Local skin pharmacokinetics of talarozole, a new retinoic acid metabolism-blocking agent

Skin Pharmacology and Physiology

Volumn 24, Issue 3, 2011, Pages 151-159

  Baert, B ^a   De Spiegeleer, B ^a  

^a GHENT UNIVERSITY   (Belgium)

Author keywords

Retinoic acid metabolism blocking agent; Skin pharmacokinetics; Talarozole

Indexed keywords

ALCOHOL; DIETHYLENE GLYCOL MONOETHYL ETHER; MYRISTIC ACID ISOPROPYL ESTER; PROPYLENE GLYCOL; RETINOID; TALAROZOLE;

ARTICLE; CLINICAL ARTICLE; CONTROLLED STUDY; DRUG CONCENTRATION; DRUG DIFFUSION; DRUG DISTRIBUTION; DRUG METABOLISM; EPIDERMIS; FEMALE; HUMAN; HUMAN TISSUE; PRIORITY JOURNAL; SKIN;

ADMINISTRATION, CUTANEOUS; ADULT; BENZOTHIAZOLES; CYTOCHROME P-450 ENZYME SYSTEM; FEMALE; HUMANS; MIDDLE AGED; SKIN ABSORPTION; SOLVENTS; TISSUE DISTRIBUTION; TRIAZOLES;

EID: 78651259874     PISSN: 16605527     EISSN: None     Source Type: Journal    
DOI: 10.1159/000323012     Document Type: Article

References (40)

1. Wolf JE: Potential anti-inflammatory effects of topical retinoids and retinoid analogues. Adv Ther 2002; 19: 109-118.
2. Miller WH: The emerging role of retinoids and retinoic acid metabolism blocking agents in the treatment of cancer. Cancer 1998; 83:1471-1482.
3. Fontana JA, Rishi AK: Classical and novel retinoids: their targets in cancer therapy. Leukemia 2002; 16: 463-472. (Pubitemid 34449726)
4. Altucci L, Gronemeyer H: The promise of retinoids to fight against cancer. Nat Rev Cancer 2001; 1:181-193. (Pubitemid 33741893)
5. Trapasso E, Cosco D, Celia C, Fresta M, Pao-lino D: Retinoids: new use by innovative drug-delivery systems. Expert Opin Drug Deliv 2009; 6:465-483.
6. Wang Y, Serradell N: R-115866-retinoic acid metabolism-blocking agent, treatment of psoriasis, treatment of acne. Drug Future 2007; 32:1040-1045. (Pubitemid 351461841)
7. Geria AN, Scheinfeld NS: Talarozole, a selec-tive inhibitor of P450-mediated all-trans ret-inoic acid for the treatment of psoriasis and acne. Curr Opin Investig Drugs 2008; 9: 1228-1237.
8. Verfaille CJ, Coel M, Boersma IH, Mertens J, Borgers M, Roseeuw D: Oral R115866 in the treatment of moderate to severe facial acne vulgaris: an exploratory study. Br J Dermatol 2007; 157:122-126. (Pubitemid 46934244)
9. Verfaille CJ, Thissen C, Bovenschen HJ, Mertens J, Steijlen PM, van de Kerkhof PCM: Oral R115866 in the treatment of moderate to severe plaque-type psoriasis. J Eur Acad Dermatol Venereol 2007; 21:1038-1046. (Pubitemid 47304603)
10. Kuijpers ALA, van Pelt JPA, Bergers M, Boegheim PJ, den Bakker JEN, Siegenthaler G, van de Kerkhof PCM, Schalkwijk J: The effects of oral liarozole on epidermal prolif-eration and differentiation in severe plaque psoriasis are comparable with those of acitretin. Br J Dermatol 1998; 139: 380-389. (Pubitemid 28430452)
11. TM for plaque psoriasis: an immunohistochemical study. Br J Dermatol 2007; 156: 263-270. (Pubitemid 46095953)
12. Griffiths C, van de Kerkhof P, Steijlen P, Shroot CB: Talarozole for moderate to severe plaque psoriasis-results of a dose-finding study. J Invest Dermatol 2008; 128: 358.
13. Thacher SM, Vasudevan J, Tsang KY, Nagpal S, Chandraratna RAS: New dermatological agents for the treatment of psoriasis. J Med Chem 2001; 44: 281-297. (Pubitemid 32113578)
14. Verfaille CJ, Steijlen PM, van de Kerkhof PCM, Stoppic P, van Wauwe JP, van Rossem K: R115866 (Rambazole): a potential alterna-tive for retinoids in the treatment of psoria-sis. J Eur Acad Dermatol Venereol 2007; 21: 21-21.
15. Van Steensel MAM: Emerging drugs for ichthyosis. Expert Opin Emerg Drugs 2007; 12:647-656.
16. Rizova E, Pagnoni A, Stoudemayer T, Poncet M, Kligman AM: Polarized light photogra-phy and videomicroscopy greatly enhances the capacity of estimating the therapeutic re-sponse to a topical retinoid (adapalene) in acne vulgaris. Cutis 2001; 68:25-33.
17. Goodman AB, Pardee AB: Evidence for de-fective retinoid transport and function in late onset Alzheimer's disease. Proc Natl Acad Sci USA 2003; 100: 2901-2905. (Pubitemid 36297596)
18. Shudo K Fukasawa H, Nakagomi M, Yamagata N: Towards retinoid therapy for Alzheimer's disease. Curr Alzheimer Res 2009; 6:302-311.
19. Vahlquist A: Retinoids and the skin: from vi-tamin A in human epidermis to the pharma-cology of oral retinoids in dermatology; in Vahlquist A, Duvic M (eds): Retinoids and Carotenoids in Dermatology. New York, In-forma Healthcare, 2007, pp 55-68.
20. Njar VCO, Gediya L, Purushottamachar P, Chopra P, Vasaitis TS, Khandelwal A, Mehta J, Huynh C, Belosay A, Patel J: Retinoic acid metabolism blocking agents (RAMBAs) for treatment of cancer and dermatological dis-eases. Bioorg Med Chem 2006; 14:4323-4340. (Pubitemid 43728662)
21. Patel JB, Khandelwal A, Chopra P, Handrat-ta VD, Njar VCO: Murine toxicology and pharmacokinetics of novel retinoic acid me-tabolism blocking agents. Cancer Chemo-ther Pharmacol 2007; 60:899-905. (Pubitemid 47389397)
22. Thatcher JE, Isoherranen N: The role of CYP26 enzymes in retinoic acid clearance. Expert Opin Drug Metab Toxicol 2009; 5: 875-886.
23. McCaffery P, Simons C: Prospective teratol-ogy of retinoic acid metabolic blocking agents (RAMBAs) and loss of CYP26 activi-ty. Curr Pharm Des 2007; 13: 3020-3037 (Pubitemid 350130968)
24. Lorie EP, Li H, Vahlquist A, Torma H: The involvement of cytochrome P450 (CYP) 26 in the retinoic acid metabolism of human epidermal keratinocytes. Biochim Biophys Acta Mol Cell Biol Lipids 2009; 1791:220-228.
25. Van de Kerckhof P, Verfaille C: Retinoids and retinoic acid metabolism blocking agents in psoriasis; in Vahlquist A, Duvic M (eds): Retinoids and Carotenoids in Derma-tology. New York, Informa Healthcare, 2007, pp 125-152.
26. Stoppie P, Borgers M, Borghgraef P, Dillen L, Goossens J, Sanz G, Szel H, Van Hove C, Van Nyen G, Nobels G, van den Bossche H, Venet M, Willemsens G, van Wauwe J: R115866 in-hibits all-trans-retinoic acid metabolism and exerts retinoidal effects in rodents. J Phar-macol Exp Ther 2000; 293: 304-312. (Pubitemid 30180953)
27. TM, a potent inhibitor of all-trans retinoic acid metabolism, applied topi-cally to mouse tail skin exerts retinoid mi-metic activity. J Invest Dermatol 2004; 122: 420.
28. Verfaille C, Borgers M, van Steensel MAM: Retinoic acid metabolism blocking agents (RAMBAs): a new paradigm in the treatment of hyperkeratotic disorders. J Dtsch Derma-tol Ges 2008; 6: 355-365.
29. Lorie EP, Cools M, Borgers M, Wouters L, Shroot B, Hagforsen E, Torma H, Vahlquist A: Topical treatment with CYP26 inhibitor talarozole (R115866) dose dependently alters the expression of retinoid-regulated genes in normal human epidermis. Br J Dermatol 2009; 160: 26-36.
30. OECD: Guidance document for the conduct of skin absorption studies: OECD series on testing and assessment. Paris, OECD 2004, p 31.
31. Jones A, Dick I, JW C: Cefic workshop on methods to determine dermal penetration for human risk assessment. Edinburgh, In-stitute of Occupational Medicine, 2004.
32. ECETOC: Percutaneous absorption. Monograph report No 20. Brussels, ECETOC; 1993.
33. Kanikkannan N, Kandimalla K, Lamba SS, Singh M: Structure-activity relationship of chemical penetration enhancers in transder-mal drug delivery. Curr Med Chem 2000; 7: 593-608. (Pubitemid 30396419)
34. Ray WJ, Bain G, Yao M, Gottlieb DI: CYP26, a novel mammalian cytochrome P450, is in-duced by retinoic acid and defines a new family. J Biol Chem 1997; 272: 18702-18708. (Pubitemid 27318214)
35. Abu-Abed SS, Beckett BR, Chiba H, Chitha-len JV, Jones G, Metzger D, Chambon P, Pet-kovich M: Mouse P450RAI (CYP26) expres-sion and retinoic acid-inducible retinoic acid metabolism in F9 cells are regulated by reti-noic acid receptor gamma and retinoid X re-ceptor alpha. J Biol Chem 1998; 273: 2409-2415. (Pubitemid 28069299)
36. Sonneveld E, van den Brink CE, van der Leede BJM, Schulkes R Petkovich M, van der Burg B, van der Saag PT: Human reti-noic acid (RA) 4-hydroxylase (CYP26) is highly specific for all-trans-RA and can be induced through RA receptors in human breast and colon carcinoma cells. Cell Growth Differ 1998; 9: 629-637. (Pubitemid 28367252)
37. Taimi M, Helvig C, Wisniewski J, Ramshaw H, White J, Amad M, Korczak B, Petkovich M: A novel human cytochrome P450, CYP-26C1, involved in metabolism of 9-cis and all-trans isomers of retinoic acid. J Biol Chem 2004; 279: 77-85. (Pubitemid 38044801)
38. Heise R, Mey J, Neis MM, Marquardt Y, Jous-sen S, Ott H, Wiederholt T, Kurschat P, Megahed M, Bickers DR Merk HF, Baron JM: Skin retinoid concentrations are modu-lated by CYP26AI expression restricted to basal keratinocytes in normal human skin and differentiated 3D skin models. J Invest Dermatol 2006; 126: 2473-2480. (Pubitemid 44582269)
39. Loudig O, Babichuk C, White J, Abu-Abed S, Mueller C, Petkovich M: Cytochrome P450RAI (CYP26) promoter: a distinct com-posite retinoic acid response element under-lies the complex regulation of retinoic acid metabolism. Mol Endocrinol 2000; 14:1483-1497.
40. Duell EA, Astrom A, Griffiths CEM, Cham-bon P, Voorhees JJ: Human skin levels of ret-inoic acid and cytochrome P-450-derived 4-hydroxyretinoic acid after topical applica-tion of retinoic acid in vivo compared to con-centrations required to stimulate retinoic acid receptor-mediated transcription in vi-tro. J Clin Invest 1992; 90: 1269-1274.