Phenylethanoic acid, phenylpropanoic acid and phenylpropenoic acid conjugates and prodrugs of hydrocodone, method of making and use thereof
View Patent ↗The presently described technology provides phenylethanoic acid, phenylpropanoic acid, phenylpropenoic acid, a salt thereof, a derivative thereof or a combination thereof chemically conjugated to hydrocodone (morphinan-6-one, 4,5-alpha-epoxy-3-methoxy-17-methyl) to form novel prodrugs or compositions of hydrocodone which have a decreased potential for abuse of hydrocodone. The present technology also provides methods of treating patients, pharmaceutical kits and methods of synthesizing conjugates of the present technology.
1. A composition comprising a conjugate, wherein the conjugate is cinnamate-hydrocodone.
2. The composition of claim 1 , wherein the conjugate is a treatment composition for treating narcotic or opioid abuse or reduces withdrawal.
3. The composition of claim 1 , wherein the conjugate reduces oral, intranasal or intravenous drug abuse.
4. The composition of claim 1 , wherein the conjugate is a pain treatment composition.
5. The composition of claim 1 , wherein the conjugate exhibits a slower rate of release over time and a higher AUC when compared to unconjugated hydrocodone over that same time period.
6. The composition of claim 1 , wherein the conjugate exhibits less variability in the oral PK profile when compared to unconjugated hydrocodone.
7. The composition of claim 1 , wherein the conjugate is provided in a dosage form selected from the group consisting of: a tablet, a capsule, a caplet, a suppository, a troche, a lozenge, an oral powder, a solution, an oral film, a thin strip, a slurry, and a suspension.
8. The composition of claim 1 , wherein the conjugate is provided in an amount sufficient to provide a therapeutically bioequivalent AUC when compared to unconjugated hydrocodone.
9. The composition of claim 1 , wherein the conjugate is provided in an amount sufficient to provide a therapeutically bioequivalent AUC and C max when compared to unconjugated hydrocodone.
10. The composition of claim 1 , wherein the conjugate is provided in an amount sufficient to provide a therapeutically bioequivalent AUC when compared to unconjugated hydrocodone but does not provide an equivalent C max .
11. A composition, comprising cinnamic acid conjugated to hydrocodone wherein the conjugate has the following structure: