Studies of Crystalline Vitamin B<sub>1</sub>. III. Cleavage of Vitamin with Sulfite

Williams, Robert R.; Waterman, Robert E.; Keresztesy, John C.; Buchman, Edwin R.

doi:10.1021/ja01306a044

Cited by 163 publications

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“…We have been unable to find any reports describing the stability of octreotide in amino acid infusions. Sodium bisulfite (SBS), which is used as a stabilizer in injectable preparations, is known to degrade various drugs, including thiamine, 9) epinephrine, 10) gabexate mesilate, 11) nafamostat mesilate, 12) urokinase, 13) morphine, 14) fluorouracil 15) and imipenem. 16) However, there are no reports of detailed kinetic studies on the degradation of octreotide in the presence of SBS.…”

Section: Octreotide Acetate Chemical Formula D-phenylalanyl-l-cysteimentioning

confidence: 99%

Prediction of the Stability of Octreotide in a Mixed Infusion

Takasu

Yoshida

Shimizu

et al. 2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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The purpose of this study was to predict the stability of octreotide in a mixed infusion containing sodium bisulfite (SBS). In aqueous solution the hydrolysis of octreotide was found to be accelerated by pH, and by increasing concentrations of SBS. Equations for the degradation rate constants (k obs ) of pH and SBS were derived. The fractional rate constants were estimated by the nonlinear least-squares method (quasiNewton method using the solver in Microsoft Excel) at 25°C. The activation energy (Ea) and frequency factor (A) were calculated using the Arrhenius equation. The pH of the mixed infusion was estimated using the pH characteristic (PHC) curve. From these results, an equation was derived giving the residual ratio (%) of octreotide at any time after mixing an infusion containing SBS at any temperature in the pH range 4.0-7.0. A high correlation was shown to exist between the estimated and determined residual ratios (%).Key words stability prediction; octreotide; pH; sodium bisulfite (SBS); pH characteristic (PHC) curve; degradation rate constant, is a long-acting octapeptide with pharmacologic actions mimicking those of the natural hormone somatostatin.1-3) The cyclic structure of octreotide ( Fig. 1) seems to play an important role in determining its unique pharmacological activity.Octreotide is increasingly used to treat symptoms of sickness and vomiting in terminal care patients suffering from gastrointestinal ileus. It is also used, in combination with standard therapies, in the symptom management of inoperable bowel obstructions in terminal cancer patients. [4][5][6] In Japan, octreotide is usually administered subcutaneously, but in the U.S. it is more often administered by deep subcutaneous (intrafat) or intravenous injection.3) The pharmacokinetics of octreotide are similar to those of many other agents administered continuously via intravenous or subcutaneous infusion, 7) and similar changes in pharmacokinetics would be expected if octreotide were to be administered by continuous intravenous administration instead of sustained subcutaneous administration, i.e., without the need for special equipment (e.g., miniature pump).We have been unable to find any reports describing the time-dependent stability of octreotide in amino acid infusions under different pH, temperature and ingredient such as sodium bisulfite. Especially, we have been unable to find reports evaluating such time-dependent stability of octreotide in amino acid infusions quantitatively.Hanamura et al. 8) report on the stability of octreotide in glucose and saline infusions, but its stability in amino acid infusion fluids was not investigated in detail. We have been unable to find any reports describing the stability of octreotide in amino acid infusions. Sodium bisulfite (SBS), which is used as a stabilizer in injectable preparations, is known to degrade various drugs, including thiamine, 9) epinephrine, 10) gabexate mesilate, 11) nafamostat mesilate, 12) urokinase, 13) morphine, 14)fluorouracil 15) and imipenem. 16) However, there ...

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Section: Octreotide Acetate Chemical Formula D-phenylalanyl-l-cysteimentioning

confidence: 99%

Prediction of the Stability of Octreotide in a Mixed Infusion

Takasu

Yoshida

Shimizu

et al. 2014

CHEMICAL & PHARMACEUTICAL BULLETIN

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“…2-(o-hydroxyethyl)-TPP [8,9]. Further characterization of the labeled material was done by using the "sulfite-cleavage" after Williams et al [10] and by treatment of "active acetaldehyde" with HJ, followed by alkaline hydrolysis which resulted in formation of 14C-labeled propionic acid. Additional evidence for the correctness of Breslow's proposal of the structure of active acetaldehyde came from experiments of Krampitz et al [11,12].…”

Section: Hcn+ch3cho•¨ch3-ch-(oh)cnmentioning

confidence: 99%

Thiamin Pyrophosphate: Catalytic Mechanism, Role in Protein Turnover

Holzer

Gubler

1992

Journal of Nutritional Science and Vitaminology, J Nutr Sci Vit

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“…When the bread extracts were purified by base exchange on synthetic zeolite (Decalso), the impurity in question accompanied the thiamine. Attempts to destroy the thiamine preferentially by the use of Na sulphite as recommended by Williams, Waterman, Keresztesy and Buchman (1935) failed; both thiamine and the impurity were destroyed by this procedure.…”

Section: Sesiiltsmentioning

confidence: 99%

The Determination of Thiamine in White Bread by the Thiochrome Method

Dawbarn

1949

Aust J Exp Biol Med

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Studies of Crystalline Vitamin B₁. III. Cleavage of Vitamin with Sulfite

Cited by 163 publications

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Prediction of the Stability of Octreotide in a Mixed Infusion

Prediction of the Stability of Octreotide in a Mixed Infusion

Thiamin Pyrophosphate: Catalytic Mechanism, Role in Protein Turnover

The Determination of Thiamine in White Bread by the Thiochrome Method

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Studies of Crystalline Vitamin B1. III. Cleavage of Vitamin with Sulfite

Cited by 163 publications

References 0 publications

Prediction of the Stability of Octreotide in a Mixed Infusion

Prediction of the Stability of Octreotide in a Mixed Infusion

Thiamin Pyrophosphate: Catalytic Mechanism, Role in Protein Turnover

The Determination of Thiamine in White Bread by the Thiochrome Method

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Studies of Crystalline Vitamin B₁. III. Cleavage of Vitamin with Sulfite