Transdermal Absorption and Skin Metabolism of Viprostol, A Synthetic Prostaglandin E₂ Analogue

References

• Scheuplein R. J. Percutaneous absorption: Theoretical aspects. Percutaneous Absorption of Steroids, P. M. Mawoais-Jarvis, et al. Academic Press, New York 1980; 1–17
   Google Scholar
• Franz T. J. Kinetics of cutaneous drug penetration. Int. J. Derm. 1983; 22: 499–505
   PubMed Web of Science ®Google Scholar
• Scheuplein R. J., Bronaugh R. L. Percutaneous absorptions. Biochemistry und Physiology of the skin, L. A. goldsmith. Oxford University Press, New York 1983/1983; Vol. 2: 1255–1295
   Google Scholar
• Panatier A., Jenner P., Testa B., Etter J. C. The skin as a drug metabolizing organ. Drug Metab. Rev. 1978; 8: 319–343
   PubMed Web of Science ®Google Scholar
• Webster R. C., Maibach M. I. Cutaneous pharmacokinetics: Steps to percutaneous absorption. Drug Metab. Rev. 1983; 14: 169–205
   PubMed Web of Science ®Google Scholar
• Noonan P. K., Webster R. C. cutaneous metabolism of xenobiotics. Percutaneous Absorption, R. L. Bronaugh, H. I. Maibach. Dekker, New York 1985; 65–85
   Google Scholar
• Guy R. H., Hadgraft J. Skin metabolism: Theoretical. Percutaneous Absorption, R. L. Bronaugh, H. I. Maibach. Dekker, New York 1985; 57
   Google Scholar
• Guy R. H., Hadgraft J. Mathematical models of percutaneous absorption. Percutaneous Absorption, R. L. Bronaugh, H. I. Maibach. Dekker, New York 1985; 3–16
   Google Scholar
• Kao J., Patterson F. K., Hall J. Skin penetration and metabolism of topically applied chemicals in six mammalian species, including man: An in vitro study with benz(a)pyrene and testosterone. Toxicol. Appl. Pharmacol. 1985; 81: 502–516
   PubMed Web of Science ®Google Scholar
• Weinstein I. B., Jeffery A. M., Jennett K. W., et al. Benzo(a) pyrene diol epoxides as intermediates in nucleic acid binding in vitro and in vivo. Sciences 1976; 3: 592–594
   Google Scholar
• Bickers D. R., Kappas A. Human skin aryl hydrocarbon hydroxylase. J. Clin. Invest. 1978; 62: 1061–1068
   PubMed Web of Science ®Google Scholar
• Tierney B., Hewer A., Walsh C., Grover P. L., Sims P. The metabolic activation of 7-methylbenzanthracene in mouse skin. Chem.–Biol. Interactions 1977; 18: 179–193
   PubMed Web of Science ®Google Scholar
• Grover P. L., Hewer A., Pal K., Sims P. The involvement of a diol-epoxide in the metabolic activation of benzo pyrene in human bronchial mucosa and in mouse skin. Int. J. Cancer 1976; 18: 1–6
   PubMed Web of Science ®Google Scholar
• Levin A., Wood A. W., Yagi M., Dansette P. M., Jerian D. M., Conney A. H. Carcinogenicity of benzo[a]pyrene 4,5,7,8-, and 9,10-oxides on mouse skin. Proc. Natl. Acad. Sci., USA 1976; 73: 243–247
   PubMed Web of Science ®Google Scholar
• Hsia S. L., Hao Y. L. Metabolic transformation of cortisol-4-[14C] in human skin. Biochemistry 1966; 5: 1469–1474
   PubMed Web of Science ®Google Scholar
• Bickers D. R. Drug carcinogen and steroid hormone metabolism in the skin. Biochemistry and Physiology of the Skin, L. A. Goldsmith. Oxford Univ. Press, New York 1983; Vol. 2: 1169–1186
   Google Scholar
• Mauvais-Jarvis P., Bercovici J. P., Gauthier F. In vivo studies on testosterone metabolism by skin of normal male and patients with the syndrome of testicular terminization. J. Clin. Endocrinol. Metab. 1969; 29: 417–421
   PubMed Web of Science ®Google Scholar
• Strobel J. L., Cady S. G., Borg T. K., Teracio L., Baynes J. W., Thorpe S. R. Identification of fibroblasts as a major site of albumin catabolism in peripheral tissues. J. Biol. Chem. 1986; 261(17)7989–7992
   PubMed Web of Science ®Google Scholar
• Pannatier A., Testa B., Etter J. C. Enzymatic hydrolysis by mouse skin homogenates: Structure-metabolism relationships of para-nitro-benzoate esters. Int. J. Pharmacol. 1981; 8: 167
   Google Scholar
• Potts R. O., McNeill S. C., Desbonnet R. Ch., Wakshull E. Transdermal drug transport and metabolism. II. The role of competing kinetic events. Pharm. Res. 1989; 6: 119–124
   PubMed Web of Science ®Google Scholar
• Camp R., Greaves M. W. The catabolism of prostaglandins by rat skin. Biochem. J. 1980; 1986: 153–160
   Google Scholar
• Fincham N., Camp R. Novel prostaglandin dehydrogenase in rat skin. Biochem. J. 1983; 212: 129–134
   PubMed Web of Science ®Google Scholar
• Chan P. S., Cervoni P., Ronsberg M. A., Accomando R. C., Quirk G. J., Scully P. A., Lipchuck L. M. Antihypertensive activity of df-15-deoxy-16-1-hydroxy-16-(α/o)vinyl prostaglandin E2 methyl ester (CL 115,347), a new orally and transdermally long-acting antihypertensive agent. J. Pharmacol. Exp. Ther. 1983; 226: 726–732
   PubMed Web of Science ®Google Scholar
• Birnbaum J. E., Chan P. S., Cervoni P., Dessy F., van Humbeeck I. Cutaneous erythema and blood pressure lowering effects of topically applied 16-vinyl prostaglandins. Prostaglandins 1982; 23(2)185–201
   PubMedGoogle Scholar
• Olivari M. T., Levine T. B., Garberg V., Rector T., Cohn J. N. Neurohumoral and hemodynamic effects of CL125,347, a transdermally absorbed prostaglandin E2 analogue in normal subjects. Circulation 1984; 70: 11242
   Google Scholar
• Given B. D., Vita N. A., Black H., Francis C., Lasseter K., Mickiewicz C., Akester J., Koury K., Dzau V. J. Chronic prostaglandins E, analog elicits renal and hormonal compensatory mechanisms in human hypertension. Circulation 1984; 70: 1163
   Google Scholar
• Uribarri J., Oh M. S., Kang S. K., Carroll H. J. Treatment of hypertension with transdermal application of a PEG2 analog. 9th Int. Congress of Nephrology, 229A (abstract).
   Google Scholar
• Belch J. J.F., Madhok R., Shaw B., Leiberman P., Sturrock R. D., Forbes C. D. Double-blind trial of CL 115,347, a transdermally absorbed prostaglandin E analogue, in treatment of Raynaud's phenomenon. Lancet 1985; 1: 1180–1183
   PubMed Web of Science ®Google Scholar
• Chan P. S., Cervoni P., Scully P. A., Ronsberg M. A., Accomando R. C. Mechanism of action of a new prostaglandin antihypertensive viprostol [CL 115,347: (dl)-15-deoxy-16-hydroxy-16(α/ω)-vinyl-prostaglandin E2 methyl ester]: 1. Vasodilation. J. Hyperten. 1986; 4: 741–747
   PubMed Web of Science ®Google Scholar
• Chan P. S., Cervoni P., Accomando C., Quirk C. J., Ronsberg M. A. Mechanism of action of a new prostaglandin antihypertensive, viprostol [CL 115,347; (do-15-deoxy-16-hydroxy-16(α/φ)-viny1-prostaglandin E2 methyl ester]: 11. Effects on the adrenergic nervous system. J. Hyperten. 1986; 4: 749–757
   PubMed Web of Science ®Google Scholar
• Gray S. J., Heptinstall S. The effects of PGE, and CL 115,347, an antihypertensive PGE, analogue in human blood platelet behavior and vascular contractility. Eur, J. Pharmacol. 1985; 114: 129–137
   PubMed Web of Science ®Google Scholar
• Birnbaum J. E., Cervoni P., Chan P. S., Chen S. M., Floyd M. B., Grudzinskas C. V., Weiss M. J., Dessy F. Prostaglandin and cogeners, (16RS)-(±)-15-deoxy-16-hydroxy-16-vinyl-prostaglandin E2, and orally and transdermally active hypotensive agent of prolonged duration. J. Med. Chem. 1982; 25: 492–494
   PubMed Web of Science ®Google Scholar
• Nicolau G., Baughman R. A., Tonelli A., McWilliams W., Shiltz J., Yacobi A. Deposition of viprostol (a synthetic PG2 vasodilator) in the skin following topical administration to laboratory animals. Xenobiotica 1987; 9: 1113–1120
   Google Scholar
• Nicolau G., Cosulich D. B., Tonelli A., Chen S. M., Pruzinsky M. S., Blum D. Metabolism of viprostol—A synthetic vasodilator PGE2 analog. Prostaglandins 1986; 31: 811–827
   PubMedGoogle Scholar
• Guzek D. B., Kennedy A. H., McNeill S., Wakshull E., Potts R. O. Transdermal drug transport and metabolism. I. Comparison of in vitro and in vivo. results, Pharm. Res. 1989; 6: 33–39
   Google Scholar
• Cosulich D. B., Perkinson N. A., Batra V. K. Capillary gas chromatographic-mass spectrometric analysis of 15-deoxy-16-hydroxy-16-vinylprostaglandin E2. J. Pharm. Sci. 1985; 74: 76–78
   PubMed Web of Science ®Google Scholar
• Nicolau G., Tonelli A. P., Cosulich D. B., Perkinson N. A., DiCioccio A. T., McWillimas W. E., Yacobi A. Pre-systemic metabolism of viprostol in the monkey following oral and topical administration. Xenobiotica 1988; 18: 797–802
   PubMed Web of Science ®Google Scholar
• Yacobi A., Baughman R. A., Cosulich D. B., Nicolau G. Method for determination of first-pass metabolism in human skin. J. Pharm. Sci. 1985; 73: 1499
   Web of Science ®Google Scholar
• Wester R. C., Noonan P. K., Smeach S., Kosobud L. Pharmacokinetics and bioavailability of intravenous and topical nitroglycerin in the Rhesus monkey, estimate of percutaneous first-pass metabolism. J. Pharm. Sci. 1983; 72: 745–748
   PubMed Web of Science ®Google Scholar