Percutaneous permeation of enantiomers and racemates of chiral drugs and prediction of their flux ratios using thermal data: A pharmaceutical perspective

Chirality

Volumn 15, Issue 5, 2003, Pages 456-465

  Afouna, Mohsen I ^a   Fincher, Timothy K ^a   Khan, Mansoor A ^b   Reddy, Indra K ^a,c  

^a UNIVERSITY OF ARKANSAS FOR MEDICAL SCIENCES   (United States)

^b TEXAS TECH UNIVERSITY HEALTH SCIENCES CENTER   (United States)

^c UNIVERSITY OF ARKANSAS FOR MEDICAL SCIENCES   (United States)

Author keywords

Chiral terpene enhancers; Enantioselectivity; Melting temperature membrane transport; MTMT; Skin permeation; Solubility

Indexed keywords

CHIRAL DRUG; DRUG; EXCIPIENT; GENACONAZOLE; KETOPROFEN; KETOROLAC; METOPROLOL; NILVADIPINE; PROPRANOLOL; SCH 42426; SCH 42427; TERPENE; TIMOLOL MALEATE; UNCLASSIFIED DRUG;

ANIMAL MODEL; CELL CULTURE; CHIRALITY; DRUG DELIVERY SYSTEM; DRUG EFFICACY; DRUG FORMULATION; DRUG SAFETY; DRUG SOLUBILITY; DRUG TRANSPORT; ENANTIOMER; ENANTIOSELECTIVITY; HUMAN; IN VITRO STUDY; IN VIVO STUDY; MATHEMATICAL MODEL; MELTING POINT; MEMBRANE TRANSPORT; NONHUMAN; PARTITION COEFFICIENT; PHYSICAL CHEMISTRY; PREDICTION; PRIORITY JOURNAL; RACEMIC MIXTURE; REVIEW; SKIN; SKIN ABSORPTION; SKIN PENETRATION; SKIN PERMEABILITY; SPECIES DIFFERENCE; STEREOCHEMISTRY; STRATUM CORNEUM; THERMODYNAMICS; VALIDATION PROCESS;

ALGORITHMS; ANIMALS; CHEMISTRY, PHYSICAL; EXCIPIENTS; HUMANS; PHARMACEUTICAL PREPARATIONS; PHARMACOKINETICS; SKIN ABSORPTION; STEREOISOMERISM;

EID: 0037273361     PISSN: 08990042     EISSN: None     Source Type: Journal    
DOI: 10.1002/chir.10211     Document Type: Review

References (57)

1. Flynn GL. Cutaneous and transdermal delivery: processes and systems of delivery. In: Banker GS, Rhodes CT, editors. Modern pharmaceutics. New York: Marcel Dekker; 1995. p 239.
2. Barry BW. Mode of action of penetration enhancers in human skin. J Control Release 1987;6:85-97.
3. Brown L, Langer R. Transdermal delivery of drugs. Annu Rev Med 1988;39:221-229.
4. Ritschel WA, Hussain AS. The principles of permeation of substances across the skin. Meth Find Exp Clin Pharmacol 1988;10:39-56.
5. Matoltsy AG, Downes AM, Sweeney TM. Studies of the epidermal water barrier. II. Investigation of the chemical nature of the water barrier. J Invest Dermatol 1968;50:19-26.
6. Scheuplein R. Permeability of the skin: a review of major concepts. Curr Prob Dermatol 1978;7:172-186.
7. Wester RC, Maibach HI. Animal models for transdermal delivery. In: Kydonieus AF, Berner B, editors. Transdermal delivery of drugs, vol. 1. Boca Raton, FL: CRC Press; 1987. p 61-70.
8. Walker M, Dugard PH, Scott RC. In vitro percutaneous absorption studies: a comparison of human and laboratory species. Hum Toxicol 1983;2:561.
9. Wester RC, Maibach HI. Percutaneous absorption in man and animal: a perspective. In: Drill V, Lazar P, editors. Cutaneous toxicity. New York: Academic Press; 1977. p 111.
10. Wester RC, Noonan PK. Topical bioavailability of a potential anti-acne agent (SC-23110) as determined by cumulative excretion and area under plasma concentration-time curve. J Invest Dermatol 1978;70:92-94.
11. Marzulli FN, Brown DWC, Maibach HI. Techniques foe studying skin penetration. Toxicol Appl Pharmacol Suppl 1969;3:76.
12. Marzulli FN, Callahan JF, Brown DWC. Chemical structure and skin penetrating capacity of a short series of organic phosphates and phosphoric acid. J Invest Dermatol 1965;44:339.
13. Denda M, Koyama J, Hori J, Horii I, Takahashi M, Hara M, Tagami H. Age- and sex-dependent change in stratum corneum sphingolipids. Arch Dermatol Res 1993;285:415-417.
14. Heard CM, Brain KR. Does solute stereochemistry influence percutaneous penetration? Chirality 1995;7:305-309.
15. Benezra C, Stampf JL, Berbier P, Ducombs G. Enantiospecificity in allergic contact dermatitis. Contact Dermatit 1985;13:110-114.
16. Papageorgiou C, Stampf JL, Benezra C. Allergic contact dermatitis to tulips: an example of enantiospecificity. Arch Dermatol Res 1988;280: 5-7.
17. Manabe E, Sugibayashi K, Morimoto Y. Analysis of skin penetration enhancing effect of drugs by ethanol-water mixed systems with hydrodynamic pore theory. Int J Pharm 1996;129:211.
18. Touitou E, Chow DD, Lawter JR, Chiral β-blockers for transdermal delivery. Int J Pharm 1994;104:19-28.
19. Vigevani A, Zampieri M, Pellizzato R. Thermal behavior and binary phase diagram of (S)-(+)-4,4′-(1-methyl-1,2-ethandiyl)-bis-(2,6-piperazinedione) (dexrazoxane), a cardioprotective agent, and of its (R)-(-)-enantiomer. J Pharm Biomed Anal 1992;10:31-36.
20. Heard CM, Suedee R. Stereoselective adsorption and trans-membrane transfer of propranolol enantiomers using cellulose derivatives. Int J Pharm 1996;139:15-23.
21. Zahir A, Kunta JR, Khan MA, Reddy IK. Effect of menthol on permeability of optically active and racemic propranolol across guinea pig skin. Drug Dev Ind Pharm 1998;24:875-878.
22. Cornwell PA, Barry BW, Stoddart CP, Bouwstra JA. Wide-angle X-ray diffraction of human stratum corneum: effects of hydration and terpene enhancer treatment. J Pharm Pharmacol 1994;46:938-950.
23. Gao S, Singh J. In vitro percutaneous absorption enhancement of a lipophilic drug tamoxifen by terpenes. J Control Release 1998;51:193-199.
24. Moghimi HR, Williams AC, Barry BW. Enhancement by terpenes of 5-fluorouracil permeation through the stratum corneum: model solvent approach. J Pharm Pharmacol 1998;50:955-964.
25. Cornwell PA, Barry BW. Sesquiterpene components of volatile oils as skin penetration enhancers for the hydrophilic permeant 5-fluorouracil. J Pharm Pharmacol 1994;46:261-269.
26. El-Kattan AF, Asbill CS, Kim N, Michniak BB. The effects of terpene enhancers on the percutaneous permeation of drugs with different lipophilicities. Int J Pharm 2001;14:215:229-240.
27. Zhao K, Singh J. Mechanism(s) of in vitro percutaneous absorption enhancement of tamoxifen by enhancers. J Pharm Sci 2000;89:771-780.
28. Jain AK, Thomas NS, Panchagnula R. Transdermal drug delivery of imipramine hydrochloride: effect of terpenes. J Control Release 2002;79:93-101.
29. El-Kattan AF, Asbill CS, Michniak BB. The effect of terpene enhancer lipophilicity on the percutaneous permeation of hydrocortisone formulated in HPMC gel systems. Int J Pharm 2000;198:179-189.
30. Vaddi HK, Ho PC, Chan SY. Terpenes in propylene glycol as skin-penetration enhancers: permeation and partition of haloperidol, fourier transform infrared spectroscopy, and differential scanning calorimetry. J Pharm Sci 2002;91:1639-1651.
31. Vaddi HK, Ho PC, Chan YW, Chan SY. Terpenes in ethanol: haloperidol permeation and partition through human skin and stratum corneum changes. J Control Release 2002;81:121-133.
32. Stott PW, Williams AC, Barry BW. Transdermal delivery from eutectic systems: enhanced permeation of a model drug, ibuprofen. J Control Release 1998;50:297-308.
33. Solinis MA, de la Cruz Y, Hernandez RM, Gascon AR, Calvo B, Pedraz JL. Release of ketoprofen enantiomers from HPMC K100M matrices-diffusion studies. Int J Pharm 2002;239:61-68.
34. Guy RH, Maibach HI, Hadgraft J. Radial transport in the dermis. In: Bronaugh RL, Maibach HI, editors. Percutaneous absorption mechanisms, methodology, drug delivery. New York: Marcel Dekker; 1985. p 335-346.
35. Elias PM. Lipids and the epidermal permeability barrier. Arch Dermatol 1981;270:95-117.
36. Gray GM, White RJ, Williams RH, Yardley HJ. Lipid composition of the superficial stratum corneum cells of pig epidermis. Br J Deramtol 1982;106:59-63.
37. Gray GM, Yardley HJ. Different population of pig epidermal cell: isolation and lipid composition. J Lipid Res 1975;13:441-447.
38. Yardley HJ, Summerly R. Lipid composition and metabolism in normal and diseased epidermis. Pharmacol Ther 1981;13:357-383.
39. Miyazaki K, Kaiho F, Inagaki A, Dohi M, Hazemoto N, Haga M, Hara H, Kato Y. Enantiomeric difference in percutaneous penetration of propranolol through rat excised skin. Chem Pharm Bull 1992;40:1075-1076.
40. Heard CM, Watkinson AC, Brain KR, Hadgraft J. In-vitro skin penetration of propranolol enantiomers. Int J Pharm 1993;90:R5-R8.
41. Sueddee R, Brain KR, Heard CM. Differential permeation of propranolol enantiomers across human skin in vitro from formulations containing an enantioselective excipient. Chirality 1999;11:860-863.
42. Udata C, Tirucherai G, Mitra AK. Synthesis, stereoselective enzymatic hydrolysis, and skin permeation of diastereomeric propranolol ester prodrugs. J Pharm Sci 1999;88:544-550.
43. Ahmed S, Imai T, Otagiri M. Evaluation of stereoselective transdermal transport and concurrent cutaneous hydrolysis of several ester prodrugs of propranolol: mechanism of stereoselective permeation. Pharm Res 1996;13:1524-1529.
44. Kunta JR, Goskonda VR, Brotherton HO, Khan MA, Reddy IK. Effect of menthol and related terpenes on the percutaneous absorption of propranolol across excised hairless mouse skin. J Pharm Sci 1997;86: 1369-1373.
45. Madiraju C. Transport of timolol across hairless mouse skin: effect of chiral terpene enhancers. Master's Thesis, University of Louisiana at Monroe, 2001.
46. Kommuru TR, Khan MA, Reddy IK. Effect of chiral enhancers on the permeability of optically active and racemic metoprolol across hairless mouse skin. Chirality 1999;11:536-540.
47. Kommuru TR, Khan MA, Reddy IK. Racemate and enantiomers of ketoprofen: phase diagram, thermodynamic studies, skin permeability, and use of chiral permeation enhancers. J Pharm Sci 1998;87:833-840.
48. Reddy IK, Kommuru RT, Zaghloul AA, Khan MA. Chirality and its implications in transdermal drug development. Crit Rev Ther Drug Carrier Syst 2000;17:285-325.
49. Roy SD, Chatterjee DJ, Manoukian E, Divor A. Permeability of pure enantiomers of ketorolac through human cadaver skin. J Pharm Sci 1995;84:49-52.
50. Barett AM, Cullum VA. The biological properties of the optical isomers of propranolol and their effects on cardiac arrhythmias. Br J Pharmacol 1968;34:43.
51. Gillespie L, Oates JA, Crout JR, Sjoerdsma H. Clinical and chemical studies with α-methyldopa in patients with hypertension. Circulation 1962;25:281.
52. O'Reilly RA. Studies on the optical enantiomorphs of warfarin in man. Clin Pharmacol Ther 1974;16:348-354.
53. Echizen H, Brecht T, Niedergesass S, Vogelgesang B, Eichelbaum M. The effect of dextro-, levo-, and racemic verapamil on atrioventricular conduction in humans. Am Heart J 1985;109:210-217.
54. Eichelbaum M. Polymorphic drug oxidation in humans. Fed Proc 1984;43:2298-2302.
55. Kim H, Radwanski E, Lovey R, Lin CC, Nomeir AA. Pharmacokinetics of the active antifungal enantiomer, SCH 42427 (RR), and evaluation of its chiral inversion in animals following its oral administration and the oral administration of its racemate genaconazole (RR/SS). Chirality 2002;14:436-441.
56. Wearley L, Antonacci B, Cacciapuoti A, Assenza S, Chaudry I, Eckhart C, Levine N, Loebenberg D, Norris C, Parmegiani R, Sequeira J, Yarosh-Maine T. Relationship among physicochemical properties, skin permeability, and topical activity of the racemic compound and pure enantiomers of a new antifungal. Pharm Res 1993;10:136-140.
57. Lawter JR, Pawelchak J. Transdermal permeation of chiral compounds. Proc Int Syrup Control Rel Bioact Mater 1989;16:308-309.