause developmental toxicity according to state or federal government labeling requirements.

이름 및 식별자

우선 이름
Netilmicin
IUPAC
(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

이름 및 동의어

netilmicin1-N-Ethylsisomicin56391-56-1NetilmicinaNetilmicineNetilmicinumNetilynVectacinNetiraNetillin1-N-AethylsisomicinNettacin
이름 더 보기
4O5J85GJJBNSC-759586(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-diolDTXSID1048542(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-hydroxy-cyclohexoxy]-5-methyl-4-(methylamino)tetrahydropyran-3,5-diolD-Streptamine, O-3-deoxy-4-C-methyl-3-(methylamino)-beta-L-arabinopyranosyl-(1-6)-O-(2,6-diamino-2,3,4,6-tetradeoxy-alpha-D-glycero-hex-4-enopyranosyl-(1-4))-2-deoxy-N1-ethyl-(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-hydroxy-cyclohexoxy)-5-methyl-4-(methylamino)tetrahydropyran-3,5-diol(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

데이터베이스 식별자

CAS
56391-56-1
PubChem CID
441306
DTXSID
DTXSID1048542
ChEMBL
CHEMBL1572
UNII
4O5J85GJJB
EC Number
260-146-8
Nikkaji
J236.025J

물성

구조 계산 물성

XLogP
-4.2
극성 표면적
200 Ų
수소 결합 공여자 수
8
수소 결합 수용자 수
12
회전 가능 결합 수
8
무거운 원자 수
33

실험 및 물리화학적 성질

Drugs · 3건

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Antibiotics

Pharmaceuticals -> Listed in ZINC15

Human DrugsOphthalmological preparations > Anti-infective agents
DecompositionWhen heated to decomposition it emits acrid smoke and irritating fumes.
Optical RotationSpecific optical rotation: +164 deg at 26 °C/D (3 in water)
Collision Cross Section216.82 Ų [M+Na]+ [CCS Type: TW; Method: calibrated with polyalanine and drug standards]

안전 및 규제

유해성 정보

FDA Requirements · 1건

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

안전 및 보호

Storage ConditionsCommercially available netilmicin sulfate injection should be stored at 2 - 30 °C. /Netilmicin sulfate/
Disposal Methods · 1건

SRP: At the time of review, criteria for land treatment or burial (sanitary landfill) disposal practices are subject to significant revision. Prior to implementing land disposal of waste residue (including waste sludge), consult with environmental regulatory agencies for guidance on acceptable disposal practices.

독성 정보

Interactions · 5건

Concurrent and/or sequential use of 2 or more aminoglycosides by any route or concurrent use of capreomycin with aminoglycosides should be avoided since the potential for ototoxicity, nephrotoxicity, and neuromuscular blockade may be increased; hearing loss may occur and may progress to deafness even after discontinuation of the drug; loss of hearing may be reversible, but usually is permanent; neuromuscular blockade may result in skeletal muscle weakness and respiratory depression or paralysis (apnea). Also, concurrent use of 2 or more aminoglycosides may result in reduced bacterial uptake of each one since the medications compete for the same uptake mechanism. /Aminoglycosides/

Concurrent use of medications with neuromuscular blocking activity, including halogenated hydrocarbon inhalation anesthetics, opioid analgesics, and massive transfusions with citrate anticoagulated blood, with aminoglycosides should be carefully monitored since neuromuscular blockade may be enhanced, resulting in skeletal muscle weakness and respiratory depression or paralysis (apnea); caution is recommended when these medications and aminoglycosides are used concurrently during surgery or in the postoperative period, especially if there is a possibility of incomplete reversal of neuromuscular blockade postoperatively; treatment with anticholinesterase agents or calcium salts may help reverse the blockade. /Aminoglycosides/

Vancomycin and aminoglycosides must often be administered concurrently in the prophylaxis of bacterial endocarditis, in the treatment of endocarditis caused by streptococci and Corynebacteria species, in the treatment of resistant staphylococcal infections, or in penicillin-allergic patients; appropriate monitoring will help to reduce the risk of nephrotoxicity or ototoxicity; renal function determinations, serum aminoglycoside and vancomycin concentrations, dosage reductions, and/or dosage interval adjustments, or alternate antibacterials, may be required. /Aminoglycosides/

Concurrent or sequential use of these medications /nephrotoxic or ototoxic medications/ with aminoglycosides may increase the potential for ototoxicity or nephrotoxicity; hearing loss may occur and may progress to deafness even after discontinuation of the drug and may be reversible, but usually is permanent; serial audiometric function determinations may be required with concurrent or sequential use of other ototoxic antibacterials; renal function determinations may be required. /Aminoglycosides/

For more Interactions (Complete) data for NETILMICIN (9 total), please visit the HSDB record page.

Human Toxicity ExcerptsPoison by intravenous, intramuscular, and subcutaneous routes. Human systemic effects by intravenous route: changes to kidney, ureter, and bladder.
Drug Induced Liver Injury · 4건

Drug-Induced Liver Injury Severity and Toxicity (DILIst)

Netilmicin

DILI Positive

DOI:10.1016/j.drudis.2019.09.022

규제 정보

FDA Requirements · 1건

Manufacturers, packers, and distributors of drug and drug products for human use are responsible for complying with the labeling, certification, and usage requirements as prescribed by the Federal Food, Drug, and Cosmetic Act, as amended (secs 201-902, 52 Stat. 1040 et seq., as amended; 21 U.S.C. 321-392).

화학 및 산업

약리 정보

ATC Code · 4건

S - Sensory organs

J - Antiinfectives for systemic use

QJ - Antiinfectives for systemic use

QS - Sensory organs

Protein BindingProtein-binding of is low and depends on the test conditions (mainly the concentration of cations in the test medium).
Pharmacodynamics · 1건

Netilmicin is a semisynthetic, water soluble antibiotic of the aminoglycoside group, produced by the fermentation of Micromonospora inyoensis, a species of actinomycete. Aminoglycosides are useful primarily in infections involving aerobic, Gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter. It is active at low concentrations against a wide variety of pathogenic bacteria including <i>Escherichia coli</i>, bacteria of the <i>Klebsiella-Enterobacter-Serratia </i>group, <i>Citrobacter </i>sp., <i>Proteus </i>sp. (indole-positive and indole-negative), including <i>Proteus mirabilis</i>, <i>P. morganii, P. rettgrei, P. vulgaris, Pseudomonas aeruginosa </i>and <i>Neisseria gonorrhoea</i>. Netilmicin is also active <i>in vitro </i>against isolates of <i>Hemophilus influenzae, Salmonella </i>sp., <i>Shigella </i>sp. and against penicillinase and non-penicillinase-producing <i>Staphylococcus </i>including methicillin-resistant strains. Some strains of <i>Providencia </i>sp., <i>Acinetobacter </i>sp. and <i>Aeromonas </i>sp. are also sensitive to netilmicin. Many strains of the above organisms which are found to be resistant to other aminoglycosides, such as kanamycin, gentamicin, tobramycin and sisomicin, are susceptible to netilmicin <i>in vitro</i>. Occasionally, strains have been identified which are resistant to amikacin but susceptible to netilmicin. The combination of netilmicin and penicillin G has a synergistic bactericidal effect against most strains of <i>Streptococcus faecalis</i> (enterococcus). The combined effect of netilmicin and carbenicillin or ticarcillin is synergistic for many strains of <i>Pseudomonas aeruginosa</i>. In addition, many isolates of <i>Serratia</i>, which are resistant to multiple antibiotics, are inhibited by synergistic combinations of netilmicin with carbenicillin, azlocillin, mezlocillin, cefamandole, cefotaxime or moxalactam. Aminoglycosides are mostly ineffective against anaerobic bacteria, fungi and viruses.

Mechanism of Action · 3건

Aminoglycosides like netilmicin "irreversibly" bind to specific 30S-subunit proteins and 16S rRNA. Specifically netilmicin binds to four nucleotides of 16S rRNA and a single amino acid of protein S12. This interferes with decoding site in the vicinity of nucleotide 1400 in 16S rRNA of 30S subunit. This region interacts with the wobble base in the anticodon of tRNA. This leads to interference with the initiation complex, misreading of mRNA so incorrect amino acids are inserted into the polypeptide leading to nonfunctional or toxic peptides and the breakup of polysomes into nonfunctional monosomes, leaving the bacterium unable to synthesize proteins vital to its growth.

Aminoglycosides are usually bacterial in action. Although the exact mechanism of action has not been fully elucidated, the drugs appear to inhibit protein synthesis in susceptible bacteria by irreversibly binding to 30S ribosomal subunits. /Aminoglycosides/

/AMINOGLYCOSIDES/ INHIBIT PROTEIN BIOSYNTHESIS & DECR FIDELITY OF TRANSLATION OF GENETIC CODE. /AMINOGLYCOSIDES/

Biological Half-Life · 2건

2.5 hours

The plasma elimination half-life on netilmicin is about 2-2.5 hr following IV or IM administration of a single dose in adults with normal renal function. The serum half-life is reported to be 18 hr in adults with creatinine clearances of 10-30 mL/min and more than 30 hr in anephric adults. The plasma elimination half-life of netilmicin in neonates is inversely related to birthweight and gestational and postnatal age and has been reported to be about 8 or 4.5 hr in neonates less than 7 days of age weighing 1.5-2 or 3-4 kg, respectively. The plasma elimination half-life for children 6 weeks of age and older is 1.5-2 hr.

Metabolism/MetabolitesNo evidence of metabolic transformation, typically 80% is recoverable in the urine within 24 hours

용도 및 제조

UsesMEDICATION

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