3S-4.4 to 3S-4.10

Continued from 3S-4. Functional groups (3S-4.0 to 3S-4.3)

Contents

3S-4. Functional groups (continued)

4.4 Oxo compounds
4.5 Alcohols
4.6 Amines
4.7 Ethers
4.8 Acetals and ketals
4.9 Trivial names of important steroids
4.10 Use of international non-proprietary names

(a) Aldehydes are named by using either the suffix -al (denotes change of -CH₃ to -CHO, i.e. without change in the number of carbon atoms), or -aldehyde (denotes change of -COOH to -CHO, i.e. without change in the number of carbon atoms; the name is derived from that of the acid). The prefix oxo- denotes the change of >CH₂ to >CO, thus also of -CH₃ to -CHO, with no change in the number of carbon atoms. Examples:

5-Androstan-19-al
5-Cholan-24-al

If the aldehyde group is formed by substitution of a hydrogen atom in CH, >CH₂ or -CH₃ by -CHO i.e. C-CHO the prefix formyl or suffix carbaldehyde is used. Examples:

3-Formyl-5-cholan-24-oic acid

(b) For ketones, the suffix is -one, and the prefix oxo-. Examples:

5-Androstan-3-one
Pregn-5-ene-3,20-dione
11-Oxo-5-cholan-24-oic acid

Notes

(1) The prefix oxo- should also be used in connection with generic terms, e.g. 17-oxo steroids. The term "17-keto steroids", often used in the medical literature, is incorrect because C-17 is specified twice, as the term keto denotes C=O.

(2) Many steroids carry hydroxyl groups as well as oxo groups. In this case, the suffix -one must be used, and hydroxyl groups indicated by prefixes, unless the compounds have trivial names (see Table 2). If the principal functional group (and hence the suffix) is preferred to either hydroxyl or oxo groups both hydroxyl and oxo groups are indicated as prefixes.

3S-4.5. Alcohols

Alcohols are named with the suffix -ol or the prefix hydroxy-, with the appropriate locants. Examples:

5-Cholestane-3,11-diol
3-Hydroxy-5-androstan-17-one (trivial name: androsterone)

Notes

(1) Composite suffixes -olone and -onol, to denote simultaneous presence of hydroxyl and ketonic groups, are not permitted by IUPAC Recommendations [3] and should not be used.

(2) A few trivial names exist for hydroxy ketones (see Table 2).

3S-4.6. Amines

Amines are named by means of the suffix -amine or the prefix amino-. Examples:

Androst-5-en-3-amine

3S-4.7. Ethers

Ethers are named as alkoxy derivatives. Examples:

17-Methoxyandrost-4-en-3-one

Ethers and partial ethers of steroid polyols are named either by using the alkoxy- prefix, or by the prefix O-alkyl- if the hydroxy group etherified is already specified in a trivial name. Examples:

(20S)-3,17,20-Trimethoxy-5-pregnane
(20S)-3,17-Dimethoxy-5-pregnan-20-ol
21-O-Methylcortisol

3S-4.8. Acetals and ketals

Acetals and ketals of oxo steroids are named as dialkoxy steroids. Examples:

Similarly, acetals formed by an oxo compound reacting with two hydroxyl groups of a steroid may be named alkylenedioxy compounds. Example:

2,3-(Methylenedioxy)pregn-5-ene (see 101)

3S-4.9. Trivial names of important steroids

Examples of trivial names retained for important steroid derivatives, these being mostly natural compounds of significant biological activity, are given in Table 2.

Click here for "table free" view if the table below is faulty.

Table 2. Trivial names of some important steroid derivatives

Trivial name	Systematic steroid name
Aldosterone	18,11-hemiacetal of 11,21-dihydroxy-3,20-dioxopregn-4-en-18-al or 11,18-epoxy-18,21-dihydroxypregn-4-ene-3,20-dione
Androsterone	3-hydroxy-5-androstan-17-one
Brassinolide	(22R,23R)-2,3,22,23-tetrahydroxy-6,7-seco-5-cmpestano-6,7-lactone
Calcidiol (93)	(5Z,7E)-(3S)-9,10-secocholesta-5,7,10(19)-triene-3,25-diol
Calciol = cholecalciferol(92)	(5Z,7E)-(3S)-9,10-secocholesta-5,7,10(19)-trien-3-ol
Calcitriol (94)	(5Z,7E)-(1S,3R)-9,10-secocholesta-5,7,10(19)-triene-1,3,25-triol
Cholesterol	cholest-5-en-3-ol
Cholic acid	3,7,12-trihydroxy-5-cholan-24-oic acid
Corticosterone	11,21-dihydroxypregn-4-ene-3,20-dione
Cortisol	11,17,21-trihydroxypregn-4-ene-3,20-dione
Cortisol acetate	21-O-acetylcortisol
Cortisone	17,21-dihydroxypregn-4-ene-3,11,20-trione
Cortisone acetate	21-O-acetylcortisone
Deoxycorticosterone	21-hydroxypregn-4-ene-3,20-dione (i.e. the 11-deoxy derivative of corticosterone)
Ecdysone	(22R)-2,3,14,22,25-pentahydroxy-5-cholest-7-en-6-one
Ercalciol = ergocalciferol	(5Z,7E,22E)-(3S)-9,10-secoergosta-5,7,10(19),22-tetren-3-ol
Ergosterol (7)	(22E)-ergosta-5,7,22-trien-3-ol
Estradiol-17	estra-1,3,5(10)-triene-3,17-diol
Estradiol-17	estra-1,3,5(10)-triene-3,17-diol
Estriol	estra-1,3,5(10)-triene-3,16,17-triol
Estrone	3-hydroxyestra-1,3,5(10)-trien-17-one
Lanosterol	lanosta-8,24-dien-3-ol
Lithocholic acid	3-hydroxy-5-cholan-24-oic acid
Progesterone	pregn-4-ene-3,20-dione
Pseudotigogenin	(25R)-5-furost-20(22)-ene-3,26-diol
Sarsasapogenin	(25S)-5-spirostan-3-ol
Smilagenin	(25R)-5-spirostan-3-ol
Testosterone (63)	17-hydroxyandrost-4-en-3-one
Tigogenin	(25R)-5-spirostan-3-ol

Note If these trivial names are used as a basis for naming derivatives or stereoisomers, the derived trivial name must make the nature of the modification completely clear and is preferably accompanied at first mention by the full systematic name. For example, in steroid papers epi is often used with trivial names to denote inversion at one centre; the name 11-epicortisol defines the compound fully since cortisol is already defined as the 11-alcohol; but the name epicortisol does not define the compound and is inadequate.

3S-4.10. Use of international non-proprietary names

International non-proprietary names (INNs) have been given to many steroids of pharmaceutical importance [6]. For convenience, a selection of some of these names is given in the appendix. If these names are used in biochemical papers, it is recommended that once in the paper, e.g. in a footnote or under Materials and Methods, the full systematic name is also given. International non-proprietary names should not be used as a basis for the names of modified compounds.

2. International Union of Biochemistry (1978) Biochemical nomenclature and related documents, The Biochemical Society, London.

3. International Union of Pure and Applied Chemistry, Nomenclature of organic chemistry, Sections A, B, C, D, E, F and H, 1979 Edition, Pergamon Press, Oxford, 1979. Section E appeared also in pp. 1-18 of [2], and section F in pp. 19-26 of [2] and in Eur. J. Biochem. 86, 1-8 (1978).

6. International non-proprietary names (INN) for pharmaceutical substances, cumulative list 6, World Health Organization, 1982.

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