From: Richard Prankerd (richard.prankerd$##$pharmacy.uq.edu.au)
Date: Mon Feb 01 1999 - 22:39:20 EST
In response to recent questions re pKa values:
There is a companion volume to Perrin's compilation (LC# QD273.P35 1965) of
organic base pKa values by G.Kortum, W.Vogel and K.Andrussow (LC# QD273.K67
1961) on weak acids. These two compilations (both originally published by
IUPAC in the 1960's) were later supplemented by one further volume each,
published in the 1970's. These volumes are the most useful source of pKa
data, in that the reliability of the data is critically assessed. However,
they refer to water only as the solvent.
Other pKa compilations are a series of volumes edited by Martell and Smith
on critical stability constants for complexation reactions (LC# QD503.M37)
of amino acids and other werak acids, in which the simplest complexed
species is the hydrogen ion. Although the CRC Handbook lists pKa values,
these are often extremely outdated values. pKa values are also listed in
the textbooks on Electrolyte Solutions (Robinson and Stokes LC#QD561.R73
1965) and Determination of Ionization Constants (Albert and Serjeant LC#
QD561.A366 1984).
Further compilations of drug pKa values are in the Medicinal Chemistry
textbooks by C.Hansch (Comprehensive Medicinal Chemistry) and by W.O.Foye.
These are smaller, more restricted and frequently give no useful
reliability information -- often not even a reference to the original data
source. Merck Index values also are usually not well referenced to the
original data source or its reliability. Two other sources, the British
Pharmaceutical Codex and Clarke's Isolation and Identification of Drugs
also give pKa values, but with no original references. The series
Analytical Profiles of Drug Substances (edited initially by Klaus Florey
and more recently by Harry Brittain usually give pKa values for drugs, but
often with no supporting reference information beyond a personal
communication.
I am currently engaged in a very large compilation of drug pKa values
(approaching 1200 entries), which will include estimates of the reliability
of the data. Watch this space!!!
Regards
Richard
Richard J. Prankerd, PhD
Senior Lecturer Phone: INT + (617) 3365-3179
School of Pharmacy Fax: INT + (617) 3365-1688
University of Queensland richard$##$uqpharmacy.pharmacy.uq.edu.au
St Lucia QLD 4072 http://www.uq.edu.au/pharmacy/academic.html
AUSTRALIA
DRUGS NEED TO BE DESIGNED WITH DELIVERY COMPONENTS IN MIND - TAKERU HIGUCHI
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