Chemical and in vitro enzymatic stability of newly synthesized celecoxib lipophilic and hydrophilic amides

International Journal of Pharmaceutics

Volumn 416, Issue 1, 2011, Pages 85-96

  Qandil, Amjad M ^a   El Mohtadi, Farah H ^a   Tashtoush, Bassam M ^a  

^a JORDAN UNIVERSITY OF SCIENCE AND TECHNOLOGY   (Jordan)

Author keywords

Celecoxib; HPLC; Hydrolysis; Hydrophobic interactions; Liver homogenate

Indexed keywords

CELECOXIB; SODIUM 2 (4 METHYLPIPERAZIN 1 YL) N [4 [5 P TOLYL 3 (TRIFLUOROMETHYL) 1H PYRAZOL 1 YL] PHENYL SULFONYL] ACETAMIDE; SODIUM 2 CHLORO N [4 [5 P TOLYL 3 (TRIFLUOROMETHYL) 1H PYRAZOL 1 YL] PHENYLSULFONYL] ACETAMIDE; SODIUM 4 CHLORO N [4 [5 P TOLYL 3 (TRIFLUOROMETHYL) 1 H PYRAZOL 1 YL]PHENYLSULFONYL] BENZAMIDE; SODIUM 4 FLUORO N [4 [5 P TOLYL 3 (TRIFLUOROMETHYL) 1 H PYRAZOL 1 YL]PHENYLSULFONYL] BENZAMIDE; SODIUM N [4 [5 P TOLYL 3 (TRIFLUOROMETHYL) 1 H PYRAZOL 1 YL] PHENYLSULFONYL] CYCLOHEXANE CARBOXAMIDE; SODIUM N [4 [5 P TOLYL 3 (TRIFLUOROMETHYL) 1 H PYRAZOL 1 YL]PHENYLSULFONYL] BENZAMIDE; UNCLASSIFIED DRUG;

ARTICLE; ATOMIC PRESSURE CHEMICAL IONIZATION; CALIBRATION; CARBON NUCLEAR MAGNETIC RESONANCE; DRUG HALF LIFE; DRUG HYDROLYSIS; DRUG SOLUBILITY; DRUG SYNTHESIS; ENZYME STABILITY; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HYDROPHILICITY; INFRARED SPECTROSCOPY; LIPOPHILICITY; LIVER HOMOGENATE; MASS SPECTROMETRY; NONHUMAN; PRIORITY JOURNAL; PROTEIN HYDROLYSIS; PROTON NUCLEAR MAGNETIC RESONANCE; RAT; REVERSED PHASE HIGH PERFORMANCE LIQUID CHROMATOGRAPHY;

AMIDES; ANIMALS; DRUG DESIGN; DRUG STABILITY; HALF-LIFE; HUMANS; HYDROGEN-ION CONCENTRATION; HYDROLYSIS; HYDROPHOBIC AND HYDROPHILIC INTERACTIONS; LIVER; MOLECULAR STRUCTURE; PLASMA; PYRAZOLES; RATS; SOLUBILITY; SULFONAMIDES;

EID: 80051799672     PISSN: 03785173     EISSN: 18733476     Source Type: Journal    
DOI: 10.1016/j.ijpharm.2011.06.013     Document Type: Article

References (35)

1. S. Baboota, F. Shakkel, A. Ahuja, J. Ali, and S. Shfiq Design, development and evaluation of novel nanoemulsion formulations for transdermal potential of celecoxib Acta Pharm. 57 2007 315 332 (Pubitemid 47429175)
2. C. Bombardier, L. Laine, A. Reicin, D. Shapiro, R. Burgos-Vargas, B. Davis, R. Day, M.B. Ferraz, C.J. Hawkey, M.C. Hochberg, T.K. Kvien, and T.J. Schnitzer Comparison of upper gastrointestinal toxicity of rofecoxib and naproxen in patients with rheumatoid arthritis N. Engl. J. Med. 343 2000 1520 1528
3. Center for Drug Evaluation and Research (CDER) Reviewer Guidance. Validation of Chromatographic Methods 1994 p. 30
4. Center for Drug Evaluation and Research (CDER) Guidance for Industry. Bioanalytical Method Validation 2001 p. 25
5. M.W. Davey, E. Sulkowski, and W.A. Carter Hydrophobic interaction of human, mouse, and rabbit interferons with immobilized hydrocarbons J. Biol. Chem. 251 1976 7620 7625
6. N. Duttaa, P. Sarotraa, S. Guptaa, R. Aggarwal, and N. Agnihotri Mechanism of action of celecoxib on normal and acid-challenged gastric mucosa Exp. Toxicol. Pathol. 61 2009 353 361
7. A. El-Medanya, A. Mahgouba, A. Mustafa, M. Arafa, and M. Morsi The effects of selective cyclooxygenase-2 inhibitors, celecoxib and rofecoxib, on experimental colitis induced by acetic acid in rats Eur. J. Pharmacol. 507 2005 291 299 (Pubitemid 40126866)
8. J. Ermer, and J.H.M. Miller Method Validation in Pharmaceutical Analysis: A Guide to Best Practice 2005 Wiley-VCH Weinheim
9. Y.K. Ho, S.F. Zakrzewski, and L.H. Mead Hydrophobic interactions between the 5-alkyl group of 2,4-diamino-6-methylpyrimidines and dihydrofolate reductase Biochemistry 12 1973 1003 1005
10. H.-W. Hung, T.-F. Lin, and C.T. Chiou Partition coefficients of organic contaminants with carbohydrates Environ. Sci. Technol. 44 2010 5430 5436
11. T. Imai, M. Taketani, M. Shii, M. Hosokawa, and K. Chiba Substrate specificity of carboxylesterase isozymes and their contribution to hydrolase activity in human liver and small intestine Drug Metab. Dispos. 34 2006 1741 1743
12. International Conference on Harmonisation (ICH) Validation of Analytical Procedures, ICH Q2A 1995 p. 9
13. International Conference on Harmonisation (ICH) Validation of Analytical Procedures Methodology, ICH Q2B 1997 p. 13
14. A. Karim, A. Laurent, M. Slater, M. Kuss, J. Qian, S. Crosby-Sessoms, and R. Hubbard A pharmacokinetic study of intramuscular (i.m.) parecoxib sodium in normal subjects Clin. Pharmacol. 41 2001 1111 1119 (Pubitemid 32880140)
15. H.T. Karnes, and C. March Precision, Accuracy, and Data Acceptance Criteria in Biopharmaceutical Analysis 1993 Springer Netherlands
16. B. Kim, H. Doh, T. Le, W. Cho, C. Yong, H. Choi, J. Kim, C. Lee, and D. Kim Ketorolac amide prodrugs for transdermal delivery: stability and invitro rat skin permeation studies Int. J. Pharm. 293 2005 193 202 (Pubitemid 40381092)
17. K. Kismet, M.T. Akay, O. Abbaso, and A. Ercan Celecoxib: a potent cyclooxygenase-2 inhibitor in cancer prevention Cancer Detect. Prev. 28 2004 127 142 (Pubitemid 38448751)
18. J.r.D. Larsen, and H. Bundgaard Prodrug forms for the sulfonamide group. I. Evaluation of N-acyl derivatives, N-sulfonylamidines, N-sulfonylsulfilimines and sulfonylureas as possible prodrug derivatives Int. J. Pharm. 37 1987 87 95 (Pubitemid 17084952)
19. J.r.D. Larsen, H. Bundgaard, and V.H.L. Lee Prodrug forms for the sulfonamide group. II. Water-soluble amino acid derivatives of N-methylsulfonamides as possible prodrugs Int. J. Pharm. 47 1988 103 110
20. W. Lew, X. Chen, and C.U. Kim Discovery and development of GS 4104 (oseltamivir): an orally active influenza neuraminidase inhibitor Curr. Med. Chem. 7 2000 663 672 (Pubitemid 30396423)
21. Lindholm, J.; 2004. Developement and Validation of HPLC methods for analytical and preparative purposes. PhD Thesis, University of Uppsala, Uppsala.
22. R. Mamidi, R. Mullangi, J. Kota, R. Bhamidipati, A. Khan, K. Katneni, S. Datla, S. Singh, K. Rao, C. Rao, N. Srinivas, and R. Rajagopalan Pharmacological and pharmacokinetic evaluation of celecoxib prodrugs in rats Biopharm. Drug Dispos. 23 2002 273 282 (Pubitemid 35203427)
23. S. Paulson, M. Vaughn, S. Jessen, Y. Awal, C.J. Gresk, B. Timothyg, M.C. Cook, and A. Karim Pharmacokinetics of celecoxib after oral administration in dogs and humans: effect of food and site of absorption J. Pharm. Exp. Ther. 297 2001 638 645 (Pubitemid 32377995)
24. A. Qandil, S. Al-Nabulsi, B. Al-Taani, and B. Tashtoush Synthesis of piperazinylalkyl ester prodrugs of ketorolac and their in vitro evaluation for transdermal delivery Drug Dev. Ind. Pharm. 34 2008 1054 1063
25. Z.A. Radi, and N.K. Khan Effects of cyclooxygenase inhibition on the gastrointestinal tract Exp. Toxicol. Pathol. 58 2006 163 173 (Pubitemid 44635152)
26. T.M. Raschke, and M. Levitt Detailed hydration maps of benzene and cyclohexane reveal distinct water structures J. Phys. Chem. B 108 2004 13492 13500
27. P. Ruelle The n-octanol and n-hexane/water partition coefficient of environmentally relevant chemicals predicted from the mobile order and disorder (MOD) thermodynamics Chemosphere 40 2000 457 512 (Pubitemid 30038621)
28. G.A. Shabir Validation of high-performance liquid chromatography methods for pharmaceutical analysis: understanding the differences and similarities between validation requirements of the US Food and Drug Administration, the US Pharmacopeia and the International Conference on Harmonization J. Chromatogr. A 987 2003 57 66 (Pubitemid 36140080)
29. F.E Silverstein, G. Faich, J.L. Goldstein, L.S. Simon, T. Pincus, A. Whelton, R. Makuch, G. Eisen, N.M. Agrawal, W.F. Stenson, A.M. Burr, W.W. Zhao, J.D. Kent, J.B. Lefkowith, K.M. Verburg, and G.S. Geis Gastrointestinal toxicity with celecoxib vs nonsteroidal anti-inflammatory drugs for osteoarthritis and rheumatoid arthritis: The CLASS Study: A Randomized Controlled Trial JAMA 284 2000 1247 1255
30. N. Subramanian, S. Ray, S.K. Ghosal, R. Bhadra, and S.P. Moulik Formulation design of self-microemulsifying drug delivery systems for improved oral bioavailability of celecoxib Biol. Pharm. Bull. 27 2004 1993 1999 (Pubitemid 41701577)
31. J.J. Talley, S.R. Bertenshaw, D.L. Brown, J.S. Carter, M.J. Graneto, M.S. Kellogg, C.M. Koboldt, J. Yuan, Y.Y. Zhang, and K. Seibert N-[[(5-Methyl-3- phenylisoxazol-4-yl)-phenyl]sulfonyl]propanamide, sodium salt, parecoxib sodium: Äâ a potent and selective inhibitor of COX-2 for parenteral administration J. Med. Chem. 43 2000 1661 1663 (Pubitemid 30304998)
32. USP Validation of Compendial Methods 1994 United States Phamracopeial Convention, Inc. Rockvill, MD p. 1982
33. J. Vane, and R. Botting Anti-inflammatory drugs and their mechanism of action Inflamm. Res. 47 1998 S78 S87
34. C.A. Ventura, I. Giannone, D. Paolino, V. Pistar, A. Corsaro, and G. Puglisi Preparation of celecoxib-dimethyl-b-cyclodextrin inclusion complex: characterization and invitro permeation study Eur. J. Med. Chem. 40 2005 624 631 (Pubitemid 40797558)
35. H.E. Vonkeman, and M.A.F.J. van de Laar Nonsteroidal anti-inflammatory drugs: adverse effects and their prevention Semin. Arthritis Rheum. 39 2010 294 312