An effective prodrug strategy to selectively enhance ocular exposure of a cannabinoid receptor (CB1/2) agonist

Journal of Medicinal Chemistry

Volumn 56, Issue 13, 2013, Pages 5464-5472

  Mainolfi, Nello ^a   Powers, James ^a   Amin, Jakal ^a   Long, Debby ^a   Lee, Wendy ^a   McLaughlin, Margaret E ^a   Jaffee, Bruce ^a   Brain, Christopher ^a   Elliott, Jason ^a   Sivak, Jeremy M ^a,b  

^a NOVARTIS INSTITUTES FOR BIOMEDICAL RESEARCH   (United States)

^b UNIVERSITY OF TORONTO   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

CANNABINOID 1 RECEPTOR AGONIST; CANNABINOID 2 RECEPTOR AGONIST;

ANIMAL EXPERIMENT; ARTICLE; DRUG ABSORPTION; DRUG DELIVERY SYSTEM; DRUG EFFICACY; DRUG EXPOSURE; DRUG FORMULATION; DRUG HALF LIFE; DRUG IDENTIFICATION; DRUG METABOLISM; DRUG PENETRATION; DRUG SAFETY; DRUG SCREENING; DRUG SELECTIVITY; DRUG SOLUBILITY; DRUG STABILITY; DRUG SYNTHESIS; MALE; NONHUMAN; RAT;

ANIMALS; AREA UNDER CURVE; EYE; GLAUCOMA; HUMANS; INTRAOCULAR PRESSURE; MALE; METABOLIC CLEARANCE RATE; MODELS, CHEMICAL; MOLECULAR STRUCTURE; OPHTHALMIC SOLUTIONS; PERMEABILITY; PRODRUGS; RATS; RECEPTOR, CANNABINOID, CB1; RECEPTOR, CANNABINOID, CB2;

EID: 84880146840     PISSN: 00222623     EISSN: 15204804     Source Type: Journal    
DOI: 10.1021/jm4004939     Document Type: Article

References (39)

1. Quigley, H. A.; Broman, A. T. The number of people with glaucoma worldwide in 2010 and 2020 Br. J. Ophthalmol. 2006, 90, 262-267
2. Vajaranant, T. S.; Wu, S.; Torres, M.; Varma, R. A 40-year forecast of the demographic shift in primary open-angle glaucoma in the United States Invest. Ophthalmol. Vis. Sci. 2012, 53, 2464-2466
3. Heijl, A.; Leske, M. C.; Bengtsson, B.; Hyman, L.; Hussein, M. Reduction of intraocular pressure and glaucoma progression: results from the Early Manifest Glaucoma Trial Arch. Ophthalmol. 2002, 120, 1268-1279
4. Kass, M. A.; Heuer, D. K.; Higginbotham, E. J.; Johnson, C. A.; Keltner, J. L.; Miller, J. P.; Parrish, R. K., II; Wilson, M. R.; Gordon, M. O. The Ocular Hypertension Treatment Study: a randomized trial determines that topical ocular hypotensive medication delays or prevents the onset of primary open-angle glaucoma Arch. Ophthalmol. 2002, 120, 701-713 discussion pp 829-830
5. Coman, O. A.; Paunescu, H.; Coman, L.; Badarau, A.; Fulga, I. Recent data on cannabinoids and their pharmacological implications in neuropathic pain J. Med. Life 2008, 1, 365-375
6. Miller, L. K.; Devi, L. A. The highs and lows of cannabinoid receptor expression in disease: mechanisms and their therapeutic implications Pharmacol. Rev. 2011, 63, 461-470
7. Hepler, R. S.; Frank, I. R. Marihuana smoking and intraocular pressure JAMA, J. Am. Med. Assoc. 1971, 217, 1392
8. Merritt, J. C.; Crawford, W. J.; Alexander, P. C.; Anduze, A. L.; Gelbart, S. S. Effect of marihuana on intraocular and blood pressure in glaucoma Ophthalmology 1980, 87, 222-228
9. Tomida, I.; Pertwee, R. G.; Azuara-Blanco, A. Cannabinoids and glaucoma Br. J. Ophthalmol. 2004, 88, 708-713
10. Allen, R. C.; Sheppard, III, J. D.; Lattanzio, Jr., F.; Lichtman, A.; Crouch, Jr., E.; Williams, P. Ocular and Systemic Effects of WIN 55-212-2 in Normotensive Rabbits. Invest. Ophthalmol. Vis. Sci. 2003, 44, ARVO E-Abstract 4423.
11. Chien, F. Y.; Wang, R. F.; Mittag, T. W.; Podos, S. M. Effect of WIN 55212-2, a cannabinoid receptor agonist, on aqueous humor dynamics in monkeys Arch. Ophthalmol. 2003, 121, 87-90
12. 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. 2001, 13, 409-412
13. Hosseini, A.; Lattanzio, F. A.; Williams, P. B.; Tibbs, D.; Samudre, S. S.; Allen, R. C. Chronic topical administration of WIN-55-212-2 maintains a reduction in IOP in a rat glaucoma model without adverse effects Exp. Eye Res. 2006, 82, 753-759
14. Straiker, A. J.; Maguire, G.; Mackie, K.; Lindsey, J. Localization of cannabinoid CB1 receptors in the human anterior eye and retina Invest. Ophthalmol. Vis. Sci. 1999, 40, 2442-2448
15. Zhong, L.; Geng, L.; Njie, Y.; Feng, W.; Song, Z. H. CB2 cannabinoid receptors in trabecular meshwork cells mediate JWH015-induced enhancement of aqueous humor outflow facility Invest. Ophthalmol. Vis. Sci. 2005, 46, 1988-1992
16. Dyson, A.; Peacock, M.; Chen, A.; Courade, J. P.; Yaqoob, M.; Groarke, A.; Brain, C.; Loong, Y.; Fox, A. Antihyperalgesic properties of the cannabinoid CT-3 in chronic neuropathic and inflammatory pain states in the rat Pain 2005, 116, 129-137
17. Adam-Worrall, J.; Hill, D. R.; Cottney, J. Synergistic combination for the treatment of pain cannabinoid receptor agonist and opiod receptor agonist. PCT Int. Appl. WO 2007006732, 2007.
18. Brain, C. T.; Dziadulewicz, E. K.; Hart, T. W. Preparation of quinazolinone derivatives as a CB agonist. PCT Int. Appl. WO 2003066603, 2003.
19. Pryce, G. Cannabinoids for the control of experimental multiple sclerosis. PhD Thesis. Queen Mary University of London, London, UK, 2010.
20. Chen, J.; Runyan, S. A.; Robinson, M. R. Novel ocular antihypertensive compounds in clinical trials Clin. Ophthalmol. 2011, 5, 667-777
21. Rautio, J.; Kumpulainen, H.; Heimbach, T.; Oliyai, R.; Oh, D.; Jarvinen, T.; Savolainen, J. Prodrugs: design and clinical applications Nature Rev. Drug Discovery 2008, 7, 255-270
22. Barot, M.; Bagui, M.; Gokulgandhi, M. R.; Mitra, A. K. Prodrug strategies in ocular drug delivery Med. Chem. 2012, 8, 753-768
23. Duvvuri, S.; Majumdar, S.; Mitra, A. K. Role of metabolism in ocular drug delivery Curr. Drug Metab. 2004, 5, 507-515
24. Cocohoba, J. M.; McNicholl, I. R. Valganciclovir: an advance in cytomegalovirus therapeutics Ann. Pharmacother. 2002, 36, 1075-1079
25. Gaudana, R.; Ananthula, H. K.; Parenky, A.; Mitra, A. K. Ocular drug delivery AAPS J. 2010, 12, 348-360
26. Jampel, H. American Glaucoma Society position statement: marijuana and the treatment of glaucoma J. Glaucoma 2010, 19, 75-76
27. Lee, V. H.; Chang, S. C.; Oshiro, C. M.; Smith, R. E. Ocular esterase composition in albino and pigmented rabbits: possible implications in ocular prodrug design and evaluation Curr. Eye Res. 1985, 4, 1117-1125
28. Chang, S. C.; Bundgaard, H.; Buur, A.; Lee, V. H. Improved corneal penetration of timolol by prodrugs as a means to reduce systemic drug load Invest. Ophthalmol. Vis. Sci. 1987, 28, 487-491
29. Bundgaard, H.; Falch, E.; Larsen, C.; Mikkelson, T. J. Pilocarpine prodrugs I. Synthesis, physicochemical properties and kinetics of lactonization of pilocarpic acid esters J. Pharm. Sci. 1986, 75, 36-43
30. Bundgaard, H.; Falch, E.; Larsen, C.; Mosher, G. L.; Mikkelson, T. J. Pilocarpine prodrugs. II. Synthesis, stability, bioconversion, and physicochemical properties of sequentially labile pilocarpine acid diesters J. Pharm. Sci. 1986, 75, 775-783
31. Cynkowska, G.; Cynkowski, T.; Al-Ghananeem, A. M.; Guo, H.; Ashton, P.; Crooks, P. A. Novel antiglaucoma prodrugs and codrugs of ethacrynic acid Bioorg. Med. Chem. Lett. 2005, 15, 3524-3527
32. Katragadda, S.; Talluri, R. S.; Mitra, A. K. Simultaneous modulation of transport and metabolism of acyclovir prodrugs across rabbit cornea: An approach involving enzyme inhibitors Int. J. Pharm. 2006, 320, 104-113
33. Tirucherai, G. S.; Dias, C.; Mitra, A. K. Corneal permeation of ganciclovir: mechanism of ganciclovir permeation enhancement by acyl ester prodrug design J. Ocul. Pharmacol. Ther. 2002, 18, 535-548
34. Prasanna, G.; Carreiro, S.; Anderson, S.; Gukasyan, H.; Sartnurak, S.; Younis, H.; Gale, D.; Xiang, C.; Wells, P.; Dinh, D.; Almaden, C.; Fortner, J.; Toris, C.; Niesman, M.; Lafontaine, J.; Krauss, A. Effect of PF-04217329 a prodrug of a selective prostaglandin EP(2) agonist on intraocular pressure in preclinical models of glaucoma Exp. Eye Res. 2011, 93, 256-264
35. Becker, U.; Ehrhardt, C.; Schneider, M.; Muys, L.; Gross, D.; Eschmann, K.; Schaefer, U. F.; Lehr, C. M. A comparative evaluation of corneal epithelial cell cultures for assessing ocular permeability ATLA, Altern. Lab. Anim. 2008, 36, 33-44
36. Dey, S. Corneal cell culture models: a tool to study corneal drug absorption Expert Opin. Drug Metab. Toxicol. 2011, 7, 529-532
37. Kadam, R. S.; Cheruvu, N. P.; Edelhauser, H. F.; Kompella, U. B. Sclera-choroid-RPE transport of eight beta-blockers in human, bovine, porcine, rabbit, and rat models Invest. Ophthalmol. Vis. Sci. 2011, 52, 5387-5399
38. Qi, H. P.; Gao, X. C.; Zhang, L. Q.; Wei, S. Q.; Bi, S.; Yang, Z. C.; Cui, H. In vitro evaluation of enhancing effect of borneol on transcorneal permeation of compounds with different hydrophilicities and molecular sizes Eur. J. Pharmacol. 2013, 705, 20-25
39. Ghate, D.; Edelhauser, H. F. Barriers to glaucoma drug delivery J. Glaucoma 2008, 17, 147-156