Preparation and physicochemical and preclinical evaluations of recrystallized celecoxib

S. Mutalik, N. Usha, A.K. Ranjith, S. Umesh, P. Musmade, N. Anup

Research output: Contribution to journalArticle

3 Citations (Scopus)

Abstract

The aim of the present study is to increase the aqueous solubility of celecoxib by recrystallization from distilled water, Tween-80, and polyethylene glycol-400. The prepared crystals were evaluated for various physicochemical evaluations, dissolution rate, and in vivo performance like analgesic activity (by writhing and hot plate method) and pharmacokinetics in mice. The practical yield of the crystals ranged between 83 and 98%, and celecoxib content was more than 99%. Celecoxib showed an almost 5-fold increase in solubility when recrystallized in the presence of Tween-80 (2%). The dissolution rates of celecoxib from the co-crystal forms were considerably higher than that of plain celecoxib. The infrared and differential scanning calorimetry studies indicated the absence of a well-defined interaction between celecoxib and carriers. The differential scanning calorimetry and X-ray diffraction studies indicated the amorphization or partial amorphization of the drug. The scanning electron microscopy showed fluffy, porous, and fine particles in recrystallized celecoxib. The particle size of prepared co-crystals was considerably reduced in comparison with plain celecoxib. The crystals prepared with Tween-80 (2%) showed significantly higher analgesic activity than plain celecoxib. In pharmacokinetic study, the prepared crystals exhibited significantly high and rapid absorption along with improved bioavailability.
Original languageEnglish
Pages (from-to)362-374
Number of pages13
JournalPDA Journal of Pharmaceutical Science and Technology
Volume61
Issue number5
Publication statusPublished - 2007

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Celecoxib
Polysorbates
Differential Scanning Calorimetry
Solubility
Analgesics
Pharmacokinetics

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@article{d222e3f56e7149e5a61cd284a2aa9044,
title = "Preparation and physicochemical and preclinical evaluations of recrystallized celecoxib",
abstract = "The aim of the present study is to increase the aqueous solubility of celecoxib by recrystallization from distilled water, Tween-80, and polyethylene glycol-400. The prepared crystals were evaluated for various physicochemical evaluations, dissolution rate, and in vivo performance like analgesic activity (by writhing and hot plate method) and pharmacokinetics in mice. The practical yield of the crystals ranged between 83 and 98{\%}, and celecoxib content was more than 99{\%}. Celecoxib showed an almost 5-fold increase in solubility when recrystallized in the presence of Tween-80 (2{\%}). The dissolution rates of celecoxib from the co-crystal forms were considerably higher than that of plain celecoxib. The infrared and differential scanning calorimetry studies indicated the absence of a well-defined interaction between celecoxib and carriers. The differential scanning calorimetry and X-ray diffraction studies indicated the amorphization or partial amorphization of the drug. The scanning electron microscopy showed fluffy, porous, and fine particles in recrystallized celecoxib. The particle size of prepared co-crystals was considerably reduced in comparison with plain celecoxib. The crystals prepared with Tween-80 (2{\%}) showed significantly higher analgesic activity than plain celecoxib. In pharmacokinetic study, the prepared crystals exhibited significantly high and rapid absorption along with improved bioavailability.",
author = "S. Mutalik and N. Usha and A.K. Ranjith and S. Umesh and P. Musmade and N. Anup",
note = "Cited By :2 Export Date: 10 November 2017 CODEN: JPHTE Correspondence Address: Mutalik, S.; School of Pharmacy, Univeristy of Queensland, Brisbane, QLD 4072, Australia; email: ssmutalik@yahoo.com Chemicals/CAS: celecoxib, 169590-42-5; polysorbate 80, 8050-83-7, 9005-65-6; Acetic Acid, 64-19-7; celecoxib, 169590-42-5; Cyclooxygenase Inhibitors; Polyethylene Glycols; Polysorbates; Pyrazoles; Solvents; Sulfonamides Manufacturers: Ranbaxy, India; lupin research park, India; Sigma, United States References: Connor, E.P., (2003) Physicians' Desk Reference, , 57th ed, Medical Economics Company Inc, Montvale, NJ; Davies, N.M., Mclachlan, A.J., Day, R.O., Williams, K.M., Clinical pharmacokinetics and pharmacodynamics of celecoxib: A selective cyclo-oxygenase-2 inhibitor (2002) Clin. Pharmacokinet, 38 (3), pp. 225-242; Jackson, L.M., Hawkey, C.J., COX-2 selective nonsteroidal anti-inflammatory drugs: Do they really offer any advantages? (2000) Drugs, 59 (6), pp. 1207-1216; Nagarsenker, M.S., Joshi, M.S., Celecoxib-cyclodextrin systems: Characterization and evaluation of in vitro and in vivo advantage (2005) Drug Dev. Ind. Pharm, 31 (2), pp. 169-178; Seedhar, N., Bhatia, S., Solubility enhancement of Cox-2 inhibitors using various solvent systems (2003) AAPS PharmSciTech, 4 (3), pp. E33; Devi, V.K., Vijayalakshmi, P., Avinash, M., Pre-formulation studies on celecoxib with a view to improve bioavailability (2003) Indian J. Pharm. Sci, 65 (5), pp. 542-545; Gupta, P., Kakumanu, V.K., Bansal, A.K., Stability and solubility of celecoxib-PVP amorphous dispersions: A molecular perspective (2004) Pharm. Res, 21 (10), pp. 1762-1769; Gupta, P., Bansal, A.K., Molecular interactions in celecoxib-PVP- meglumine amorphous system (2005) J. Pharm. Pharmacol, 57 (3), p. 303; Gupta, P., Bansal, A.K., Spray drying for generation of a ternary amorphous system of celecoxib, PVP and meglumine (2005) Pharm. Dev. Technol, 10 (2), pp. 273-281; Rawat, S., Jain, S.K., Solubility enhancement of celecoxib using beta-cyclodextrin inclusion complexes (2004) Eur. J. Pharm. Biopharm, 57 (2), pp. 263-267; Chandra Sekhara Rao, G., Satish Kumar, M., Mathivanan, N., Bhanoji Rao, M.E., Improvement of physical stability and dissolution rate of celecoxib suspensions by complexation with beta-cyclodextrins (2004) Pharmazie, 59, p. 627; Reddy, M.N., Rehana, T., Ramakrishna, S., Chowdhary, K.P., Diwan, P.V., Beta cyclodextrin complexes of celecoxib: Molecular modeling, characterization and dissolution studies (2004) AAPS PharmSciTech, 6 (1), pp. E7; Ventura, C.A., Giannone, I., Paolino, D., Pistara, V., Corsaro, A., Puglisi, G., Preparation of celecoxib-dimethyl-beta-cyclodextrin inclusion complex: Characterization and in vitro permeation study (2005) Eur. J. Med. Chem, 40 (7), pp. 624-631; Sinha, V.R., Anitha, R., Ghosh, S., Nanda, A., Kumria, R., Complexation of celecoxib with β-cyclodextrin: Characterization of the interaction in solution and solid state (2005) J. Pharm. Sci, 94, pp. 676-687; Manzoori, J.L., Abdolmohammad-Zadeh, H., Amjadi, M., Study on the inclusion complex between beta-cyclodextrin and celecoxib by spectrofluorimetry and its analytical application (2005) Farmaco, 60, p. 575; Subramanian, N., Ray, S., Ghosal, S.K., Bhadra, R., Moulik, S.P., Formulation design of self-microemulsifying drug delivery systems for improved oral bioavailability of celecoxib (2004) Biol. Pharm. Bull, 27, pp. 1993-1999; Lu, G.W., Hawley, M., Smith, M., Geiger, B.M., Pfund, W., Characterization of a novel polymorphic form of celecoxib (2006) J. Pharm. Sci, 95, pp. 305-317; Paradkar, A., Maheshwari, M., Kambli, R., Grimsey, I., York, P., Design and evaluation of celecoxib porous particles using melt sonocrystallization (2006) Pharm. Res, 23 (6), pp. 1395-1400; Mutalik, S., Venkatesh, M., Udupa, N., Fast analgesic activity from recrystallized nimesulide and its solid dispersion (2002) Indian J. Physiol. Pharmacol, 46 (1), pp. 115-118; Kapoor, A., Mujumdar, D.K., Yadav, M.R., Crystal forms of nimesulide-a sulfonanilide (non-steroidal anti-inflammatory drug) (1998) Indian J. Chem., B, 37 (6), pp. 572-575; Ghosh, M.N., (1984) Fundamentals of Experimental Pharmacology, , 2nd ed, Scientific Book Agency: Calcutta, India; Hossinzadeh, H., Ramezani, M., Fadishei, M., Mahmoudi, M., Antinociceptive, antiinflammatory and acute toxicity effects of zhumeria majdae extracts in mice and rats (2002) Phytomedicine, 9 (2), pp. 135-141; Kulkarni, S.K., (1999) Hand Book of Experimental Pharmacology, p. 23. , 3rd ed, Vallabh Prakashan: New Delhi, India; Reddy, M.N., Sujatha, P., Chauhan, A.S., Ramakrishna, S., Diwan, P.V., A simple and sensitive reverse-phase high performance liquid chromatographic method for the determination of celecolxib in rat plasma (2003) Indian J. Pharm. Sci, 65, p. 260; Betageri, G.V., Makarla, K.R., Enhancement of dissolution of glyburide by solid dispersion and lyophilization techniques (1995) Int. J. Pharm, 126 (1), pp. 155-160; Liu, C., Liu, C., Desai, K.G.H., Enhancement of dissolution rate of valdecoxib using solid dispersions with polyethylene glycol 4000 (2005) Drug Dev. Ind. Pharm, 31 (1), pp. 1-10; Serajuddin, A.T.M., Sheen, P.C., Augustine, M.A., Improved dissolution of a poorly water-soluble drug from solid dispersions in polyethylene glycol: Polysorbate 80 mixtures (1990) J. Pharm. Sci, 79 (5), pp. 463-464; Babu, M.M.G.V., Gouri Shankar, V., Hima Sankar, K., Sheshashayana, A., Kishore Kumar, N., Ramana Murthy, K.V., Development of dissolution medium for a poorly water soluble drug, celecoxib (2002) Indian J. Pharm. Sci, 64 (6), pp. 588-591; Paradkar, A.R., Pawar, A.P., Chordiya, J.K., Patil, V.B., Ketkar, A.R., Spherical crystallization of celecoxib (2002) Drug Dev. Ind. Pharm, 28 (10), pp. 1213-1220; Chiou, W.L., Chen, S.J., Athanikar, N., Enhancement of dissolution rates of poorly water-soluble drugs by crystallization in aqueous surfactant solutions. I: Sulfathiazole, prednisone and chloramphenicol (1976) J. Pharm. Sci, 65 (11), pp. 1702-1704",
year = "2007",
language = "English",
volume = "61",
pages = "362--374",
journal = "PDA Journal of Pharmaceutical Science and Technology",
issn = "1079-7440",
publisher = "Parenteral Drug Association Inc.",
number = "5",

}

Preparation and physicochemical and preclinical evaluations of recrystallized celecoxib. / Mutalik, S.; Usha, N.; Ranjith, A.K.; Umesh, S.; Musmade, P.; Anup, N.

In: PDA Journal of Pharmaceutical Science and Technology, Vol. 61, No. 5, 2007, p. 362-374.

Research output: Contribution to journalArticle

TY - JOUR

T1 - Preparation and physicochemical and preclinical evaluations of recrystallized celecoxib

AU - Mutalik, S.

AU - Usha, N.

AU - Ranjith, A.K.

AU - Umesh, S.

AU - Musmade, P.

AU - Anup, N.

N1 - Cited By :2 Export Date: 10 November 2017 CODEN: JPHTE Correspondence Address: Mutalik, S.; School of Pharmacy, Univeristy of Queensland, Brisbane, QLD 4072, Australia; email: ssmutalik@yahoo.com Chemicals/CAS: celecoxib, 169590-42-5; polysorbate 80, 8050-83-7, 9005-65-6; Acetic Acid, 64-19-7; celecoxib, 169590-42-5; Cyclooxygenase Inhibitors; Polyethylene Glycols; Polysorbates; Pyrazoles; Solvents; Sulfonamides Manufacturers: Ranbaxy, India; lupin research park, India; Sigma, United States References: Connor, E.P., (2003) Physicians' Desk Reference, , 57th ed, Medical Economics Company Inc, Montvale, NJ; Davies, N.M., Mclachlan, A.J., Day, R.O., Williams, K.M., Clinical pharmacokinetics and pharmacodynamics of celecoxib: A selective cyclo-oxygenase-2 inhibitor (2002) Clin. Pharmacokinet, 38 (3), pp. 225-242; Jackson, L.M., Hawkey, C.J., COX-2 selective nonsteroidal anti-inflammatory drugs: Do they really offer any advantages? (2000) Drugs, 59 (6), pp. 1207-1216; Nagarsenker, M.S., Joshi, M.S., Celecoxib-cyclodextrin systems: Characterization and evaluation of in vitro and in vivo advantage (2005) Drug Dev. Ind. Pharm, 31 (2), pp. 169-178; Seedhar, N., Bhatia, S., Solubility enhancement of Cox-2 inhibitors using various solvent systems (2003) AAPS PharmSciTech, 4 (3), pp. E33; Devi, V.K., Vijayalakshmi, P., Avinash, M., Pre-formulation studies on celecoxib with a view to improve bioavailability (2003) Indian J. Pharm. Sci, 65 (5), pp. 542-545; Gupta, P., Kakumanu, V.K., Bansal, A.K., Stability and solubility of celecoxib-PVP amorphous dispersions: A molecular perspective (2004) Pharm. Res, 21 (10), pp. 1762-1769; Gupta, P., Bansal, A.K., Molecular interactions in celecoxib-PVP- meglumine amorphous system (2005) J. Pharm. Pharmacol, 57 (3), p. 303; Gupta, P., Bansal, A.K., Spray drying for generation of a ternary amorphous system of celecoxib, PVP and meglumine (2005) Pharm. Dev. Technol, 10 (2), pp. 273-281; Rawat, S., Jain, S.K., Solubility enhancement of celecoxib using beta-cyclodextrin inclusion complexes (2004) Eur. J. Pharm. Biopharm, 57 (2), pp. 263-267; Chandra Sekhara Rao, G., Satish Kumar, M., Mathivanan, N., Bhanoji Rao, M.E., Improvement of physical stability and dissolution rate of celecoxib suspensions by complexation with beta-cyclodextrins (2004) Pharmazie, 59, p. 627; Reddy, M.N., Rehana, T., Ramakrishna, S., Chowdhary, K.P., Diwan, P.V., Beta cyclodextrin complexes of celecoxib: Molecular modeling, characterization and dissolution studies (2004) AAPS PharmSciTech, 6 (1), pp. E7; Ventura, C.A., Giannone, I., Paolino, D., Pistara, V., Corsaro, A., Puglisi, G., Preparation of celecoxib-dimethyl-beta-cyclodextrin inclusion complex: Characterization and in vitro permeation study (2005) Eur. J. Med. Chem, 40 (7), pp. 624-631; Sinha, V.R., Anitha, R., Ghosh, S., Nanda, A., Kumria, R., Complexation of celecoxib with β-cyclodextrin: Characterization of the interaction in solution and solid state (2005) J. Pharm. Sci, 94, pp. 676-687; Manzoori, J.L., Abdolmohammad-Zadeh, H., Amjadi, M., Study on the inclusion complex between beta-cyclodextrin and celecoxib by spectrofluorimetry and its analytical application (2005) Farmaco, 60, p. 575; Subramanian, N., Ray, S., Ghosal, S.K., Bhadra, R., Moulik, S.P., Formulation design of self-microemulsifying drug delivery systems for improved oral bioavailability of celecoxib (2004) Biol. Pharm. Bull, 27, pp. 1993-1999; Lu, G.W., Hawley, M., Smith, M., Geiger, B.M., Pfund, W., Characterization of a novel polymorphic form of celecoxib (2006) J. Pharm. Sci, 95, pp. 305-317; Paradkar, A., Maheshwari, M., Kambli, R., Grimsey, I., York, P., Design and evaluation of celecoxib porous particles using melt sonocrystallization (2006) Pharm. Res, 23 (6), pp. 1395-1400; Mutalik, S., Venkatesh, M., Udupa, N., Fast analgesic activity from recrystallized nimesulide and its solid dispersion (2002) Indian J. Physiol. Pharmacol, 46 (1), pp. 115-118; Kapoor, A., Mujumdar, D.K., Yadav, M.R., Crystal forms of nimesulide-a sulfonanilide (non-steroidal anti-inflammatory drug) (1998) Indian J. Chem., B, 37 (6), pp. 572-575; Ghosh, M.N., (1984) Fundamentals of Experimental Pharmacology, , 2nd ed, Scientific Book Agency: Calcutta, India; Hossinzadeh, H., Ramezani, M., Fadishei, M., Mahmoudi, M., Antinociceptive, antiinflammatory and acute toxicity effects of zhumeria majdae extracts in mice and rats (2002) Phytomedicine, 9 (2), pp. 135-141; Kulkarni, S.K., (1999) Hand Book of Experimental Pharmacology, p. 23. , 3rd ed, Vallabh Prakashan: New Delhi, India; Reddy, M.N., Sujatha, P., Chauhan, A.S., Ramakrishna, S., Diwan, P.V., A simple and sensitive reverse-phase high performance liquid chromatographic method for the determination of celecolxib in rat plasma (2003) Indian J. Pharm. Sci, 65, p. 260; Betageri, G.V., Makarla, K.R., Enhancement of dissolution of glyburide by solid dispersion and lyophilization techniques (1995) Int. J. Pharm, 126 (1), pp. 155-160; Liu, C., Liu, C., Desai, K.G.H., Enhancement of dissolution rate of valdecoxib using solid dispersions with polyethylene glycol 4000 (2005) Drug Dev. Ind. Pharm, 31 (1), pp. 1-10; Serajuddin, A.T.M., Sheen, P.C., Augustine, M.A., Improved dissolution of a poorly water-soluble drug from solid dispersions in polyethylene glycol: Polysorbate 80 mixtures (1990) J. Pharm. Sci, 79 (5), pp. 463-464; Babu, M.M.G.V., Gouri Shankar, V., Hima Sankar, K., Sheshashayana, A., Kishore Kumar, N., Ramana Murthy, K.V., Development of dissolution medium for a poorly water soluble drug, celecoxib (2002) Indian J. Pharm. Sci, 64 (6), pp. 588-591; Paradkar, A.R., Pawar, A.P., Chordiya, J.K., Patil, V.B., Ketkar, A.R., Spherical crystallization of celecoxib (2002) Drug Dev. Ind. Pharm, 28 (10), pp. 1213-1220; Chiou, W.L., Chen, S.J., Athanikar, N., Enhancement of dissolution rates of poorly water-soluble drugs by crystallization in aqueous surfactant solutions. I: Sulfathiazole, prednisone and chloramphenicol (1976) J. Pharm. Sci, 65 (11), pp. 1702-1704

PY - 2007

Y1 - 2007

N2 - The aim of the present study is to increase the aqueous solubility of celecoxib by recrystallization from distilled water, Tween-80, and polyethylene glycol-400. The prepared crystals were evaluated for various physicochemical evaluations, dissolution rate, and in vivo performance like analgesic activity (by writhing and hot plate method) and pharmacokinetics in mice. The practical yield of the crystals ranged between 83 and 98%, and celecoxib content was more than 99%. Celecoxib showed an almost 5-fold increase in solubility when recrystallized in the presence of Tween-80 (2%). The dissolution rates of celecoxib from the co-crystal forms were considerably higher than that of plain celecoxib. The infrared and differential scanning calorimetry studies indicated the absence of a well-defined interaction between celecoxib and carriers. The differential scanning calorimetry and X-ray diffraction studies indicated the amorphization or partial amorphization of the drug. The scanning electron microscopy showed fluffy, porous, and fine particles in recrystallized celecoxib. The particle size of prepared co-crystals was considerably reduced in comparison with plain celecoxib. The crystals prepared with Tween-80 (2%) showed significantly higher analgesic activity than plain celecoxib. In pharmacokinetic study, the prepared crystals exhibited significantly high and rapid absorption along with improved bioavailability.

AB - The aim of the present study is to increase the aqueous solubility of celecoxib by recrystallization from distilled water, Tween-80, and polyethylene glycol-400. The prepared crystals were evaluated for various physicochemical evaluations, dissolution rate, and in vivo performance like analgesic activity (by writhing and hot plate method) and pharmacokinetics in mice. The practical yield of the crystals ranged between 83 and 98%, and celecoxib content was more than 99%. Celecoxib showed an almost 5-fold increase in solubility when recrystallized in the presence of Tween-80 (2%). The dissolution rates of celecoxib from the co-crystal forms were considerably higher than that of plain celecoxib. The infrared and differential scanning calorimetry studies indicated the absence of a well-defined interaction between celecoxib and carriers. The differential scanning calorimetry and X-ray diffraction studies indicated the amorphization or partial amorphization of the drug. The scanning electron microscopy showed fluffy, porous, and fine particles in recrystallized celecoxib. The particle size of prepared co-crystals was considerably reduced in comparison with plain celecoxib. The crystals prepared with Tween-80 (2%) showed significantly higher analgesic activity than plain celecoxib. In pharmacokinetic study, the prepared crystals exhibited significantly high and rapid absorption along with improved bioavailability.

M3 - Article

VL - 61

SP - 362

EP - 374

JO - PDA Journal of Pharmaceutical Science and Technology

JF - PDA Journal of Pharmaceutical Science and Technology

SN - 1079-7440

IS - 5

ER -