(2R,3R,4S,5S,6R)-4-Amino-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-hydroxy-cyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol
![(2R,3R,4S,5S,6R)-4-Amino-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-hydroxy-cyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol Structure](CAS/GIF/34493-98-6.gif)
- CAS No.
- 34493-98-6
- Chemical Name:
- (2R,3R,4S,5S,6R)-4-Amino-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-hydroxy-cyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol
- Synonyms
- ibekacin;DIBEKACIN;Aids070753;Brn 1441606;Aids-070753;4)]-2-deoxy-;Dibekacin USP/EP/BP;4'-Dideoxykanamycin B;Dibekacin（Dideoxykanamycin B）;D-StreptaMine,O-3-aMino-3-deoxy-a-D-glucopyranosyl-(1®
- CBNumber:
- CB02130442
- Molecular Formula:
- C18H37N5O8
- Molecular Weight:
- 451.52
- MOL File:
- 34493-98-6.mol
- MSDS File:
- SDS
- Modify Date:
- 2024/3/19 15:37:51
(2R,3R,4S,5S,6R)-4-Amino-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-hydroxy-cyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol Properties
| alpha | D20 +132° (c = 0.65) |
|---|---|
| Boiling point | 559.28°C (rough estimate) |
| Density | 1.3132 (rough estimate) |
| refractive index | 1.7600 (estimate) |
| pka | 13.07±0.70(Predicted) |
| CAS DataBase Reference | 34493-98-6 |
SAFETY
Risk and Safety Statements
| Toxicity | LD50 in mice (mg/kg): 61.0-68.0 i.v., 373.0-380.0 i.m. (Komiya) |
|---|
(2R,3R,4S,5S,6R)-4-Amino-2-[(1S,2S,3R,4S,6R)-4,6-diamino-3-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-hydroxy-cyclohexyl]oxy-6-(hydroxymethyl)oxane-3,5-diol Chemical Properties,Uses,Production
Description
Dibekacin was synthesized in 1967 by Umezawa et al. by the removal of the 3 - and 4 -hydroxyl groups of kanamycin B. Studies by the same workers on the mechanisms of bacterial resistance to kanamycin-group antibiotics preceded the discovery. Dibekacin shows excellent activity, as expected, against a variety of bacteria, including kanamycin-resistant strains. It shows higher activity than kanamycin against Pseudomonas aeruginosa, Proteus, and other pathogens.
Uses
Dideoxykanamycin B is an antibacterial compound.
Definition
ChEBI: A kanamycin that is kanamycin B lacking the 3- and 4-hydroxy groups on the 2,6-diaminosugar ring.
Antimicrobial activity
3′,4′-Dideoxy kanamycin B. A semisynthetic aminoglycoside
closely related to the natural compound tobramycin (3′-deoxy
kanamycin B). Supplied as the sulfate.
It is active against staphylococci including methicillinresistant
strains, a wide range of enterobacteria, Acinetobacter
and Pseudomonas spp. It is also active against M. tuberculosis
and the M. avium complex (MICs 4–16 mg/L). It exhibits
the usual aminoglycoside properties of bactericidal activity
at concentrations close to the MIC and bactericidal synergy
with selected β-lactam antibiotics.
Absence of hydroxyl groups present in the parent kanamycin
B renders dibekacin resistant to phosphorylation
by APH(3′). It is also resistant to some forms of ANT(4′).
However, the type of this enzyme, ANT(4′), found in
some Gram-positive organisms modifies dibekacin at the
2″-hydroxyl group; nevertheless dibekacin has much greater
activity than tobramycin against organisms that produce the
enzyme.
A 1 mg/kg intravenous bolus dose achieves a peak plasma
concentration of around 5 mg/L. The plasma half-life is
2.3 h. Protein binding is 3–12%. It is eliminated principally
by the renal route, 75–80% of the dose appearing in
the urine in the first 24 h. Elimination is inversely related to
renal function. In patients maintained on chronic hemodialysis,
the half-life rises to 54 h between dialyses and falls to
6–7 h on dialysis.
Toxic effects are those typical of aminoglycosides with a
frequency similar to or less than those of gentamicin.
It is used for severe infections caused by susceptible microorganisms,
especially those resistant to established aminoglycosides,
but availability is limited.
Safety Profile
Poison by intraperitoneal, subcutaneous, intramuscular, and intravenous routes. Moderately toxic by ingestion. Experimental teratogenic and reproductive effects. An antibacterial agent. When heated to decomposition it emits toxic fumes of NOx.
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