Steroid nomenclature

J. steroid Biochem. Vol. 28, No. 1, pp. v-vii, 1987 Pergamon Journals Ltd. Printed in Great Britain

STEROID

NOMENCLATURE I. S.wemulic

These must conform l(1970) 143-1751.

to the IUPAC-IUB

numes

1967 Revised Tentative

Rules for Steroid

Nomenclature

[J. steroid Biochem.

II. Trivial names The following

are examples

of trivial

Aetiocholanolone* Aldosterone Androsteronc Cholesterol Cholic acid Corticosterone Cortisol Cortisone Dehydroepiandrosterone (DHA) Deoxycorticosterone (DOC) Ergosterol Oestradiol-l7B* Oestriol’ Oestrone* Progesterone Testosterone *The diphthongs

names

which

may be used without

reference

to their systematic

names:

3a-Hydroxy-SP-androstanI7-one IS,1 I-Hernia&al of I I~,21-dihydroxy-3,20-dioso-4-pregnen-lS-al 3a-Hydroxy-Sa -androstan- I7-one S-Cholesten-3P-ol 3a,7a, l2a-Trihydroxy-5/?-cholan-24-oic acid I I/?,21-Dihydroxy-4-pregnene-3,20-dione I Ip,l7,21-Trihydroxy-4-pregnene-3,20-dione 17,21-Dihydroxy-4-pregnene-3.1 l,20-trione 3/?-Hydroxy-S-androsten17-one 2l-Hydroxy-4-pregnene-3,20-dione 5,7,22-Ergostatrien-38-01 1,3,5(10)-Oestratriene-3,17p-dial’ 1,3,5(10)-Oestratriene-3,16a-l7/?-triol’ 3-Hydroxy- 1,3,5( IO)-oestratrien- l7-one’ 4-Pregnene-3,20-dione l7a-Hydroxy-4-androsten-3-one

z and ae may be replaced

by the letter e

Trivial names may be prefixed to denote their derivatives or stereoisomers. In addition to prefixes used in systematic nomenclature (hydroxy, 0x0, etc.) the following are frequently used: “epi” (inversion of a substituent), “dehydro” (removal of two hydrogen atoms from two adjacent carbon atoms or from a carbinol grouping) and “deoxy” (replacement of a etc. may be used to indicate addition of hydrogen to double hydroxy group by a hydrogen atom). “Dihydro”, “tetrahydro”, bonds but not to carbonyl groups. Names so derived should indicate the site and when necessary the steric outcome of the structural change defined by the prefix. Examples of correctly derived names are: I I-oxoaetiocholanolone. 6a-hydroxycortisone, epitestosterone, I I-epicortisol (not epicortisol), 7-dehydrocholesterol, I I-dehydrocorticosterone. I I-deoxycortisol, and 22-dihydroergosterol. With a few generally accepted exceptions such as deoxycorticosterone (I I-deox!corticosterone), deoxycholic acid (7-deoxycholic acid) and dehydroepiandrosterone (5-dehydroepiandrosterone) trivial names should be unambiguous. The prefix “allo” (change from Sp to 5a configuration) and the symbol A.‘ (unsaturation at position x) may not be used. The following are examples of trivial names not generally accepted but frequently used in specialized publications: Androstenedione 202 -Cortol 20/I-Cortol 202~Cortolone ZOB-Cortolone Dihydrotestosterone Pregnanediol Pregnanetriol Preenenolone Tetrahydroaldosterone* Tetrahydrocortisol* Tetrahydrocortisone* 201-Dihydroprogesterone *In this instance,

4-Androstene-3, I ‘I-dione 5p-Pregnane-3a, I I /?. 17,20a,2 I -pent01 5/?-Pregnane-3a. 1I/I. I7,20/?,2 I-pentol 3a, I7.2Oa.2 I -Tetrahydroxy-Sfi-pregnanI 1-one 3a, I7,208.2 I-Tetrahydroxy-5/?-pregnanI l-one l7P-Hydroxy-5a-androstan-3-one 5fi-Pregnane-3a,20a-diol 5b-Pregnane-3a.l7.20z-trio1 3fi-Hydroxy-5-pregnen-20-one l8,l I-Hemiacetal of 31,11/1,21-trihydroxy-20-oxo-5~-pregnan-18-al 3a, I I p, 17.2 I -Tetrahydroxy-5/I-pregnan-20-one 3a,I 7,21-Trihydroxy-S/j’-pregnane-I l.20-dione 20a-Hydroxy-4-pregnen-3-one “Tetrahydro”

indicates

addition

of hydrogen

to a double

bond and a carbonyl

group

Such names may not be used in the title nor in the summary. They may be used in the text when their meaning is clearly defined by the subject-matter (e.g. pregnenolone as an intermediate in the biosynthesis of progesterone or pregnanediol estimated in the urine). Otherwise, they should be used in the same manner as less familiar trivial names (see below). Less familiar trivial names are acceptable only when their use leads to a substantial sating of space, i.e. when they arc much shorter than their systematic names and when they are frequently referred to. Their systematic names should be given at their first mention when only one or a few such trivial names are used. Otherwise, their systematic names should be listed in a footnote or tabulated in the text. No trivial name may designate an impossible structure (e.g. 20-hydroxyprogesterone).

Abbreviations

vi

The use of abbreviations should be largely conlined to tables and figures. Commonly used abbreviations such as DHA (dchydroepiandrostcrone) or DOC (deoxycorticosterone) are acceptable in the text. Less common abbreviations may be used in the text only when this leads fo a substantial saving af Space without loss of clarity. All abbreviations must be defined in the text, in a footnote to the text, a footnote to a table, or in the legend to a figure, as appropriate.

OTHER

ABBREVIATIONS

AND SYMBOLS

The Journal of Steroid Biochemistry will in general use the recommended Sl symbols for units Wsteme international d’Unites; see Symho/.s, Signs cmd Ahhr>c+ariom kmmmended_for British S~iejltificPtcbfi~nrions (I 969): London, The Royal

Society]. The symbol for the plural of a unit is the same as that for the singular: thus “centimetres” is “cm”, not “ems”. The principles given in the Tentative Rules of the IUPAC-IUB Commission on Biochemical Nomenclature [see ~j~~r~ie~~cff~ Jolour~l 101 (1966) 11 will be followed for abbreviations. Abbreviations of names of compounds except those listed below must be defined together in a footnote. ACTH ADP. CDP. GDP, IDP. UPD, XDP AMP etc. ATP etc. CoA and acetyl-CoA DEAR-cellulose DNA EDTA FAD FSH GH HCG LH LtH NAD+, NADH NADP+, NADPH P, PTH RNA nRNA, mRNA, rRNA. tRNA Tris Other

accepted

Adrenocorticotrophin The S-pyrophosphates

(or tropin) of adenosine,

cytidine,

guanosine,

inosine,

uridine,

Adenosine 5’-mo~ophosphate, etc. Adenosine S-triphosphate, etc. Coenzyme A and its acyl derivatives Diethylaminoethyl cellulose Deoxyribonucleic acid Ethylenediaminetetra-acetate Flavin-adenine dinucleotide Follicle-stimulating hormone Growth hormone Chlorionic gonadotrophin (or tropin), human Luteinizing hormone Luteotrophic (or tropic) hormone Nicotinamide-adenine dinucleotide (oxidized and reduced forms) Nicotinamide-adenine dinucleotide phosphate (oxidized and reduced Inorganic orthophosphate Parathyroid hormone Ribonucleic acid Nuclear, messenger, ribosomal and transfer ribonucleic acid species 2-Amino-2-hydroxymethylpropane-

abbreviations

acceleration due to gravity approximateiy aqueous centimetre compare concentration counts/minute crystalline curie (3-7 x 10’” d.o.s.1 diffusion coefficien; dilfusion coefficient. correlated water, at zero conccntratmn dilute disintegrations/minute disintegrations/second equilibrium constant gas -liquid chromatt~~rapt~y gram(me) gram(me)-molecule hour infrared kilogramtme) litre logarithm (base IO) logarithm (base c) maximum median effective dose median lethal dose melting pomt Michaelis constant microgram

which

I .3-diol

need not be defined: R approx aq. cm Cf.

cont. cpm tryst. Ci D to 20’ in

El. dil. dpm dps K GLC g IllOl

h i.r. kg

log Ill max. ED,,, LDw m.p. Y,, I’ g

(not c. or ca.)

forms)

xanthosine

Abbreviations micromolar (conccntralion) micromolc milliiilrc millimicron (lO-uni) millimolar (concentration) millimolar (amount) minimum minute (60 s) molar (cont.) mole nanogram(me) nuclear magnetic resonance

11M jtmol ml

(not PM)

nm (not m,u) mM or mmol/l mmol (not mM) min. min M or mol/l mol ng NMR

per per cent picogram(me) precipitate preparation probability that an event is due to chance recrystallized relative band or spot speed in chromatography revolutionsjminute second (time) sedimentation coefficient soluble solution solvent systems

specific activity standard deviation Svedberg unit of sedimentation (10-1s) thin-layer chromatography time (symbol) ultraviolet uncorrected wavelength wave number (unit) weight weight in volume

% Pg PPt. prep.

P recryst R,: plural R, values rev./min (or rpm) S s

sol. soln e.g. benzene-hexane-water (4:2: I, by vol.) benzene-water (2: I, v/v) SA or sp.act. SD

coefficient

s TLC U.V.

uncorr. i cm-’ wt w/v

The symbols [see Biochent. J. 102 (1967) 23) are to be used only when representing

These symbols [see Biochem.

The symbols [see Biochem.

vii

J. 101 (1966)

J. 101 (1966)

polymers,

and need not be defined.

polymers,

and need not be defined.

I] need not be defined.

I] are to be used only when representing

The recommendations of Enz~~ntc Nontenriafure (Edited by Marcel Florkin and Elmer H. Stotz, Comprehensive Biology, Vol. 13, Elsevier, 1965) are to be followed as far as possible and the EC numbers should be quoted as suggested on p. 42 of that publication.

Symbols for the isotope introduced are placed in square brackets in front of the name, e.g. [4-‘Qtestosterone, 4 indicating the position of the isotope in the compound.

the figure