305
Views
1
CrossRef citations to date
0
Altmetric
Research Article

Transdermal permeation of novel n-acetyl-glucosamine/NSAIDs mutual prodrugs

, , , , , , , , & show all
Pages 48-54 | Received 25 Apr 2010, Accepted 26 Jul 2010, Published online: 21 Sep 2010

References

  • Albert A. Chemical aspects of selective toxicity. Nature 1958;182(4633):421–423.
  • Rao H, Surya Prakash. Capping drugs: Development of prodrugs. Accessed February 2003 from the website: Http://www.ias.ac.in/resonance/Feb2003/pdf/Feb2003p19-27.pdf.
  • Capelli L, Chianese V, La Montagna G, Giordano M. Further studies on glucametacin in rheumatoid arthritis and in other chronic types of rheumatism. Curr Med Res Opinion 1981;7(4):227–233.
  • Singh G, Sharma PD. Review article: Mutual prodrugs – A recent trend in prodrug design. Indian J Pharm Sci 1994;56(3):69–79.
  • Ueda I, Tani M. Histamine and its related active substances: Synthesis and pharmacological properties a new chimera drug derived from the combination of anti-inflammatory agent histamine H2 receptor antagonist. Mem Inst Sci Ind Res Osaka Univ 1990;43–54.
  • Imai T, Fukuhara Ueda I, Otagiri M. An evaluation of an anti-inflammatory-histamine H2 antagonist drug complex on gastric corrosions in the rat. J Pharmacol Exp Ther 1994;265: Exp. 328–333.
  • Fukuhara A, Imai T, Inoue K, Otagiri M. Effect of oral multiple-dose administration Fukuhara, Imai, Inoue, of anti-inflammatory flurbiprofen chimera drug on gastric lesion, other toxicities and disposition toxicities. Biol Pharm Bull 1995;18:140–147.
  • Fukuhara A, Imai T, Otagiri M. Stereoselective disposition of flurbiprofen from a Fukuhara, Imai, disposition from mutual prodrug with a histamine H2-antagonist to reduce gastrointestinal lesions in the rat. Chirality 1996;8:494–502.
  • Otagiri M, Imai T, Fukuhara A. Improving the pharmacokinetic and pharmacodynamic properties of a drug by chemical conversion to a chimer drug. J Con Release 1999;62:223–229.
  • Capomacchia AC, and, US Provisional patent application No. 60/560,128, filed 7 April 2004. Glucosamine and glucosamine/anti-inflammatory mutual prodrugs, compositions, and methods.
  • Capomacchia AC, Garner ST. US Patent application 235.00560201, filed 7 April 2005. Glucosamine and glucosamine/anti-inflammatory mutual prodrugs, compositions, and methods.
  • Ghodeswar BC, Pophalikar RN, Bhojani MR, Nagpal D, Dhaneshwar SS. Synthesis and pharmacological evaluation of mutual prodrugs of some nonsteroidal antiflammatory drugs with glucosamine. Indian J Pharm Sci 2004;66:773–777.
  • Bhosale AV, Agrawal GP, Mishra P. Preparation and characterization of mutual prodrugs of ibuprofen. Indian J Pharm Sci 2003;66(2):158–163.
  • Garner ST, et al. Transdermal permeability of NAG. Pharmaceut Dev Tech 2007;12:169–174.
  • Yuan X, Capomacchia AC. The binary eutectic of NSAIDs and two-phase liquid system for enhanced membrane permeation. Pharmaceut Develop Technol 2005;1:1–10.
  • Qandil et al. Synthesis of piperazinylalkyl ester prodrugs of ketorolac and their in vitro evaluation for transdermal delivery. Drug Dev Ind Pharm 2008;34:1054–1063.
  • Babazadeh M. Design, synthesis and in vitro evaluation of vinyl ether type polymeric prodrugs of ibuprofen, ketoprofen and naproxen. Int J Pharm 2008;356:167–173.
  • Silva DJ, et al. J Org Chem 1999;64:5926–5929 (Supplemental material).
  • Itoh T, Xia J, Magavi R, Nishihata T, Rytting JH. Use of shed snake skin as a model membrane for in vitro percutaneous penetration studies: Comparison with human skin. Pharm Res 1990;7:1042–1047.
  • Higuchi T, Konishi R. In vitro testing and transdermal delivery. Proceedings of the 2nd Transdermal Therapeutic Symposium. Therapeutic Res 1987;6:280–288.
  • Ngawhirunpat T, Panomsuk S, Opanasopit P, Rojanarata T, Hatanaka T. Comparison of the percutaneous absorption of hydrophilic and lipophilic compounds in shed snake skin and human skin. Pharmazie 2006;61(4):331–335.
  • Ngawhirunpat T, Opansopit P, Rojanarata T, Panomsuk S. Evaluation of simultaneous permeation and metabolism of methyl nicotinate in human, snake, and shed snake skin. Pharmaceut Develop Technol 2008; 13:75–83.
  • Franz TJ, Lehman PA, Kagy MK. Dimethyl sulfoxide. In: Smith EW, Maibach HI, editors. Percutaneous enhancers. Boca Raton, FL: CRC Press; 1995:112–127.
  • Swart H, et al. Synthesis and transdermal penetration of NSAID glycoside esters. Int J Pharm 2005;301:71–79.
  • Bonina FP, Puglia C, Barbuzzi T, Caprariis PD, Rimoli MG. In vitro and in vivo evaluation of polyoxyethenene esters as dermal prodrugs of ketoprofen, naproxen and diclofenac. Eur J Pharm Sci 2001;14:123–134.
  • Doh H-J Cho, WJ, Yong CS, Choi HG, Kim JS, Lee CH. Synthesis and evaluation of ketorolac ester prodrugs for transdermal delivery. J Pharm Sci 2003;92:1008–1017.
  • Kim B-Y, et al. Ketorolac amide prodrugs for transdermal delivery: Stability and in vivo transdermal stability rat skin permeation studies. Int J Pharm 2004;293:193–202.
  • Lipinski CA, Lombardo F, Dominy BW, Feeney PJ. Experimental and computational approaches to estimate solubility and permeability in drug discovery and development settings. Adv Drug Deliv Rev 1997;23(1–3):3–25.
  • The Merck Index. 12th ed. Whitehouse Station, NJ: Merck & Co, 1996; pp 758, 839, 905.
  • D’Souza AJM, Topp EM. Release from polymeric prodrugs: Linkages and their degradation. J Pharm Sci 2004;93(8):1962–1979.
  • McClain DA, Crook ED. Hexosamines and insulin resistance. Diabetes 1996;45:1003–1009.
  • Singh LP, Andy J, Anyamale V, Greene K, Alexander M, Crook ED. Hexosamine-induced fibronectin protein synthesis in mesangial cells is associated with increases in cAMP responsive element binding (CREB) phosphorylation and nuclear CREB: The involvement of protein kinases A and C. Diabetes 2001;50:2355–2362.
  • Miwa I, Mita Y, Murata T, Okuda J, Sugiura M, Hamada Y, Chiba T. Utility of 3-O-methyl-N-acetyl-D-glucosamine, an N-acetylglucosamine kinase inhibitor, for accurate assay of glucokinase in pancreatic islets and liver. Enzyme Protein 1994;48:135–142.
  • Van Schaftigen E. Glucosamine-sensitive and -insensitive detritiation of [2-3H] glucose in isolated rat hepatocytes: A study of the contributions of glucokinase and glucose-6- phosphatase. Biochem J 1995;308:23–29.
  • Virkamaki A, Yki-Jarvinen H. Allosteric regulation of glycogen synthase and hexokinase by glucosamine-6-phosphate during glucosamine-induced insulin resistance in skeletal muscle and heart. Diabetes 1999;48:1101–1107.
  • Gouze JN, Bianchi A, Becuwe P, Dauca M, Netter P, Magdalou J, Terlain B, Bordji K. Glucosamine modulates IL-1-induced activation of rat chondrocytes at a receptor level and by inhibiting the NF-B pathway. FEBS Lett 2002;510:166–170.
  • Poustie MW, Carran J, McEleney K, Dixon SJ, Anastassiades TP, Bernier SMJ. N-butyryl glucosamine increases matrix gene expression by chondrocytes. Pharmacol Exp Ther 2004;311(2):610–616.
  • Anastassiades TP. Treatment of arthritis and compositions therefore. 2001. United States Patent Application No. 20020045597.
  • Anastassiades TP. Methods and compositions using N-acyl 2-glucosamine derivatives for the treatment of arthritis. 2002. PCT Int. Appl. WO 2002017890 A2 20020307 CAN 136:210563 AN 2002:171660.
  • Anastassiades TP. Amelioration of decreased weight and growth by N-acylated glucosamines. 2003. United States Patent Application No. 20040152665.
  • Setnikar I, Giacchetti C, Zanolo G. Pharmacokinetics of glucosamine in the dog and in man. Arzneimittel-Forschung 1986;36(4):729–735.
  • Setnikar I, Palumbo R, Canali S, Zanolo G. Pharmacokinetics of glucosamine in man. Arzneimittel-Forschung 1993;43(10):1109–1113.
  • Setnikar I, Rovati LC. Absorption, distribution, metabolism,and excretion of glucosamine sulfate. A review. Arzneimittel-Forschung 2001;51(9):699–725.
  • Setnikar et al. The bioavailability and pharmacokinetics of glucosamine hydrochloride and chondroitin sulfate after oral and intravenous single dose administration in the horse. Biopharmaceut Drug Disposit 2004;25(3):109–116.
  • Du J, White N, Eddington ND. The bioavailability and pharmacokinetics of pharmacokinetics glucosamine hydrochloride and chondroitin sulfate after oral and intravenous single dose administration in the horse. Biopharmaceut Drug Disposit 2004;25(3):109–116.
  • Aghazadeh-Habashi A, Sattari S, Pasutto F, Jamali F. Single dose pharmacokinetics and bioavailability of glucosamine in the rat. J Pharm Pharmaceut Sci 2000;5(2):181–184.

Reprints and Corporate Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

To request a reprint or corporate permissions for this article, please click on the relevant link below:

Academic Permissions

Please note: Selecting permissions does not provide access to the full text of the article, please see our help page How do I view content?

Obtain permissions instantly via Rightslink by clicking on the button below:

If you are unable to obtain permissions via Rightslink, please complete and submit this Permissions form. For more information, please visit our Permissions help page.