Cannabinoids in the treatment of glaucoma

Pharmacology and Therapeutics

Volumn 95, Issue 2, 2002, Pages 203-220

  Järvinen, Tomi ^a   Pate, David W ^b   Laine, Krista ^a  

^a UNIVERSITY OF EASTERN FINLAND   (Finland)

^b HortaPharm BV   (Netherlands)

Author keywords

Cannabinoids; CB receptor; Endocannabinoids; Glaucoma; Intraocular pressure; Topical

Indexed keywords

CANNABINOID; CANNABINOID RECEPTOR; N METHYL DEXTRO ASPARTIC ACID RECEPTOR;

APOPTOSIS; ARTICLE; CENTRAL NERVOUS SYSTEM; DRUG EFFECT; DRUG MECHANISM; DRUG RESEARCH; GLAUCOMA; HUMAN; HYPOTENSION; INTRAOCULAR PRESSURE; MICROCIRCULATION; OPTIC NERVE INJURY; PRIORITY JOURNAL;

EID: 0036669783     PISSN: 01637258     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0163-7258(02)00259-0     Document Type: Review

References (184)

1. Adachi K., Fujita Y., Morizane C., Akaike A., Ueda M., Satoh M., Masai H., Kashii S., Honda Y. Inhibition of NMDA receptors and nitric oxide synthase reduces ischemic injury of the retina. Eur J Pharmacol. 350:1998;53-57.
2. Adachi K., Kashii S., Masai H., Ueda M., Morizane C., Kaneda K., Kume T., Akaike A., Honda Y. Mechanism of the pathogenesis of glutamate neurotoxicity in retinal aschemia. Graefes Arch Clin Exp Ophthalmol. 236:1998;766-774.
3. Ahmed I., Gokhale R.D., Shah M.V., Patton T.F. Physicochemical determinants of drug diffusion across the conjunctiva, sclera, and cornea. J Pharm Sci. 76:1987;583-586.
4. Alward W.L.M. Medical management of glaucoma. Engl J Med. 339:1998;1298-1307.
5. Arsenovic, J. (1997). Formulation of aqueous opthalmic solutions of cannabinoids for use in glaucoma therapy. M.Ph. Thesis, University of Otago.
6. Bary A.R., Tucker I.G., Davies N.M. Considerations in the use of hydroxypropyl-β-cyclodextrin in the formulation of aqueous ophthalmic solutions of hydrocortisone. Eur J Pharm Biopharm. 50:2000;237-244.
7. Beilin M., Neumann R., Belkin M., Green K., Bar-Ilan A. Pharmacology of the intraocular pressure (IOP) lowering effect of systemic dexanabinol (HU-211), a non-psychotropic cannabinoid. J Ocul Pharmacol Ther. 16:2000;217-230.
8. Beltramo M., Piomelli D. Carrier-mediated transport and enzymatic hydrolysis of the endogenous cannabinoid 2-arachidonoyl glycerol. Neuroreport. 11:2000;1231-1235.
9. Beltramo M., Stella N., Calignano A., Lini S.Y., Makriannis A., Piomelli D. Functional role of high-affinity anandamide transport, as revealed by selective inhibition. Science. 277:1997;1094-1096.
10. Biegon A., Joseph A.B. Development of HU-211 as a neuroprotectant for ischemic brain damage. Neurol Res. 17:1995;275-280.
11. Bisogno T., Delton-Vandenbrouke I., Milone A., Lagarde M., Di Marzo V. Biosynthesis and inactivation of N-arachidonoylethanolamine (anandamide) and N-docosahexaenoylethanolamine in bovine retina. Arch Biochem Biophys. 370:1999;300-307.
12. Bisogno T., Maccarrone M., De Petrocellis L., Jarrahian A., Finazzi-Agro A., Hillard C., Di Marzo V. The uptake by cells of 2-arachidonoylglycerol, an endogenous agonist of cannabinoid receptors. Eur J Biochem. 268:2001;1982-1989.
13. Bodor N. Recent advances in retrometabolic drug design and targeting approaches. Pharmazie. 55:2000;163-166.
14. Borchardt R.T. Assessment of transport barriers using cell and tissue culture systems. Drug Dev Ind Pharm. 16:1990;2595-2612.
15. Bouaboula M., Perrachon S., Milligan L., Canat X., Rinaldi-Carmona M., Portier M., Barth F., Calandra B., Pecceu F., Lupker J., Maffrand J.P., Le Fur G., Casellas P. A selective inverse agonist for central cannabinoid receptor inhibits mitogen-activated protein kinase activation stimulated by insulin or insulin-like growth factor 1. Evidence for a new model of receptor/ligand interactions. J Biol Chem. 272:1997;22330-22339.
16. Brechue W.F., Maren T.H. pH and drug ionization affects ocular pressure lowering of topical carbonic anhydrase inhibitors. Invest Ophthalmol Vis Sci. 34:1993;2581-2587.
17. Buchwald A., Browne C.E., Wu W.-M., Bodor N. Soft cannabinoid analogues as potential anti-glaucoma agents. Pharmazie. 55:2000;196-201.
18. Calignano A., La Rana G., Beltramo M., Makriyannis A., Piomelli D. Potentiation of anandamide hypotension by the transport inhibitor, AM404. Eur J Pharmacol. 337:1997;R1-R2.
19. Carney L.G., Hill R.M. Human tear buffering capacity. Arch Ophthalmol. 97:1979;951-952.
20. Chang S.C., Lee V.H.L. Nasal and conjunctival contributions to the systemic absorption of topical timolol in the pigmented rabbit: implications in the design of strategies to maximize the ratio of ocular to systemic absorption. J Ocul Pharmacol. 3:1987;159-169.
21. 9-tetrahydrocannabinol after ophthalmic administration to the rabbit. J Pharm Sci. 72:1983;136-138.
22. Chien D.-S., Sasaki H., Bundgaard H., Buur A., Lee V.H.L. Role of enzymatic lability in the corneal and conjunctival penetration of timolol ester prodrugs in the pigmented rabbits. Pharm Res. 8:1991;728-733.
23. Chrai S.S., Patton T.F., Mehta A., Robinson J.R. Lacrimal and instilled fluid dynamics in rabbit eye. J Pharm Sci. 62:1973;1112-1121.
24. Colasanti B.K. Ocular hypotensive effect of marihuana cannabinoids: correlate of central action or separate phenomenon? J Ocul Pharmacol. 2:1986;295-304.
25. Colasanti B.K., Brown R.E., Craig C.R. Ocular hypotension, ocular toxicity, and neurotoxicity in response to marijuana extract and cannabidiol. Gen Pharmacol. 15:1984;479-484.
26. Colasanti B.K., Craig C.R., Allara R.D. Intraocular pressure, ocular toxicity and neurotoxicity after administration of cannabinol or cannabigerol. Exp Eye Res. 39:1984;251-259.
27. Colasanti B.K., Powell S.R., Craig C.R. Intraocular pressure, ocular toxicity and neurotoxicity after administration of D9-tetrahydrocannabinol or cannabichromene. Exp Eye Res. 38:1984;63-71.
28. Collaborative Normal Tension Glaucoma Study Group Comparison of glaucomatous progression between untreated patients with normal-tension glaucoma and and patients with therapeutically reduced introcular pressures. Am J Ophthalmol. 126:1998;487-497.
29. Collaborative Normal Tension Glaucoma Study Group The effectiveness of intraocular pressure reduction in the treatment of normal-tension glaucoma. Am J Ophthalmol. 126:1998;498-505.
30. 9-tetrahydrocannabinol. J Pharmacol Exp Ther. 263:1992;1118-1126.
31. Cooler P., Gregg J.M. The effect of delta-9-tetrahydrocannabinol on intraocular pressure in humans. South Med J. 70:1977;951-954.
32. Cravatt B.F., Giang D.K., Mayfield S.P., Boger D.L., Lerner R.A., Gilula N.B. Molecular characterization of an enzyme that degrades neuromodulatory fatty-acid amides. Nature. 384:1996;83-87.
33. Crawford W.J., Merritt J.C. Effect of tetrahydrocannabinol on arterial and intraocular hypertension. Int J Clin Pharmacol Biopharm. 17:1979;191-196.
34. Davies N.M. Biopharmaceutical considerations in topical ocular drug delivery. Clin Exp Pharmacol Physiol. 27:2000;558-562.
35. Davies N.M., Wang G., Tucker I.G. Evaluation of a hydrocortisone/hydroxypropyl-β-cyclodextrin solution for ocular drug delivery. Int J Pharm. 156:1997;201-209.
36. De Petrocellis L., Bisogno T., Davis J.B., Pertwee R.G., Di Marzo V. Overlap between the ligand recognition properties of the anandamide transporter and VR1 vanilloid receptor: inhibitors of anandamide uptake with negligible capsaicin-like activity. FEBS Lett. 483:2000;52-56.
37. Deutsch D.G., Chin S.A. Enzymatic synthesis and degradation of anandamide, a cannabinoid receptor agonist. Biochem Pharmacol. 46:1993;791-796.
38. Devane W.A., Dysarz I.F.A., Johnson M.R., Melvin L.S., Howlett A.C. Determination and characterization of a cannabinoid receptor in rat brain. Mol Pharmacol. 34:1988;605-613.
39. Devane W.A., Breuer A., Sheskin T., Jarbe T.U.C., Eisen M.S., Mechoulam R. A novel probe for the cannabinoid receptor. J Med Chem. 35:1992;2065-2069.
40. Devane W.A., Hanus L., Breuer A., Pertwee R.G., Stevenson L.A., Griffin G., Gibson D., Mandelbaum A., Etinger A., Mechoulam R. Isolation and structure of a brain constituent that binds to the cannabinoid receptor. Science. 258:1992;1946-1949.
41. Di Marzo V., Fontana A., Cadas H., Schinelli S., Cimino C., Schwartz J.-C., Piomelli D. Formation and inactivation of endogenous cannabinoid anandamide in central neurons. Nature. 372:1994;686-691.
42. Di Marzo V., Bisogno T., Melck D., Ross R., Brockie H., Stevenson L., Perwee R., De Petrocellis L. Interactions between synthetic vanilloids and the endogenous cannabinoid system. FEBS Lett. 436:1998;449-454.
43. Di Marzo V., Bisogno T., Sugiura T., Melck D., De Petrocellis L. The novel endogenous cannabinoid 2-arachidonoylglycerol is inactivated by neuronal- and basophil-like cells: connections with anandamide. Biochem J. 331:1998;15-19.
44. Doane M.G., Jensen A.D., Dohlman C.H. Penetration routes of topically applied eye medication. Am J Ophthalmol. 85:1978;383-386.
45. Duarte C.B., Ferreira I.L., Santos P.F., Carvalho A.L., Agostinho P.M., Carvalho A.P. Glutamate in life and death of retinal amacrine cells. Gen Pharmacol. 30:1998;289-295.
46. ElSohly M.A., Harland E.C., Murphy J.C., Wirth P., Waller C.W. Cannabinoids in glaucoma: a primary screening procedure. J Clin Pharmacol. 21:1981;472S-478S.
47. ElSohly M.A., Harland E.C., Benigni D.A., Waller C.W. Cannabinoids in glaucoma II: the effect of different cannabinoids on intraocular pressure of the rabbit. Curr Eye Res. 3:1984;841-850.
48. Eshhar N., Striem S., Biegon A. HU-211, a non-psychotropic cannabinoid, rescues cortical neurones from excitatory amino acid toxicity in culture. Neuroreport. 5:1993;237-240.
49. Feigenbaum J.J., Bergmann F., Richmond S.A., Mechoulam R., Nadler V., Kloog Y., Sokolovsky M. A non-psychotropic cannabinoid acts as a functional N-methyl-D-aspartate (NMDA) receptor blocker. Proc Natl Acad Sci USA. 86:1989;9584-9587.
50. Felder C.C., Glass M. Cannabinoid receptors and their endogenous agonists. Annu Rev Pharmacol Toxicol. 38:1998;179-200.
51. Felder C.C., Nielsen A., Briley E.M., Palkovits M., Priller J., Axelrod J., Nguyen D.N., Richardson J.M., Riggin R.M., Koppel G.A., Paul S.M., Becker G.W. Isolation and measurement of the endogenous cannabinoid receptor agonist, anandamide, in brain and peripheral tissues of human and rat. FEBS Lett. 393:1996;321-325.
52. Freedman K.A., Klein J.W., Crosson C.E. Beta-cyclodextrins enhanced biovailability of pilocarpine. Curr Eye Res. 12:1993;641-647.
53. Fridriksdottir H., Loftsson T., Stefansson E. Formulation and testing of methazolamide cyclodextrin eye drop solutions. J Controlled Release. 44:1997;95-99.
54. Frijlink H.W., Eissens A.C., Schoonen A.J.M., Lerk C.F. The effect of cyclodextrins on drug absorption. II. In vivo observation. Int J Pharm. 64:1990;195-205.
55. Frömming K.-H., Szejtli J. Cyclodextrins in Pharmacy. 1994;Kluwer Academic Publishers, Dordrecht.
56. Gallily R., Yamin A., Waksmann Y., Ovadia H., Weidenfeld J., Bar-Joseph A., Biegon A., Mechoulam R., Shohami E. Protection against septic shock and suppression of tumor necrosis factor alpha and nitric oxide production by dexanabinol (HU-211), a nonpsychotropic cannabinoid. J Pharmacol Exp Ther. 283:1997;918-924.
57. Garrett E.R., Hunt C.A. Physico-chemical properties, solubility and protein binding of delta-9-tetrahydrocannabinol. J Pharm Sci. 63:1974;1056-1064.
58. Goparaju S.K., Ueda N., Taniguchi K., Yamamoto S. Enzymes of porcine brain hydrolyzing 2-arachidonoylglycerol, an endogenous ligand of cannabinoid receptors. Biochem Pharmacol. 57:1999;417-423.
59. Green K. Marijuana smoking vs cannabinoids for glaucoma therapy. Arch Ophthalmol. 116:1998;1433-1437.
60. Green K. Marihuana and intraocular pressure. Nahas G.G., Sutin K.N., Agurell S. Marihuana and Medicine. 2000;581-589 Humana Press Inc. Totawa.
61. Green K., Bowman K. Effect of marihuana and derivatives on aqueous humor dynamics in the rabbit. Braude M.C., Szara S. The Pharmacology of Marihuana. Vol 2:1976;803-813 Raven Press, New York.
62. Green K., Mcdonald T.F. Ocular toxicology of marijuana: an update. J Toxicol Cutaneous Ocul Toxicol. 6:1987;309-334.
63. Green K., Bigger J.F., Kim K., Bowman K. Cannabinoid penetration and chronic effects in the eye. Exp Eye Res. 24:1977;197-205.
64. Green K., Wynn H., Bowman K.A. A comparison of topical cannabinoids on intraocular pressure. Exp Eye Res. 27:1978;239-246.
65. Green K., Symonds M.C., Oliver N.W., Elijah R.D. Intraocular pressure following systemic administration of cannabinoids. Curr Eye Res. 2:1983;247-253.
66. Hampson A.J., Bornheim L.M., Scanziani M., Yost C.S., Gray A.T., Hansen B.M., Leonoudakis D.J., Bickler P.E. Dual effects of anandamide on NMDA receptor-mediated responses and neurotransmission. J Neurochem. 70:1998;671-676.
67. Hepler R.S., Frank I.M. Marihuana smoking and intraocular pressure. JAMA. 217:1971;1392.
68. Hochmann A.G., Herkenham M. Cannabinoid receptors undergo axonal flow in sensory nerves. Neuroscience. 92:1999;1171-1175.
69. Hodges L.C., Reggio P.H., Green K. Evidence against cannabinoid receptor involvement in intraocular pressure effects of cannabinoids in rabbits. Ophthalmol Res. 29:1997;1-5.
70. Howes J.F. Antiglaucoma effects of topically and orally administered cannabinoids. Agurell S., Dewey W.L., Willette R.E. The Cannabinoids: Chemical, Pharmacologic and Therapeutic Aspects. 1984;881-890 Academic Press Inc. New York.
71. Howlett A.C., Champion T.M., Wilken G.H., Mechoulam R. Stereochemical effects of 11-OH-D-8-tetrahydrocannabinol-dimethylheptyl to inhibit adenylate cyclase and bind to the cannabinoid receptor. Neuropharmacology. 29:1990;161-165.
72. Huang H.-S., Schoenwald R.D., Lach J.L. Corneal penetration behavior of beta-blocking agents II: assessment of barrier contributions. J Pharm Sci. 72:1983;1272-1286.
73. Irie T., Uekama K. Pharmaceutical applications of cyclodextrins. III. Toxicological issues and safety evaluation. J Pharm Sci. 86:1997;147-162.
74. Jansen T., Xhonneux B., Mensensm J., Borgers M. Beta-cyclodextrins as vehicles in eye-drop formulations: an evaluation of their effects on rabbit corneal epithelium. Lens Eye Toxic Res. 7:1990;459-468.
75. Jarho P., Järvinen K., Urtti A., Stella V., Järvinen T. Modified β-cyclodextrin (SBE7-β-CyD) with viscous vehicle improves the ocular delivery and tolerability of pilocarpine prodrug in rabbits. J Pharm Pharmacol. 48:1996;263-269.
76. Jarho P., Urtti A., Pate D.W., Suhonen P., Järvinen T. Increase in aqueous solubility, stability and in vitro corneal permeability of anandamide by hydroxypropyl-β-cyclodextrin. Int J Pharm. 137:1996;209-217.
77. Jarho P., Järvinen K., Urtti A., Stella V.J., Järvinen T. The effect of SBE7-β-cyclodextrin with viscous vehicle on ocular delivery of pilocarpine prodrug in rabbits. Szejtli J., Szente L. Proceedings of the Eigth International Symposium on Cyclodextrins. 1997;299-402 Kluwer Academic Publishers, Dordrecht.
78. 9-tetrahydrocannabinol. Life Sci. 63:1998;PL381-PL384.
79. Järvinen K., Järvinen T., Thompson D.O., Stella V.J. The effect of a modified β-cyclodextrin, SBE4-β-CD, on the aqueous stability and ocular absorption of pilocarpine. Curr Eye Res. 13:1994;897-905.
80. Järvinen K., Järvinen T., Urtti A. Ocular absorption following topical delivery. Adv Drug Delivery Rev. 16:1995;3-19.
81. Järvinen T., Järvinen K. Prodrugs for improved ocular drug delivery. Adv Drug Delivery Rev. 19:1996;203-224.
82. Järvinen T., Järvinen K., Urtti A., Thompson D.O., Stella V.J. Sulfobutyl ether β-cyclodextrin (SBE4-β-CD) in eyedrops improves the tolerability of a topically applied pilocarpine prodrug in rabbits. J Ocul Pharmacol Ther. 11:1995;95-106.
83. Järvinen T., Juntunen J., Huuskonen J., Nevalainen T., Pate D.W., Laine K. Water-soluble prodrugs of anandamides. Abstracts of the International Cannabinoid Research Society Meeting, June 28-30, 2001, San Lorenzo de El Escorial, Spain. 2001;15 International Cannabinoid Research Society, Burlington.
84. 9-tetrahydrocannabinol in human eyes. Arch Opthalmol. 101:1983;591-593.
85. Johnson M.R., Melvin L.S. The discovery of nonclassical cannabinoid analgetics. Mechoulam R. Cannabinoids as Therapeutic Agents. 1986;121-145 CRC Press, Boca Raton.
86. Kaufman P.L., Wis M. Marijuana and glaucoma. Arch Ophthalmol. 116:1998;1512-1513.
87. 9-tetrahydrocannabinol. Curr Eye Res. 20:2000;496-501.
88. Keipert S., Fedder J., Böhm A., Hanke B. Interactions between cyclodextrins and pilocarpine - as an example of a hydrophilic drug. Int J Pharm. 142:1996;153-162.
89. Korczyn A.D. The ocular effects of cannabinoids. Gen Pharmacol. 11:1980;419-423.
90. Kristinsson J.K., Fridriksdottir H., Thorisdottir S., Sigurdardottir A.M., Stefansson E., Loftsson T. Dexamethasone-cyclodextrin-polymer co-complexes in aqueous eye drops. Invest Ophthalmol Vis Sci. 37:1996;1199-1203.
91. Kublik H., Bock T.K., Schreier H., Müller B.W. Nasal absorption of 17β-estradiol from different cyclodextrin inclusion formulations in sheep. Eur J Pharm Biopharm. 42:1996;320-324.
92. Kurahashi Y., Ueda N., Suzuki N., Suzuki M., Yamamoto S. Reversible hydrolysis and synthesis of anandamide demonstrated by recombinant rat fatty-acid amide hydrolysis. Biochem Biophys Res Commun. 237:1997;512-515.
93. Laine K., Järvinen T., Savinainen J., Laitinen J.T., Pate D.W., Järvinen K. Effects of topical anandamide uptake inhibitors, AM404 and olvanil, on intraocular pressure in normotensive rabbits. Pharm Res. 18:2001;494-499.
94. Laine K., Järvinen K., Pate D.W., Urtti A., Järvinen T. Effect of the enzyme inhibitor, phenylmethylsulfonyl fluoride, on the IOP profiles of topical anandamides. Invest Ophthalmol Vis Sci. 43:2002;393-397.
95. Leist M., Fava E., Montecucco C., Nicotera P. Peroxynitrite and nitric acid donors induce neuronal apoptosis by eliciting autocrine excitotoxicity. Eur J Neurosci. 9:1997;1488-1498.
96. Leker R.R., Shohami E., Abramsky O., Ovadia H. Dexanabinol; a novel neuroprotective drug in experimental focal cerebral ischemia. J Neurol Sci. 162:1999;114-119.
97. Liaw J., Robinson J.R. The effect of polyethylene glycol molecular weight on corneal transport and the related influence of penetration enhancers. Int J Pharm. 88:1992;125-140.
98. Liaw J., Rojanasakul Y., Robinson J.R. The effect of drug charge type and charge density on corneal transport. Int J Pharm. 88:1992;111-124.
99. Liu J.H.K., Dacus A.C. Central nervous system and peripheral mechanisms in ocular hypotensive effect of cannabinoids. Arch Ophthalmol. 105:1987;245-258.
100. Loftsson T. Effects of cyclodextrins on the chemical stability of drugs in aqueous solutions. Drug Stability. 1:1995;22-33.
101. Loftsson T., Brewster M.E. Pharmaceutical applications of cyclodextrins. 1. Drug solubilization and stabilization. J Pharm Sci. 85:1996;1017-1025.
102. Loftsson T., Järvinen T. Cyclodextrins in ophthalmic drug delivery. Adv Drug Delivery Rev. 36:1999;59-79.
103. Loftsson T., Stefansson E. Effect of cyclodextrins on topical drug delivery to the eye. Drug Dev Ind Pharm. 23:1997;473-481.
104. Loftsson T., Fridriksdottir H., Thorisdottir S., Stefansson E. The effect of hydroxypropyl methylcellulose on release of dexamethazone from aqueous 2-hydroxypropyl-β-cyclodextrin formulations. Int J Pharm. 104:1994;181-184.
105. Loftsson T., Fridriksdottir H., Thorisdottir S., Stefansson E., Sigurdardottir A.M., Gudmundsson Ö., Sigthorsson T. 2-Hydroxypropyl-β-cyclodextrinin topical carbonic anhydrase inhibitor formations. Eur J Pharm Sci. 1:1994;175-180.
106. Love S. Oxidative stress in brain ischemia. Brain Pathol. 9:1999;119-131.
107. Lu Q., Straiker A., Lu G., Maguire G. Expression of CB2 receptor mRNA in adult rat retina. Vis Neurosci. 17:2000;91-95.
108. Mandell A.I., Stentz F., Kitabchi A.E. Dipivalyl epinephrine: a new prodrug in the treatment of glaucoma. Ophthalmology. 85:1978;268-275.
109. Maren T.H., Jankowska L. Ocular pharmacology of sulfonamides: the cornea as barrier and depot. Curr Eye Res. 4:1985;399-408.
110. Matsuda S., Kanemitsu N., Nakamura A., Mimura Y., Ueda N., Kurahashi Y., Yamamoto S. Metabolism of anandamide, an endogenous cannabinoid receptor ligand, in porcine ocular tissues. Exp Eye Res. 64:1997;707-711.
111. Mechoulam R., Feigenbaum J.J., Lander N., Segal M., Jarbe T.U.C., Hiltunen A.J., Consroe P. Enantiomeric cannabinoids: stereospecificity of psychotropic activity. Experientia. 44:1988;762-764.
112. Mechoulam R., Ben-Shabat S., Hanus L., Ligumsky M., Kaminski N.E., Schatz A.R., Gopher A., Almog S., Martin B.R., Compton D.R., Pertwee R.G., Griffin G., Bayewitch M., Barg J., Vogel Z. Identification of an endogenous 2-monoglyceride, present in canine gut, that binds to cannabinoid receptors. Biochem Pharmacol. 50:1995;83-90.
113. Mechoulam R., Fride E., Di Marzo V. Endocannabinoids. Eur J Pharmacol. 359:1998;1-18.
114. Merritt J.C., Crawfford W.J., Alexander P.C., Anduze A.L., Gelbart S.S. Effect of marihuana on intraocular and blood pressure in glaucoma. Ophthalmology. 877:1980;222-228.
115. 9-tetrahydrocannabinol in heterogenous glaucomas. Ann Ophthalmol. 12:1980;947-950.
116. 9-tetrahydrocannabinol and aqueous dynamics in glaucoma. J Clin Pharmacol. 21:1981;471S-476S.
117. 9-tetrahydrocannabinol and vehicle constituents on intraocular pressure in normotensive dogs. Res Comm Subst Abuse. 7:1986;29-35.
118. Mikawa Y., Matsuda S., Kanagawa T., Tajika T., Ueda N., Mimura Y. Ocular activity of topically administered anandamide in the rabbit. Jpn J Ophthalmol. 41:1997;217-220.
119. Muchtar S., Almog S., Torracca M.T., Saettone M.F., Benita S. A sub-micron emulsion as ocular vehicle for delta-8-tetrahydrocannabinol: effect on intraocular pressure in rabbits. Ophthalmic Res. 24:1992;142-149.
120. Munro S., Thomas K.L., Abu-Shaar M. Molecular characterization of a peripheral receptor for cannabinoids. Nature. 365:1993;61-65.
121. 2+ influx through the N-methyl-D-aspartate receptor ion channel by the non-psychoactive cannabinoid HU-211. Brain Res. 622:1993;79-85.
122. Nakanishi K., Masada M., Nadai T., Miyajima K. Effect of the interaction of drug-β-cyclodextrin complex with bile salts on the drug absorption from rat small intestinal lumen. Chem Pharm Bull. 37:1989;211-214.
123. Naveh N., Weissman C., Muchtar S., Benita S., Mechoulam R. A submicron emulsion of HU-211, a synthetic cannabinoid, reduces intraocular pressure in rabbits. Graefes Arch Exp Ophthalmol. 238:2000;334-339.
124. Netland P.A., Chaturvedi N., Dreyer E.B. Calcium channel blockers in the management of low-tension and open-angle glaucoma. Am J Ophthalmol. 115:1993;608-613.
125. Nickells R.W. Apoptosis of retinal ganglion cells in glaucoma: an update of the molecular pathways involved in cell death. Surv Ophthalmol. 43:1999;S151-S161.
126. Nickells R.W., Zack D.J. Apoptosis in ocular disease: a molecular overview. Ophthalmic Paediatr Genet. 17:1996;145-165.
127. Pate D.W., Järvinen K., Urtti A., Jarho P., Järvinen T. Ophthalmic arachidonyl ethanolamide decreases intraocular pressure in normotensive rabbits. Curr Eye Res. 14:1995;791-797.
128. Pate D.W., Järvinen K., Urtti A., Jarho P., Fich M., Mahadevan V., Järvinen T. Effects of topical anandamides on intraocular pressure in normotensive rabbits. Life Sci. 58:1996;1849-1860.
129. Pate D.W., Järvinen K., Urtti A., Jarho P., Mahadevan V., Järvinen T. Effects of topical alpha-substituted anandamides on intraocular pressure in normotensive rabbits. Pharm Res. 14:1997;1738-1743.
130. Pate D.W., Järvinen K., Urtti A., Mahadevan V., Järvinen T. Effect of the CB1 receptor antagonist, SR 141716A, on cannabinoid-induced ocular hypotension in normotensive rabbits. Life Sci. 63:1998;2181-2188.
131. + channels involved in neuronal cell death. Protection by flunarizine. Life Sci. 48:1991;1881-1893.
132. Pertwee R.G. Pharmacology of cannabinoid CB1 and CB2 receptors. Pharmacol Ther. 74:1997;129-180.
133. Pertwee R.G., Gibson T.M., Stevenson L.A., Ross R.A., Banner W.K., Saha B., Razdan R.K., Martin B.R. O-1057, a potent water-soluble cannabinoid receptor agonist with antinociceptive properties. Br J Pharmacol. 129:2000;1577-1584.
134. Piomelli D., Giuffrida A., Calignano A., de Fonseca F.R. The endocannabinoid system as a target for therapeutic drugs. Trends Pharmacol Sci. 21:2000;218-224.
135. Podos S.M., Becker B., Kass M.A. Prostaglandin synthesis, inhibition, and intraocular pressure. Invest Ophthalmol. 12:1973;426-433.
136. Podos S.M., Becker B., Kass M.A. Indomethacin blocks arachidonic acid-induced elevation of intraocular pressure. Prostaglandins. 3:1973;7-16.
137. Porcella A., Casellas P., Gessa G.L., Pani L. Cannabinoid receptor CB1 mRNA is highly expressed in the rat ciliary body: implications for the antiglaucoma properties of marihuana. Mol Brain Res. 58:1998;240-245.
138. Porcella A., Maxia C., Gessa G.L., Pani L. The human eye expresses high levels of CB1 cannabinoid receptor mRNA and protein. Eur J Neurosci. 12:2000;1123-1127.
139. Porcella A., Maxia C., Gessa G.L., Pani L. The synthetic cannabinoid WIN55212-2 decreases the intraocular pressure in human glaucoma resistant to conventional therapies. Eur J Neurosci. 13:2001;409-412.
140. Prunte C., Orgul S., Flammer J. Abnormalities of microcirculation in glaucoma: facts and hints. Curr Opin Ophthalmol. 9:1998;50-55.
141. Rajewski R.A., Stella V.J. Pharmaceutical applications of cyclodextrins. 2. In vivo drug delivery. J Pharm Sci. 85:1996;1142-1169.
142. Reddy I.K., Khan M.A., Wu W.-M., Bodor N.S. Permeability of a soft steroid loteprednol etabonate, through an excised rabbit cornea. J Ocul Pharmacol Ther. 12:1996;159-167.
143. Reer O., Bock T.K., Müller B.W. In vitro corneal permeability of diclofenac sodium in formulations containing cyclodextrins compared to commercial product voltaren ophtha. J Pharm Sci. 83:1994;1345-1349.
144. Resul B., Stjernschantz J., No K., Liljebris C., Selen G., Astin M., Bito L.Z. Phenyl-substituted prostaglandins: potent and selective antiglaucoma agents. J Med Chem. 36:1993;243-248.
145. Ritch R. Neuroprotection: is it already applicable to glaucoma therapy. Curr Opin Ophthalmol. 11:2000;78-84.
146. Rojanasakul Y., Wang L.-Y., Bhat M., Glover D.D., Malanga C.J., Ma J.K.H. The transport barrier of epithelia: a comparative study on membrane permeability and charge selectivity in the rabbit. Pharm Res. 9:1992;1029-1034.
147. Salminen L., Urtti A. Disposition of ophthalmic timolol in treated and untreated rabbit eyes. A multiple and single dose study. Exp Eye Res. 38:1984;203-206.
148. Sasaki H., Yamamura K., Mukai T., Nishida K., Nakamura J., Nakashima M., Ichikawa M. Enhancement of ocular drug penetration. Crit Rev Ther Drug Carrier Syst. 16:1999;85-146.
149. Schlicker E., Timm J., Göthert M. Cannabinoid receptor-mediated inhibition of dopamine release in the retina. Naunyn Schmiedebergs Arch Pharmacol. 354:1996;791-795.
150. Schoenwald R.D., Huang H.-S. Corneal penetration behaviour of β-blocking agents. I: physicochemical factors. J Pharm Sci. 72:1983;1266-1272.
151. Schoenwald R.D., Ward R. Relationship between steroid permeability across excited rabbit cornea and octanol-water partition coefficients. J Pharm Sci. 67:1978;786-788.
152. 2+ and other second messengers in excitatory amino acid receptor mediated neurodegeneration: clinical perspectives. Clin Neurosci. 4:1997;194-198.
153. Schwartz M., Yoles E. Optic nerve degeneration and potential neuroprotection: implications for glaucoma. Eur J Ophthalmol. 9:1999;S9-S11.
154. Schwartz M., Yoles E. Neuroprotection: a new treatment modality for glaucoma. Curr Opin Ophthalmol. 11:2000;107-111.
155. Shohami E., Gallily R., Mechoulam R., Bass R., Ben-Hur T. Cytokine production in the brain following closed head injury: dexanabinol (HU-211) is a novel TNF-alpha inhibitor and an effective neuroprotectant. J Neuroimmunol. 72:1997;169-177.
156. Showalter V.M., Compton D.R., Martin B.R., Abood M.E. Evaluation of binding in a transfected cell line expressing a peripheral cannabinoid receptor (CB2): identification of cannabinoid receptor subtype selective ligands. J Pharmacol Exp Ther. 278:1996;989-999.
157. Siefert B., Keipert S. Influence of alpha-cyclodextrin and hydroxylated β-cyclodextrin derivatives on the in vitro corneal uptake and permeation of aqueous pilocarpine-HCL solutions. J Pharm Sci. 86:1997;716-720.
158. Siefert B., Pleyer U., Muller M., Hartmann C., Keipert S. Influence of cyclodextrins on the in vitro corneal permeability and in vivo ocular distribution of thalidomide. J Ocul Pharmacol Ther. 15:1999;429-438.
159. Sigurdardottir A.M., Loftsson T. The effect of polyvinylpyrrolidone on cyclodextrin complexation of hydrocortisone and its diffusion through hairless mouse skin. Int J Pharm. 126:1995;73-78.
160. Skaper S.D., Buriani A., Dal-Toso R., Petrelli L., Romanello S., Facci L., Leon A. The ALIAmide palmitoylethanolamide and cannabinoids, but not anandamide, are protective in a delayed postglutamate paradigm of excitotoxic death in cerebellar granule neurons. Proc Natl Acad Sci USA. 93:1996;3984-3989.
161. Sommer A., Tielsch J.M., Katz J., Quigley H.A., Gottsch J.D., Javitt J., Singh K. Relationship between intraocular pressure and primary open angle glaucoma among white and black Americans. Arch Ophthalmol. 109:1991;1090-1095.
162. Song Z.-H., Slowey C.-A. Involvement of cannabinoid receptors in the intraocular pressure-lowering effects of WIN55212-2. J Pharmacol Exp Ther. 292:2000;136-139.
163. Stella V.J., Rao V.M., Zannou E.A., Zia V. Mechanisms of drug release from cyclodextrin complexes. Adv Drug Delivery Rev. 36:1999;3-16.
164. Straiker A.J., Maguire G., Mackie K., Lindsey J. Localization of the cannabinoid CB1 receptors in human anterior eye and retina. Invest Ophthalmol Vis Sci. 40:1999;2442-2448.
165. Straiker A., Stella N., Piomelli D., Mackie K., Karten H.J., Maguire G. Cannabinoid CB1 receptors and ligands in vertebrate retina: localization and function of an endogenous signalling system. Proc Natl Acad Sci USA. 96:1999;14565-14570.
166. Sucher N.J., Lipton S.A., Dreyer E.B. Molecular basis of glutamate toxicity in retinal ganglion cells. Vision Res. 37:1997;3483-3493.
167. Sugiura T., Kondo S., Sukagawa A., Nakane S., Shinoda A., Itoh K., Yamashita A., Waku K. 2-Arachidonoylglycerol: a possible endogenous cannabinoid receptor ligand in brain. Biochem Biophys Res Commun. 215:1995;89-97.
168. Sugrue M.F. New approaches to antiglaucoma therapy. J Med Chem. 40:1997;2793-2809.
169. Sugrue M.F., Funk H.A., Leonard Y., O'Neill-Davis L., Labelle M. The ocular hypotensive effects of synthetic cannabinoids. Invest Ophthalmol Vis Sci. 37:1996;S831.
170. Szejtli J. Cyclodextrin Technology. 1988;Kluwer Academic Publishers, Dordrecht.
171. Szente L., Szejtli J. Highly soluble cyclodextrin derivatives: chemistry, properties, and trends in development. Adv Drug Delivery Rev. 36:1999;17-28.
172. Thompson D.O. Cyclodextrins-enabling excipients: their present and future use in pharmaceuticals. Crit Rev Ther Drug Carrier Syst. 14:1997;1-328.
173. Ueda N., Kurahashi Y., Yamamoto S., Tokunaga T. Partial purification and characterization of the porcine brain enzyme hydrolyzing and synthesizing anandamide. J Biol Chem. 40:1995;23823-23827.
174. Urtti A., Salminen L. A comparison between iris-ciliary body concentration and receptor affinity of timolol. Acta Ophthalmol. 63:1985;16-18.
175. Urtti A., Salminen L. Minimizing systemic absorption of topically administered ophthalmic drugs. Surv Ophthalmol. 37:1993;435-456.
176. Waller C.W., Benigni Q.A., Harland E.C., Bedford J.A., Murphy J.C., ElSohly M.A. Cannabinoids in glaucoma III: the effects of different cannabinoids on intraocular pressure in the monkey. Agurell S., Dewey W.L., Wllette R.E. The Cannabinoids: Chemical, Pharmacologic and Therapeutic Aspects. 1984;871-880 Academic Press Inc. New York.
177. Wang W., Sasaki H., Chien D.-S., Lee V.H.L. Lipophilicity influence on conjunctival drug penetration in the pigmented rabbit: a comparison with corneal penetration. Curr Eye Res. 10:1991;571-579.
178. Watsky M.A., Jablonski M.M., Edelhauser H.F. Comparison of conjunctival and corneal surface areas in rabbit and human. Curr Eye Res. 7:1988;483-486.
179. Woodward D.F., Krauss A.H.-P., Chen J., Lai R.K., Spada C.S., Burk
180. Yazulla S., Studholme K.M., McIntosh H.H., Deutsch D.G. Immunocytochemical localization of cannabinoid CB1 receptor and fatty acid amide hydrolase in rat retina. J Comp Neurol. 415:1999;80-90.
181. Yazulla S., Studholme K.M., McIntosh H.H., Fan S.-F. Cannabinoid receptors on goldfish retinal bipolar cells: electron-microscope immunocytochemistry and whole-cell recordings. Vis Neurosci. 17:2000;391-401.
182. Yoles E., Belkin M., Schwartz M. HU-211, a nonpsychoactive cannabinoid, produces short- and long-term neuroprotection after optic nerve axotomy. J Neurotrauma. 13:1996;49-57.
183. + efflux and neuronal apoptosis. Science. 284:1999;336-339.
184. Zhang M.-Q., Rees D.C. A review of recent applications of cyclodextrins for drug discovery. Expert Opin Ther Patents. 9:1999;1697-1717.