Arbekacin

The Arbekacin, with the CAS registry number 51025-85-5, is also known as 1-N-[(S)-4-Amino-2-hydroxybutyryl]dibekacin. It belongs to the classification codes of Anti-Infective Agents; Drug / Therapeutic Agent. This chemical's molecular formula is C₂₂H₄₄N₆O₁₀ and molecular weight is 552.62. What's more, its IUPAC name is called (2S)-4-Amino-N-[(1R,2S,3S,4R,5S)-5-amino-4-[(2R,3R,6S)-3-amino-6-(aminomethyl)oxan-2-yl]oxy-2-[(2S,3R,4S,5S,6R)-4-amino-3,5-dihydroxy-6-(hydroxymethyl)oxan-2-yl]oxy-3-hydroxycyclohexyl]-2-Hydroxybutanamide. Arbekacin is a semisynthetic aminoglycoside antibiotic. It is primarily used for the treatment of infections caused by multi-resistant bacteria including methicillin-resistant Staphylococcus aureus.

Physical properties about Arbekacin are: (1)# of Rule of 5 Violations: 3; (2)ACD/BCF (pH 5.5): 1; (3)ACD/BCF (pH 7.4): 1; (4)ACD/KOC (pH 5.5): 1; (5)ACD/KOC (pH 7.4): 1; (6)#H bond acceptors: 16; (7)#H bond donors: 16; (8)#Freely Rotating Bonds: 20; (9)Polar Surface Area: 297.27 Å²; (10)Index of Refraction: 1.634; (11)Molar Refractivity: 134 cm³; (12)Molar Volume: 374.5 cm³; (13)Flash Point: 500.5 °C; (14)Enthalpy of Vaporization: 149.21 kJ/mol; (15)Boiling Point: 904 °C at 760 mmHg; (16)Vapour Pressure: 0 mmHg at 25 °C.

Preparation of Arbekacin: this chemical can be prepared by 6-N-Boc-3, 4 -didanosine kanamycin B. This reaction needs reagent t-BuoCON₃. The yield is 12 %.

You can still convert the following datas into molecular structure:
(1) SMILES: NCCC(O)C(=O)N[C@@H]3C[C@H](N)[C@@H](O[C@H]1O[C@H](CN)CC[C@H]1N)[C@H](O)[C@H]3O[C@H]2O[C@H](CO)[C@@H](O)[C@H](N)[C@H]2O
(2) InChI: InChI=1S/C22H44N6O10/c23-4-3-12(30)20(34)28-11-5-10(26)18(37-21-9(25)2-1-8(6-24)35-21)17(33)19(11)38-22-16(32)14(27)15(31)13(7-29)36-22/h8-19,21-22,29-33H,1-7,23-27H2,(H,28,34)/t8-,9+,10-,11+,12?,13+,14-,15+,16+,17-,18+,19-,21+,22+/m0/s1
(3) InChIKey: MKKYBZZTJQGVCD-DGBUGYMQSA-N

The toxicity data is as follows:

Organism	Test Type	Route	Reported Dose (Normalized Dose)	Effect	Source
mouse	LD50	intravenous	80mg/kg (80mg/kg)		Antimicrobial Agents and Chemotherapy. Vol. 29, Pg. 543, 1986.
rat	LD50	intraperitoneal	588mg/kg (588mg/kg)	BEHAVIORAL: ALTERED SLEEP TIME (INCLUDING CHANGE IN RIGHTING REFLEX) LUNGS, THORAX, OR RESPIRATION: CYANOSIS	Kiso to Rinsho. Clinical Report. Vol. 27, Pg. 1905, 1993.