Physical and thermal characterisation of chiral omeprazole sodium salts

Markovic, Nov; Agotonovic-Kustrin, Snezana; Glass, Beverley; Prestidge, Clive A.

doi:10.1016/j.jpba.2005.12.039

Cited by 17 publications

(15 citation statements)

References 25 publications

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“…It has been reported that omeprazole is a heat labile drug. [18][19][20] Therefore, the amount of intact omeprazole was quantified by HPLC after wet-milling followed by lyophilization to confirm that this process did not cause significant product degradation. No omeprazole was degraded, indicating that the impact energy generated during wet-milling using the ULTRA APEX MILL is very low (data not shown).…”

Section: Discussionmentioning

confidence: 99%

“…In order to develop pharmaceutical techniques to improve dissolution rate and oral bioavailability, we have utilized the ULTRA APEX MILL to produce nanopowders of poorly [18][19][20] and albendazole (solubility: 10 mg/ml) and danazol (solubility: 0.56 mg/ml) are also poorly soluble. [21][22][23] Furthermore, we carried out a physico-chemical characterization of these drugs after they were subjected to wet-milling.…”

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confidence: 99%

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Nanoparticulation of Poorly Water Soluble Drugs Using a Wet-Mill Process and Physicochemical Properties of the Nanopowders

Tanaka

Inkyo²,

Yumoto

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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Section: Discussionmentioning

confidence: 99%

mentioning

confidence: 99%

Nanoparticulation of Poorly Water Soluble Drugs Using a Wet-Mill Process and Physicochemical Properties of the Nanopowders

Tanaka

Inkyo²,

Yumoto

et al. 2009

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…In OMP-Na, the loss in mass was observed in two steps, the first one from 85°C 3 Journal of Spectroscopy to 110°C and the second one from 120°C to 160°C. Both steps are in the accordance with the release of two water molecules [5,6,8,[23][24][25]. In OMP-Mg, the loss in mass in two steps was also observed, from 85°C to 105°C and from 135°C to 170°C which is in accordance with the release of two water molecules [12].…”

Section: Resultsmentioning

confidence: 74%

“…It was suggested that the water molecule in the OMP-Na probably establishes one hydrogen bond with nitrogen of the imidazole ring and the other with a sulfoxide group. Markovic et al [8] studied both OMP isomers. By using DSC method, they identified that both optical isomers of OMP-Na are thermodynamically more stable (melting of S isomer at 227°C and R isomer at 229°C) than the OMP in neutral form which melts at 159°C.…”

Section: Introductionmentioning

confidence: 99%

Spectroscopic Characterization of Omeprazole and Its Salts

Vrbanec

Šket

Merzel

et al. 2017

Journal of Spectroscopy

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During drug development, it is important to have a suitable crystalline form of the active pharmaceutical ingredient (API). Mostly, the basic options originate in the form of free base, acid, or salt. Substances that are stable only within a certain pH range are a challenge for the formulation. For the prazoles, which are known to be sensitive to degradation in an acid environment, the formulation is stabilized with alkaline additives or with the application of API formulated as basic salts. Therefore, preparation and characterization of basic salts are needed to monitor any possible salinization of free molecules. We synthesized salts of omeprazole from the group of alkali metals (Li, Na, and K) and alkaline earth metals (Mg, Ca). The purpose of the presented work is to demonstrate the applicability of vibrational spectroscopy to discriminate between the OMP and OMP-salt molecules. For this reason, the physicochemical properties of 5 salts were probed using infrared and Raman spectroscopy, NMR, TG, DSC, and theoretical calculation of vibrational frequencies. We found out that vibrational spectroscopy serves as an applicable spectroscopic tool which enables an accurate, quick, and nondestructive way to determine the characteristic of OMP and its salts.

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“…The chosen model drug is omeprazole (OME), a proton pump inhibitor in gastric parietal cells (16,17). This drug is poorly soluble in water and sensitive to heat, moisture, organic solvents, and, to some degree, light (18,19). OME shows low physicochemical stability at acidic conditions, degrades very rapidly in the stomach and undergoes hepatic first-pass metabolism (20)(21)(22), with a bioavailability not exceeding 35%.…”

Section: Introductionmentioning

confidence: 99%

A Comprehensive Development Strategy in Buccal Drug Delivery

2010

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Abstract. This work combines several methods in an integrated strategy to develop a matrix for buccal administration. For this purpose, tablets containing selected mucoadhesive polymers loaded with a model drug (omeprazole), free or in a complexed form with cyclodextrins, and in the absence and presence of alkali agents were subjected to a battery of tests. Mucoadhesion studies, including simple factorial analysis, in vitro release studies with both model-dependent and model-independent analysis, and permeation studies were performed. Mucoadhesive profiles indicated that the presence of the drug decreases the mucoadhesion profile, probably due its hydrophobic character. In tablets loaded with the drug complexed with β-cyclodextrin or methyl-β-cyclodextrin, better results were obtained with the methylated derivative. This effect was attributed to the fact that in the case of β-cyclodextrin, more hydroxyl groups are available to interact with the mucoadhesive polymers, thus decreasing the mucoadhesion performance. The same result was observed in presence of the alkali agent (L-arginine), in this case due to the excessive hydrophilic character of L-arginine. Drug release from tablets was also evaluated, and results suggested that the dissolution profile with best characteristics was observed in the matrix loaded with omeprazole complexed with methyl-β-cyclodextrin in the presence of L-arginine. Several mathematical models were applied to the dissolution curves, indicating that the release of the drug, in free or in complexed state, from the mucoadhesive matrices followed a super case II transport, as established on the basis of the Korsmeyer-Peppas function. The feasibility of drug buccal administration was assessed by permeation experiments on porcine buccal mucosa. The amount of drug permeated from mucoadhesive tablets presented a maximum value for the system containing drug complexed with the methylated cyclodextrin derivative in presence of L-arginine. According to these results, the system containing the selected polymer mixture and the drug complexed with methyl-β-cyclodextrin in presence of L-arginine showed a great potential as a buccal drug delivery formulation, in which a good compromise among mucoadhesion, dissolution, and permeation properties was achieved.

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Physical and thermal characterisation of chiral omeprazole sodium salts

Cited by 17 publications

References 25 publications

Nanoparticulation of Poorly Water Soluble Drugs Using a Wet-Mill Process and Physicochemical Properties of the Nanopowders

Nanoparticulation of Poorly Water Soluble Drugs Using a Wet-Mill Process and Physicochemical Properties of the Nanopowders

Spectroscopic Characterization of Omeprazole and Its Salts

A Comprehensive Development Strategy in Buccal Drug Delivery

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