The Schistosomicidal Activity of Symmetrical Diaminodiphenoxyalkanes

Raison, C. G.; Standen, O. D.

doi:10.1111/j.1476-5381.1955.tb00082.x

Cited by 23 publications

(22 citation statements)

References 11 publications

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“…Secondary and tertiary amines with odd-and even-numbered carbon chains alternated in toxicity, those with 6 and 8 carbon atoms being more toxic than those with 5, 7, or 9. It is of interest that the schistosomicidal activity of tertiary methylamines also alternates, but in this instance compounds with even numbers of carbon atoms are a little less active than those with odd numbers (Raison and Standen, 1955).…”

Section: Resultsmentioning

confidence: 99%

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The Toxicity of Diaminodiphenoxyalkanes

Goodwin

Richards

Udall

1957

British Journal of Pharmacology and Chemotherapy

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Representative members of a series of schistosomicidal diaminodiphenoxyalkanes were examined for their toxic effects in laboratory animals. Primary amino-derivatives were, in general, more toxic than secondary methylamino-compounds; tertiary compounds were less toxic than either. Large doses given by mouth or by injection to mice or rabbits produced intravascular haemolysis; the haemoglobin and erythrocyte counts began to increase again about a week after the dose. Mice which had been given large doses of diaminodiphenoxyalkanes developed symmetrical bald patches 2 to 3 weeks after treatment. The exposed skin appeared normal and new fur grew to cover the hairless areas in about 6 weeks. Large doses of drug delayed water diuresis in mice.Many compounds of the series caused visual impairment when given to cats. In order to obtain a quantitative assessment of retinotoxic potency, a method was devised in which the ability of the retina of the frog to resynthesize rhodopsin was measured in treated and control animals. Compounds that produced blindness in cats also inhibited rhodopsin synthesis in frogs; the most toxic compounds were primary amines. Treatment with some tertiary amines caused retinal damage if the drugs were given for long periods. Diaminodiphenoxyalkanes may perhaps interfere in some way with the biological activity of vitamin A. However, toxic effects on the hair and retina were not prevented by supplements of synthetic or natural vitamin A.

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Section: Resultsmentioning

confidence: 99%

“…The activity of a series of diphenoxyalkanes (I) against experimental schistosomiasis in mice has been reported by Standen and his colleagues (Raison andStanden, 1954, 1955;Caldwell and Standen, 1956;Standen and Walls, 1956 When large doses of drugs were given by mouth, suspensions were prepared with compound powder of tragacanth.…”

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The Toxicity of Diaminodiphenoxyalkanes

Goodwin

Richards

Udall

1957

British Journal of Pharmacology and Chemotherapy

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“…Variation of the Amino Group The influence of the changes in structure indicated in Table I (A, B, and C) on schistosomicidal activity is best assessed by comparison with the corresponding parent compounds, results for which have already been published by Raison and Standen (1955). Considering first the hydroxyalkylamines (Table I, A), the simplest examples are the secondary hydroxyethylaminocompounds; this series shows the same general picture as the ethylamino-compounds, with a well-marked peak of activity at n=7, but the level of activity is lower.…”

Section: Discussionmentioning

confidence: 99%

“…The animals were killed 7 days after completion of treatment and were examined to determine the drug effects against the parasites. Assessment of results was made-according to the methods described by Raison and Standen (1955).…”

Section: Methodsmentioning

confidence: 99%

“…Many variations of the central chain lead to compounds of reduced activity, the outstanding exceptions being a number of but-2-ene derivatives, which retain full activity. Previous papers from these laboratories (Raison and Standen, 1955;Caldwell and Standen, 1956;Standen and Walls, 1956) have reported the schistosomicidal activities of diaminodiphenoxyalkanes (I) and related compounds. Two further variations of this structure are now considered, H2N O{CH2)n-0 JNH2 (I) namely that of the terminal amino-group, apart from mono-and di-alkyl substitution (Raison and Standen, 1955), and that of the aliphatic chain linking the two benzene rings.…”

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THE ACTION OF SUBSTANCES ANALOGOUS TO DIAMINODIPHENOXYALKANES AGAINST SCHISTOSOMA MANSONI

Gorvin

Raison

Solomon

et al. 1957

British Journal of Pharmacology and Chemotherapy

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The effects on activity against Schistosoma mansoni of further modifications of the diaminodiphenoxyalkanes are reported. Replacement of the amino‐group by any of a large number of other groups destroys activity. Activity is retained in the presence of certain substituted (hydroxyalkyl, carboxyalkyl) amino‐groups and in some of their aldehyde‐bisulphite derivatives. Many variations of the central chain lead to compounds of reduced activity, the outstanding exceptions being a number of but‐2‐ene derivatives, which retain full activity.

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Observations in Mice on the Schistosomicidal Properties of 1:7‐BIS( p ‐Aminophenoxy)Heptane in vivo and in vivo/in vitro

Standen

1962

Ciba Foundation Symposium ‐ Bilharziasis

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The Schistosomicidal Activity of Symmetrical Diaminodiphenoxyalkanes

Cited by 23 publications

References 11 publications

The Toxicity of Diaminodiphenoxyalkanes

The Toxicity of Diaminodiphenoxyalkanes

THE ACTION OF SUBSTANCES ANALOGOUS TO DIAMINODIPHENOXYALKANES AGAINST SCHISTOSOMA MANSONI

Observations in Mice on the Schistosomicidal Properties of 1:7‐BIS( p ‐Aminophenoxy)Heptane in vivo and in vivo/in vitro

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