(2R,3S,4S,5R,6R)-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-3-{[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}oxane-3,4,5-triol

• ChemBase ID: 1043
• Molecular Formular: C18H36N4O11
• Molecular Mass: 484.49864
• Monoisotopic Mass: 484.23805799
• SMILES: O([C@H]1O[C@@H]([C@H]([C@@H]([C@H]1O)O)O)CN)[C@@H]1[C@H](C[C@H]([C@@H]([C@H]1O)O[C@@H]1[C@@H]([C@H]([C@@H]([C@H](O1)CO)O)N)O)N)N
• Canonical SMILES: OC[C@H]1O[C@H](O[C@H]2[C@H](N)C[C@@H]([C@H]([C@@H]2O)O[C@H]2O[C@H](CN)[C@H]([C@@H]([C@H]2O)O)O)N)[C@@H]([C@H]([C@@H]1O)N)O
• InChI: InChI=1S/C18H36N4O11/c19-2-6-10(25)12(27)13(28)18(30-6)33-16-5(21)1-4(20)15(14(16)29)32-17-11(26)8(22)9(24)7(3-23)31-17/h4-18,23-29H,1-3,19-22H2/t4-,5+,6-,7-,8+,9-,10-,11-,12+,13-,14-,15+,16-,17-,18-/m1/s1
• InChIKey: SBUJHOSQTJFQJX-NOAMYHISSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R,3S,4S,5R,6R)-2-(aminomethyl)-6-{[(1R,2R,3S,4R,6S)-4,6-diamino-3-{[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy}-2-hydroxycyclohexyl]oxy}oxane-3,4,5-triol
• IUPAC Traditional name: kanamycin
• Brand Name: Bekanamycin; Kanamycin A; Kanamycin B; Kenamycin A; Klebcil
• Synonyms: KAN; Aminodeoxykanamycin; Kanamycin Base; Kanamycin Sulfate; Nebramycin Factor 5; Kanamycin; Kanamycin solution from Streptomyces kanamyceticus

Database IDs

• CAS Number: 25389-94-0; 8063-07-8
• MDL Number: MFCD00070289
• PubChem SID: 160964506; 46508178
• PubChem CID: 6032

CALCULATED PROPERTIES

JChem

• Acid pKa: 12.109839
• H Acceptors: 15
• H Donor: 11
• LogD (pH = 5.5): -18.059649
• LogD (pH = 7.4): -12.666778
• Log P: -7.0609136
• Molar Refractivity: 106.1345 cm^3
• Polarizability: 45.27121 Å^3
• Polar Surface Area: 282.61 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: false

ALOGPS 2.1

• Log P: -3.1
• LOG S: -0.72
• Solubility (Water): 9.23e+01 g/l

PROPERTIES

Physical Property

• Apperance: liquid
• Hydrophobicity(logP): -6.3

Safety Information

• European Hazard Symbols: Toxic (T)
• German water hazard class: 2
• Risk Statements: 61
• Safety Statements: 53-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360
• GHS Precautionary statements: P201-P308 + P313
• Storage Temperature: 2-8°C

Product Information

• Concentration: 10 mg/mL in 0.9% NaCl; 50 mg/mL in 0.9% NaCl
• Suitability: suitable for cell culture
• Impurities: endotoxin, tested
• Sterility: sterile-filtered

DETAILS

DrugBank - DB01172

• Drug Groups: approved
• Description: Antibiotic complex produced by Streptomyces kanamyceticus from Japanese soil. Comprises 3 components: kanamycin A, the major component, and kanamycins B and C, the minor components. [PubChem]
• Indication: For treatment of infections where one or more of the following are the known or suspected pathogens: E. coli, Proteus species (both indole-positive and indole-negative), E. aerogenes, K. pneumoniae, S. marcescens, and Acinetobacter species.
• Pharmacology: Kanamycin 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: Mild and reversible nephrotoxicity may be observed in 5 - 25% of patients. Amikacin accumulates in proximal renal tubular cells. Tubular cell regeneration occurs despite continued drug exposure. Toxicity usually occurs several days following initiation of therapy. May cause irreversible ototoxicity. Otoxocity appears to be correlated to cumulative lifetime exposure. Drug accumulation in the endolymph and perilymph of the inner ear causes irreversible damage to hair cells of the cochlea or summit of ampullar cristae in the vestibular complex. High frequency hearing is lost first with progression leading to loss of low frequency hearing. Further toxicity may lead to retrograde degeneration of the 8th cranial (vestibulocochlear) nerve. Vestibular toxicity may cause vertigo, nausea, vomiting, dizziness and loss of balance.; Oral LD50 is 17500 mg/kg in mice, over 4 g/kg in rats, and over 3 g/kg in rabbits.
• Affected Organisms: Enteric bacteria and other eubacteria
• Absorption: Kanamycin is rapidly absorbed after intramuscular injection and peak serum levels are generally reached within approximately one hour. Poor oral and topical absorption except with severe skin damage.
• Half Life: 2.5 hours
• External Links: Wikipedia; RxList; Drugs.com

Sigma Aldrich - K0129

Application
Recommended for use in cell culture applications at 10 ml/L.
Biochem/physiol Actions
Mode of Action: Binds to 70S ribosomal subunit; inhibits translocation; elicits miscoding.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria, and mycoplasma.
Caution
Stable at 37°C for 5 days.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - K0254

Application
Used as a selection agent for cells transformed with kanamycin B (neoR, kanR) resistance gene. Recommended for use in cell culture applications at 2 ml/L.
Biochem/physiol Actions
Mode of Action: Binds to 70S ribosomal subunit; inhibits translocation; elicits miscoding.Antimicrobial spectrum: Gram-negative and Gram-positive bacteria, and mycoplasma.
Caution
Stable at 37 °C for 5 days.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information