A Terlipressin-Albumin Conjugate for Increased Stability

NU2018-179

INVENTORS
Nathan Gianneschi*
Or Berger
Wonmin Choi

SHORT DESCRIPTION
A new compound consisting of terlipressin coupled to an 18-carbon (C-18) fatty acid that allows the drug to bind to albumin, providing increased stability.

BACKGROUND
Terlipressin, an analogue of vasopressin, is used in many countries around the world to treat a variety of life threating diseases like hepatorenal syndrome, esophageal varices, and septic shock.  Both vasopressin and terlipressin constrict blood vessels and increase reabsorption of water.  Several companies manufacture and sell terlipressin outside of the United States; however, it has not been approved by the FDA for any indication. A primary reason is that terlipressin possesses a poor pharmacokinetic profile. As a short peptide, it is quickly metabolized and eliminated from the body. Therefore, frequent IV administration of the drug is required to maintain therapeutic levels.

ABSTRACT
Northwestern researchers have designed a novel drug carrier system based on naturally evolved interactions between long-chain fatty acids (LCFAs) and Human Serum Albumin (HSA).  Mono-functionalizing octadecanedioic acid (ODDA) with terlipressin produces a prodrug that is capable of binding to HSA and shows differentiated pharmacokinetics, as well as remarkable tolerability. The fatty acid moiety interacts with human serum albumin (HSA), a ubiquitous protein in the body. The terlipressin-HSA conjugate is more stable than terlipressin alone, allowing the drug to avoid degradation and elimination. Currently, terlipressin requires intermittent IV administration, but with this novel carrier system would enable less frequent dosing, overcoming a significant drawback of terlipressin therapy.

APPLICATIONS

  • Terlipressin therapy (possible indications in hepatorenal syndrome (HRS), esophageal varices, septic shock, low blood pressure, paracentesis-induced circulatory dysfunction)

ADVANTAGES

  • Improved pharmacokinetic profile for terlipressin:  reduced number of injections and decreased treatment period
  • Low immunogenicity

IP STATUS
A US patent application has been filed.

Patent Information: