Cholesterol → Amikacin

HRID 2403068Notes

Reaction equation

HRID 2403068 reaction equation
[CH2:1]1[C@@H:6]([NH:7][C:8]([C@@H:10]([OH:14])[CH2:11][CH2:12][NH2:13])=[O:9])[C@H:5]([O:15][C@H:16]2[O:21][C@H:20]([CH2:22][OH:23])[C@@H:19]([OH:24])[C@H:18]([NH2:25])[C@H:17]2[OH:26])[C@@H:4]([OH:27])[C@H:3]([O:28][C@H:29]2[O:34][C@H:33]([CH2:35][NH2:36])[C@@H:32]([OH:37])[C@H:31]([OH:38])[C@H:30]2[OH:39])[C@H:2]1[NH2:40].OS(O)(=O)=O.[OH-].[Na+].CCCCCCCCCCCCCCCC(OC[C@@H](OC(CCCCCCCCCCCCCCC)=O)COP(OCC[N+](C)(C)C)([O-])=O)=O.CC(CCC[C@H]([C@@H]1[C@]2(C)[C@H]([C@H]3[C@H](CC2)[C@]2(C)C(C[C@H](CC2)O)=CC3)CC1)C)C>O.C(O)C>[CH2:1]1[C@@H:6]([NH:7][C:8]([C@@H:10]([OH:14])[CH2:11][CH2:12][NH2:13])=[O:9])[C@H:5]([O:15][C@H:16]2[O:21][C@H:20]([CH2:22][OH:23])[C@@H:19]([OH:24])[C@H:18]([NH2:25])[C@H:17]2[OH:26])[C@@H:4]([OH:27])[C@H:3]([O:28][C@H:29]2[O:34][C@H:33]([CH2:35][NH2:36])[C@@H:32]([OH:37])[C@H:31]([OH:38])[C@H:30]2[OH:39])[C@H:2]1[NH2:40]

Participants

7

Reactant 4

HCID 5997CholesterolHCID 14798Sodium HydroxideHCID 452110Colfosceril PalmitateHCID 5458175Amikacin Sulfate Salt

Product 1

HCID 37768Amikacin

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

Amikacin sulfate 12.0 g was dissolved in 200 mL water and pH was adjusted to 6.5 by adding necessary amounts of 25% NaOH solution. Lipids, 1.480 g DPPC and 0.520 g cholesterol, were dissolved in a mixture of 60 mL ethanol and 10 mL water. These amounts result in a 300 mL batch after infusion at a lipid/amikacin flow rate of 300/500 mL/min, respectively. Volumes can be proportionally adjusted for larger scale or if different flow rates are desired.

Sources & evidence

ORD record
ord-f7b7f0a566d040a3805b8825a1273395
Source dataset
uspto-grants-2014_08
Patent number
US08802137B2

Reaction notes

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