The Impact of Co-crystal Formation on the Stability of Camylofin Dihydrochloride Immediate Release Tablets

Year 2024, Volume: 44 Issue: 2, 108 - 123, 01.06.2024

Sanika Kole Rutuja Vinchurkar Ashwini Gawade Ashwin Kuchekar

https://doi.org/10.52794/hujpharm.1331991

Abstract

The objective of this study was to select an appropriate co-former and investigate its impact on the formation of co-crystals involving Camylofin dihydrochloride and Fumaric acid. To determine co-former, a molecular docking study was conducted, and among the compounds evaluated, fumaric acid exhibited the highest number of hydrogen bonds formed with Camylofin dihydrochloride and demonstrated a favorable Glide score of -5.21 kcal/mol. The kneading method was employed after optimizing the molar ratio of Camylofin dihydrochloride to Fumaric acid, which was found to be 1:1, 1:2, and 1:3. The resulting Camylofin dihydrochloride co-crystals underwent various analytical techniques, including Fourier Transform Infrared Spectroscopy, Scanning Electron Microscopy, Powder X-ray Diffraction, and Differential Scanning Calorimetry. The Camylofin dihydrochloride-Fumaric acid co-crystals, immediate-release tablets were formulated. A result of ex-vivo study revealed that Camylofin dihydrochloride-Fumaric acid co-crystals and their immediate release tablets were more potent than plain Camylofin dihydrochloride, with the immediate release tablets being the most potent of all. Stability analysis demonstrated that the final batch F5 remained stable under accelerated ambient stability conditions (40°C±2°C, 75% RH±5%RH) and accelerated stability conditions (25°C±2°C,62% RH±5%RH). The co-crystal technology utilized in this study successfully improved the stability of Camylofin dihydrochloride without altering its chemical composition.

Keywords

Camylofin dihydrochloride, Co-crystals, Immediate release tablets, Stability Drug release, Ex-vivo study

References

• 1. Palshetkar N, Purandare A, Mehta H, et al. Effectiveness and Safety of Camylofin in Augmentation of Labor: A Systema- tic Review and Meta-Analysis. IJOGR. 2020; 70:425–439. https://doi.org/10.1007/s13224-020-01343-3
• 2. Mayadeo N, Gangadhar A, Das S. Camylofin in the mana- gement of prolonged labor: a review of evidence. Int J Rep- rod Contraception, Obstet Gynecol. 2017; 6:776. https://doi. org/10.18203/2320-1770.ijrcog20170545
• 3. Sarbhjit K, Bajwa SK, Parmjit K, et al. To compare the effect of camylofin dihydrochloride (Anafortin) with combination of valethamate bromide (epidosin) and hyoscine butyl-n-bormide (buscopan) on cervical dilation. J Clin Diagnostic Res. 2013; 7:1897–1899. https://doi.org/10.7860/JCDR/2013/6231.3345
• 4. Singh RKR, Rathnam M V., Singh SJ, et al. Determination of Camylofin Dihydrochloride and Nimesulide in Pharmace- utical Preparation by Gas Chromatography. Am J Anal Chem. 2011; 2:944-952 https://doi.org/10.4236/ajac.2011.28110
• 5. Kokilambigai KS, Lakshmi KS. Camylofin dihydrocloride - A review of analytical methods. Int J Pharm and Pharm Sci. 2014; 6:36–37
• 6. Singh RKR, Rathnam M V., Singh SJ, et al. Stability Indi- cating Method for Simultaneous RP HPLC Determination of Camylofin Dihydrochloride and Nimesulide in Pharma- ceutical Preparations. ISRN Anal Chem. 2012. https://doi. org/10.5402/2012/586415
• 7. Singh RR, Rathnam M V., Singh SJ, et al. A stability indica- ting GC-FID method for camylofin dihydrochloride and dic- lofenac potassium in pharmaceutical preparation. Int J Pharm Pharm Sci. 2012; 4(1):317-324
• 8. Guo M, Sun X, Chen J, et al. Pharmaceutical cocrystals: A review of preparations, physicochemical properties and app- lications. Acta Pharm Sin B. 2021; 11:2537–2564. https://doi. org/ 10.1016/j.apsb.2021.03.030
• 9. Chauhan V, Mardia R, Patel M, et al. Technical and Formu- lation Aspects of Pharmaceutical Co-Crystallization: A Syste- matic Review. ChemistrySelect. 2022; 37:e202202588. https:// doi.org/10.1002/slct.202202588
• 10. Shete AS, Shah V V., Bhosale PA, et al. Fenofibrate-Nicotina- mide Cocrystals: Molecular Docking Studies and Evaluation in Tablet Dosage Form. Indian J Pharm Sci. 2022; 84(3):560- 568. https://doi.org/10.36468/pharmaceutical-sciences.950
• 11. Mangesh B, Sumedh P, Sumedh M, et al. Scientific Coformer Screening, Preparation and Evaluation of Fenofibrate Tartaric Acid Cocrystal. J Drug Deliv Ther. 2019; 9:406–410. https:// doi.org/10.22270/jddt.v9i4.3199
• 12. Dhibar M, Chakraborty S, Basak S, et al. Critical Analysis and Optimization of Stoichiometric Ratio of Drug-Coformer on Cocrystal Design: Molecular Docking, In Vitro and In Vivo Assessment. Pharmaceuticals. 2023; 16(2): 284. https://doi. org/10.3390/ph16020284
• 13. Trott oleg, Arthur J. Olson. AutoDock Vina: Improving the Speed and Accuracy of Docking with a New Scoring Function, Efficient Optimization, and Multithreading. J Comput Chem. 2010; 31(2):455–461. https://doi.org/10.1002/jcc.21334
• 14. Kumar Bandaru R, Rout SR, Kenguva G, et al. Recent Ad- vances in Pharmaceutical Cocrystals: From Bench to Market. Front pharmacol. 2021;12:780582. https://doi.org/10.3389/ fphar.2021.780582
• 15. Gawade A, Kuchekar A, Boldhane S, et al. Improvement of Physicochemical and Solubility of Dipyridamole by Cocry- stallization Technology. J Drug Deliv Ther. 2021; 11:43–48. https://doi.org/10.22270/jddt.v11i1-s.4696
• 16. Industry G for. Q1A(R2) Stability Testing of New Drug Subs- tances and Products. Ich
• 17. Anand R, Nanda A. Formulation and Evaluation of Cocry- stals of a Bcs Class Ii Drug Using Glycine As Coformer. Int J Appl Pharm. 2022; 14:68–76. https://doi.org/10.22159/ ijap.2022v14i6.46090
• 18. Ouyang J, Xing X, Zhou L, et al. Cocrystal design of vanillin with amide drugs: Crystal structure determination, solubility enhancement, DFT calculation. Chem Eng Res Des. 2022; 183:170–180. doi: 10.1016/j.cherd.2022.05.009
• 19. Kara DD, Rathnanand M. Cocrystals and Drug–Drug Cocry- stals of Anticancer Drugs: A Perception towards Screening Techniques, Preparation, and Enhancement of Drug Proper- ties. Crystals. 2022; 12(10):1337. https://doi.org/10.3390/ cryst12101337
• 20. Garbacz P, Wesolowski M. Benzodiazepines co-crystals scre- ening using FTIR and Raman spectroscopy supported by dif- ferential scanning calorimetry. Spectrochim Acta - Part A Mol Biomol Spectrosc. 2020; 234:118242. https://doi.org/10.1016/j. saa.2020.118242
• 21. Madhuri G, Nagaraju R, Killari KN. Enhancement of the physicochemical properties of poorly soluble lovastatin by co- crystallization techniques - In vivo studies. Indian J Pharm Sci. 2020; 82:249–259. doi: 10.36468/pharmaceutical-scien- ces.645
• 22. USP. Chapter 616 Bulk Density and Tapped Density of Pow- ders. United States Pharmacopeial Conv
• 23. The United States Pharmacopeial Convention. Basic Methods for Angle of Repose - 1174 - Powder Flow. The United States of Pharmacopoeia
• 24. Jain S, Bansal M, Sharma A. Formulation And In-Vitro Eva- luation Of Cocrystals Of Pantoprazole Sodium For Immedia- te Release. Int J Pharm Biol Sci Arch. 2021; 9(1). https://doi. org/10.32553/ijpba.v9i1.176
• 25. Dhahir RK, Al-Kotaji MYASAR. Formulation of orally disin- tegrating tablets of cinnarizine by using direct compression method. Int J Appl Pharm. 2019; 11:117–123. doi: 10.22159/ ijap.2019v11i1.29599
• 26. Trivedi HR, Borkar DS, Puranik PK. Experimental design approach for development of cocrystals and immediate relea- se cocrystal tablet of atorvastatin calcium for enhancement of solubility and dissolution. J Res Pharm. 2020; 24(5):720-737. https://doi.org/10.35333/jrp.2020.226
• 27. Al-Dulaimi A, Al-kotaji M, Abachi F. Paracetamol/ naproxen co-crystals; a simple way for improvement of flowability, tab - leting and dissolution properties. Iraqi J Pharm. 2021; 18:1– 19. https://doi.org/10.33899/iphr.2021.168798
• 28. Panzade P, Shendarkar G, Shaikh S, et al. Pharmaceutical Cocrystal of Piroxicam: Design, formulation and evalu- ation. Adv Pharm Bull. 2017; 7:399–408. doi: 10.15171/ apb.2017.048
• 29. Alam K, Shareef H, Bushra R. Formulation development & evaluation of caffeine tablets (200mg) by direct compression. Int J Drug Dev Res.2013; 5(3):371-376
• 30. The United States Pharmacopeial Convention. USP 1216 Tab- let Friability. Usp30 - Nf25
• 31. Osei-Yeboah F, Sun CC. Validation and applications of an ex- pedited tablet friability method. Int J Pharm. 2015; 484:146- 155. https://doi.org/10.1016/j.ijpharm.2015.02.061
• 32. Budiman A, Husni P, Shafira, et al. The development of gli- benclamide-saccharin cocrystal tablet formulations to increa- se the dissolution rate of the drug. Int J Appl Pharm. 2019; 11:359–364. doi: 10.22159/ijap.2019v11i4.33802
• 33. Rodríguez-Ruiz C, Montes-Tolentino P, Domínguez-Chávez JG, et al. Tailoring Chlorthalidone Aqueous Solubility by Cocrystallization: Stability and Dissolution Behavior of a Novel Chlorthalidone-Caffeine Cocrystal. Pharmaceutics. 2022; 30; 14(2):334. https://doi.org/10.3390/pharmaceu- tics14020334
• 34. Marzouk MA, Osman DA, Mohamed OS. In vitro and in vivo evaluation of taste-masked orodispersible tab- lets of fluoxetine hydrochloride for the treatment of dep - ression. Drug Dev Ind Pharm. 2021; 47:645–653. doi: 10.1080/03639045.2021.1908336
• 35. Tembhare E, Gupta KR, Umekar MJ. An Approach to Drug Stability Studies and Shelf-life Determination. Arch Curr Res Int. 2019; 19(1):1-20. https://doi.org/10.9734/acri/2019/ v19i130147
• 36. Vinet L, Zhedanov A. A ‘missing’ family of classical ortho- gonal polynomials. J. Phys. A-Math. 2011; 44. https://doi. org/10.1088/1751-8113/44/8/085201
• 37. Al-kazemi R, Al-basarah Y, Nada A. Atorvastatin Cocrystals : Tablet. Asian J Pharm. 2020; 14:578–595
• 38. Undale VR. An isolated chicken ileum: Alternative to labo- ratory animals for isolated tissue experimentation. IOSR J Pharm. 2012; 2(5):39-45. doi: 10.9790/3013-25203. https:// doi.org/10.9790/3013-25203945
• 39. Jain G, Bodakse SH, Mishra S, et al. Development of an ex vivo model for pharmacological experimentation on isolated tissue preparation. J Adv Pharm Technol Res. 2012; 3(3):176- 81. doi: 10.4103/2231-4040.101013
• 40. Rahman Z, Agarabi C, Zidan AS, et al. Physico-mechani- cal and stability evaluation of carbamazepine cocrystal with nicotinamide. AAPS Pharm Sci Tech. 2011; 12:693–704. doi: 10.1208/s12249-011-9603-4
• 41. Zhou Q, Tan Z, Yang D, et al. Improving the solubility of ari- piprazole by multicomponent crystallization. Crystals. 2021; 11(4):343. https://doi.org/10.3390/cryst11040343
• 42. Guo C, Zhang Q, Zhu B, et al. Pharmaceutical Cocrystals of Nicorandil with Enhanced Chemical Stability and Susta- ined Release. Cryst Growth Des. 2020; 20:6995–7005. doi: 10.1021/acs.cgd.0c01043
• 43. Panzade P, Shendarkar G. Superior solubility and dissolution of zaltoprofen via pharmaceutical cocrystals. Turkish J Pharm Sci. 2019; 16:310–316. doi: 10.4274/tjps.galenos.2018.15013
• 44. Khan MS, Vishakante GD, Bathool A. Preparation and evalua- tion of sodium alginate porous dosage form as carriers for low dosed active pharmaceutical ingredients. Turkish J Pharm Sci. 2012; 9:183–198
• 45. Yang D, Cao J, Jiao L, et al. Solubility and Stability Advan- tages of a New Cocrystal of Berberine Chloride with Fuma- ric Acid. ACS Omega. 2020; 5(14):8283–8292. https://doi. org/10.1021/acsomega.0c00692