Tìm theo
Neomycin
Thuốc trị ký sinh trùng, chống nhiễm khuẩn
Thuốc Gốc
Small Molecule
CAS: 1404-04-2
ATC: A01AB08, A07AA01, B05CA09, D06AX04, J01GB05, R02AB01, S01AA03, S02AA07, S03AA01
ĐG : Akorn Inc. , http://www.akorn.com
CTHH: C23H46N6O13
PTK: 614.6437
A component of neomycin that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed). Neomycin is a bactericidal aminoglycoside antibiotic that binds to the 30S ribosome of susceptible organisms. Binding interferes with mRNA binding and acceptor tRNA sites and results in the production of non-functional or toxic peptides.
Nhận Dạng Quốc Tế & Đặc Tính Hóa Học
Công thức hóa học
C23H46N6O13
Phân tử khối
614.6437
Monoisotopic mass
614.312285588
InChI
InChI=1S/C23H46N6O13/c24-2-7-13(32)15(34)10(28)21(37-7)40-18-6(27)1-5(26)12(31)20(18)42-23-17(36)19(9(4-30)39-23)41-22-11(29)16(35)14(33)8(3-25)38-22/h5-23,30-36H,1-4,24-29H2/t5-,6+,7-,8+,9-,10-,11-,12+,13-,14-,15-,16-,17-,18-,19-,20-,21-,22-,23+/m1/s1
InChI Key
InChIKey=PGBHMTALBVVCIT-VCIWKGPPSA-N
IUPAC Name
(2R,3S,4R,5R,6R)-5-amino-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-2-{[(2S,3R,4S,5R)-4-{[(2R,3R,4R,5S,6S)-3-amino-6-(aminomethyl)-4,5-dihydroxyoxan-2-yl]oxy}-3-hydroxy-5-(hydroxymethyl)oxolan-2-yl]oxy}-3-hydroxycyclohexyl]oxy}oxane-3,4-diol
Traditional IUPAC Name
framycetin
SMILES
NC[C@@H]1O[C@H](O[C@@H]2[C@@H](CO)O[C@@H](O[C@@H]3[C@@H](O)[C@H](N)C[C@H](N)[C@H]3O[C@H]3O[C@H](CN)[C@@H](O)[C@H](O)[C@H]3N)[C@@H]2O)[C@H](N)[C@@H](O)[C@@H]1O
Độ tan chảy
6 mg/mL (as sulfate form)
Độ hòa tan
6.47e+01 g/l
logP
-7.8
logS
-0.98
pKa (strongest acidic)
12.29
pKa (Strongest Basic)
9.97
PSA
353.11 Å2
Refractivity
135.9 m3·mol-1
Polarizability
60.87 Å3
Rotatable Bond Count
9
H Bond Acceptor Count
19
H Bond Donor Count
13
Physiological Charge
6
Number of Rings
4
Bioavailability
0
MDDR-Like Rule
true
Dược Lực Học : Neomycin is an aminoglycoside antibiotic. Aminoglycosides work by binding to the bacterial 30S ribosomal subunit, causing misreading of t-RNA, leaving the bacterium unable to synthesize proteins vital to its growth. Aminoglycosides are useful primarily in infections involving aerobic, Gram-negative bacteria, such as Pseudomonas, Acinetobacter, and Enterobacter. In addition, some mycobacteria, including the bacteria that cause tuberculosis, are susceptible to aminoglycosides. Infections caused by Gram-positive bacteria can also be treated with aminoglycosides, but other types of antibiotics are more potent and less damaging to the host. In the past the aminoglycosides have been used in conjunction with penicillin-related antibiotics in streptococcal infections for their synergistic effects, particularly in endocarditis. Aminoglycosides are mostly ineffective against anaerobic bacteria, fungi and viruses.
Cơ Chế Tác Dụng : A component of neomycin that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed). Neomycin is a bactericidal aminoglycoside antibiotic that binds to the 30S ribosome of susceptible organisms. Binding interferes with mRNA binding and acceptor tRNA sites and results in the production of non-functional or toxic peptides. Aminoglycosides like neomycin "irreversibly" bind to specific 30S-subunit proteins and 16S rRNA. Specifically neomycin 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.
Dược Động Học :
▧ Absorption :
Poorly absorbed from the normal gastrointestinal tract. Although only approximately 3% of neomycin is absorbed through intact intestinal mucosa, significant amounts may be absorbed through ulcerated or denuded mucosa or if inflammation is present.
▧ Protein binding :
Protein binding studies have shown that the degree of aminoglycoside protein binding is low and, depending upon the methods used for testing, may be between 0% and 30%.
▧ Metabolism :
Neomycin undergoes negligible biotransformation after parenteral administration.
▧ Route of Elimination :
The small absorbed fraction is rapidly distributed in the tissues and is excreted by the kidney in keeping with the degree of kidney function.
▧ Half Life :
2 to 3 hours
Độc Tính : LD50 = 200 mg/kg (rat). Because of low absorption, it is unlikely that acute overdosage would occur with oral neomycin. However, prolonged administration could result in sufficient systemic drug levels to produce neurotoxicity, ototoxicity and/or nephrotoxicity. Nephrotoxicity occurs via drug accumulation in renal proximal tubular cells resulting in cellular damage. Tubular cells may regenerate despite continued exposure and nephrotoxicity is usually mild reversible. Neomycin is the most toxic aminoglycoside agent, which is thought to be due to its large number of cationic amino groups. Otoxocity occurs via drug accumulation in the endolymph and perilymph of the inner ear causing irreversible damage to hair cells in the cochlea or summit of ampullar cristae in the vestibular complex. High frequency hearing loss is followed by low frequency hearing loss. Further toxicity may cause retrograde degeneration of the auditory nerve. Vestibular toxicity may result in vertigo, nausea and vomiting, dizziness and loss of balance.
Chỉ Định : Topical uses include treatment for superficial eye infections caused by susceptible bacteria (used in combination with other antiinfectives), treatment of otitis externa caused by susceptible bacteria, treatment or prevention of bacterial infections in skin lesions, and use as a continuous short-term irrigant or rinse to prevent bacteriuria and gram negative rod bacteremia in abacteriuric patients with indwelling catheters. May be used orally to treat hepatic encephalopathy, as a perioperative prophylactic agent, and as an adjunct to fluid and electrolyte replacement in the treatment of diarrhea caused to enteropathogenic E. coli (EPEC).
Tương Tác Thuốc :
  • Cefotaxime Increased risk of nephrotoxicity
  • Cefotetan Increased risk of nephrotoxicity
  • Cefoxitin Increased risk of nephrotoxicity
  • Ceftazidime Increased risk of nephrotoxicity
  • Ceftriaxone Increased risk of nephrotoxicity
  • Colistimethate Aminoglycosides may enhance the nephrotoxic effect of Colistimethate. Aminoglycosides may enhance the neuromuscular-blocking effect of Colistimethate. Due to the potential for additive or synergistic toxicities (including both nephrotoxicity and neuromuscular blockade) between colistimethate and the aminoglycoside antibiotics, this combination should be avoided whenever possible. If these agents must be used together, patients' renal and neuromuscular function should be monitored closely.
  • Tacrolimus Additive renal impairment may occur during concomitant therapy with aminoglycosides such as Neomycin. Use caution during concomitant therapy.
  • Ticarcillin Ticarcillin may reduce the serum concentration of Neomycin. Ticarcillin may inactivate Neomycin in vitro and the two agents should not be administered simultaneously through the same IV line.
Liều Lượng & Cách Dùng : Dressing - Topical
Ointment - Ophthalmic
Solution / drops - Ophthalmic
Dữ Kiện Thương Mại
Giá thị trường
Nhà Sản Xuất
  • Công ty :
    Sản phẩm biệt dược : Myacyne
  • Công ty :
    Sản phẩm biệt dược : Mycifradin
  • Công ty :
    Sản phẩm biệt dược : Myciguent
  • Công ty :
    Sản phẩm biệt dược : Neo-Fradin
  • Công ty :
    Sản phẩm biệt dược : Neo-Rx
  • Công ty :
    Sản phẩm biệt dược : Neobiotic
  • Công ty :
    Sản phẩm biệt dược : Nivemycin
Đóng gói
Tài Liệu Tham Khảo Thêm
drugbank
http://www.drugbank.ca/drugs/DB00994
PubChem Substance
http://pubchem.ncbi.nlm.nih.gov/summary/summary.cgi?sid=46505525
KEGG Compound
http://www.genome.jp/dbget-bin/www_bget?cpd:C00384
National Drug Code Directory
http://www.hipaaspace.com/Medical_Billing/Coding/National.Drug.Codes/PDF/39822-0310-5
PharmGKB
http://www.pharmgkb.org/drug/PA450608
Wikipedia
http://en.wikipedia.org/wiki/Neomycin
RxList
http://www.rxlist.com/cgi/generic3/neomy.htm
Drugs.com
http://www.drugs.com/cdi/neomycin.html
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