Name | bekanamycin |
Synonyms | kdm NK 1006 nebramycinv Bekanamycin bekanamycin Kanamycin B kanendomycin nebramycinfactor5 Nebramycin factor 5 d-streptamine,o-3-amino-3-deoxy-alpha-d-glucopyranosyl-(1-4)-o-(2,6-diamino-2, 4,6-diamino-3-[(3-amino-3-deoxyhexopyranosyl)oxy]-2-hydroxycyclohexyl 2,6-diamino-2,6-dideoxyhexopyranoside (2R,3S,4R,5R,6R)-5-Amino-2-(aminomethyl)-6-[(1R,2S,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]oxyoxane-3,4-diol |
CAS | 4696-76-8 |
EINECS | 225-170-5 |
InChI | InChI=1/C18H37N5O10/c19-2-6-11(26)12(27)9(23)17(30-6)32-15-4(20)1-5(21)16(14(15)29)33-18-13(28)8(22)10(25)7(3-24)31-18/h4-18,24-29H,1-3,19-23H2 |
Molecular Formula | C18H37N5O10 |
Molar Mass | 483.51 |
Density | 1.3771 (rough estimate) |
Melting Point | 178-182° (dec) |
Boling Point | 580.49°C (rough estimate) |
Specific Rotation(α) | D18 +130° (c = 0.5 in water); D21 +114° (c = 0.98 in water) |
Flash Point | 442.3°C |
Solubility | Aqueous Acid (Slightly), Methanol (Slightly, Heated, Sonicated), Water (Sparingl |
Vapor Presure | 3.43E-30mmHg at 25°C |
Appearance | Solid |
Color | Crystals |
pKa | 13.07±0.70(Predicted) |
Storage Condition | under inert gas (nitrogen or Argon) at 2–8 °C |
Stability | Hygroscopic |
Refractive Index | 1.7600 (estimate) |
Use | It is an antibiotic drug and an intermediate for the production of deca-star sulfate and abecacin sulfate |
In vitro study | Bekanamycin (Kanamycin B) is a precursor for semisynthetic antibiotics such as Arbekacin and Dibekacin and is generally extracted from the broth of S. kanamyceticus . Bekanamycin (Kanamycin B) in a concentration-dependent fashion reduces reversibly the quantal content of the end-plate potentials while it has no observable effect on the configuration of the extracellularly recorded presynaptic action potential. The reduction in evoked transmitter release produced by Bekanamycin could be antagonized either by increasing the external calcium concentration or by drugs like the aminopyridines which are to greatly enhance transmitter release from motor nerve terminals. Bekanamycin exerts potent inhibitory effects on transmitter release probably by interfering with the influx of calcium that occurs during depolarization of motor nerve terminals. |
Toxicity | LD50 i.v. in mice: 136 mg/kg (Wakazawa) |