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1404-04-2 molecular structure
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(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

ChemBase ID: 335
Molecular Formular: C23H46N6O13
Molecular Mass: 614.64374
Monoisotopic Mass: 614.31228556
SMILES and InChIs

SMILES:
O([C@H]1[C@H](O[C@H]2O[C@@H]([C@@H](O)[C@H](O)[C@H]2N)CN)[C@@H](N)C[C@@H](N)[C@@H]1O)[C@@H]1O[C@@H]([C@@H](O[C@H]2O[C@H]([C@@H](O)[C@H](O)[C@H]2N)CN)[C@H]1O)CO
Canonical SMILES:
OC[C@H]1O[C@H]([C@@H]([C@@H]1O[C@H]1O[C@@H](CN)[C@H]([C@@H]([C@H]1N)O)O)O)O[C@@H]1[C@@H](O)[C@H](N)C[C@@H]([C@H]1O[C@H]1O[C@H](CN)[C@H]([C@@H]([C@H]1N)O)O)N
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
InChIKey:
PGBHMTALBVVCIT-VCIWKGPPSA-N

Cite this record

CBID:335 http://www.chembase.cn/molecule-335.html

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NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
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
IUPAC Traditional 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
Brand Name
Actilin
Actiline
Antibiotique
Dekamycin V
Enterfram
Fradiomycin B
Framygen
Nebramycin X
Negamicin
Neomycin A
Soframycin
Soframycin Ophthalmic
Soframycine
Biosol
Bykomycin
Endomixin
Fradiomycin
Fradiomycin Sulfate
Fraquinol
Lidamycin Creme
Myacine
Myacyne
Mycifradin
Mycifradin-N
Myciguent
Neo-Fradin
Neo-Mantle Creme
Neo-Rx
Neobiotic
Neobrettin
Neofracin
Neolate
Neomix
Neosulf
Nivemycin
Tuttomycin
Vonamycin Powder V
Synonyms
Framycetinum [INN-Latin]
Neomycin B
Streptothricin B
Framycetin
Neomycin solution
Caswell No. 595
Neomycin B Sulfate
Neomycin Sulfate
Neomycin Sulphate
Neomycin trisulfate salt hydrate
USAF CB-19
Neomycin
新霉素 溶液
CAS Number
1404-04-2
119-04-0
PubChem SID
46505525
24897464
24886366
160963798
46508892
PubChem CID
8378

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 12.291083  H Acceptors 19 
H Donor 13  LogD (pH = 5.5) -24.511583 
LogD (pH = 7.4) -15.933928  Log P -8.415177 
Molar Refractivity 135.9003 cm3 Polarizability 58.22208 Å3
Polar Surface Area 353.11 Å2 Rotatable Bonds
Lipinski's Rule of Five false 
Log P -2.81  LOG S -0.98 
Solubility (Water) 6.47e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Safety Information Pharmacology Properties Product Information Bioassay(PubChem)
Apperance
liquid expand Show data source
Hydrophobicity(logP)
-7.8 expand Show data source
European Hazard Symbols
Harmful Harmful (Xn) expand Show data source
MSDS Link
Download expand Show data source
Download expand Show data source
German water hazard class
2 expand Show data source
Risk Statements
42/43 expand Show data source
Safety Statements
23-36/37-45 expand Show data source
GHS Pictograms
GHS08 expand Show data source
GHS Signal Word
Danger expand Show data source
GHS Hazard statements
H317-H334 expand Show data source
GHS Precautionary statements
P261-P280-P342 + P311 expand Show data source
Personal Protective Equipment
Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter expand Show data source
Eyeshields, Gloves expand Show data source
Storage Temperature
2-8°C expand Show data source
Gene Information
human ... TERT(7015) expand Show data source
Concentration
1 mg/mL expand Show data source
Suitability
suitable for cell culture expand Show data source
Impurities
endotoxin, tested expand Show data source
Sterility
sterile-filtered expand Show data source
Product Line
BioReagent expand Show data source

DETAILS

DETAILS

DrugBank DrugBank Sigma Aldrich Sigma Aldrich
DrugBank - DB00994 external link
Item Information
Drug Groups approved
Description 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.
Indication 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).
Pharmacology 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.
Toxicity 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.
Affected Organisms
Enteric bacteria and other eubacteria
Biotransformation Neomycin undergoes negligible biotransformation after parenteral administration.
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.
Half Life 2 to 3 hours
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%.
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.
External Links
Wikipedia
RxList
Drugs.com
DrugBank - DB00452 external link
Item Information
Drug Groups approved
Description A component of neomycin that is produced by Streptomyces fradiae. On hydrolysis it yields neamine and neobiosamine B. (From Merck Index, 11th ed)
Indication For the treatment of bacterial blepharitis, bacterial bonjunctivitis, corneal injuries, corneal ulcers and meibomianitis. For the prophylaxis of ocular infections following foreign body removal
Pharmacology Framycetin is used for the treatment of bacterial eye infections such as conjunctivitis. Framycetin is an antibiotic. It is not active against fungi, viruses and most kinds of anaerobic bacteria. Framycetin works by binding to the bacterial 30S ribosomal subunit, causing misreading of t-RNA, leaving the bacterium unable to synthesize proteins vital to its growth. Framycetin is useful primarily in infections involving aerobic bacteria bacteria.
Affected Organisms
Enteric bacteria and other eubacteria
External Links
Wikipedia
Sigma Aldrich - N1142 external link
Application
Broadly used in molecular biology and cell culture as a selection agent for prokaryotic cells that have been transformed using the selectable marker gene (neo). Recommended for use in cell culture applications at 5 ml/L.
Biochem/physiol Actions
Mode of action: binds to the 30S and in some cases the 50S subunit causing miscoding; inhibits initiation and elongation during protein synthesis.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria.
Caution
Stable at 37 °C for 5 days.
Other Notes
Formulated to contain 10 mg/ml neomycin in 0.9% sodium chloride.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

REFERENCES

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