UNIT – IV DRUGS ACTING ON ENDOCRINE SYSTEM
STEROIDS: REACTION: 3 CH
Steroids are tetracyclic compounds
O
Se,300 C
characterized by the presence of a 1,2- STEROID
Distillation
cyclopenteno perhydrophenanthrene ring
system. Diels hydrocarbon
Definition of Steroids
Widely distributed in animals and plants.
Basic Steroid Nucleus: Any compound which undergoes
1,2-Cyclopentanoperhydrophenanthrene reduction in the presence of selenium
3
4 2
5 and gives Diels hydrocarbon is called a
6 1
7
steroid.
10
8 9 STEROLS
Diels’ Identified:
Sterols are crystalline compounds
Steroids undergo distillation in the presence containing a secondary alcoholic (–OH)
of selenium, which acts as a reducing agent, group.
to give Diels hydrocarbon at 300°C. They may be divided into three groups.
21
CLASSIFICATION OF STEROLS H3C 22
26
Sterols are classified based on their source as 18
CH 20
23 CH3
12 3
17
follows: 19 11 13 24
25
H3C
C D 16 CH
[Link]: Obtained from animals 1 9 14 27 3
15
2 10 H 8 H
Example: Cholesterol A 5 B 7
3
4 6
[Link]: Obtained from plants H
Example: Stigmasterol Important Points in Steroid Nomenclature
[Link]: Obtained from yeast and [Link] line (– – –) Indicates α-configuration.
fungi [Link] wedge In dicates β-configuration.
Example: Ergosterol [Link] line (~~~) Indicates that the
NOMENCLATURE OF STEROIDS: configuration is not determined.
The IUPAC system of nomenclature is
used for naming steroids.
[Link] a methylene group (–CH₂–) is These prefixes are preceded by a small
missing from the side chain, it is indicated by letter indicating the ring affected.
the prefix “nor”, preceded by the number of Examples:A-nor-5α-androstane (ring A
the carbon atom which has disappeared. contracted)
Example:23-nor-5β-cholane B-homo-5β-pregnane (ring B enlarged)
21
H3C CH2CH3
22 CH3 CH3
23
18 20 CH3 D C D
C
12 CH3 17 CH3 CH3
19 11 13 H
A B A B
H3C
9
C 14 D 16
1
H H
2 10 H 8 H 15
A 5 B A-Nor-5-α-androstane B-homo-5β-pregnane
7
3
4 H 6
5. Ring Contraction and Ring Enlargement
When a ring has been contracted or enlarged, it
is indicated by the prefixes “nor” and “homo”
respectively.
6. Loss of Angular Methyl Group
The numbers showing the position of the
The prefix “nor” is also used to indicate the
bond broken, followed by the prefix
loss of an angular methyl group.
“seco”
In this case, it is preceded by the number
Examples:3,4-seco-5α-cholane , 2,3-seco-
designating the methyl group lost.
5α-pregnane
Examples: 18-nor ,19-nor
CH2CH3
CH3
C D CH3
C D
D CH3
A B CH3 C
H A B
A B
19-nor-5-α-cholane
H
H
[Link] Fission (Seco Steroids) 2,3-Seco5-α-pregnane
3,4-Seco5-α-cholane
When ring fission occurs with the addition of
a hydrogen atom to each new terminal
group, it is indicated by:
8. Cyclo Prefix
The prefix “cyclo”, preceded by the
numbers of the positions concerned, is used
to indicate the formation of an additional
ring.
Example: 3α,5α-cyclocholestane (or) 3,5-
Cyclo5-α-cholestane
CH3
C D
CH3
A B
H
3,5-Cyclo5-α-cholestane
STEREOCHEMISTRY OF STEROIDS R
21 H
H3C 22
18 *20 23 26
12 CH 3 CH3 C D
19 11 17
1 CH3 C 13 * D* 24 25
16 A B H
*
9 * *
14 CH
2 8 15 27 3
A * 10 B AB = Cis
* * H
HO 3 5 6 7 BC,CD } Trans
4
H
Saturated sterols (cholestane) shows that they
possess nine dissimilar asymmetric carbon atoms R
(eight in the nucleus and one in the side chain, CH3
namely at carbon atoms:C-3, C-5, C-8, C-9, C-10, CH3 C D
C-13, C-14, C-17 and C-20)
A B H
The number of possible optical isomers is AB
H
calculated by the formula:2n[29=512] . Therefore, BC,CD } Trans
Cholestane
512 optical isomers are possible.
STEROID RING SYSTEM Normal and Allo Series of Steroids
Steroids are derivatives of the In the normal series of steroids (5α-
cyclopentanoperhydrophenanthrene ring series), the AB ring junction is cis.
system. In the allo-steroids (derived from
The four fused rings are designated as A, cholestane), the AB ring junction is trans.
B, C and D.
X-ray analysis and chemical studies have
shown that in all naturally occurring
steroid hormones, the BC and CD ring
junctions are trans.
The AB ring junction may be either cis or
trans.