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Book Review Biotransformation von Arzneimitteln (Bio-Transformation of Drugs). By S. Pfeifer

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Coumarins in the Rutaceae are the theme of a review article
by A . 1. Gray and P. G. Waterman. The biogenesis, structural
variants, and occurrence of simple coumarins as well as furanoand pyranocoumarins are described. In addition the compounds are discussed regarding their possible biological significance and their usefulness in taxonomic considerations. [Coumarins in the Rutaceae. Phytochemistry 17, 845-864 (1978);
301 references]
[Rd 43 IE]
The fine control of the conversion of pyruvate (phosphoenolpyruvate) into oxaloacetate in various species is described in an
article by M . C. Scrutton. Depending upon the species, the
catalysts for this reaction are the enzymes pyruvate carboxylase, phosphoenolpyruvate carboxylase and phosphoenolpyruvate carboxytransphosphorylase. Owing to these enzymatic
reactions, which enhance the supply of intermediates, the citric
acid cycle can serve for both degradation as well as synthesis.
Effectors for the above mentioned enzymes are acetyl coenzyme A and other acyl coenzymes A as well as glutamate,
aspartate, and a-ketoglutarate. It is hoped,that an investigation
of the regulation will provide a detailed explanation of the
biological function of the enzymes. [Fine Control of the Conversion of Pyruvate (Phosphoenolpyruvate) to Oxaloacetate
in Various Species. FEBS Lett. 89, 1-9 (1978); 60 references]
[Rd 44 IE]
The connection between photosynthetic carbon reduction and
photorespiration is discussed in an article by 7: J . Andrews
and G . H . Lorimer. The primary reaction of photorespiration
consists of the oxidative cleavage of ribulose 1,5-bisphosphate
( 1 1 to give 3-phosphoglycerate and phosphoglycolate. Photorespiration thus counteracts, in part, the result of photosynthesis. The question arises whether this apparently meaningless
debilitating effect on the plants might not be avoidable. The
authors show with the aid of experimental findings that all
carboxylases for (1) are at the same time also oxygenases
for (1 ). The ratio of carboxylation to oxygenation depends
upon the relative concentrations of the substrates C 0 2 and
02.It would appear that photorespiration, though of no
particular advantage to plants could not be dispensed with
in the course of evolution because it is an unevadable consequence of the chemical structure of the active center of ribulose
1,5-bisphosphate carboxylase. [Photorespiration. Still Unavoidable? FEBS Lett. 90, 1-9 (1978); 103 references]
[Rd 45 IE]
Steric aspects of dopaminergic drugs are dealt with in a
report by D. D. Miller. At the physiological pH value,
dopamine occurs in a variety of molecular species, the
phenolic ammonium salt being predominant. Nevertheless,
it is still unknown which of these forms is optimal for a
dopaminergic action. Hence, a series of analogs which are
fixed in their conformation and some more complex molecules
with dopaminergic segments have been investigated. The
experiments showed that the stretched form is optimal for
binding to dopamine receptors, but also that rotamers have
to be taken into consideration. The dopaminergic action is
largely dependent upon the stereochemistry. [Steric Effects of
Dopaminergic Drugs. Fed. Proc. 37, 2392-2395 (1 978); 33 references]
[Rd 46 IE]
Template reactions are the theme of a review by M . de Sousa
H e d y and A . J . Rest. Macrocycles were hitherto mainly accessible only via laborious routes and in small yields. One of
the first examples of the ability of metals and metal ions
to promote the formation of macrocycles was the self-condensation of o-phthalonitrile to give metal phthalocyanine complexes from which the free ligand was easily displaced. From
the formation of macrocycles such as (1) using Niz+ ions
it was recognized that the coordination sphere of the metal ion
would hold the reacting groups in the correct positions for
cyclization reactions, i. e., the metal ion acts as a “template”.
K + has proven suitable for the synthesis of crown ethers,
Ni2+ or Cu2+ are preferably used for the synthesis of planar
macrocycles containing four nitrogen atoms. [Template Reactions. Adv. Inorg. Chem. Radiochem. 21, 1 4 0 (1978); 143
referencesJ
[Rd 48 IE]
The use of liquid crystals in chromatography is dealt with
in an article by H . Kelker. Liquid crystals can be used as stationary phase in gas-liquid chromatography for the separation
ofisomers whose separation is not easy to achieve with normal
isotropic liquids. An example is the resolution of a mixture
of m- and p-xylene using liquid-crystalline 4,4-azooxyanisole.
Otherwise, m- and p-xylene necessitate the use of highly efficient columns, e. g. modified bentonites, for their separation.
The article contains, inter alia, a list of all the previous applications of liquid crystals as stationary phases in chromatography.
[Liquid Crystals in Chromatography. Adv. Liq. Cryst. 3,237273 (1 978); references]
[Rd 49 IE]
BOOK REVIEWS
Biotransformation von Anneimitteln (Bio-Transformation of
Drugs). By S . Pfeifer, Verlag Chemie GmbH, WeinheimNew York. Vol. 1: 1977 reprint of the 1st edition of 1975,
484 pp., bound, DM 90.00. Vol. 2: 1st edition, 424 pp.,
bound, DM 70.00,
Volume 1 contains 329 monographs on the metabolism
of various antibacterial sulfonamides, antidiabetic preparaAngew. Chem. Int. Ed. Engl. 17 (1978) N o . 1 1
tions, antiepileptic agents, psychopharmaceuticals, sedatives
and hypnotics, and synthetic steroid hormones and estrogens
with a different structure. The literature is covered up to
1972/73, and a literature supplement gives publications up
to the middle of 1975.
Volume 2 contains 211 monographs on the metabolism
of analgesics, antineuralgic drugs, antirheumatic preparations,
871
non-steroidal anti-inflammatory drugs, analgesic antagonists,
drugs for arrhythmias, 0-receptor blocking agents, antihypertensive agents, chemotherapeutic preparations (nitrogen-containing heterocyclic systems), coronary dilators, and tuberculostatics. The literature is covered up to 1973/74, and a literature supplement gives publications up to the middle of 1976.
Besides, the references for volume 1 are also extended.
The third volume is expected to appear this year.
More and more work is being done on the biotransformation
of drugs and the field is in a stage of rapid growth. It is
therefore extremely difficult to give an account here that is
both up to date and comprehensive.
The two volumes reviewed describe over 500 substances.
This series of monographs differs from previous reviews by
having a high information content and by being based on
very recent literature; it is expected that the literature will
be updated by special supplements in the following volumes.
Unfortunately, the naming of the substances is not uniform:
the international short names are often used, but mainly in
the Latin form (e.g. calcii benzamidosalicylas and acidum
flufenamicum). This causes unnecessary confusion. Furthermore, it is difficult to see how the substances were selected:
some of those which have been included are not yet used
as drugs, or are no longer used in this way, while others
that are very common (e.g. reserpine) are missing.
All the monographs a;e drawn up in the same form. In
a condensed and clear manner, they give schemes of biotransformation, routes of elimination, and detection of metabolites
in various species, together with the analytical methods used
for this purpose. In a final section, called Remarks, we find
e. g. incomplete or contradictory literature data. The author
also gives supplementary data on individual metabolites (e.g.
activity and distribution in the body) and-without any claims
to completeness-further information e. g. on pharmacokinetics and drug interactions. In the presentation of this material,
clearly no attempt was made to follow a systematic approach.
The collection can be recommended as a reference work
for all those involved with the biotransformation of drugs.
K O . Vollmer [NB 433 IE]
Molecular Structure and Dimensions. Guide to the Literature
1935-1976. Organic and Organometallic Crystal Structures. Edited by 0. Kennard, F . H . Allen, and D. G. Watson
for the Cambridge Crystallographic Data Centre and the
International Union of Crystallography. Bohn, Scheltema
& Holtema, Utrecht 1977. 683 pp., bound, fl. 150.00.
While this volume, like the “60-year Structure Index” of
“Structure Reports” consists of indexes (indexes of substance
names, formulas, authors, and literature references), this time
all the indexes have been developed with computer programs
from the data bank of organic and organometallic crystal
structures of the Cambridge Crystallographic Data Centre
and printed from magnetic tape with photosetting. This is
a prerequisite for greater up-to-dateness, variety, and reliability.
A substance name may contain many structural elements
of a chemical compound. The index built up according to
the KWIC (Keyword in context) concept records each compound under the word segment relevant to that compound
and thus provides not only access to defined substances whose
exact nomenclature is difficult but above all to related substances and groups of substances. In Part A are collected
10 1 56 organic compounds and metal-containing organic compounds that include an interesting organic portion. One finds,
for example, 49 adenine derivatives, 77 porphine derivatives
and complexes, as well as 50 deuterated compounds. In Part
B 5777 organometallic compounds and complexes are listed
872
in two-fold arrangement: all the compounds of each metal
are sorted again according to their relevant word segments,
e. g. 139 phosphane complexes of platinum o r 8 carbene complexes of chromium.
In Part A the molecular formula index lists all compounds
in the usual way (C, H, all other elements in alphabetical
order) but in Part B the formulas are permuted once more
so that, e.g. all the fluorine or all the silicon compounds
occur together. In both cases it is not always the true molecular
formula that is used, but-when useful-partial molecular
formulas of the “residues”, i.e. of the discrete units of the
compound. All the indexes lead, inter alia, directly to the
original reference.
The printed book cannot offer the variety of entry that
is provided in a data bank, because the extent and the’ cost
force compromises. Victims of the compromises are keywords
such as “hydrates” and “inclusion compounds”, but also the
possibility of finding in one place all the complexes of ligands
such as salicylaldehyde or thiocyanate.
The reliability of the index is guaranteed by the programmed
setting and automatic printing, provided that the basic material
is faultless. To this end the material taken into the data
bank is subjected on entry to numerous test programs. The
logic of our language and spelling are, however, so complicated
that variation in nomenclature and mode of writing must
sometimes be recognized and corrected mentally, because
heterogeneity in naming in conjunction with the strict logic
of the sorting program leads sometimes to primitive errors
on introduction into the index. The user accustomed to the
working of a computer does not stumble over, for example,
the separated positions of “vitamin B 12” and “vitamin B(12)”;
more serious is that compounds of the same type may be
named according to different principles, e. g. “dichlorophthalocyanato-tin(1v)” or “stannic phthalocyanine”.
Such failings are of little account when measured against
the value of the total undertaking, and they are shared with
traditionally prepared indexes. However, the data bank makes
it possible to prepare cumulative indexes relatively easily,
and when doing so to eradicate mistakes gradually during
further developments of the programs.
Statistical data readily accessible by modern programming
show by the numerous replications of the same structure,
by the corrections to the data that become necessary, by
the distribution of references in the original literature (which
enables the completeness of the entries to be tested), and
by the content of 28000 structures estimated for 1980 the
importance now attaching to joint international efforts in
connection with the collection and retrieval of scientific data.
It is to be hoped that the development started with this
project will not remain restricted to crystal structures.
Giinter Bergerhoff [NB 440b IE]
Microbiological Aspects of Pollution Control. By R. K. Dart
and R. J . Stretton. Elsevier Scientific Publishing Company,
Amsterdam-Oxford-New
York, 1977, 1st edit., vi, 215
pp., bound, Dfl. 85.00.
We read in a publication of the Fonds der Chemischen
Industrie, dated October 27, 1977 that “This additional
expense, necessitated by environmental protection, can become
the ‘eye of the needle’ for productivity and research. This
means that nowadays every chemist should know something
about the microbial aspects of environmental protection. The
book is aimed at engineers and therefore gives a detailed
description of methods, e. g. for microbial water control, that
have long been known to microbiologists and hygienists. The
eleven chapters deal with the microbial formation of polluting
compounds, atmospheric pollution and microorganisms,
A n g e w Chem. Int. E d . Enyl. 17 ( 1 9 7 8 ) N o . 11
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