Pharmaceutical formulations containing lipoic acid derivatives
Inventors
Shorr, Robert G. L. • RODRIGUEZ, ROBERT J. • BHASIN, RAJINDER
Assignees
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Publication Number
US-8263653-B2
Publication Date
2012-09-11
Expiration Date
Abstract
The invention provides ion pairs of a lipoic acid derivative and an ion pairing agent, pharmaceutical formulations containing such ion pairs, and methods of using the ion pairs and pharmaceutical formulations in the treatment of medical disorders, such as cancer. An exemplary ion pair is the ion pair formed by bis-benzyl lipoate and triethanolamine. The pharmaceutical formulations may comprise a dextrose solution as a diluent.
Core Innovation
The disclosed subject matter relates to ion-pair pharmaceutical formulations formed between a lipoic acid derivative and an ion pairing agent. The lipoic acid derivative is expressed by Formula I and Formula II with variable substituents R1 and R2, including exemplified compounds such as bis-benzyl lipoate and 6,8-bis(benzylthio)octanoic acid. The ion pairing agent is used to form the ion pair for a pharmaceutical formulation.
Triethanolamine is identified as an ion pairing agent suitable for forming ion pairs with the lipoic acid derivative, and the ion pairing agent classes include amines, organic Bronsted bases, and polymer-conjugated ion pairing agents. The formulation includes pharmaceutical formulation components such as diluents, including dextrose/D5W, and salt formation related to the ion pairing approach.
The formulations are described as improving solubility and providing substantially increased tumor/cell kill compared with conventional vehicles. Viability decreases with increasing concentrations of the lipoic acid derivative in TEA, and apoptosis/necrosis profiling indicates TEA favors necrotic death while a sodium-salt favors apoptotic death.
Claims Coverage
The provided independent claim identifies one inventive concept: an ion pair that includes at least one triethanolamine component. No additional independent claims are provided in the supplied claim list.
Ion pair including triethanolamine
An ion pair consisting of at least one triethanolamine component.
The claim coverage is limited to an ion pair that includes at least one triethanolamine component.
Stated Advantages
Improved solubility.
Improved antitumor efficacy relative to conventional formulations.
Substantially increased tumor/cell kill compared with conventional vehicles.
Documented Applications
Antitumor use supported by tumor cell killing characterization in A2780 tumor cells.
Therapeutic and anticancer use as an ion pair pharmaceutical formulation.
Antimicrobial use as an ion pair pharmaceutical formulation.
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