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Observations on the biopharmaceutical importance of chain length in chemically related compounds

Buckton, G., Beezer, A. E., Denyer, Stephen Paul and Russell, S. J. 1991. Observations on the biopharmaceutical importance of chain length in chemically related compounds. International Journal of Pharmaceutics 73 (1) , pp. 1-7. 10.1016/0378-5173(91)90093-4

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The physicial properties of compounds which have a common parent structure, and differ only by the sequential addition of a methylene group to an alkyl side chain might be expected to demonstrate a linear variation in behaviour as a function of the length of the alkyl carbon chain. Although this is indeed so in many instances, there are many examples in the literature in which a break in the pattern of the behaviour of the product is observed at a chain length of five carbons (±1). In this paper, examples are highlighted in which this is true for solid-state properties (melting point, wettability), solubility, liquid properties, partition and biological response. NMR data demonstrate that certain substituent alkyl chains are essentially rigid until a chain length of 5 carbons is exceeded, after which the freedom of movement is increased; this is used as a basis to explain the observed behaviour.

Item Type: Article
Date Type: Publication
Status: Published
Schools: Pharmacy
Subjects: R Medicine > RM Therapeutics. Pharmacology
Uncontrolled Keywords: QSAR; Wetting; Melting point; Solubility; Partition; Biological response
Publisher: Elsevier
ISSN: 0378-5173
Last Modified: 19 Mar 2016 23:14

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