Scope and limitations of the co-drug approach to topical drug delivery

Current Pharmaceutical Design

Volumn 14, Issue 8, 2008, Pages 794-802

  Lau, W M ^a   White, A W ^a   Gallagher, S J ^b   Donaldson, M ^b   McNaughton, G ^b   Heard, C M ^a  

^a CARDIFF UNIVERSITY   (United Kingdom)

^b Stiefel Laboratories   (United Kingdom)

Author keywords

Co drug; Combination therapy; Dermal drug delivery; Drug design; Pro drug; Skin; Transdermal drug delivery

Indexed keywords

ACETYLSALICYLIC ACID; ALPHA TOCOPHEROL; ANALGESIC AGENT; ANTIBIOTIC AGENT; ANTIINFECTIVE AGENT; ANTIOXIDANT; ASCORBIC ACID; ASCORBIC ACID DERIVATIVE; ATENOLOL; AZELAIC ACID; BETAMETHASONE VALERATE; CALCIPOTRIOL; CARBONIC ACID; COCODAMOL; ETACRYNIC ACID; FAMCICLOVIR; IBUPROFEN; KERATOLYTIC AGENT; LINOLEIC ACID; METFORMIN PLUS ROSIGLITAZONE; NALTREXOL; NALTREXONE; POLYUNSATURATED FATTY ACID; PRODRUG; RADAFAXINE; RETINOIC ACID; RETINYLASCORBIC ACID; SALICYLIC ACID; UNINDEXED DRUG; VALACICLOVIR;

ACNE; ALCOHOLISM; CONJUNCTIVAL HYPEREMIA; CORNEA EPITHELIUM; COVALENT BOND; DRUG DELIVERY SYSTEM; DRUG PENETRATION; DRUG SOLUBILITY; DRUG STABILITY; DRUG STRUCTURE; DRUG SYNTHESIS; EYELID EDEMA; GLAUCOMA; HUMAN; HYDROLYSIS; MONOTHERAPY; NARCOTIC DEPENDENCE; NONHUMAN; OXIDATIVE STRESS; PHYSICAL CHEMISTRY; PRIORITY JOURNAL; PSORIASIS; REVIEW; SKIN DISEASE; SKIN PENETRATION; SKIN PROTECTION; TOPICAL TREATMENT;

ADMINISTRATION, TOPICAL; DERMATOLOGIC AGENTS; DRUG COMBINATIONS; DRUG DELIVERY SYSTEMS; DRUG DESIGN; DRUG SYNERGISM; EYE; HUMANS; OCULAR PHYSIOLOGY; OPHTHALMIC SOLUTIONS; PERMEABILITY; PRODRUGS; SKIN ABSORPTION; SKIN DISEASES;

EID: 44349122974     PISSN: 13816128     EISSN: None     Source Type: Journal    
DOI: 10.2174/138161208784007653     Document Type: Review

References (50)

1. Bonina FP, Puglia C, Barbuzzi T, de Caprariis P, Palagiano F, Rimoli MG. et al. In vitro and in vivo evaluation of polyoxyethylene esters as dermal prodrugs of ketoprofen, naproxen and declofenac. Eur J Pharm Sci 2001; 14: 123-34.
2. Prausnitz MR. Microneedles for transdermal drug delivery. Adv Drug Del Rev 2004; 56: 581-7.
3. Kassan DG, Lynch AM, Stiller MJ. Physical enhancement of dermatologic drug delivery: Lontophoresis and phomphoresis. J Am Acad Dermatol 1996; 34: 657-66.
4. Vanbever R, Leroy M-A, Preat V. Transdermal permeation of neutral molecules by skin electroporation. J Control Release 1998; 54: 243-50
5. Barry BW. Novel mechanisms and devices to enable successful transdermal drug delivery. Eur J Pharm Sci 2001; 14: 101-14.
6. Williams AC, Barry BW. Penetration enhancers. Adv Drug Del Rev 2004; 56: 603-188.
7. De Clercq E. Antiviral drugs: Current state of the art. J Clin. Virol. 2001; 22: 73-89.
8. De Clercq E, Field HJ Antiviral prodrugs - the development of successful prodrug strategies for antiviral chemotherapy. Br. J Pharmacol 2006; 147: 1-11.
9. Ormrod D, Goa K. Valaciclovir - A review of its use in the management of herpes zoster. Drugs 2000; 59: 1317-40.
10. Guo AL, Hu PD, Balimane PV, Leibach FH, Sinko PJ interactions of a nonpeptidic drug, valacyclovir, with the human intestinal peptide transporter (hPEPT1) expressed in a mammalian cell line. J Pharmacol Exp Ther 1999; 299: 449-54.
11. Gupta AK, Chow M. A review of prednicarbate (Dermatop). Skin Ther Lett 2004; 9: 5-6.
12. Hammell DC, Hamad M, Vaddi HK, Crooks PA, Stinchcomb AL. A duplex "Gemini" prodiug of naltrexone for transdermal delivery. J Control Release 2004; 97: 293-90.
13. Berger AS, Cheng CK, Pearson PA, Ashton P, Crooks PA, Cynkowski T, et al. Intravitreal sustained release corticosteroid-5-fluoruracil conjugate in the treatment of experimental proliferative vitteoretinopathy. Invest Ophthalmol Vis Sci 1996; 37: 2318-25.
14. Howard-Sparks M, Al-Ghananeem A, Pearson A, Crooks P. Evaluation of O3α-, O21-Di-(N1-methyloxycarbonyl-2, 4-dioxo-5-fluoropyrimidinyl)17α-hydroxy-5β-pregnan-20-one as a novel potential antiangiogenic codrug. J Enzyme Inhib Med Chem 2005; 20: 417-28.
15. Kiptoo PK, Hamad MO, Crooks PA, Stinchcomb AL. Enhancement of transdermal delivery of 6-beta-naltrexol via a coding linked to hydroxybupropion. J Control Release 2006: 113: 137-45.
16. Hamad MO, Kiptoo PK, Stinchcomb AL, Crooks PA. Synthesis and hydrolytic behavior of two novel tripartate codrugs of naltrexone and 6[beta]-naltrexol with hydroxybopropion as potential alcohol abuse and smoking cessation agents. Bioorg Med Chem 2006; 14: 7051-61.
17. Jones RN, Barry AL, Thornsberry C. Antimicrobial activity of Ro 23-9424, a novel ester-linked codrug of fleroxacin and desacetylcefotaxime. Antimicrob Agents Chemother 1989; 33; 944-50.
18. Jones RN, Croco JL, Barrett MS, Novick WJ, Erwin ME. Antimicrobial spectrum of cefpirome combined with tazobactam against the Bacteroides fragilis group. Diagn Microbiol Infect Dis 1990; 13: 371-3.
19. Jones RN, Marshall SA, Varnam DJ. Activity of a broad-spectrum cephalosporin (Ro 49-9391) alone and in combination with two novel [beta]-lactamase inhibitors (Ro 48-5545 and Ro 48-8724). Diagn Microbiol Infect Dis 1998; 32: 85-94.
20. DiStefano A, Sozio P, Cocco A, Iannitelli A, Santucci E, Costa M, et al. L-dopa- and dopamine-(R)-α-lipoic acid conjugates as multifunctional codrugs with antioxidant properties. J Med Chem 2006; 49: 1486-3.
21. Leppanen J, Huuskonen J, Nevalainen T, Gynther J, Taipale H, Jarvinen T. Design and synthesis of a novel L-dopa-entacapone codrug. J Med Chem 2002; 45: 1379-82.
22. Sheba M, Khedr A, Elsherief H. Biological and metabolic study of naproxen-propyphenazone mutual prodrug. Eur J Pharm Sci 2002; 17: 121-30.
23. Otagiri M, Imai T, Fukuhara A. Improving the pharmacokinetic and pharmacodynamic properties of a drug by chemical conversion to a chimera drug. J Control Release 1999; 62: 223-9.
24. Sun X-F, Wu Q, Wang N, Cai Y, Lin X-F. Novel mutual pro-drugs of 2′,3′-dideoxyinosine with 3-octadecyloxy-propane-1,2-diol by straightforward enzymatic regioselective synthesis in acetone. Biotechnol Lett 2005; 27: 113-7.
25. Coradini D, Pellizzaro C, Scarlata I, Zorzet S, Garrovo C, Abolafio G, et al. A novel retinoic/butyric hyaluronan ester for the treatment of acute promyelocytic leukemia: Preliminary preclinical results. Leukemia 2006; 20: 785-92.
26. Nudelman A, Rephaeli A. Novel mutual prodrug of retinoic and butyric acids with enhanced anticancer activity. J Med Chem 2000; 43: 2962-6
27. Menger FM, Rourk MJ Synthesis and reactivity of 5-fluorouracil/ cytarabine mutual prodrugs. J Org Chem 1997; 62: 9083-8.
28. Bos JD, Meinardi MMHM. The 500 Dalton rule for the skin penetration of chemical compounds and drugs. Exp Dermatol 2000; 9: 165-9.
29. Nazemi MH, Brain KR, Heard CM. In: Brain KR, Walters KA, Eds.; Perspectives in percutaneous penetration. STS Publishing: Cardiff 2000; Vol. 7: 67.
30. Guy RH, Potts RO. Structure-permeability relationships in percutaneous penetration. J Pharm Sci 1992; 81: 603-4.
31. Shindo Y, Witt E, Han D, Epstein W, Packer L. Enzymic and non-enzymic antioxidants in epidermis and dermis of human skin. J Invest Dermatol 1994; 102: 122-4.
32. Lupo MP. Antioxidants and vitamins in cosmetics. Clin Dermatol 2001; 19: 467-73.
33. Abdulmajed K, Heard CM. Topical delivery of retinyl ascorbate co-drug: 1. Synthesis, penetration into and permeation across human skin. Int J Pharm 2004; 280: 113-24.
34. Abdulmajed K, McGuigan C, Heard CM. Topical delivery of retinyl ascorbate co-drug: 5. In vitro degradation studies. Skin Pharmacol Phys 2006; 19: 248-58.
35. Abdulmajed K, Heard CM, McGuigan C, Pugh WJ Topical delivery of retinyl ascorbate co-drug: 2. Comparative skin tissue and keratin binding studies. Skin Pharmacol Phys 2004; 17: 274-82.
36. Abdulmajed K, McGuigan C, Heard CM. Topical delivery of retinyl ascorbate: 4. Comparative anti-oxidant activity towards DPPH. Free Radic Res 2005; 39: 491-8.
37. Abdulmajed K, McGuigan C, Heard CM. Topical delivery of retinyl ascorbate co-drug: 6. Determination of toxic dose and antioxidant activity in cultured human epidermal keratinocytes. Pharmazie 2005; 60: 794-5.
38. Ostacolo C, Marra F, Laneri S, Sacchi A, Nicoli S, Padula C, et al. α-Tocopherol pro-vitamins: Synthesis, hydrolysis and accumulation in tabbit ear skin. J Control Release 2004; 99; 403-14
39. Sintov AC, Behar-Canetti C, Friedman Y, Tamarkin D. Percutaneous penetration and skin metabolism of ethylsalicylate-containing agent, TU-2100: in-vitro and in-vivo evaluation in guinea pigs. J Control Release 2002; 79: 113-22.
40. Christophers E, Mrowietz U. In: Freedberg IM, Eisen AZ, Wolff K, Austen KF, Goldsmith LA, Katz SI, Eds. Fitzpatrick's dermatology in general medicine, Mc Graw-Hill: New York 2003; Vol. 6.
41. Lebwohl M, Menter A, Koo J, Feldman SR. Combination therapy to treat moderate to severe psoriasis. J Am Acad Dermatol 2004; 50: 416-30.
42. Kragballe K, Noerrelund KL, Liu H, Ortonne JP, Wozel G, Uurasmaa T, et al. Efficacy of once-daily treatment regimens with calcipotriol/betamethasone dipropionate ointment and calcipotriol ointment in psoriasis vulgaris. Br. J Dermatol 2004; 150: 1167-73.
43. Kirby C, Davison M, Emerson Z, Chalmers S, Barker N, Griffiths A. Combination treatment with methotre-xate and cyclosporin for severe recalcitrant psoriasis. Br J Dermatol 1999; 141: 279-82.
44. Ben-Shabat S, Benisty R, Wormser U, Sintov AC. Vitamin D3-based conjugates for topical treatment of psoriasis: Synthesis, antiproliferative activity, and cutaneous penetration studies. Pharm Res 2005; 22: 50-7.
45. Mayser P, Grimm H, Grimminger F. n-3 Fatty acids in psoriasis. Br J Nutr 2002; 87: 77.
46. Jarvinen K, Jarvinen T, Urtti A. Ocular absorption following topical delivery. Adv Drug Deliv Rev 1995; 16: 3-19.
47. Cynkowska G, Cynkowski T, Al-Ghananeem AA, Guo H, Ashton P, Crooks PA. Novel antiglaucoma prodrugs and codrugs of ehtacrynic acid. Bioorg Med Chem Lett 2005; 15: 3524-7.
48. Fry FH, Jacob C. Sensor/effector drug design with potential relevance to cancer. Curr Pharm Des 2006; 12(34): 4479-99.
49. Lefebvre HP, Brown SA, Chetboul V, King JN, Pouchelon JL, Toutain PL. Angiotensin-converting enzyme inhibitors in veterinary medicine. Curr Pharm Des 2007; 13(13): 1347-61.
50. Leonetti C, Zupi G. Targeting different signaling pathways with antisense oligonucleotide combination for cancer therapy. Curr Pharm Des 2007; 13(5): 463-70.