Preparation and physicochemical characterization of sildenafil cocrystals

Sildenafil is a specific inhibitor of the phosphodiesterase type 5 (PDE-5) enzyme that protects cyclic guanosine monophosphate from breakdown by PDE-5. It is a biopharmaceutical categorization system Class II medication with low bioavailability because it is almost insoluble in water. The objectives...

Descripción completa

Guardado en:

Detalles Bibliográficos
Autores principales:	Somchai Sawatdee, Apichart Atipairin, Supitchaya Rakkummerd, Onsinee Suriyaphol, David J Harding, Poowadon Muenraya, Phimphaka Harding
Formato:	article
Lenguaje:	EN
Publicado:	Wolters Kluwer Medknow Publications 2021
Materias:	aspirin benzoic acid cocrystal fumaric acid physicochemical properties sildenafil solubility Therapeutics. Pharmacology RM1-950 Pharmacy and materia medica RS1-441
Acceso en línea:	https://doaj.org/article/fc7af6e60a36430497abad6a089bd338
Etiquetas:	Agregar Etiqueta Sin Etiquetas, Sea el primero en etiquetar este registro!

id	oai:doaj.org-article:fc7af6e60a36430497abad6a089bd338
record_format	dspace
spelling	oai:doaj.org-article:fc7af6e60a36430497abad6a089bd3382021-11-12T10:17:53ZPreparation and physicochemical characterization of sildenafil cocrystals2231-40400976-209410.4103/japtr.japtr_72_21https://doaj.org/article/fc7af6e60a36430497abad6a089bd3382021-01-01T00:00:00Zhttp://www.japtr.org/article.asp?issn=2231-4040;year=2021;volume=12;issue=4;spage=408;epage=419;aulast=Sawatdeehttps://doaj.org/toc/2231-4040https://doaj.org/toc/0976-2094Sildenafil is a specific inhibitor of the phosphodiesterase type 5 (PDE-5) enzyme that protects cyclic guanosine monophosphate from breakdown by PDE-5. It is a biopharmaceutical categorization system Class II medication with low bioavailability because it is almost insoluble in water. The objectives of this study were to prepare sildenafil cocrystals with co-former molecules including aspirin (acetylsalicylic acid [ASA]), fumaric acid (FMA), and benzoic acid (BZA) to improve the water solubility of sildenafil. The cocrystals were prepared by antisolvent addition (AA) and slow solvent evaporation (SE) methods. The stoichiometric ratios of sildenafil and co-former molecules were varied. The obtained crystals were characterized by stereomicroscope, Fourier transformed infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR), and powder X-ray diffraction (PXRD). The water solubility of sildenafil cocrystals was compared with sildenafil base. In the AA method, the crystals only form in sildenafil-ASA reaction. These crystals were not cocrystals between sildenafil and ASA because they were formed to new substances that were confirmed by single-crystal X-ray diffraction. In the SE method, the cocrystals were successfully prepared in the reaction of sildenafil with ASA, FMA, and BZA which use acetone or ethyl acetate as a solvent. The obtained crystals are irregular shapes and their FT-IR, NMR, and PXRD results exhibited the characteristics of sildenafil and its co-former. The stoichiometric ratios of sildenafil and co-formers after cocrystallization were different from an initial of crystallization. The sildenafil cocrystals with ASA, FMA, and BZA by SE method had higher water solubility than sildenafil base. The sildenafil-FMA cocrystals had the highest water solubility and increased up to five times when compared with sildenafil base.Somchai SawatdeeApichart AtipairinSupitchaya RakkummerdOnsinee SuriyapholDavid J HardingPoowadon MuenrayaPhimphaka HardingWolters Kluwer Medknow Publicationsarticleaspirinbenzoic acidcocrystalfumaric acidphysicochemical propertiessildenafilsolubilityTherapeutics. PharmacologyRM1-950Pharmacy and materia medicaRS1-441ENJournal of Advanced Pharmaceutical Technology & Research, Vol 12, Iss 4, Pp 408-419 (2021)
institution	DOAJ
collection	DOAJ
language	EN
topic	aspirin benzoic acid cocrystal fumaric acid physicochemical properties sildenafil solubility Therapeutics. Pharmacology RM1-950 Pharmacy and materia medica RS1-441
spellingShingle	aspirin benzoic acid cocrystal fumaric acid physicochemical properties sildenafil solubility Therapeutics. Pharmacology RM1-950 Pharmacy and materia medica RS1-441 Somchai Sawatdee Apichart Atipairin Supitchaya Rakkummerd Onsinee Suriyaphol David J Harding Poowadon Muenraya Phimphaka Harding Preparation and physicochemical characterization of sildenafil cocrystals
description	Sildenafil is a specific inhibitor of the phosphodiesterase type 5 (PDE-5) enzyme that protects cyclic guanosine monophosphate from breakdown by PDE-5. It is a biopharmaceutical categorization system Class II medication with low bioavailability because it is almost insoluble in water. The objectives of this study were to prepare sildenafil cocrystals with co-former molecules including aspirin (acetylsalicylic acid [ASA]), fumaric acid (FMA), and benzoic acid (BZA) to improve the water solubility of sildenafil. The cocrystals were prepared by antisolvent addition (AA) and slow solvent evaporation (SE) methods. The stoichiometric ratios of sildenafil and co-former molecules were varied. The obtained crystals were characterized by stereomicroscope, Fourier transformed infrared spectroscopy (FT-IR), nuclear magnetic resonance (NMR), and powder X-ray diffraction (PXRD). The water solubility of sildenafil cocrystals was compared with sildenafil base. In the AA method, the crystals only form in sildenafil-ASA reaction. These crystals were not cocrystals between sildenafil and ASA because they were formed to new substances that were confirmed by single-crystal X-ray diffraction. In the SE method, the cocrystals were successfully prepared in the reaction of sildenafil with ASA, FMA, and BZA which use acetone or ethyl acetate as a solvent. The obtained crystals are irregular shapes and their FT-IR, NMR, and PXRD results exhibited the characteristics of sildenafil and its co-former. The stoichiometric ratios of sildenafil and co-formers after cocrystallization were different from an initial of crystallization. The sildenafil cocrystals with ASA, FMA, and BZA by SE method had higher water solubility than sildenafil base. The sildenafil-FMA cocrystals had the highest water solubility and increased up to five times when compared with sildenafil base.
format	article
author	Somchai Sawatdee Apichart Atipairin Supitchaya Rakkummerd Onsinee Suriyaphol David J Harding Poowadon Muenraya Phimphaka Harding
author_facet	Somchai Sawatdee Apichart Atipairin Supitchaya Rakkummerd Onsinee Suriyaphol David J Harding Poowadon Muenraya Phimphaka Harding
author_sort	Somchai Sawatdee
title	Preparation and physicochemical characterization of sildenafil cocrystals
title_short	Preparation and physicochemical characterization of sildenafil cocrystals
title_full	Preparation and physicochemical characterization of sildenafil cocrystals
title_fullStr	Preparation and physicochemical characterization of sildenafil cocrystals
title_full_unstemmed	Preparation and physicochemical characterization of sildenafil cocrystals
title_sort	preparation and physicochemical characterization of sildenafil cocrystals
publisher	Wolters Kluwer Medknow Publications
publishDate	2021
url	https://doaj.org/article/fc7af6e60a36430497abad6a089bd338
work_keys_str_mv	AT somchaisawatdee preparationandphysicochemicalcharacterizationofsildenafilcocrystals AT apichartatipairin preparationandphysicochemicalcharacterizationofsildenafilcocrystals AT supitchayarakkummerd preparationandphysicochemicalcharacterizationofsildenafilcocrystals AT onsineesuriyaphol preparationandphysicochemicalcharacterizationofsildenafilcocrystals AT davidjharding preparationandphysicochemicalcharacterizationofsildenafilcocrystals AT poowadonmuenraya preparationandphysicochemicalcharacterizationofsildenafilcocrystals AT phimphakaharding preparationandphysicochemicalcharacterizationofsildenafilcocrystals
_version_	1718431028275576832

Preparation and physicochemical characterization of sildenafil cocrystals

Ejemplares similares