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Cocrystallization of Etodolac: Prediction of Cocrystallization, Synthesis, Solid State Characterization And In Vitro Drug Release

Year 2017, Volume: 21 Issue: 1, 78 - 88, 20.09.2016

Dipak D Gadade Sanjay S Pekamwar Swaroop R Lahoti Santosh D Patni Mahesh C Sarode

https://doi.org/10.12991/marupj.259884

Abstract

The present investigation deals with determination of Hansen solubility parameters, synthesis and characterization of Etodolac co-crystals with various coformers. Various coformers were screened under the study to prepare cocrystals of Etodolac for improving its solubility and dissolution. The prepared cocrystals were characterized by saturation solubility study, Fourier transform infrared spectroscopy (FTIR), differential scanning calorimetry (DSC), powder X-ray diffraction (PXRD), in vitro dissolution studies and stability study. The outcome of study show that the significant improvement in solubility with Para Amino Benzoic Acid, Ferulic Acid and Salicylic acid. Etodolac:Salicylic acid cocrystal 1:1M were formulated as immediate release tablets. The results reveal that solubility and dissolution of etodolac was improved by cocrystallization and it possess adequate pharmaceutical stability.

Keywords

Etodolac Cocrystal Solubility Dissolution Hansen Solubility Parameter

References

  • Vijayaraj S, Omshanthi B, Anitha S, Sampathkumar KP. Synthesis and characterization of novel sulphoxide prodrug of famotidine. Indian J Pharm Educ 2014; 48: 35-44.
  • Blagden N, De Matas M, Gavan PT, York P. Crystal engineering of active pharmaceutical ingredients to improve solubility and dissolution rates. Adv Drug Deliver Rev 2007; 59(7): 617-30.
  • Yadav AV, Shete AS, Dabke AP, Kulkarni PV, Sakhare SS. Co-crystals: a novel approach to modify physicochemical properties of active pharmaceutical ingredients. Indian J Pharm Sci 2009; 71(4): 359.
  • Zhou Z, Li W, Sun WJ, Lu T, Tong HH, Sun CC, Zheng Y. Resveratrol cocrystals with enhanced solubility and tabletability. Int. J. Pharm 2016; 509: 391-399.
  • Sravani E, Mannava MC, Kaur D, Annapurna BR, Khan RA, Suresh K, Mittapalli S, Nangia A, Kumar BD. Preclinical bioavailability–bioequivalence and toxico-kinetic profile of stable succinc acid cocrystal of temozolomide. Current Sci 2015; 108(6): 1097.
  • Childs SL, Kandi P, Lingireddy SR. Formulation of a danazol cocrystal with controlled supersaturation plays an essential role in improving bioavailability. Mol Pharmaceut 2013; 10(8): 3112-27.
  • Mulye SP, Jamadar SA, Karekar PS, Pore YV, Dhawale SC. Improvement in physicochemical properties of ezetimibe using a crystal engineering technique. Powder Tech 2012; 222: 131-8.
  • Goud NR, Gangavaram S, Suresh K, Pal S, Manjunatha SG, Nambiar S, Nangia A. Novel furosemide cocrystals and selection of high solubility drug forms. J Pharm Sci 2012; 101(2): 664-680.
  • Trask AV, Motherwell WS, Jones W. Solvent-drop grinding: green polymorph control of cocrystallisation. Chem Comm 2004; (7) :890-1.
  • Humber LG. Etodolac: The chemistry, pharmacology, metabolic disposition, and clinical profile of a novel anti‐inflammatory pyranocarboxylic acid. Medicinal research reviews. 1987; 7(1): 1-28.
  • Glaser K, Sung ML, O'Neill K, Hartman D, Carlson R, Kreft A, Kubrak D, Hsiao CL, Weichman B. Etodolac selectively inhibits human prostaglandin G/H synthase 2 (PGHS-2) versus human PGHS-1. Euro J Pharm 1995; 281(1): 107-11.
  • Naito Y, Matsuda H, Shimomura K, Kurihara K, Tochigi K, Tomono K. Measurement and correlation of solubilities of the poorly water-soluble pharmaceutical compound etodolac by addition of co-solvents. Fluid Phase Equilibria. 2013; 357: 43-9.
  • Kitak T, Dumičić A, Planinšek O, Šibanc R, Srčič S. Determination of solubility parameters of ibuprofen and ibuprofen lysinate. Molecules. 2015; 20(12): 21549-68.
  • Shewale S, Shete AS, Doijad RC, Kadam SS, Patil VA, Yadav AV. Formulation and solid state characterization of nicotinamide-based co-crystals of fenofibrate. Indian J Pharm Sci 2015; 77(3): 328.
  • Mohammad MA, Alhalaweh A, Velaga SP. Hansen solubility parameter as a tool to predict cocrystal formation. Int J Pharm . 2011; 407(1): 63-71
  • Greenhalgh DJ, Williams AC, Timmins P, York P. Solubility parameters as predictors of miscibility in solid dispersions. J Pharm Sci 1999; 88(11): 1182-90.
  • Nguyen KL, Friščić T, Day GM, Gladden LF, Jones W. Terahertz time-domain spectroscopy and the quantitative monitoring of mechanochemical cocrystal formation. Nat materials. 2007; 6(3): 206-209.
  • Higuchi, KA Connors. Phase-solubility techniques. Adv Anal Chem Instrum 1965; 4: 117–212.

Etodolak’ın Ko-kristalizasyonu: Ko-kristalizasyon Tahmini, Ko-kristal Sentezi, Katı Faz Yapı Aydınlatma Çalışmaları ve In Vitro İlaç Salımı

Year 2017, Volume: 21 Issue: 1, 78 - 88, 20.09.2016

Dipak D Gadade Sanjay S Pekamwar Swaroop R Lahoti Santosh D Patni Mahesh C Sarode

https://doi.org/10.12991/marupj.259884

Abstract

Bu araştırma kapsamında, etodolak
ko-kristallerinin sentezi  ve farklı
koformerlerin yapılarının aydınlatılması ile Hansen  çözünürlük paratmetrelerinin tayini
çalışılmıştır. Etodolak’ın  çözünürlüğünün
arttırılması ve dissolüsyon özelliğinin  iyileştirilmesi
amacıyla hazırlanan etodolak ko-kristallerinin 
farklı koformerleri izlenmiştir. Ko-Kristallerin yapısı; Fourier  dönüşümlü infrared spektroskopisi (FTIR),
diferansiyal  taramalı kalorimetri (DSC)
tayini, X-ışını kırınım (PXRD)  tayini
ile aydınlatılmış, ayrıca çözünürlük ve çözelti doygunluğu  çalışmaları, in vitro dissolüsyon ve
stabilite çalışmaları  yapılmıştır.
Çalışma sonucunda etodolak’ın, p-amino benzoik 
asit, ferrulik asit ve salisilik asit ile kokristalleri hazırlandığında  çözünürlüğünün arttığı tespit edilmiştir.
Etodolak:Salisilik  ait 1:1M
kokristalinin hızlı ilaç salımı için formüle edilen  tablet içeriğinde kullanılması öngörülmüştür.
Etodolak kokristallerinin  yeterli
farmasötik stabiliteye sahip oldukları ve 
etodolak’ın çözünürlük ve dissolüsyon özelliğini arttırdıkları  sonucuna ulaşılmıştır.  

Keywords

Etodolak Ko-Kristal Çözünürlük Dissolüsyon Hansen Çözünürlük Parametresi

References

  • Vijayaraj S, Omshanthi B, Anitha S, Sampathkumar KP. Synthesis and characterization of novel sulphoxide prodrug of famotidine. Indian J Pharm Educ 2014; 48: 35-44.
  • Blagden N, De Matas M, Gavan PT, York P. Crystal engineering of active pharmaceutical ingredients to improve solubility and dissolution rates. Adv Drug Deliver Rev 2007; 59(7): 617-30.
  • Yadav AV, Shete AS, Dabke AP, Kulkarni PV, Sakhare SS. Co-crystals: a novel approach to modify physicochemical properties of active pharmaceutical ingredients. Indian J Pharm Sci 2009; 71(4): 359.
  • Zhou Z, Li W, Sun WJ, Lu T, Tong HH, Sun CC, Zheng Y. Resveratrol cocrystals with enhanced solubility and tabletability. Int. J. Pharm 2016; 509: 391-399.
  • Sravani E, Mannava MC, Kaur D, Annapurna BR, Khan RA, Suresh K, Mittapalli S, Nangia A, Kumar BD. Preclinical bioavailability–bioequivalence and toxico-kinetic profile of stable succinc acid cocrystal of temozolomide. Current Sci 2015; 108(6): 1097.
  • Childs SL, Kandi P, Lingireddy SR. Formulation of a danazol cocrystal with controlled supersaturation plays an essential role in improving bioavailability. Mol Pharmaceut 2013; 10(8): 3112-27.
  • Mulye SP, Jamadar SA, Karekar PS, Pore YV, Dhawale SC. Improvement in physicochemical properties of ezetimibe using a crystal engineering technique. Powder Tech 2012; 222: 131-8.
  • Goud NR, Gangavaram S, Suresh K, Pal S, Manjunatha SG, Nambiar S, Nangia A. Novel furosemide cocrystals and selection of high solubility drug forms. J Pharm Sci 2012; 101(2): 664-680.
  • Trask AV, Motherwell WS, Jones W. Solvent-drop grinding: green polymorph control of cocrystallisation. Chem Comm 2004; (7) :890-1.
  • Humber LG. Etodolac: The chemistry, pharmacology, metabolic disposition, and clinical profile of a novel anti‐inflammatory pyranocarboxylic acid. Medicinal research reviews. 1987; 7(1): 1-28.
  • Glaser K, Sung ML, O'Neill K, Hartman D, Carlson R, Kreft A, Kubrak D, Hsiao CL, Weichman B. Etodolac selectively inhibits human prostaglandin G/H synthase 2 (PGHS-2) versus human PGHS-1. Euro J Pharm 1995; 281(1): 107-11.
  • Naito Y, Matsuda H, Shimomura K, Kurihara K, Tochigi K, Tomono K. Measurement and correlation of solubilities of the poorly water-soluble pharmaceutical compound etodolac by addition of co-solvents. Fluid Phase Equilibria. 2013; 357: 43-9.
  • Kitak T, Dumičić A, Planinšek O, Šibanc R, Srčič S. Determination of solubility parameters of ibuprofen and ibuprofen lysinate. Molecules. 2015; 20(12): 21549-68.
  • Shewale S, Shete AS, Doijad RC, Kadam SS, Patil VA, Yadav AV. Formulation and solid state characterization of nicotinamide-based co-crystals of fenofibrate. Indian J Pharm Sci 2015; 77(3): 328.
  • Mohammad MA, Alhalaweh A, Velaga SP. Hansen solubility parameter as a tool to predict cocrystal formation. Int J Pharm . 2011; 407(1): 63-71
  • Greenhalgh DJ, Williams AC, Timmins P, York P. Solubility parameters as predictors of miscibility in solid dispersions. J Pharm Sci 1999; 88(11): 1182-90.
  • Nguyen KL, Friščić T, Day GM, Gladden LF, Jones W. Terahertz time-domain spectroscopy and the quantitative monitoring of mechanochemical cocrystal formation. Nat materials. 2007; 6(3): 206-209.
  • Higuchi, KA Connors. Phase-solubility techniques. Adv Anal Chem Instrum 1965; 4: 117–212.
There are 18 citations in total.

Details

Subjects Health Care Administration
Journal Section Articles
Authors

Dipak D Gadade This is me

Sanjay S Pekamwar This is me

Swaroop R Lahoti This is me

Santosh D Patni This is me

Mahesh C Sarode This is me

Publication Date September 20, 2016
Published in Issue Year 2017 Volume: 21 Issue: 1

Cite

APA Gadade, D. D., Pekamwar, S. S., Lahoti, S. R., Patni, S. D., et al. (2016). Cocrystallization of Etodolac: Prediction of Cocrystallization, Synthesis, Solid State Characterization And In Vitro Drug Release. Marmara Pharmaceutical Journal, 21(1), 78-88. https://doi.org/10.12991/marupj.259884
AMA Gadade DD, Pekamwar SS, Lahoti SR, Patni SD, Sarode MC. Cocrystallization of Etodolac: Prediction of Cocrystallization, Synthesis, Solid State Characterization And In Vitro Drug Release. Marmara Pharm J. September 2016;21(1):78-88. doi:10.12991/marupj.259884
Chicago Gadade, Dipak D, Sanjay S Pekamwar, Swaroop R Lahoti, Santosh D Patni, and Mahesh C Sarode. “Cocrystallization of Etodolac: Prediction of Cocrystallization, Synthesis, Solid State Characterization And In Vitro Drug Release”. Marmara Pharmaceutical Journal 21, no. 1 (September 2016): 78-88. https://doi.org/10.12991/marupj.259884.
EndNote Gadade DD, Pekamwar SS, Lahoti SR, Patni SD, Sarode MC (September 1, 2016) Cocrystallization of Etodolac: Prediction of Cocrystallization, Synthesis, Solid State Characterization And In Vitro Drug Release. Marmara Pharmaceutical Journal 21 1 78–88.
IEEE D. D. Gadade, S. S. Pekamwar, S. R. Lahoti, S. D. Patni, and M. C. Sarode, “Cocrystallization of Etodolac: Prediction of Cocrystallization, Synthesis, Solid State Characterization And In Vitro Drug Release”, Marmara Pharm J, vol. 21, no. 1, pp. 78–88, 2016, doi: 10.12991/marupj.259884.
ISNAD Gadade, Dipak D et al. “Cocrystallization of Etodolac: Prediction of Cocrystallization, Synthesis, Solid State Characterization And In Vitro Drug Release”. Marmara Pharmaceutical Journal 21/1 (September 2016), 78-88. https://doi.org/10.12991/marupj.259884.
JAMA Gadade DD, Pekamwar SS, Lahoti SR, Patni SD, Sarode MC. Cocrystallization of Etodolac: Prediction of Cocrystallization, Synthesis, Solid State Characterization And In Vitro Drug Release. Marmara Pharm J. 2016;21:78–88.
MLA Gadade, Dipak D et al. “Cocrystallization of Etodolac: Prediction of Cocrystallization, Synthesis, Solid State Characterization And In Vitro Drug Release”. Marmara Pharmaceutical Journal, vol. 21, no. 1, 2016, pp. 78-88, doi:10.12991/marupj.259884.
Vancouver Gadade DD, Pekamwar SS, Lahoti SR, Patni SD, Sarode MC. Cocrystallization of Etodolac: Prediction of Cocrystallization, Synthesis, Solid State Characterization And In Vitro Drug Release. Marmara Pharm J. 2016;21(1):78-8.