Hydrolysis kinetics of diacetyl nadolol. 1987

C H Chiang, and C Y Wu, and H S Huang
National Defense Medical Center, School of Pharmacy, Taipei, Taiwan, Republic of China.

Diacetyl nadolol, a prodrug of nadolol and a beta-blocker, has corneal permeability approximately 20 times higher than that of its parent compound due to its higher lipophilicity. Hydrolysis studies were conducted for diacetyl nadolol at various elevated temperatures and pH values to provide stability information for its ophthalmic preparations. The apparent rate constants for diacetyl nadolol hydrolysis to acetyl nadolols and nadolol were determined. Within the neutral pH range (6.8 to 8.2), the hydrolysis of diacetyl nadolol may be proposed as specific base catalysis. Various constants for diacetyl nadolol hydrolysis to acetyl nadolols and acetyl nadolols to nadolol were respectively listed as following: activation energy, 9.78 and 11.39 kcal/mol; entropy at 25 degrees C, -9.78 and -5.86 cal/mol.deg; second-order rate constant at 75 degrees C, 3.47 X 10(4) and 2.22 X 10(4) M-1h-1. According to these kinetic constants, a diacetyl nadolol aqueous solution with pH 6.5 may be prepared as an antiglaucoma agent. The shelf-life was estimated to be only 43 d at room temperature (25 degrees C). However, when the storage temperature is lowered to 5 degrees C, the shelf-life can be extended to greater than 2 years.

UI MeSH Term Description Entries
D009248 Nadolol A non-selective beta-adrenergic antagonist with a long half-life, used in cardiovascular disease to treat arrhythmias, angina pectoris, and hypertension. Nadolol is also used for MIGRAINE DISORDERS and for tremor. Corgard,SQ-11725,Solgol,SQ 11725,SQ11725
D011355 Prodrugs A compound that, on administration, must undergo chemical conversion by metabolic processes before becoming the pharmacologically active drug for which it is a prodrug. Drug Precursor,Drug Precursors,Pro-Drug,Prodrug,Pro-Drugs,Precursor, Drug,Precursors, Drug,Pro Drug,Pro Drugs
D002851 Chromatography, High Pressure Liquid Liquid chromatographic techniques which feature high inlet pressures, high sensitivity, and high speed. Chromatography, High Performance Liquid,Chromatography, High Speed Liquid,Chromatography, Liquid, High Pressure,HPLC,High Performance Liquid Chromatography,High-Performance Liquid Chromatography,UPLC,Ultra Performance Liquid Chromatography,Chromatography, High-Performance Liquid,High-Performance Liquid Chromatographies,Liquid Chromatography, High-Performance
D004355 Drug Stability The chemical and physical integrity of a pharmaceutical product. Drug Shelf Life,Drugs Shelf Lives,Shelf Life, Drugs,Drug Stabilities,Drugs Shelf Life,Drugs Shelf Live,Life, Drugs Shelf,Shelf Life, Drug,Shelf Live, Drugs,Shelf Lives, Drugs
D004356 Drug Storage The process of keeping pharmaceutical products in an appropriate location. Drug Storages,Storage, Drug,Storages, Drug
D006868 Hydrolysis The process of cleaving a chemical compound by the addition of a molecule of water.
D013696 Temperature The property of objects that determines the direction of heat flow when they are placed in direct thermal contact. The temperature is the energy of microscopic motions (vibrational and translational) of the particles of atoms. Temperatures
D013816 Thermodynamics A rigorously mathematical analysis of energy relationships (heat, work, temperature, and equilibrium). It describes systems whose states are determined by thermal parameters, such as temperature, in addition to mechanical and electromagnetic parameters. (From Hawley's Condensed Chemical Dictionary, 12th ed) Thermodynamic

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