Hormones

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 Hormones
• Hormones are the organic substances which are secreted by the

ductless glands (endocrine glands).

• They are brought to the different organs of the body by means

of blood stream to produce the various physiological functions.

• They are required in small quantities and are specific in their

functions.

• The deficiency of a hormones leads to a particular disease which

can only be cured by the administration of that hormone.

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Classification of hormones

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 Androgens or Male sex hormones
• The testes produce mainly one androgen, testosterone.

• It is excreted in the urine as such or mainly as

metabolites like androsterone and
dehydroepiandrosterone.

• Even these metabolized products are also found to be

biologically active.

• The main function is to maintain the function of prostate

gland, seminal vesicles, cowper’s glands, penis and
develop the secondary male sex characteristics.
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Testosterone and its synthetic
anabolic androgenic steroids

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Androgens of pharmaceutical
importance

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 Testosterone

1. Molecular formula: C19H28O2

2. The usual tests show that it has one double bond, one
ketonic and one 2°alcoholic groups.

3. By calculating the formula of the parent hydrocarbon it

is shown to be a tetracyclic compound.
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4. As it is very sensitive to alkali showing thereby the presence of
α, β-unsaturated ketonic group which is also confirmed by its UV
spectrum.

5. On oxidation it gives the diketone as obtained by

dehydroepiandrosterone. The formation this diketone can only
be explained if II is the structure of testosterone.

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Synthesis (Ruzicka and Butenandt, 1935)

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 Oestrogens (Follicular hormones)
• Oestradiol is the most important member of
this group, secreted by ovaries.

• Metabolised to many products and is excreted

in urine not as such but as metabolites, some
of which still exhibit biological activity.

E.g: Oestrone and Oestriol.

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 Therapeutic uses of oestrogens
1. Involved in the inhibition of ovulation in
combination with progestins (Birth control).

2. Used in hormone replacement therapy for

postmenopausal women.

3. Used in the treatment of advanced,

inoperable breast cancer and prostate cancer.

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 Classification of oestrogens
1. Steroidal oestrogens and their derivatives
• Oestrone
• Oestradiol
• Oestriol
• Ethinyl oestradiol
• Mestranol
• Sodium oestrone sulphate
• Sodium 17α-dihydroequillin sulphate
• Sodium 17β-dihydroequillin sulphate
• Sodium 17α-oetradiol sulphate
• Sodium 17β-dihydroequilenin sulphate
• Sodium 17β-oetradiol sulphate
• Sodium 17α-dihydroequilenin sulphate
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2. Nonsteroidal or synthetic oestrogens or artificial
hormones

• Diethylstilboestrol

• Dienestrol

• Benzestrol

• Hexoestrol

3. Oestrogens of plant origin

• Coumestrol

• Genistein 13
Oestrogens of pharmaceutical importance

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Gestogens or corpus luteum hormones
or Progestins
• Progesterone is the most important member
of this group.

• This hormone is mainly secreted by the corpus

luteum part of the ovary and is metabolised to
various inactive products mainly
pregnanediol.

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 Classification of progesterones

1. Derivatives of progesterone

• Progesterone

• Hydroxyprogesterone caproate

• Megesterol acetate

• Medroxyprogesterone acetate

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 2. Synthetic progesterone
• Ethisterone
• Norethindrone
• Dimethisterone
• Norethynodrel
• Ethynodiol diacetate
• Desogestrel
• Etonogestrel
• Norgestromin
• Norgestrel
• Norgestimate 17
 Classification of progesterones
1. Derivatives of progesterone

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2. Synthetic progesterones

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 Constitution of progesterone
1. Molecular formula: C22H30O2

2. It shows the presence of two ketonic groups as it forms

dioxime.

3. On catalytic reduction it takes up three molecules of

hydrogen forming diol showing thereby the presence of one
double bond, because two hydrogen molecules are utilized
in the formation of two -CHOH groups. Thus the parent
hydrocarbon C21H26 which corresponds to the general
formula CnH2n-6 for tetracyclic compounds.

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4. X-ray analysis shows the presence of steroid
nucleus which is further confirmed by its
synthesis from cholesterol and stigmasterol.

5. The hormone is very sensitive to alkali

showing the presence of α, β-unsaturated
ketonic group which is also confirmed by its UV
spectrum (λmax 240 nm). This suggests that the
position of the double bond is 4,5.
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6. Progesterone undergoes haloform reaction
(forms haloform with halogen and NaOH) which
shows the presence of C=OCH3 group.

On the basis of all these, progesterone may be

assigned the following structure.

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Synthesis of progesterone from Diosgenin

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 Adrenal cortical hormones
• There is a small gland over the kidney known
as adrenal gland.

• It is divided mainly into two parts

1. The cortex (outer) and

2. Medulla (inner)

• The later secretes mainly known as

adrenaline, whereas the cortex secretes
mainly cortical hormones. 24
• The cortical hormones are classified into four groups according
to the structure and biological action.

i. Oestrogens

ii. Androgens

iii. Progesterones

iv. Corticoids

• Out of these the first three types are mainly secreted by sex
organs, whereas the corticoids are the characteristic adrenal
cortical hormones.

• The production of these adrenocortical hormones has been

controlled by adrenocorticotropic hormone (ACTH) which is
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produced in the anterior lobe of the pituitary.
 Classification of coticosteroids

1. Mineralocorticoids with high salt retention

• Aldosterone

• 11-deoxycorticosterone

• Fludrocotisone acetate

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2. Glucocorticoids with moderate to low salt
retention
• Cortisone acetate
• Hydrocortisone (cortisol)
• Prednisone
• Prednisolone
• Methylprednisolone
• Betamethasone
• Dexamethasone

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Corticosteroids of pharmaceutical importance
Cortisone Cortisol

Aldosterone Presdnisolone

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Dexamethasone

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