(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; sulfuric acid

• ChemBase ID: 72953
• Molecular Formular: C18H38N4O15S
• Molecular Mass: 582.57712
• Monoisotopic Mass: 582.20543754
• SMILES: [C@@H]1([C@@H]([C@H](O[C@@H]([C@@H]1O)O[C@@H]1[C@H](C[C@H]([C@@H]([C@H]1O)O[C@H]1O[C@@H]([C@H]([C@@H]([C@H]1O)N)O)CO)N)N)CN)O)O.S(=O)(=O)(O)O
• Canonical SMILES: OS(=O)(=O)O.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.H2O4S/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;1-5(2,3)4/h4-18,23-29H,1-3,19-22H2;(H2,1,2,3,4)/t4-,5+,6-,7-,8+,9-,10-,11-,12+,13-,14-,15+,16-,17-,18-;/m1./s1
• InChIKey: OOYGSFOGFJDDHP-KMCOLRRFSA-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; sulfuric acid
• IUPAC Traditional name: kanamycin; sulfuric acid
• Synonyms: Kanamycin monosulfate; Kantrex; Kanamycin sulfate; Kanamycin sulfate Streptomyces kanamyceticus; Kanamycin sulfate; O-3-Amino-3-deoxy-α-D-glucopyranosyl-(16)-O-[6-amino-6-deoxy-α-D-glucopyranosyl-(14)]-2-deoxy-D-streptamine Sulfate; Cantrex; Cristalomicina; Enterokanacin; Kamycin; Kanabristol; Kanamytrex; Kanaqua; Kanasig; Kanatrol; Kanescin; Otokalixin; Resistomycin; Kanamycin A Sulfate; Kanamycin sulfate from Streptomyces kanamyceticus; Kanamycin A; Kanamycin sulfate salt; 卡那霉素 硫酸酯 来源于卡那霉素链霉菌; 硫酸卡那霉素（来自卡那霉素链霉菌）; 卡那霉素 A; 卡那霉素碱 硫酸盐; 卡那霉素 硫酸酯 来源于卡那霉素链霉菌

Database IDs

• CAS Number: 70560-51-9; 25389-94-0
• EC Number: 246-933-9
• MDL Number: MFCD00070253
• Beilstein Number: 3874279
• PubChem SID: 24896209; 24896204; 162037873; 24881933; 24896236; 24896199; 24896240
• PubChem CID: 441374

CALCULATED PROPERTIES

• 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

PROPERTIES

Physical Property

• Solubility: H2O: soluble10-50 mg/mL (As a stock solution. Stock solutions should be stored at 2-8°C. Stable at 37°C for 5 days.); Water
• Apperance: powder; White Solid
• Melting Point: >250°C (dec.)

Safety Information

• Storage Condition: -20°C; -20°C Freezer
• RTECS: NZ3225030
• European Hazard Symbols: Toxic (T)
• German water hazard class: 2; 3
• Risk Statements: 61
• Safety Statements: 53-45
• GHS Pictograms: GHS08
• GHS Signal Word: Danger
• GHS Hazard statements: H360
• GHS Precautionary statements: P201-P308 + P313
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: 2-8°C

Product Information

• Grade: Biotechnology Performance Certified
• Salt Data: sulfate
• Potency: ≥750 μg per mg; ≥750 μg per mg ((dry basis)); ≥750 μg per mg (dry basis)
• Suitability: cell culture tested; meets USP testing specifications; plant cell culture tested; suitable for cell culture; suitable for plant cell culture
• Ignition Residue: ≤0.2% (as SO4)
• Impurities: <5% kanamycin B; ≤5% Kanamycin B; ≤5% kanamycin B; endotoxin, tested
• Sterility: γ-irradiated
• Loss on Drying: ≤2% loss on drying
• Quality Level: PREMIUM
• Linear Formula: C18H36-37N4-5O10-11 · H2SO4
• Empirical Formula (Hill Notation): C18H36N4O11 · H2O4S

DETAILS

Selleck Chemicals - S2315

Research Area: Infection
Biological Activity:
Kanamycin sulfate(Kanamycin monosulfate) is an aminoglycoside antibiotic, available in oral, intravenous, and intramuscular forms, and used to treat a wide variety of infections. Kanamycin interacts with the 30S subunit of prokaryotic ribosomes. It induces substantial amounts of mistranslation and indirectly inhibits translocation during protein synthesis. [1]

Sigma Aldrich - K4378

Application
Used in biotechnology applications to inhibit protein synthesis. Used as a selection agent for cells transformed with kanamycin B (neoR, kanR) resistance gene.
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.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - K0879

Application
在生物技术中用于抑制蛋白质合成。建议以 10-50μg/mL 的量用于分子生物学应用。
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.
Reconstitution
直接在小瓶中用无菌水配制储备液 (10mg/mL)。储备液应储存在 2-8°C 下。在 37°C 下可稳定 5 天。
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - K3763

Application
Use in biotechnology applications to inhibit protein synthesis.
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.

Sigma Aldrich - 60615

Other Notes
Aminoglycoside-antibiotic with broad antibacterial spectrum, (including mycobacteria, many gram-positive and most gram-negative organisms); Additive in culture media for the isolation of group D streptococci on Kanamycin Esculin Azide Agar (Mossel et al.) or for selection of transformed plant cells containing the neomycin phosphotransferase (for kanamycin resistance); on a kanamycin-medium1,2
Application
Aminoglycoside-antibiotic with broad antibacterial spectrum, (including mycobacteria, many gram-positive and most gram-negative organisms); Additive in culture media for the isolation of group D streptococci on Kanamycin Esculin Azide Agar (Mossel et al.) or for selection of transformed plant cells containing the neomycin phosphotransferase (for kanamycin resistance); on a kanamycin-medium1,2
Biochem/physiol Actions
Kanamycin interacts with the 30S subunit of prokaryotic ribosomes thereby inhibiting translocation during protein synthesis 3.

Sigma Aldrich - K1377

Application
在生物技术中用于抑制蛋白质合成。建议以 100mg/L 的量用于细胞培养应用。
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.
Protocols & Applications
Antibiotic Selector for application, solubility, solution stability, working concentration, and mode of action information

Sigma Aldrich - K4000

Application
Used as a selection agent for cells transformed with kanamycin B (neoR, kanR) resistance gene.
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.

Sigma Aldrich - K1637

Application
Used in biotechnology applications to inhibit protein synthesis. Used as a selection agent for cells transformed with kanamycin B (neoR, kanR) resistance gene.
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.

Toronto Research Chemicals - K137500

Antibiotic complex produced by Streptomyces kanamyceticus Okami & Umezawa from Japanese soil. Comprised of three components, kanamycin A, the major component, and kanamycins B and C, two minor congeners. Antibacterial.

REFERENCES

• http://en.wikipedia.org/wiki/Kanamycin
• Ito, et al.: J. Antibiot., 17, 189 (1964)
• Toda, S., et al.: J. Antibiot., 30, 1002 (1964)
• Claes, P.J., et al.: Anal. Profiles Drug. Subs., 6, 259 (1964)