(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: 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

NAMES AND DATABASE IDS

Names

• 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

Database IDs

• CAS Number: 1404-04-2; 119-04-0
• PubChem SID: 46505525; 24897464; 24886366; 160963798; 46508892
• PubChem CID: 8378

CALCULATED PROPERTIES

JChem

• 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 cm^3
• Polarizability: 58.22208 Å^3
• Polar Surface Area: 353.11 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -2.81
• LOG S: -0.98
• Solubility (Water): 6.47e+01 g/l

PROPERTIES

Physical Property

• Apperance: liquid
• Hydrophobicity(logP): -7.8

Safety Information

• European Hazard Symbols: Harmful (Xn)
• German water hazard class: 2
• Risk Statements: 42/43
• Safety Statements: 23-36/37-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H317-H334
• GHS Precautionary statements: P261-P280-P342 + P311
• Personal Protective Equipment: Eyeshields, Faceshields, full-face respirator (US), Gloves, multi-purpose combination respirator cartridge (US), type ABEK (EN14387) respirator filter; Eyeshields, Gloves
• Storage Temperature: 2-8°C

Pharmacology Properties

• Gene Information: human ... TERT(7015)

Product Information

• Concentration: 1 mg/mL
• Suitability: suitable for cell culture
• Impurities: endotoxin, tested
• Sterility: sterile-filtered
• Product Line: BioReagent

DETAILS

DrugBank - DB00994

• 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

• 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

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