Carbonate Ion → Levobupivacaine

HRID 2273577Notes

Reaction equation

HRID 2273577 reaction equation
[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[C@H:10]([C:11]([NH:13][C:14]2[C:15]([CH3:21])=[CH:16][CH:17]=[CH:18][C:19]=2[CH3:20])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6]1.Cl.C(=O)([O-])[O-]>>[CH3:1][CH2:2][CH2:3][CH2:4][N:5]1[C@H:10]([C:11]([NH:13][C:14]2[C:15]([CH3:21])=[CH:16][CH:17]=[CH:18][C:19]=2[CH3:20])=[O:12])[CH2:9][CH2:8][CH2:7][CH2:6]1

Participants

3

Reactant 2

HCID 19660Carbonate IonHCID 1179652-Piperidinecarboxamide, 1-butyl-N-(2,6-dimethylphenyl)-, hydrochloride (1:1), (2S)-

Product 1

HCID 92253Levobupivacaine

Procedure

In a first vial, levobupivacaine-HCl (6, 12.5 or 25 mg), tetrafunctional PEG, pentaerythritol poly(ethylene glycol) ether tetra-N-hydroxy-succinimidyl glutarate (10,000 g/mol) (SG-PEG) (50 mg) and tetrafunctional PEG, pentaerythritol poly(ethylene glycol) ether tetra-sulfhydryl (10,000 g/mol) (PEG-SH) (50 mg) were dissolved in 250 μL of pH 2.2 buffer. This solution was combined with an equal volume of carbonate buffer (pH 9.7) using a spray kit. Levobupivacaine precipitated within the gel upon mixing. All levobupivacaine-loaded gels swelled 1.5-2 times their original volume except for the gel containing the highest amount of levobupivacaine, which swelled about 4 times its initial volume. In vitro release studies showed a steady release of levobupivacaine from the gel. At 9 days, 30% of the drug was released.

Workup

  1. customLevobupivacaine precipitated within the gel
  2. additionupon mixing
  3. additioncontaining the highest amount of levobupivacaine, which

Sources & evidence

ORD record
ord-5206d7f8b8694c67807cda50a1c3bc32
Source dataset
uspto-grants-2015_09
Patent number
US09125814B2

Reaction notes

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