Introduction to the Dictionary of Drugs Online

• Introduction to the DOD database
• Compound selection and presentation
• Chemical names and synonyms
• Description of data types
• Hazard and Toxicity Information
• Bibliographic references and literature coverage
• Entry under review
• Abbreviations
• References

Introduction to the DOD database

The Chapman & Hall/CRC Chemical Database is a structured database holding information on chemical substances. It includes descriptive and numerical data on chemical, physical and biological properties of compounds; systematic and common names of compounds; literature references; structure diagrams and their associated connection tables. The Dictionary of Drugs Online is a subset of this database and includes all compounds contained in the Dictionary of Drugs (Main Work and Updates).

Compound selection and presentation

General

In general the following compounds are included:

1. all currently marketed drugs
2. all drugs listed in the generic name compilations (US Adopted Names, International Nonproprietary Names, British Approved Names, Japanese Accepted Names) [1-4]
3. compounds used as pharmacological tools in biochemical research
4. biologically active natural products.
5. compounds undergoing clinical trials
6. drugs which are no longer marketed
7. compounds whose toxicity or adverse side-effects preclude clinical use, but which possess interesting or novel pharmacological properties.

Derivatives and variants

Derivatives of compounds containing common functional groups are normally given under the parent compound e.g. hydrochlorides, esters, oximes, ethers, N- or S-oxides. Exceptions occur when a derivative has an extensive literature of its own, or where the derivative requires special stereochemical description which is best suited to diagrammatic representation e.g. chiral sulfoxides. In these cases the derivative entry is cross-referenced to the parent compound.

Molecular formulae are included in DOD for nearly all of these derivatives and they can therefore readily be traced using the Molecular Formula Index whether they are documented as derivatives or have their own entry. Molecular formulae are not in general given for salts or hydrates. Where a derivative appears to have been characterised only as a salt, the properties of this salt may be given under the heading for the derivative. In such cases the data is clearly labelled e.g. Mp 179° (as hydrochloride).

Where a compound can exist in several stereoisomeric forms, these isomers are grouped together into a single entry. Where known, physical properties, CAS registry numbers and pharmacological activity are assigned for each isomer.

Antibiotic complexes and biologicals

Many structurally related antibiotics co-occur as metabolites of the same producing organism, and these are presented within a single entry e.g. Actaplanin.

Usually these components will only differ from each other in side chains or sugar residues and can be presented with a single structure diagram, suitably annotated.

Complex biological molecules such as hormones have been treated in a manner, with closely related species variants subsumed into a single entry. An example is Calcitonin.

Anions and cations

For ionic substances such as quaternary ammonium salts, the entry refers to the anion or cation, and the molecular formula and molecular weight given are those of the ion. The various salts (e.g. chloride, nitrate) are treated as derivatives, each with its own molecular formula.

Isotopically labelled compounds

In general the coverage of DOD does not extend to isotopic variants. In cases where isotopes are used either medicinally or diagnostically, an entry for the unlabelled compound has been compiled and contains an explanation of the uses, plus additional CAS numbers applying to the isotopically labelled compound.

Chemical names and synonyms

Entry names

Most entries are headed by a generic name but for some simpler compounds the systematic name is preferred as the entry name, in which case the entry name may be found from the generic name by using the Name Index. All generic names have suffixes to indicate their source (eg BAN, USAN).

In some cases a generic name may strictly apply to a specific stereoisomer - Such examples carry annotations in the entry text.

Synonyms

The Dictionary contains a wide range of synonyms which may be (a) those found in the chemical literature (b) Chemical Abstracts names (these are omitted when excessively long) (c) company codes (d) tradenames used by pharmaceutical companies.

Care has been taken to include as many tradenames, company codes and alternative names as possible. Most of these have been authenticated from the primary literature but in cases where this has not been possible the principal authorities are Negwer's Organic-Chemical Drugs and their Synonyms [5] and Martindale's Extra Pharmacopoeia [6]. Where a common drug has a very large number of tradenames, a cross reference is given to Negwer which should be consulted for the full listing. Proprietary ownership of drug names is not indicated, and the Dictionary should not be considered as an authoritative source on the proprietary ownership or use of these names.

Synonyms are presented in the following order:

• CAS names. Names corresponding to those used by CAS during the 8th and 9th Collective Index Periods (1967- 1971 and 1972-1976 respectively) are labelled with the suffixes 8CI, 9CI. Names first introduced since 1976 are referred to as 9CI as there have been no substantial changes to CAS nomenclature affecting organic compounds since that date.
• Other systematic names
• Generic names (when not used as entry names), including alternative generic names. Generic names from USAN, BAN, JAN and INN follow different spelling conventions, and all variants are listed in DOD.
• Tradenames
• Company codes

Spelling conventions

American spelling is generally used for chemical names:

• sulf- not sulph-
• estr- not oestr-

with some exceptions:

• caesium not cesium
• aluminium not aluminium

UK spelling is used throughout the text.

Description of data types

Fig. 1 illustrates the format of a typical entry within which individual types of data have been labelled.

CAS Registry Numbers

CAS Registry Numbers are identifying numbers allocated to each distinctly definable chemical substance indexed by the Chemical Abstracts Service since 1965 (plus retrospective allocation of numbers by CAS to compounds from the sixth and seventh collective index periods). The numbers have no chemical significance but they provide a label for each substance independent of any system of nomenclature.

In DOD, much effort has been expended to ensure that accurate CAS numbers are given for as many substances as possible. If a CAS number is not given for a particular compound, it may be (a) because CAS have not allocated one, or (b) very occasionally because an editorial decision cannot be made as to the correct number to cite.

Additional registry numbers

At the foot of the DOD entry, immediately before the references, may be shown additional registry numbers. These are numbers which have been recognised by the editors as belonging to the entry concerned but which cannot be unequivocally assigned to any of the compounds covered by the entry. Their main use will be in helping those who need to carry out additional searches, especially online searches in the CAS or other databases and who will be able to obtain additional hits using these numbers. Clearly, discretion is needed in their use for this purpose.

Additional registry numbers may arise for a variety of reasons:

1. Some may refer to stereoisomers or other variants of the main entry compound which may or may not be mentioned in the entry, but for which no physical properties or other useful information is available. For example, an entry may state that a compound has so far only been obtained as an inseparable mixture of stereoisomers. Although no physical properties are available, individual CAS numbers for each stereoisomer will have been assigned, and will be listed in the additional registry number field.
2. A CAS number may refer to a mixture, in which case it is added to the DOD entry referring to the most significant component.
3. The number may refer to an undefined isomer, e.g. there is a CAS number for 'Sulfobenzoic acid' (where the original document does not make it clear which isomer is referred to) in addition to the separate numbers for 2-,3- and 4 -sulfobenzoic acids. Such a number may appear as an additional registry number in all three appropriate entries.
4. Replaced numbers, duplicate numbers and other numbers arising from CAS indexing procedures of, occasionally, from errors or inconsistencies by CAS, are also reported. CAS frequently replace a given number with one that more accurately represents what they now know about a substance, and the replaced number remains on their files for searching.
5. In the case of compounds with more than one stereogenic centre, additional registry numbers frequently refer to levels of stereochemical description which cannot be assigned to a particular stereoisomer described in DOD.
6. Numbers may refer to derivatives similar to those described in the DOD entry for which no data is available.
7. Some DOD entries cover families of compounds such as natural products. An example is the entry for Calcitonins, where only the porcine and human variants are described in detail. The additional registry numbers given in this entry refer to a number of other species variants which appear to have been identified according to CAS but for which no attempt has been made to collate full data for DOD.
8. Isotopically labelled variants e.g. for ^l3lI-labelled compounds such as iodocholesterol. Isotopically labelled variants are not generally included in DOD, but some are used as radioactive agents or diagnostic aids.

Structural formulae

Every attempt has been made to present the structures of Chemical substance as accurately as possible according to best current practice and IUPAC recommendations. Structurally related compounds are presented Consistently and ring systems are oriented in a standard manner to allow ready comparison of structures. The pseudoatom abbreviations Me, Et and Ac for methyl, ethyl and acetyl respectively are used only when attached to a heteroatom. Ph is used throughout whether attached to carbon or a heteroatom. Other pseudoatom abbreviations such as Prⁱ for isopropyl and Bz for benzoyl are not used.

Peptides are usually drawn using the standard three letter abbreviations. The configurations of constituent amino acids are assumed to be L- unless otherwise stated.

Stereochemical conventions [24]

The absolute configuration of a compound is indicated where known . Where only one stereoisomer is referred to in the text of the entry, the structure diagram refers to that stereoisomer. Wherever possible, stereo structures are described using the Cahn-Ingold-Prelog sequence rule (R,S) and (E,Z) conventions [7], but in cases where these are cumbersome or inapplicable, alternatives such as the α,ß-system are used instead. Structure diagrams for compounds containing one or two chiral centres are given in DOD as Fischer-type diagrams showing the stereochemistry unequivocally. True Fischer diagrams in which the configuration is implied by the North-South-East-West positions of the substituents are widespread in the literature: although unambiguous they need to be used with caution by the inexperienced as they cannot be reoriented without the risk of introducing errors.

In a simple case, the four substituents about a Tetrahedral carbon atom are assigned priorities according to the CIP rules, and the molecule is then viewed from the side remote from the substituent of lowest priority. The configuration is (R) if the order of the three other groups from highest to lowest is clockwise, and (S) if it is anticlockwise.

Extensions of the (R,S)-system refer to situations such as axial and planar chirality (e.g. biaryls, cyclophanes) and to molecules with central atoms other than carbon (e.g. sulfoxides).

Where only the relative configuration of a compound containing more than one chiral centre is known, the symbols (R*) and (S*) are used, the lowest-numbered chiral centre being arbitrarily assigned the symbol (R*). For racemic modifications of compounds containing more than one chiral centre the symbols (RS) and (SR) are used, with the lowest-numbered chiral centre being arbitrarily assigned the symbol (RS). The racemate of a compound with a single chiral centre is described in DOD as (±)-.

Molecular formula and molecular weight

The elements in the molecular formulae are given according to the Hill convention (C,H, then other elements in alphabetical order). Molecular weights given are formula weights and are rounded to 3 places of decimals. In the case of high molecular mass substances, such as proteins, the value quoted may be that taken from an original literature source and may be an aggregate molar mass.

Molecular formulae are not generally quoted for derivatives such as salts or hydrates.

Pharmacological activity and therapeutic use

Practically every compound in this Dictionary has been classified according to its mechanism of action (where this is known) and its therapeutic use and are assigned a Type of Compound code. Compounds which have several claimed therapeutic uses are indexed separately in each category. A full list of Type of Compound codes are given in the Help file.

The assignment of drugs into each category is based on information given in Martindale [6], the most recent lists of approved names [l-4] or in the primary literature. This Dictionary is intended for medicinal and pharmaceutical chemists as an aid to research and is not intended as a guide to prescription or use of drugs. The information is given in good faith but the Editors cannot be held responsible for any inaccuracies therein. Nomenclature recommended in the annual supplements to Trends in Pharmacological Sciences [8] is used to summarise drug-receptor properties. Key papers on the biochemical mechanisms of drug actions are identified, and the main therapeutic effects of drugs are described together with any recent observations of new activities for existing drugs.

For many drugs with chiral centres pharmacological activity can reside predominantly with one enantiomer. Any differences in potency between the different Stereoisomers of a particular compound are noted in DOD.

The optimisation of drug activity is a continuing challenge for the medicinal chemist. Crystallographic and conformational studies as well as conventional structure-activity relationships (sar) are used in drug research to achieve this goal, and for many recently marketed products references to these areas of research are mentioned in DOD. Two indicators of drug absorption and distribution, pK_a values and log P partition coefficients (octanol/water), are quoted for many entries.

Development status

This field gives information (when available) about whether a compound has been marketed, or is undergoing clinical trials. If a compound has been withdrawn from the market, this is also stated. Although a variety of sources have been consulted [2, 9], the transient nature of this type of information means that this dictionary should not be considered as an authoritative or up to date source for a drug's marketing status. Details of the worldwide top 100 prescription drugs (in 1994) are also provided [9].

Physical data

Appearance

Organic compounds are assumed to be colourless unless otherwise stated. An indication of crystal form and of recrystallisation solvent is often given but these are imprecise items of data- most organic compounds can be crystallised from several solvent systems and the crystal form often varies.

Melting points and boiling points

These are reported in degrees Celsius. The policy followed in cases of conflicting data is as follows:

• Where the literature melting points are very similar, only one figure (the highest or most probable) is quoted
• where two or more melting points are recorded and differ by several degrees (the most likely explanation being that one sample was impure), the lower figure is given in parentheses; thus Mp 139° (135-136°).
• where quoted figures differ widely and some other explanation such as polymorphism or incorrect identity seems the most likely explanation, both figures are quoted without parentheses; thus Mp 142°, Mp 205- 206°).
• Known cases of polymorphism or double melting point are noted.
• Boiling points are given at atmospheric pressure unless otherwise indicated. The pressure in mmHg (if not atmospheric) is given as a subscript, e.g. Bp₁₀₀85°. Some boiling points are now quoted in the literature with the pressure in kilopascals (kPa, SI units). The conversion factor is; 1 mmHg - 0. 133222 kPa; 1 kPa = 7.50064 mmHg.
• Boiling point determination is less precise than that of melting points and conflicting boiling point data is not usually reported except when there appears to be a serious discrepancy between different authors. o Sublimation temperatures are recorded in a similar style to boiling points e.g. Subl.₂₀ 130°.

Optical rotations

These are given wherever possible and are expressed in the form: [α]_D ²⁰ + 30.6 (c, 1.2 in MeOH). This denotes a temperature of 20°C , wavelength at the sodium D line (589 nm) and a concentration of 1.2 9/100 ml in methanol solution. Where reported in the literature, an indication of optical purity (op) or enantiomeric excess (ee) is recorded after the rotation value.

The degree sign following optical rotations, although still extensively found in the primary literature, has been dropped from DOD as it is dimensionally incorrect.

Densities and refractive indices

Although these are now of less importance for the identification of liquids than has been the case in the past, they are still quoted for common substances. Densities and refractive indices are not quoted where the determination appears to refer to an undefined mixture of stereoisomers.

Solubilities

Solubilities are quoted only where the solubility is unusual for an organic compound. Typical organic compounds are soluble in the usual organic solvents such as ether and chloroform, and virtually insoluble in water.

pK_a values

Experimentally determined pK_a values are given for both acids and bases. The pK_a of a base can be obtained by subtracting its pK_a from 14.17(at 20° C) or from 14.00 (at 25° C).

An indication of the ionisation of a compound at a particular pH is invaluable for predicting its potential pharmacological profile, hence pK_a values are reported for as many compounds as possible.

Octanol-water partition cofficients

Octanol-water partition coefficients are a useful measure of a compound's lipophilicity, and hence its potential biodistribution [10]. In an attempt to provide comprehensive coverage of this important area, both experimental and calculated values have been included for as many compounds as possible.

Experimental partition coefficients are denoted by the suffix 'exp' in parentheses. The majority of values have been supplied by the LOGKOW database* and these are indicated by the symbol ^s. Experimental values without the ^s symbol are as reported in the primary literature.

Calculated partition coefficients are denoted by the suffix 'calc' in parentheses. These have been calculated by Tripos, Inc.† using the Hansch and Leo algorithm CLOGP [11]. In special circumstances the degree of error is unusually large - such values carry the epithet 'uncertain' to highlight this.

Hazard and Toxicity Information

General

Toxicity and hazard information is highlighted by the sign .

An important function of DOD is to alert the user to Potential hazards associated with the use of a compound. All hazard and toxicity data in DOD has been carefully and critically assessed by a specialist editor. Brief summaries of hazard and toxicity information have been included for many pharmacological agents, although the absence of such data cannot be taken as an indication of safety in use and the publishers cannot be held responsible for any inaccuracies in the reported information.

Physical, reactive and toxic properties all contribute to the hazard associated with a particular chemical. As part of the physical data, flash points, explosive limits and autoignition temperatures have been included where appropriate. Flammability classifications, which are based on flash point measurements and boiling points, are also mentioned, and the opportunity has been taken to include UK occupational exposure standards, or for some compounds threshold limit values published by the American Conference of Governmental Industrial Hygienists (ACGIH).

For the reactive hazards, a brief comment is made on any explosive (or violent polymerisation) properties and aspects of the chemical reactivity of a substance which are of concern. These include the potential for peroxidation, oxidising/reducing properties and incompatibility with commonly available chemicals.

Toxicity information has been chosen to show hazardous effects from short-term or long-term exposure. Observations from human exposure are summarised if available (including adverse effects when handling drugs), otherwise experimental tests are quoted. Included in the toxicity data are results of irritancy tests, acute lethality data, target organ toxicity, and carcinogenic and reproductive properties where appropriate. Those chemicals which have been classified by the International Agency for Research on Cancer (IARC) as human carcinogens, probable carcinogens or possible human carcinogens have been identified in the Dictionary accordingly.

Although drug toxicity usually implies any adverse effects following the administration of a drug, the hazards of handling many classes of drugs in the workplace should not be overlooked [12-18]. Strict hygiene and compliance with local safety rules are necessary when handling prostaglandins, antineoplastic alkylating agents, immunosuppressants, synthetic estrogens and adrenocorticosteroids and known allergens, in addition to the usual precautions for working with pharmacological agents whatever their hazard profile.

The selection of drug-induced toxicity data for DOD is drawn mainly from available animal studies and reviews of adverse effects in humans. Acute lethality data (usually expressed as LD₅₀ or sometimes LD_Lo - the lowest dose reported to have caused death) are quoted for one animal species (usually a rodent) by an oral and one parenteral route of administration.

Information on the chronic toxicity of drugs following long-term or repeated exposure in animals is relatively scarce in the literature. Pertinent references are included, however, as is a mention of any effects on the male and female reproductive systems and the developmental toxicity of drugs. For many drugs a fuller explanation of the observations of reproductive and teratogenic tests quoted in DOD is available [19]. Genotoxicity rests and long-term safety evaluation studies used by the pharmaceutical industry for drug development and licence applications are currently being scrutinised [20,21].

Brief comments in DOD on the adverse human effects of drugs are intended to reinforce the general precautions necessary when handling pharmacological agents. More comprehensive reviews of adverse drug reactions, particularly for the major classes of drugs in use today, have been published [6, 22].

No attempt has been made in DOD to summarise the enhancement(or otherwise) of drug potency and toxicity by interaction with other drugs or with dietary components [23].

RTECS^® Accession Numbers**

Many entries in DOD contain one or more RTECS^®; Accession Numbers. Possession of these numbers allows users to locate toxicity information on relevant substances from the MOSH Registry of Toxic Effects of Chemical Substances, which is a compendium of toxicity data extracted from the scientific literature.

For each Accession Number the RTECS^®; database provides the following data when available: substance prime name and synonyms; date when the substance record was last updated; CAS Registry Numbers; molecular formula and weight; reproductive, tumorigenic, and toxic dose data; citations to aquatic toxicity ratings, IARC reviews, ACGIH Threshold Limit Values, toxicological reviews, existing Federal standards, the NIOSH criteria document program for recommended standards, the NIOSH current intelligence program, the NCI Carcinogenesis Testing Program, and the EPA Toxic Substances Control Act inventory.

The NIOSH Registry of Toxic Effects of Chemical Substances is available in the following forms:

1. Printed version available only from: Superintendent of Documents, US Government Printing Office, Washington DC 2M02.
2. RTECS^® Online Database available from:
   Chemical Information Systems, Inc.
   Knight-Ridder Information Services, Inc.
   National Library of Medicine
   STN International
   DataStar
   
3. RTECS^® CD-ROM Database available from:
   Micromedex
   Silverplatter Information Inc.
   Canadian Centre for Occupational Health and Safety
4. RTECS^® Computer tape available from:
   National Technical Information Service (NTIS).

Bibliographic references and literature coverage

Each entry is accompanied by a selection of literature references, the aim of which is to facilitate entry into the literature for the user who wishes to locate more detailed information about a particular compound. Thus in general, recent references are preferred to older ones, particularly for chiral compounds where optical purity and absolute configuration may have been determined only relatively recently. Extensive use is made of review articles, especially for very widely used compounds which have been known for a long time. Therefore, the number of references quoted cannot be taken as a measure of relative importance of a compound.

References are given in date order except for references to spectroscopic library collections, which sort at the top of the list, and those to hazard/toxicity sources which sort at the bottom.

For many compounds, especially those still undergoing clinical trials, the only information available may be in the patent literature. Wherever possible the original patents (or English language equivalents) have been consulted, and details of biological activity and physical properties are as quoted in these documents. When referring to a patent no distinction is made between patent applications and granted patents. As well as quoting the patent office and patent number, a CAS reference and the patenting company are also given. Patents are usually quoted in the following format:

Eur Pat., 247 458 (1987) (Glaxo); CA, 116, 7887q (synth)

Extensive reference has been made to post- 1990 pharmacological and biochemical literature. These changes reflect current interests in, for example, drug receptor interactions, anti-HIV agents, drugs which modulate the immune system, and the therapeutic uses of natural products and their derivatives.

In addition to citations of pharmacological mechanisms, references to pharmacokinetic and metabolic studies and to clinical trials are included for many entries together with the more recent hplc/capillary gc methods for analysing drugs in biological matrices.

The contents of most references are indicated by means of suffixes eg (synth), (pharmacokinet). Some suffixes are now given in boldface type, where the editors consider the reference to be especially important. In general journal abbreviations are uniform with the Chemical Abstracts Service Source Index (CASSI) except for a short list of very common journals where we have been able to save space by using well understood short-form abbreviations. The full list of these is as follows:

DOD ABBREVIATION	CASSI
Acta Cryst. (and sections thereof)	Acta Crystallogr. (and sections thereof)
Angew. Chem., Int Ed	Agnew. Chem., Ind. Ed. Engl.
Annalen	Justus Liebigs Ann. Chem.
Coll. Czech. Chem. Comm.	Collect. Czech. Chem. Commun.
Chem. Comm.	J. Chem. Soc., Chem. Commun.
J.A.C.S.	J. Am. Chem. Soc.
J.C.S. (and various subsections thereof)	J. Chem. Soc. (and various subsections thereof)
J. Het. Chem.	J. Heterocycl. Chem.
J. Nat. Prod.	J. Nat. Prod. (Lloydia)
J.O.C.	J. Org. Chem.
Recl. Trav. Chim. (J.R. Neth. Chem. Soc.)	Recl. Trav. Chim. Pays-Bas (J.R. Neth. Chem. Soc.)
Tet. Lett.	Tetrahedron Lett

Entry under review

The database is continually under updated. When an entry is undergoing revision at the time of an on-line release (e.g. by addition of further derivatives or references), this is indicated by a message at the head of the entry.

Abbreviations

Abbreviation	Meaning
[α]	specific rotation
acac	acetylacetonato
Ac	acetyl
ACGIH	American Conference of Governmental Industrial Hygienists
Ac2O	acetic anhydride
AcOH	acetic acid
ADI	Acceptable Daily Intake
alk.	alkaline
amorph.	amorphous
ANSI	American National Standards Institute
anhyd.	anhydrous
approx.	approximately
aq.	aqueous
asym.	asymmetrical, unsymmetrical
B	base
BAN	British Approved Name
biol.	biological
bipy	2,2¢-bipyridine
Bp	boiling point
br	broad
BSI	British Standards Institution
Bu	butyl (But for tert-butyl etc.)
bwd	bird (wild)
Bz	benzyl
c.	concentration
ca.	(circa) about
CAS	Chemical Abstracts Service
Ccp	cubic close packed
cdt	1,5,9-cyclododecatriene
C6H6	benzene
C5Me5	pentamethylcyclopentadienyl
CNS	central nervous system
cod	1,5-cyclooctadiene
col.	colour, coloration
comly.	commercially
compd(s)	compounds(s)
conc.	concentrated
const.	constant
constit.	constituent
coord	coordinate(d), coordination
cot	1,3,5,7-cyclooctatetraene
Cp	cyclopentadienyl
C5Ph5	pentaphenylcyclopentadienyl
cryst.	crystal(s)
cv	cultivar
CVD	chemical vapour deposition
Cy	cyclohexyl
d	density
dba	dibenzylideneacetone
dck	duck
dec.	decomposes, decomposition
degradn.	degradation
depe	1,2-bis(diethylphosphino)ethane
descr.	described
diars	diarsine (generalised ligand)
dil.	dilute, dilution
dimorph.	dimorphic
diphos	diphosphine (generalised ligand)
diss.	dissolves, dissolved
dissoc.	dissociates
dist.	distil, distillation
DMA	dimethylacetamide
DMF	dimethylformamide
dmpe	1,2-bis(dimethylphosphino)ethane
dmpm	bis(dimethylphosphino)methane
DMSO	dimethyl sulfoxide
dppe	1,2-bis(diphenylphosphino)ethane
dppm	bis(diphenylphosphino)methane
dppp	1,3-bis(diphenylphosphino)propane
EDTA	ethylenediaminetetracetate(4-)
ee	enantiomeric excess
Eg	band gap (electron volts)
en	ethylenediamine
equilib.	equilibrium
esp.	especially
Et	ethyl
EtOAc	ethyl acetate
EtOH	ethanol
EtOH	aq. aqueous ethanol
evapn.	evaporation
exp.	exposure
exp.	experimental
fac	facial
Fc	ferrocenyl
fl. p.	flash point
fluor.	fluoresces, fluorescence
formn.	formation
Fp	freezing point
g	gram(s)
ΔG0f	standard free energy of formation
Glc	β-D-glucopyranosyl
gpg	guinea pig
ham	hamster
ΔH0f	standard enthalpy of formation
hcp	hexagonal close packed
hydrol.	hydrolyses, hydrolysed, hydrolysis
ihl	inhalation
im	imidazolato
ims	intramuscular
INN	International Non-proprietary Name
inorg.	inorganic
insol.	insoluble
intermed.	intermediate
ipr	intraperitoneal
ISO	International Standards Organisation
Ivg	intravaginal
ivn	intravenous
JAN	Japanese Accepted Name
JMAF	Japanese Ministry for Agriculture, Forestry and Fisheries
K	temperature (Kelvin)
L	generalised ligand
LC	lethal concentration
LD	Lethal dose; LD50: a dose which is lethal to 50% of the animals tested
M	relative molecular mass (formula weight)
M	metal
m	medium
mcd	magnetic circular dichroism
Me	methyl
MEL	maximum exposure limit
MeOH	methanol
mer	meridional
mes	mesityl (1,3,5-trimethylphenyl)
Me2CO	acetone
misc.	miscible
misc.	miscellaneous
mixt.	mixture
mky	monkey
MOCVD	metal-organic chemical vapour deposition
mod.	moderately
Mp	melting point
mus	mouse
n	index of refraction eg. (n20D for 20° and sodium light).
Nbd	norbornadiene
nqr	nuclear quadrupole resonance spectrum
obt.	obtained
oc	open cup
oep	octaethylporphyrinato
OES	occupational exposure standard
Oh	octahedral
op	optical purity
org.	organic
orl	oral
ox	oxalato
Ph	phenyl (C6H5)
pH	Measure of soln. acidity where pH = log10 (1/[H+]) where [H+] is the hydrogen ion
Phen	1,10-phenanthroline
phys.	physical
pK	Measure of dissoc. const. (K) where pK = Log10(1/K)
Pm	picometres (10–12 m)
PMDET	pentamethyldiethylenetriamine
polarog.	polarography
polym.	polymerised, polymerisation
ppm	parts per million
Pr	propyl (Pri for isopropyl)
prob.	probably
purifn.	purification
Py	pyridine
pz	pyrazolato
R	generalised alkyl group
rbt	rabbit
ref.	reference
rel.	relative(ly)
r.t.	room temperature
s	strong
S0	standard entropy
scu	subcutaneous
skn	skin
sl.	slightly
sol.	soluble
soln(s)	solution(s)
solv(s)	solvent(s)
soly.	solubility
sp.	species (singular)
spar.	sparingly
spp.	species (plural)
ssp.	subspecies
subl.	sublimation, sublimes
tbp	triagonal bipyramidal
Td	tetrahedral
Tf	triflate
THF	tetrahydrofuran
tht	tetrahydrothiophene
TLV	Threshold Limit Value
TMED	tetramethylethylenediamine
tpp	tetraphenylporphyrinato
triphos	triphosphine (generalised ligand)
Ts	tosyl
μeff	effective magnetic moment (in Bohr magnetons μB)
unsatd.	unsaturated
USAN	United States Adopted Name
Uv	ultraviolet spectrum
v.	very
var.	variety
vis.	visible
vol.	volume
w	weak
WSSA	Weed Science Society of America
X	generalised anion, usually halide

References

[1]	USP Dictionary of USAN and International Drug Names,US Pharmacopeial Convention Inc., Rockville, USA, 1995.
[2]	International Nonproprietary Names for Pharmaceutical Substances. Cumulative list no. 8, World Health Organisation, Geneva, 1992.
[3]	British Approved Names, British Pharmacopoeia Commission, London, 1994
[4]	Japanese Accepted Names for Pharmaceuticals, Society of Japanese Pharmacopoeia, 1992
[5]	Negwer, M., Organic-Chemical Drugs and their Synonyms, 7th edn., Akademie-Verlag, 1994.
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