Preparation and Physicochemical Characterizations of p-Methoxycinnamic acid – Succinic Acid Cocrystal by Solvent Evaporation Technique

Authors

  • Melanny Ika Sulistyowaty Department of Pharmaceutical Sciences, Faculty of Pharmacy, Universitas Airlangga, Surabaya, East Java, Indonesia https://orcid.org/0000-0002-9510-6822
  • Dwi Setyawan Department of Pharmaceutical Sciences, Faculty of Pharmacy, Universitas Airlangga, Surabaya, East Java, Indonesia; Department of Nanotechnology, Faculty of Advanced Technology and Multidiscipline, Universitas Airlangga, Surabaya, East Java, Indonesia https://orcid.org/0000-0001-8009-6054
  • Retno Sari Department of Pharmaceutical Sciences, Faculty of Pharmacy, Universitas Airlangga, Surabaya, East Java, Indonesia https://orcid.org/0000-0002-3391-1877
  • Abhimata Paramanandana Department of Pharmaceutical Sciences, Faculty of Pharmacy, Universitas Airlangga, Surabaya, East Java, Indonesia
  • Nofika Agung Maharani Department of Pharmaceutical Sciences, Faculty of Pharmacy, Universitas Airlangga, Surabaya, East Java, Indonesia
  • Timbul Partogi Simorangkir Department of Pharmaceutics, Faculty of Military Pharmacy, The Republic of Indonesia Defense University, Bogor, West Java, Indonesia

DOI:

https://doi.org/10.3889/oamjms.2022.10193

Keywords:

Physicochemical characterization, Cocrystal, p-methoxycinnamic acid, Succinic acid, Solvent evaporation

Abstract

Background: PMCA (p-Methoxycinnamic acid) is an active pharmaceutical ingredient derived from Kaempheria galanga L (known as kencur in Indonesia), which is poorly soluble in water. It can cause problems in the development of pharmaceutical dosage forms. Several methods have been carried out to increase the solubility of PMCA such as complex formation with β-cyclodextrin, or solid dispersion. The cocrystal formation method is a solubility enhancement method that has been developed recently.

Aim: The aim of the study was the preparation and physicochemical characterization of PMCA co-crystal with succinic acid (SA) as its conformer by solvent evaporation technique.

Methods: PMCA-SA cocrystal was made by the solvent evaporation method with a 1:1 molar ratio. Physicochemical characterization of PMCA and SA cocrystal was performed by differential scanning calorimetry (DSC), powder X-ray diffraction (PXRD), and scanning electron microscope (SEM).

Results: The DSC thermogram showed a decrease in the melting point of cocrystal compared to PMCA (173.55˚C), SA (187.55˚C), and its physical mixture (159.53˚C). The cocrystal thermogram displayed an endothermic peak at 158.46 ° C. Diffractogram of PMCA- SA cocrystal exhibited new diffraction peaks at an angle of 2θ = 21.92; 25.91 and 39.25˚ which was not found in the diffractogram of every single component nor its physical mixture. SEM photomicrograph showed PMCA-SA cocrystal as a rod-shaped crystal that had a different surface morphology and smaller size than the constituent materials.

Conclusions: Based on the physicochemical characterization data above, it could be ascertained that PMCA-SA cocrystals had formed, these cocrystals were expected to increase the solubility of PMCA in water.

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References

Isadiatuti D, Rosita N, Ekowati J, Syahrani A, Ariyani T, Rifqi MA. The thermodynamic study of p-methoxycinnamic acid in inclusion complex formation, using β-cyclodextrin and hydroxypropyl-β-cyclodextrin. J Basic Clin Physiol Pharmacol. 2021;32(4):663-7. https://doi.org/10.1515/jbcpp-2021-0008 PMid:34214343 DOI: https://doi.org/10.1515/jbcpp-2021-0008

Adisakwattana S, Roengsamran S, Hsu WH, Yibchok-anun S. Mechanisms of anti hyperglycaemic effect of p-methoxycinnamic acid in normal and streptozotocin-induced diabetic rats. Life Sci. 2005;78(4):406-12. https://doi.org/10.1016/j.lfs.2005.04.073 PMid:16139846 DOI: https://doi.org/10.1016/j.lfs.2005.04.073

Wicaksono Y, Rosidi VA, Saragih SY, Fauziah L and Setyawan D. Preparation of spray dried coamorphous solids to improve the solubility and dissolution rate of atorvastatin calcium. J Teknologi. 2021;83(2):77-83. https://doi.org/10.11113/jurnalteknologi.v83.14706 DOI: https://doi.org/10.11113/jurnalteknologi.v83.14706

Thakuria R, Delori A, Jones W, Lipert M, Roy L, Rodríguez-Hornedo N. Pharmaceutical cocrystals and poorly soluble drugs. Int J Pharm. 2013;453(1):101-25. https://doi.org/10.1016/j.ijpharm.2012 PMid:23207015 DOI: https://doi.org/10.1016/j.ijpharm.2012.10.043

Bavishi DD, Borkhataria CH. Spring and parachute: How cocrystals enhance solubility. Prog Crystal Growth Character Mater. 2016;62(3):1-8. https://doi.org/10.1016/j.pcrysgrow.2016.07.001 DOI: https://doi.org/10.1016/j.pcrysgrow.2016.07.001

Wicaksono Y, Setyawan D, Siswandono S, Siswoyo TA. Preparation and characterization of a novel cocrystal of atorvastatin calcium with SA coformer. Indones J Chem. 2019;19(3):660-7. https://doi.org/10.22146/ijc.35801 DOI: https://doi.org/10.22146/ijc.35801

Lin HL, Wu TK, Lin SY. Screening and characterization of cocrystal formation of metaxalone with short-chain dicarboxylic acids induced by solventassisted grinding approach. Thermochim Acta. 2014;575:313-21. https://doi.org/10.1016/j.tca.2013.10.029 DOI: https://doi.org/10.1016/j.tca.2013.10.029

Fulias A, Vlase G, Vlase T, Suta LM, Soica C, Ledeti I. Screening and characterization of cocrystal formation between carbamazepine and SA. J Therm Anal Calorim. 2015;121(3):1-6. https://doi.org/10.1007/s10973-015-4473-8 DOI: https://doi.org/10.1007/s10973-015-4473-8

Setyawan D, Oktavia IP, Farizka R, Sari R. Physicochemical characterization and in vitro dissolution test of quercetin-SA co-crystals prepared using solvent evaporation. TurkJ Pharm Sci. 2017;14(3):280-4. https://doi.org/10.4274/tjps.16362 PMid:32454625 DOI: https://doi.org/10.4274/tjps.16362

Setyawan D, Permata SA, Zainul A, Lestari M. Improvement in vitro dissolution rate of quercetin using cocrystallization of quercetin-malonic acid. Indones J Chem. 2018;18(3):531-6. https://doi.org/10.22146/ijc.28511 DOI: https://doi.org/10.22146/ijc.28511

Yamashita H, Yutaka H, Masamich Y, Toshio T, Katsuhide T. Detection of cocrystal formation based on binary phase diagrams using thermal analysis. Pharm Res. 2013;30(1):70-80. https://doi.org/10.1007/s11095-012-0850-1 PMid:22907418 DOI: https://doi.org/10.1007/s11095-012-0850-1

Perpetuo GL, Chierice GO, Ferreira LT, Fraga-Silva TF, Venturini J, Arruda MS, et al. A combined approach using differential scanning calorimetry with polarized light thermomicroscopy in the investigation of ketoprofen and nicotinamide cocrystal. Thermochim Acta. 2017;651:1-10. https://doi.org/10.1016/j.tca.2017.02.014 DOI: https://doi.org/10.1016/j.tca.2017.02.014

Yuliandra Y, Zaini E, Syofyan S, Pratiwi W, Putri LN, Pratiwi YS, et al. Cocrystal of ibuprofen-nicotinamide: Solid-state characterization and in vivo analgesic activity evaluation. Sci Pharm. 2018;86(2):23-33. https://doi.org/10.3390/scipharm86020023 PMid:29867030 DOI: https://doi.org/10.3390/scipharm86020023

Sci C, Musumeci D, Hunter CA, Prohens R, Mccabe JF. Edge Article Virtual Cocrystal Screening. London, United Kingdom: The Royal Society of Chemistry; 2019. p. 883-90. DOI: https://doi.org/10.1039/c0sc00555j

Athiyah U, Kusuma PA, Tutik T, Lestari ML, Isadiartuti D, Paramita DP, et al. Crystal engineering of quercetin by liquid assisted grinding method. J Teknologi. 2019;81(1):12639. https://doi.org/10.11113/jt.v81.12639 DOI: https://doi.org/10.11113/jt.v81.12639

Wisudyaningsih B, Setyawan D, Siswodihardjo S. Co-crystallization of quercetin and isonicotinamide using solvent evaporation method. Trop J Pharma Res. 2019;18(4):697-702. https://doi.org/10.4314/tjpr.v18i4.3 DOI: https://doi.org/10.4314/tjpr.v18i4.3

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Published

2022-07-07

How to Cite

1.
Sulistyowaty MI, Setyawan D, Sari R, Paramanandana A, Maharani NA, Simorangkir TP. Preparation and Physicochemical Characterizations of p-Methoxycinnamic acid – Succinic Acid Cocrystal by Solvent Evaporation Technique. Open Access Maced J Med Sci [Internet]. 2022 Jul. 7 [cited 2024 Nov. 23];10(A):1444-9. Available from: https://oamjms.eu/index.php/mjms/article/view/10193

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