The Spectrophotometric Determination of Thalidomide in Body Fluids

Green, J. N.; Benson, B. C.

doi:10.1111/j.2042-7158.1961.tb10501.x

Cited by 16 publications

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“…Spectrophotometric study of spontaneous hydrolysis Thalidomide in aqueous ethanol or dilute acid exhibits two absorption peaks in the ultraviolet region of the spectrum. An intense absorption occurs at 220 m~u and a weak one at about 300 mpu (Beckmann & Kampf, 1961;Green & Benson, 1961). At an alkaline pH the phthalimide ring opens and this is accompanied by a marked fall in the extinction at 220 mpu.…”

Section: Reference Compoundsmentioning

confidence: 99%

“…An intense absorption occurs at 220 m~u and a weak one at about 300 mpu (Beckmann & Kampf, 1961;Green & Benson, 1961). At an alkaline pH the phthalimide ring opens and this is accompanied by a marked fall in the extinction at 220 mpu.…”

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“…of distilled water for 3 min and filtering. The final concentration of this solution (estimated spectrophotometrically) was 45 to 50 ptg/ml., taking the E"0-m at 220 mu as 1,950 (Green & Benson, 1961).…”

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The Metabolism of Thalidomide: The Spontaneous Hydrolysis of Thalidomide in Solution

Schumacher

Smith

1965

British Journal of Pharmacology and Chemotherapy

104

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The sedative, neurotoxic and embryotoxic effects of (±)-a-phthalimidoglutarimide or thalidomide are now well known. Any of these effects could be due to thalidomide, or to its metabolites, and it is therefore important to identify these metabolites and to study their biological properties. Our studies on thalidomide began with an investigation of the urinary metabolites excreted by rabbits dosed orally with thalidomide and, as will be described in the succeeding paper (Schumacher, Smith & Williams, 1965), it was soon found that a large number of metabolites occurred. In fact, we succeeded in isolating or detecting by colour reactions and paper chromatography all twelve of its possible hydrolysis products.This caused us to suspect that thalidomide might be unstable in solution and in this paper we shall describe the conditions for the spontaneous hydrolysis of thalidomide in aqueous solution at various pH values.In describing the spontaneous hydrolysis and metabolites of thalidomide, it will be useful to refer to Fig. 1, which shows how thalidomide could break down by simple hydrolysis of its substituted amide bonds. METHODS AND RESULTS Reference compoundsThese compounds were either obtained as gifts or prepared in this laboratory. A list is given in Table 1 of the sources of reference compounds, their melting points and any other relevant data. The following compounds were synthesized and their properties are described.2-and 4-(o-carboxybenzamido)glutaramic acid and 2-(o-carboxybenzamido)glutaric acid and their sodium salts. (±)-4-Phthalimidoglutaramic acid (5 g) was stirred into an amount of aqueous sodium hydroxide (40% w/v) calculated to yield the disodium salt of (±)-4-(o-carboxybenzamido)glutaramic acid. The greenish solution was allowed to stand at room temperature for 10 min and then methanol (100 ml.) was added. The mixture was kept for 4 to 5 hr. The precipitate which had formed was filtered, washed with methanol and then recrystallized five times from aqueous methanol and dried in a desiccator. The disodium salt of (±)-4-(o-carboxybenzamido)glutaramic acid was obtained as a white crystalline powder in a yield of 80

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The Metabolism of Thalidomide: The Spontaneous Hydrolysis of Thalidomide in Solution

Schumacher

Smith

1965

British Journal of Pharmacology and Chemotherapy

104

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“…Because of its limited solubility in water, solutions of the drug were prepared in either water or water: dimethyl sulphoxide (50:50) to provide an adequate range of concentrations. The concentration of each solution was checked spectrophotometrically prior to use, according to the method of Green and Benson (1961). The final concentrations of thalidomide in the cell incubations were 3 x 10"* M, 5 X 10"' M and 3 X 10"^ M. This concentration range spans the peak blood level of 6 x io~® M measured after a single oral dose of 150 mg of thalidomide (Green & Benson, 1961).…”

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“…The concentration of each solution was checked spectrophotometrically prior to use, according to the method of Green and Benson (1961). The final concentrations of thalidomide in the cell incubations were 3 x 10"* M, 5 X 10"' M and 3 X 10"^ M. This concentration range spans the peak blood level of 6 x io~® M measured after a single oral dose of 150 mg of thalidomide (Green & Benson, 1961). It was not possible to test concentrations of the drug greater than 3 x 10"* M because of its limited solubility.…”

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The effect of thalidomide on arachidonic acid metabolism in human polymorphonuclear leukocytes and platelets

1986

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Thalidomid‐Analoga, 6. Mitt.: Die biologische Halbwertszeit der Thalidomid‐ähnlichen Verbindung K‐2004 bei der Ratte

Pischek¹,

Koch²

1975

Archiv der Pharmazie

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Dic Resorption aus dem Gastrointestinaltrakt und die Ausscheidung im Urin dcr Testverbindung K 2004, cines nicht tcratogcnen Thalidomid-Analogen, wurde an der Rattc untersucht. Aus den Ergebnisxn von 8 identischen Vcrsuchen wurdc cine mittlere Resorption von 61 * 1 2 % bei oraler Verabrcichung von 10 mg pro Ratte und cine mittlere Halbwertszeit von 4,s h berechnet. The Biologic Half-life of the ThaSdornideEke Compound K-2004The absorption from the gastrointestinal tract and the urinary elimination in the rat of the test compound K-2004, a non-tcratogenic congener of thalidomide, have been investigated. From thc data of eight identical experiments a mean absorption of 61 5 12 % of an orally administered dose of 10 mg/rat and a mean half-life of 4,s h have been calculated.

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The Spectrophotometric Determination of Thalidomide in Body Fluids

Cited by 16 publications

References 0 publications

The Metabolism of Thalidomide: The Spontaneous Hydrolysis of Thalidomide in Solution

The Metabolism of Thalidomide: The Spontaneous Hydrolysis of Thalidomide in Solution

The effect of thalidomide on arachidonic acid metabolism in human polymorphonuclear leukocytes and platelets

Thalidomid‐Analoga, 6. Mitt.: Die biologische Halbwertszeit der Thalidomid‐ähnlichen Verbindung K‐2004 bei der Ratte

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