Abuse-resistant hydrocodone compounds

• US 7,375,082 B2
• Filed: 09/30/2004
• Issued: 05/20/2008
• Est. Priority Date: 02/22/2002
• Status: Expired due to Term

• Current Assignee: Takeda Pharmaceutical Company Limited
• Original Assignee: Shire LLC (Shire plc)
• Inventors: Piccariello, Thomas, Krishnan, Suma, Mickle, Travis, Moncrief, James Scott, Lauderback, Christopher, Mickle, Christal
• Primary Examiner(s): Tsang; Cecilia J.
• Assistant Examiner(s): Audet; Maury
• Application Number:
  US10/953,116
• Publication Number:
  US 20050176645A1
• Time in Patent Office: 1,328 Days
• Field of Search: 514/9
• US Class Current: 514/1.3
• CPC Class Codes: A61K 31/485 Morphinan derivatives, e.g. morphine, codeine
• CPC Class Codes: A61K 47/549 Sugars, nucleosides, nucleotides or nucleic acids
• CPC Class Codes: A61K 47/62 the modifying agent being a protein, peptide or polyamino acid

Abstract

The present invention decreases the potential for abuse of opioids, particularly hydrocodone, by covalent modification. The invention provides methods of delivering hydrocodone as conjugates that release the hydrocodone following oral administration while being resistant to abuse by circuitous routes such as intravenous (“shooting”) injection and intranasal administration (“snorting”). Further, hydrocodone compositions of the invention are resistant to oral abuse as well, since release of the hydrocodone at suprapharmacological doses reaches saturation.

Claims

1. A composition comprising hydrocodone covalently bound at the 6′

position to a single amino acid or an oligopeptide of 15 or fewer amino acids through the N-terminus or side chain of said oligopeptide or said amino acid, or a pharmaceutically acceptable salt thereof, and a pharmaceutically acceptable additive in a form suitable for oral administration.

2. The composition of claim 1, wherein said oligopeptide comprises fewer than 10 amino acids.

3. The composition of claim 1, wherein said oligopeptide comprises fewer than 6 amino acids.

4. The composition of claim 1, wherein the oligopeptide is selected from a dipeptide, a tripeptide, a tetrapeptide, a pentapeptide, and a hexapeptide.

5. The composition of claim 1, wherein the oligopeptide is a pentapeptide.

6. The composition of claim 5, wherein said pentapeptide consists essentially of naturally occurring amino acids.

7. The composition of claim 1 wherein said hydrocodone is resistant to release from said amino acid or said oligopeptide when the composition is manipulated for parenteral administration.

8. The composition of claim 1, wherein said form suitable for oral administration is a tablet, a capsule, a caplet, an oral solution, or an oral suspension.

9. The composition of claim 6, wherein said form suitable for oral administration is a tablet, a capsule, a caplet, an oral solution, or an oral suspension.