In-vitro corneal permeation of cannabinoids and their water-soluble phosphate ester prodrugs

Journal of Pharmacy and Pharmacology

Volumn 57, Issue 9, 2005, Pages 1153-1157

  Juntunen, Juha ^a   Järvinen, Tomi ^a   Niemi, Riku ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

Author keywords

[No Author keywords available]

Indexed keywords

2 HYDROXYPROPYL BETA CYCLODEXTRIN; ANANDAMIDE; CANNABINOID; CANNABINOID RECEPTOR; CAVASOL W7 HP PHARMA; METHANANDAMIDE; NOLADIN ETHER; ORGANOPHOSPHATE; PRODRUG; UNCLASSIFIED DRUG; WATER;

ANIMAL TISSUE; ARTICLE; CATTLE; CORNEA; CORNEA ENDOTHELIUM; DRUG EFFECT; DRUG FORMULATION; DRUG HYDROLYSIS; DRUG PENETRATION; DRUG RECEPTOR BINDING; DRUG RELEASE; DRUG SOLUBILITY; DRUG STRUCTURE; DRUG TRANSPORT; FEMALE; IN VITRO STUDY; INTRAOCULAR PRESSURE; ISOLATED ORGAN; LIPOPHILICITY; MALE; NONHUMAN; PHYSICAL CHEMISTRY; RABBIT; SUSPENSION;

ALKALINE PHOSPHATASE; ANIMALS; ARACHIDONIC ACIDS; BETA-CYCLODEXTRINS; CANNABINOIDS; CATTLE; CORNEA; DIFFUSION CHAMBERS, CULTURE; DOSE-RESPONSE RELATIONSHIP, DRUG; ESTERS; HALF-LIFE; PERMEABILITY; PHOSPHATES; PRODRUGS; RABBITS; SOLUBILITY; SUSPENSIONS; TROMETHAMINE; WATER;

EID: 25844481538     PISSN: 00223573     EISSN: None     Source Type: Journal    
DOI: 10.1211/jpp.57.9.0009     Document Type: Article

References (17)

1. Abadji, V., Lin, S., Taha, G., Griffin, G., Stevenson, L. A., Pertwee, R. G., Makriyannis, A. (1994) (R)-methanandamide: a chiral novel anandamide possessing higher potency and metabolic stability. J. Med. Chem. 37: 1889-1893
2. Cooler, P., Gregg, J. M. (1977) Effect of delta-9-tetrahydrocannabinol on intraocular pressure in humans. South Med. J. 70: 951-954
3. Devane, W. A., Dysarz, F. A., Johnson, M. R., Melvin, L. S., Howlett, A. C. (1988) Determination and characterization of a cannabinoid receptor in rat brain. Mol. Pharmacol. 34: 605-613
4. Devane, W. A., Hanus, L., Breuer, A., Pertwee, R. G., Stevenson, L. A., Griffin, G., Gibson, D., Mandelbaum, A., Etinger, A., Mechoulam, R. (1992) Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science 258: 1946-1949
5. Hanus, L., Saleh, A.-L., Fride, E., Breuer, A., Vogel, Z., Shalev, D. E., Kustanovich, I., Mechoulam, R. (2001) 2-Arachidonyl glyceryl ether, an endogenous agonist of the cannabinoid cb1 receptor. Proc. Natl Acad. Sci. U S A 98: 3662-3665
6. Hepler, R. S., Frank, I. R. (1971) Marihuana smoking and intraocular pressure. JAMA 217: 1392
7. Jarho, P., Urtti, A., Pate, D. W., Suhonen, P., Järvinen, T. (1996a) Increase in aqueous solubility, stability and in vitro corneal permeability of anandamide by hydroxypropyl-β-cyclodextrin. Int. J. Pharm. 137: 209-216
8. Jarho, P., Urtti, A., Järvinen, K., Pate, D. W., Järvinen, T. (1996b) Hydroxypropyl-beta-cyclodextrin increases aqueous solubility and stability of anandamide. Life Sci. 58: 181-185
9. Järvinen, T., Pate, D. W., Laine, K. (2002) Cannabinoids in the treatment of glaucoma. Pharmacol. Ther. 95: 203-220
10. Juntunen, J., Huuskonen, J., Laine, K., Niemi, R., Taipale, H., Nevalainen, T., Pate, D. W., Järvinen, T. (2003a) Anandamide prodrugs. 1. Water-soluble phosphate esters of arachidonylethanolamide and r-methanandamide. Eur. J. Pharm. Sci. 19: 37-43
11. Juntunen, J., Vepsäläinen, J., Niemi, R., Laine, K., Järvinen, T. (2003b) Synthesis, in vitro evaluation, and intraocular pressure effects of water-soluble prodrugs of endocannabinoid noladin ether. J. Med. Chem. 46: 5083-5086
12. Kearse, C., Green, K. (2000) Effect of vehicle upon in vitro transcorneal permeability and intracorneal content of d9-tetrahydrocannabinol. Curr. Eye Res. 20: 496-501
13. Lojda, Z., Cejkova, J., Bolkova, A., Havrankova, E. (1976) Uneven distribution of alkaline phosphatase in individual layers of rabbit and ox cornea. Histochemical and biochemical study. Histochemistry 49: 237-243
14. Musson, D. G., Bidgood, A. M., Olejnik, O. (1991) Comparative corneal penetration of prednisolone sodium phosphate and prednisolone acetate in nzw rabbits. J. Ocul. Pharmacol. 7: 175-182
15. Pate, D. W., Järvinen, K., Urtti, A., Jarho, P., Järvinen, T. (1995) Ophthalmic arachidonylethanolamide decreases intraocular pressure in normotensive rabbits. Curr. Eye Res. 14: 791-797
16. Porcella, A., Casellas, P., Gessa, G. L., Pani, L. (1998) Cannabinoid receptor cb1 mrna is highly expressed in the rat ciliary body: implications for the antiglaucoma properties of marihuana. Brain Res. Mol. Brain Res. 58: 240-245
17. Schoenwald, R. D. (1990) Ocular drug delivery. Pharmacokinetic considerations. Clin. Pharmacokinet. 18: 255-269