7 Jun PDF | This review aim to demonstrate the role of bioisosterism in rational drug design as well as in the molecular modification and optimization. (pharmacology) The relationship between bioisosteres, substituents or groups with similar physical or chemical properties that impart similar biological. This chapter reviews progress in the use of bioisosterism in drug design. The broadest definition of bioisosteres is, “groups or molecules those have chemical.

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The bioisosteric relationship between aminoalkyl, 2-imidazolidine and 4-imidazole moieties in histamine H 1 receptor antagonists and the similarity between amidines and 2-amino pyridines led to bioisosteric design of the histamine H 2 -receptor antagonist.


Bioisosterism is part of the spectrum of QSAR. By continuing you agree to the use of cookies. Recommended articles Citing articles 0. Elsevier About ScienceDirect Remote access Shopping cart Contact and support Terms and conditions Bioisisterism policy We use cookies to help provide and enhance our service and tailor content and ads. We use cookies to help provide and enhance our service and tailor content and ads.

Bioisosterism is used to reduce toxicity, change bioavailabilityor modify the activity of the lead compound, and may alter the metabolism of the lead. Bioisosyerism Isosteres in Drug Discovery”. For example, the bioisosherism of a hydrogen atom with a fluorine atom at a site of metabolic oxidation in a drug candidate may prevent such metabolism from taking place.

Publisher Summary This chapter reviews progress in the use of bioisosterism in drug design. In medicinal chemistrybioisosteres are chemical substituents or groups with similar physical or chemical properties which produce broadly similar biological properties to another chemical compound. The main use of this term and its techniques are related to pharmaceutical sciences. In theory, bioisosterism lends itself to computer substructure searching especially as a means of developing new leads or new series.



Promising Starting Points for Drug Design”. It has been proposed that key force field features, that is the pharmacophorebe patented instead.

Whereas classical bioisosteres commonly conserve much of the same structural properties, nonclassical bioisosteres are much more dependent on the specific binding needs of the ligand in question and may substitute a linear functional group for a cyclic moiety, an alkyl group for a complex heteroatom moiety, or other changes that go far beyond a simple atom-for-atom switch.

Published by Bioisisterism Inc. Wiley-VCH,p. By modifying certain substituents, the pharmacological activity of the chalcone and its toxicity are bioisossterism modified.

bioisosterism – Wiktionary

This chapter reviews progress in the use of bioisosterism in drug design. From Wikipedia, the free encyclopedia. Bioisosteres of some patented compounds can be discovered automatically and used to circumvent Markush structure patent claims.

Classical bioisosterism was originally formulated by James Moir and refined by Irving Langmuir [2] as a response to the observation that different atoms with the same valence electron structure had similar biological properties. Retrieved from ” https: By using this site, you agree to the Terms of Use and Privacy Policy.

Another example is aromatic rings, a phenyl -C 6 H 5 ring can often be replaced by a different aromatic ring such as thiophene or naphthalene which may improve efficacy, change specificity of binding, or reduce metabolically labile sites on the molecule, resulting in better pharmacokinetic properties.


Silafluofen is an organosilicon analogue of pyrethroid insecticidewherein a carbon center has been replaced by isosteric silicon. Similar effects in two functional groups does not imply atom upon atom overlap. However, with a blocked pathway for metabolism, the drug candidate may have biousosterism longer half-life.

Because the fluorine atom is similar in size to the hydrogen atom the overall topology of the molecule is not significantly affected, leaving the desired biological activity unaffected. Non-classical bioisosteres may differ in a multitude of ways from classical bioisostsrism, but retain the focus on providing similar sterics and electronic profile to the original functional group. Bioisosterjsm drug design[1] the purpose of exchanging one bioisostere for another is to enhance the desired biological or physical properties of a compound without making significant changes in chemical structure.

In practice, examples of new lead generation using bioisosteric principles are few. Bioisosteric substitution of the ammonium group by a sulfonium group finds application in studies on dopamine agonists such as and the isolevorphanol opiate analog. Bioisosteres in Medicinal Chemistry.

This page was last edited on 31 Octoberat Another example are chalcones bioisosteres. The chapter describes peptide and dipeptide bioisosteres, amide carbonyl group bioisosteres, ketone carbonyl bioisosteres, bioisosyerism carbonyl bioisosteres, ester ether oxygen bioisosteres, phosphate bioisosteres, catechol bioisosteres, urea, thiourea bioisosteres, carboxylic acid bioisosteres, ring equivalents, and some basic groups.

Retrieved 15 Jan Author links open overlay panel Christopher A.

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