Biomaterial Database

Synthesis, properties and microemulsion formulation of ibuprofen eugenol ester. 2005

X L Zhao, and D W Chen, and P Gao, and Y F Luo, and K X Li

School of Pharmacy, Shenyang Pharmaceutical University, Shenyang, People's Republic of China.

Ibuprofen-eugenol ester (IEE), a highly lipophilic compound, was synthesized from ibuprofen in order to reduce the common side effects induced by this classic anti-inflammatory drug. IEE was isolated as an amorphous whitish solid with a melting point at 40.2 +/- 0.1 degrees C, whose structure was confirmed by IR, 1H NMR and MS spectra. The hydrolysis results showed that the ester was stable over a wide pH range from 1.1-9.96. However, it could be hydrolyzed easily by enzymes from rat plasma and rat liver homogenate. A pharmaceutically acceptable microemulsion system was presented and characterized in terms of stability, droplet size distribution (DSD) and their solubilization capacity for IEE. The solubility of IEE in the optimized microemulsion formulation was about 21,000 times higher than that in water. The AUC of ibuprofen from the prodrug showed a remarkable increase compared to oral ibuprofen suspension. These results suggest that synthesizing the ibuprofen prodrug was justified and the presented microemulsion system might be a promising oral dosage form for poorly water-soluble drugs.

UI	MeSH Term	Description	Entries
D007052	Ibuprofen	A non-steroidal anti-inflammatory agent with analgesic, antipyretic, and anti-inflammatory properties	Advil,Benzeneacetic Acid, alpha-methyl-4-(2-methylpropyl)- trimethylsilyl ester,Brufen,Ibumetin,Ibuprofen, (+-)-Isomer,Ibuprofen, (R)-Isomer,Ibuprofen, (S)-Isomer,Ibuprofen, Aluminum Salt,Ibuprofen, Calcium Salt,Ibuprofen, Copper (2+) Salt,Ibuprofen, Magnesium Salt,Ibuprofen, Potassium Salt,Ibuprofen, Sodium Salt,Ibuprofen, Zinc Salt,Ibuprofen-Zinc,Motrin,Nuprin,Rufen,Salprofen,Trauma-Dolgit Gel,alpha-Methyl-4-(2-methylpropyl)benzeneacetic Acid,Ibuprofen Zinc,Trauma Dolgit Gel
D007202	Indicators and Reagents	Substances used for the detection, identification, analysis, etc. of chemical, biological, or pathologic processes or conditions. Indicators are substances that change in physical appearance, e.g., color, at or approaching the endpoint of a chemical titration, e.g., on the passage between acidity and alkalinity. Reagents are substances used for the detection or determination of another substance by chemical or microscopical means, especially analysis. Types of reagents are precipitants, solvents, oxidizers, reducers, fluxes, and colorimetric reagents. (From Grant & Hackh's Chemical Dictionary, 5th ed, p301, p499)	Indicator,Reagent,Reagents,Indicators,Reagents and Indicators
D008099	Liver	A large lobed glandular organ in the abdomen of vertebrates that is responsible for detoxification, metabolism, synthesis and storage of various substances.	Livers
D008297	Male		Males
D002626	Chemistry, Pharmaceutical	Chemistry dealing with the composition and preparation of agents having PHARMACOLOGIC ACTIONS or diagnostic use.	Medicinal Chemistry,Chemistry, Pharmaceutic,Pharmaceutic Chemistry,Pharmaceutical Chemistry,Chemistry, Medicinal
D002627	Chemistry, Physical	The study of CHEMICAL PHENOMENA and processes in terms of the underlying PHYSICAL PHENOMENA and processes.	Physical Chemistry,Chemistries, Physical,Physical Chemistries
D004655	Emulsions	Colloids formed by the combination of two immiscible liquids such as oil and water. Lipid-in-water emulsions are usually liquid, like milk or lotion. Water-in-lipid emulsions tend to be creams. The formation of emulsions may be aided by amphiphatic molecules that surround one component of the system to form MICELLES.	Emulsion
D004798	Enzymes	Biological molecules that possess catalytic activity. They may occur naturally or be synthetically created. Enzymes are usually proteins, however CATALYTIC RNA and CATALYTIC DNA molecules have also been identified.	Biocatalyst,Enzyme,Biocatalysts
D005054	Eugenol	A cinnamate derivative of the shikimate pathway found in CLOVE OIL and other PLANTS.	Phenol, 2-methoxy-4-(2-propenyl)-
D005260	Female		Females