Ultrapure tetrahydrocannabinol-11-oic acids
This application is in the field of medicinal chemistry and relates to ultrapure ajulemic acid, its synthesis, pharmaceutical compositions and methods of use thereof for the treatment and/or prevention of inflammation, pain, and fibrotic diseases including scleroderma, systemic sclerosis, scleroderma-like disorders, sine scleroderma, liver cirrhosis, interstitial pulmonary fibrosis, idiopathic pulmonary fibrosis, Dupuytren's contracture, keloids, chronic kidney disease, chronic graft rejection, and other scarring-wound healing abnormalities, post-operative adhesions, and reactive fibrosis.
1. A pharmaceutical composition comprising one or more cannabinoids and a pharmaceutically acceptable excipient, wherein said one or more cannabinoids comprise at least 98% (w/w) ajulemic acid or a pharmaceutically acceptable salt thereof, and wherein no significant antinociception is observed in a hot plate test of mice following oral administration to the mice of 10 mg/kg of said one or more cannabinoids.
2. The pharmaceutical composition of claim 1 , wherein said one or more cannabinoids comprise at least 99% (w/w) ajulemic acid or a pharmaceutically acceptable salt thereof.
3. The pharmaceutical composition of claim 1 , wherein the pharmaceutical composition is in the form of a tablet or a capsule.
4. The pharmaceutical composition of claim 3 , wherein the tablet or the capsule comprises from about 5 mg to about 180 mg ajulemic acid or a pharmaceutically acceptable salt thereof.
5. The pharmaceutical composition of claim 4 , wherein the tablet or the capsule comprises from about 10 mg to about 120 mg ajulemic acid or a pharmaceutically acceptable salt thereof.
6. The pharmaceutical composition of claim 3 , wherein the tablet or the capsule comprises a biocompatible matrix.
7. The pharmaceutical composition of claim 3 , wherein the tablet is prepared by compressing a mixture comprising the one or more cannabinoids and one or more polymers.
8. The pharmaceutical composition of claim 3 , wherein the tablet comprises a binding agent.
9. The pharmaceutical composition of claim 8 , wherein the binding agent comprises hydroxyalkylcellulose, hydroxyalkylalkylcellulose, or polyvinylpyrrolidone.
10. The pharmaceutical composition of claim 3 , wherein the tablet or the capsule comprises a lubricating agent.
11. The pharmaceutical composition of claim 3 , wherein the tablet or the capsule comprises colloidal silica.
12. The pharmaceutical composition of claim 3 , wherein the tablet or the capsule is coated with a semipermeable coating.
13. The pharmaceutical composition of claim 3 , wherein the tablet or the capsule is coated with a rate-controlling polymer.
14. The pharmaceutical composition of claim 1 , wherein the one or more cannabinoids comprises less than about 0.1% (w/w) of 11-hydroxy-(6aR,10aR)-3-(1′,1′-dimethylheptyl)-Δ8-tetrahydrocannabinol (HU-210).
15. The pharmaceutical composition of claim 1 , wherein the one or more cannabinoids has an affinity for the CB2 receptor ranging from about 2 times to about 100 times greater than the affinity for the CB1 receptor.
16. The pharmaceutical composition of claim 15 , wherein the one or more cannabinoids has an affinity for the CB2 receptor ranging from about 10 times to about 40 times greater than the affinity for the CB1 receptor.