Arbekacin

ChEBI: A kanamycin that is kanamycin B bearing an N-(2S)-4-amino-2-hydroxybutyryl group on the aminocyclitol ring.

Solid

Arbekacin is a kanamycin that is kanamycin B bearing an N-(2S)-4-amino-2-hydroxybutyryl group on the aminocyclitol ring. It has a role as an antimicrobial agent, a protein synthesis inhibitor, an antibacterial agent and an antibacterial drug. It is a member of kanamycins and an aminoglycoside. It derives from a kanamycin B.|An semisynthetic aminoglycoside antibiotic. Often used for treatment of multi-resistant bacterial infection such as methicillin-resistant Staphylococcus aureus (MRSA).|Arbekacin is a semisynthetic aminoglycoside antibiotic derived from dibekacin with activity against both gram-positive and gram-negative bacteria. Arbekacin is most commonly used in the treatment of multi-resistant bacterial infections.

3', 4'-dideoxykanamycin B and equivalent tert-butoxycarbonyl azide, in a mixed solution of water, pyridine and triethylamine (10:10:1), react at room temperature for 18h . Then use Amberlite CG50 (NH4+) column chromatography to obtain 6'-N-tert-butoxycarbonyl-3', 4'-dideoxykanamycin B with a yield of 49% and a melting point of 136～140℃ (decomposition). [α] {D}^26+112°(C=1.0, water). At the same time, 36% of unreacted 3', 4'-dideoxykanamycin B was recovered. 6'-N-tert-butoxycarbonyl-3', 4'-dideoxykanamycin B (1.1g, 2.0mmo1) and tert-butoxycarbonyl azide (320mg, 2.2mmo1) under the same conditions as above The next reaction yielded 1.41 g of yellow powder. Without purification, dissolve in 20ml water and 10ml dimethoxyethane, and use (S)-4-tert-butoxycarbonylamino-2-hydroxybutyric acid (N-hydroxysuccinimide) ester (696mg, 2.2mmo1) ) A solution in 10ml of dimethoxyethane, acylation at room temperature for 20h. React with 10ml 90% trifluoroacetic acid at room temperature for 40min, and remove the tert-butoxycarbonyl group. The reaction solution was concentrated until it was chromatographed with Amberlite CG50 (NH4+) column, eluted with water and 0.5 mol/L ammonia, and then eluted with 0.75 mol/L ammonia. 162 mg of arbekacin dicarbonate was obtained, the yield was 12%, the melting point was 178°C (decomposition), [α]{D}^24+87°(C=0.77, water).

It has strong antibacterial activity against kanamycin, gentamicin and amikacin-resistant bacteria. Used for sepsis and pneumonia caused by sensitive bacteria.

Molecular Weight:552.6
XLogP3:-6.8
Hydrogen Bond Donor Count:11
Hydrogen Bond Acceptor Count:15
Rotatable Bond Count:10
Exact Mass:552.31189162
Monoisotopic Mass:552.31189162
Topological Polar Surface Area:297
Heavy Atom Count:38
Complexity:757
Defined Atom Stereocenter Count:14
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes