| |
| |
| Steroid Nomenclature |
|
|
|
The compounds listed on this website are named essentially according to
the systematic nomeclature of Fieser and Fieser, Steroids, Rheinhold
Publishing Corp., New York, 1959.
|
|
All compounds are related to the parent Hydrocarbons - Cholestane and Coprostane
specifically referred to as 5a-Cholestane and 5b-Cholestane respectively.
Etioallocholane and Etiocholane are refergreen to as 5a-Androstane and
5b-Androstane respectively. Allo-pregnane and Pregnane similarly,
5a-Pregnane and 5b-Pregnane. The compounds listed are given by both systematic
as well as trivial designation.
|
|
|
 |
|
|
| The substituents at a specific position, if known, are designated:
|
| "a" ( down; or dotted line )
( Figure I ) or "b" (up; or solid line) ( Figure II ). If the configuration has
not been determined it is designated by a wavy line ( Figure III ).
|
|
|
|
|
|
| The designation of double bonds
uses sequential numbering; however, under certain circumstances, there are
deviations. For example, as shown below, the double bond in the compound,
5-Cholenic Acid-3b-ol is between positions 5 and 6, and in the compound 5
(10)-Estren-3, 17-Dione the double bond is between the 5 and 10 position of the
steroid nuclei.
|
|
|
|
|
|
|
|
| Prefixes & Suffixes |
|
|
| Acetoxy: |
Ester of acetic acid
|
| Allo: |
Opposite isomer usually restricted
to isomers at C-5 in most instances
|
| Alpha: |
Opposite side of cholesterol
CH3 groups |
| Anhydr: |
Removal of CH group |
| Beta: |
On same side of molecule as
CH3 group of cholesterol |
| Benzoate: |
Ester of benzoic acid
|
| Bisnor: |
Ethylene group eliminated or 2
carbon atoms
|
| Bromo: |
Bromine atom replaces H atom
|
| Carboxylic: |
Acid group |
| Chloro: |
Chlorine atom replaces H atom
|
| Cis: |
Same side of molecule as
CH3 goups of cholesterol |
| Cyclo (i): |
Loss of hydrogens across ring
|
| Delta: |
Unsatturated (when "ene" is
used, "delta"is greenundant) |
| Dehydro: |
Loss of Hydrogen |
| Desoxy: |
Loss of Oxygen |
| Dihydro: |
Two hydrogen atoms added
|
| Epi: |
Isomer differing in spatial
orientation at a single carbon atom (Hydroxyl) |
| Etio: |
Last degradation product retaining
the basic spatial characteristics |
| of the parent compound
|
| Fluoro: |
Fluorine atom replaces H atom
|
| Homo: |
On carbon atom added |
| Hydro: |
One hydrogen atom added
|
| Hydroxy: |
Alcohol group |
| Iso: |
Orientation of side chain
|
| Keto: |
Carboxy (Ketone) gpoup
|
| Methyl: |
CH3 group
|
| Nor: |
Loss of one CH2group
|
| Oxy: |
Ketone or alcohol (oxygen) group
present |
| Propionate: |
Ester of propionic acid
|
| Seco: |
Ring fission in which 2 "H" atoms
have been added at terminal |
| | groups by fission
|
| Tetrahydro: |
Four hydrogen atoms added
|
| Trans: |
Opposite side of cholesterol
CH3 group |
| al: |
Aldehyde |
diene:
|
double unsaturation |
| ane: |
Saturated hydrocarbon |
triene:
|
triple unsaturation |
| ene: |
Unsaturated |
tetraene:
|
quadruple unsaturation |
| ic: |
Acid
| |
|
| ol: |
Alcohol |
|
|
| one: |
Ketone group |
|
|
| DEFINITIONS OF COMMONLY USED TERMS IN ENDOCRINOLOGY |
|
|
| Hormone:
|
A regulatory substance, active at
low concentration with three basic functions.
|
|
|
|
|
a) Regulation and maintenance of a
constant internal environment as it relates to extra and
intracellular fluids.
|
|
|
b) Inter-relationships between
different hormones, i.e., the nervous systems, fluid flow and blood
pressure.
|
|
|
c) Morphogenetic function relating
to type and rates of growth of tissues.
|
|
|
| Animal Hormone:
|
Classified as a protein, polypeptide
or steroid principally secreted by the endocrine gland which directly
or indirectly aids in regulation of processes such as
metabolism, reproduction and growth.
|
|
|
| Plant Hormone:
|
An organic compound principally
controlling growth, i.e., gibberillins, cytokinins and auxins.
|
|
|
| Steroid:
|
Bile acids, sex hormones, sterols,
some vitamins and adrenocortical compounds are typical steroids.
They are cyclic compounds whose basic nucleus consists of three
6-membered rings and a 5-membered cyclopentane ring fused together to
yield perhydrocyclopento- phenanthrene structure.
|
| |
| Steroid Hormone:
|
Term used for androgens, estrogens,
corticoids and gestagens
|
| |
| Androgen:
|
19-Carbon steroids. A male sex
hormone or one of its metabolites.
|
| |
Synthesized by the testes, cortex of
the adrenal gland and to some extent, the ovary.
|
| |
| Bile acid:
|
24-Carbon steroids occurring in bile
in the form of a bile salt.
|
| |
| Bufadienolids:
|
24-Carbon homologue of a cardenolide
occurring as a cardiac glycoside in plants or toads.
|
| |
| Cardenolide: |
23-Carbon steroid noted by a
14b-hydroxy group and a alpha, beta-unsaturated gamma lactone ring.
|
| |
| Corticosteroids:
|
21-Carbon steroid-hormone derived
from the cortex and metabolites of such hormones. |
| |
| Estrogens: |
18-Carbon steroid. A female sex
hormone or one of its metabolites. |
| |
| Glucuronide: |
Glucuronic acid linked to a steroid,
hormone or other compound by means of a glycosidic bond.
|
| |
| Sterols: |
An alcoholic hydroxyl group attached
to position 3 and an aliphatic side chain of 8 or more carbon atoms
attached to position 17 of the steroid nucleus.
|
|
|
|
| |