Subject: Pharmaceutical Chemistry-II

Chapter: Steroidal Drugs

 Steroidal Drugs

Steroids are the complex polynuclear compounds occurs widely in the plant and animal kingdoms. They have common steroidal
nucleus as shown in figure.

They contain tetracyclic structural consisting of rings A, B, C and D.

• Chemical name:1,2- cyclopentanoperhydrophenanthrene

The ring A, B, and C are six-membered and D is five membered. A group attached to any position and shown by continuous thick line is
taken to be above the plane of the nucleus and is designated as beta (ꞵ) and a group shown by dotted line is below the plane and is
termed as alpha (α).
 5α-Androstane(19C) 5α- Estrane(18C) 5α-Pregnane(21C)

Androstane is a simple parent hydrocarbon containing 19 carbon atom.

The common derivative of this is the male sex hormone, testosterone.
Estrane has 18 carbon atoms.
The oestrogenic hormone oestradiol is a derivative of estrane present in female sex harmones.
The pregnane has 21 carbon atoms.
The progestogen hormone, progesterone is a derivative of pregnane.
The polycyclic saturated hydrocarbon of steroid skeleton containing 18, 19 and 21 carbon atoms, are called oestrane, androstane and
pregnane respectively.
1. Oestrane derivative:e.g. Ostradiol
2. 19-nor androstane or oestrane derivative. E.g. Nandrolone
3. Androstane derivatives: e.g. testosterone
4. Pregnane derivatives: e.g.Progesterone, cortisone, hydrocortisone. Prednisolone, betamethasone
 Sex Hormone
Adrenocorticoids and in small proportion, sex hormones have been isolated from cortex of adrenal gland. The male sex hormone
testosterone, is secreted by interstitial cells of testes. It plays important role in the reproductive physiology of the male. It has both
anabolic and androgenic activity. The androgenic activity includes the development of secondary sex characters (e. g. voice deepening.
growth of hair, formation of semen etc.) in males. The anabolic activity includes increase in the rate of protein synthesis. They also
increase nitrogen and water retention and stimulate skeletal growth which is known as anabolic activity. Important androgenic
compound produced by testes include testosterone.
Oestradiol and Progesterone are main female sex hormones.
Oestradiol is the oestrogenic are the female sex hormone secreted by ovary. It is concerned with development and maintenance of
secondary female characters and growth and development of female reproductive organs. It is necessary for onset of puberty and
menses. Oestrogens are also needed for maintenance of pregnancy and also have anabolic effect on protein metabolism and water
retention.
Progesterone is the progestational hormone. Progestogens are the female sex hormones produced by corpus luteum and the placenta.
After ovulation, the follicle tissue ruptures to form corpus luteus which secretes progesterone. It helps to prepare endometrium for
conception, to implant land maintain fertilized ovum, to stop spontaneous rhythmic contraction of uterus. It also prevents ovulation
during pregnancy and hence is a natural contraceptive. If fertilization does not occur then it maintains normal menstrual bleeding.
 Adrenocorticoids hormones
The adrenal glands consisting of medulla and cortex, secretes two different types of hormones, Medulla secreting adrenaline and cortex, a
group of closely related steroidal hormones. The adrenocortical hormones are broadly group into three main categories :

1.Glucocorticoids

2.Mineralocorticoids

3.Sex corticoids.

1)Glucocorticoids: These are cortisone, hydrocortisone, betamethasone and prednisolone, primarily involved in intermediary metabolism and
have their principal action on gluconeogenesis, glycogen deposition and protein and calcium metabolism. They cause inhibition of
corticotrophin excretion. Glucocorticoids are used to treat:
1. Diseases of connective tissues like rheumatism, rheumatic arthritis etc.
2. Allergic and anaphylactic reactions.
3. Dermatological diseases e. g. (eczematous conditions)
4. Collagen diseases like lupus erythematosus.
5. Addison’s disease (upset of electrolyte)
6. Asthma and other respiratory tract diseases.
7. They are used as anti-inflammatory and antiallergic.
2)Mineralocorticoids : Namely, deoxycortone and aldosterone, have their main action on electrolyte and water
metabolism causing sodium and fluid retention and potassium excretion.

3)Sex corticoids :It includes mainly androgens.

The glucocorticoid actions are related to the apparently inseparable anti-inflammatory, anti-allergic, and
antirheumatic properties and are useful in conditions such as asthma and rheumatoid arthritis. The
mineralocorticoid actions are used in conditions such as Addison's disease.
 Testosterone

Properties:

1. Testosterone occurs as white, odourless, tasteless crystal.

2. It is practically insoluble in water and soluble in fixed oils.

3. It is incompatible with oxidizing agent It should be stored in a well tight closed container and protected from light It is official as
propionate, phenylpropionate, enanthate and isocaproate salt
Uses :
4. As substitute or replacement therapy in male hypogonadal disorder (hypogonadism)
5. To correct penile size in childhood (In the treatment of micropenis in childhood).
6. To stimulate erythropoiesis (to treat patient with aplastic anaemia)
7. For muscle development (anabolic property).
8. To treat male infertility.
9. In treatment of gynaecomastla.(excessive development of male mammary glands.)
10. In females :
a)To treat menopausal symptoms (dysmenorrhoea)
b)In treatment of chronic mastitis.
c)For suppression of lactation.
d)For relief of after-pain in labour.
e)In palliative treatment of disseminated breast cancer

Official Preparation :

1. Testosterone B.P.,

2. Testosterone Implants B.P.

3. Testosterone Propionate B.P., I.P.,

4. Testosterone Propionate Injection B.P., LP.

5. Testosterone Phenylpropionate, B.P.

6. Testosterone Phenyl Propionate Injection B.P.

7. Testosterone Decanoate B.P.,

8. Testosterone Enanthate B.,P.

9. Testosterone Isocaproate B.P.

Brand names : Tastoform, Testoviron depot, Hormondrin, Mixogen injection

 Nandrolone

Properties:

1. Nandrolone is an androgen having anabolic effect on protein metabolism.

2. It is official as phenylpropionate and decanoate salts, both the salts occurs as a creamy white powder with a faint characteristic odour

3. Insoluble in water and soluble in alcohol ,chloroform and fixed oil. The oily injection is given by intramuscular route.

4. It is stored in well closed light resistant containers.

Uses :

5. It is a anabolic steroid used for the retention of nitrogen and building up of muscle and help in protein metabolism.

6. It is also used as adjunctive therapy in the treatment of osteoporosis.

7. It is also used in the treatment of advanced malignant neoplasm of the breast in postmenopausal women.

Official preparation:

8. Nandrolone Decanoate, B.P., l.P.

9. Nandrolone Decanoate Injection, B.P., l.P.

10. Nandrolone Phenylpropionate, B.P., l.P.

11. Nandrolone Phenylpropionate Injection, B.P.

Popular Brand Names : Docabolin, Durabolin,Metamol, Unabol, Biodebol.

 Oestradiol
Properties:
1.It occurs as a white or creamy white crystalline powder and is odourless.
2.It is practically insoluble in water and sparingly soluble in vegetable oil and in acetone.
3.It is stored in well-closed light resistant containers.
Uses :
4.It is used in hormone replacement therapy in females i. e. after menopause or ovariectomy.
5.It is used in to treat menopausal symptoms.
6.It is used in to treat primary amenorrhoea(Abnormal ceassation of the menses),delayed onset of puberty(The sequence of
events by which a child is transformed into a young adult).
7.It is used in to treat breast cancer in post menopausal women.
8.It is used in to treat prostatic carcinoma in men.
Official preparation:
9.Oestradiol Benzoate, B.P., l.P.
10.
Oestradiol Benzoate Injection, B.P.
11.
Oestradiol Dipropionate, l.P.
12.
Oestradiol Injection, l.P.
Brand names : Ovocept, Aprocrine.
 Progesterone.
Properties:
1. Progesterone is the main hormone of corpus luteum and the placenta.
2. It occurs as a colourless crystals or a while or slightly yellowish white crystalline powder.
3. It is practically insoluble in water and sparingly soluble in arachis oil.
4. The solutions in oil are sterilized by maintaining a temperature at 150° for 1 hour.
5. It should be stored in a well tight closed container and protected from light.
Uses :
6. To treat dysfunctional uterine bleeding, dysmenorrhoea and endometrosis.
7. To treat habitual or threatened abortions.
8. To maintain pregnancy.
9. To treat premenstrual syndrome (like stress and anxiety)
10. To prepare endometrium for reception. Implantation and for maintenance of fertilized ovum (to maintain pregnancy)
11. For prophylaxis of postnatal depression (sudden fall of progesterone concentration after delivery).
12. To treat cancer of breast and endometrium

Official Preparation: Progesterone, B.P., Progesterone Injection, B.P.

Brand Names : Mestrogen Forte, Osterone.

 Cortisone
Properties
1. Cortisone acetate Is a white or creamy white crystalline powder which odourless.
2. It is very slightly soluble in water but freely soluble in chloroform.
3. It is stable in air but is affected by light. Hence It is stored in well- dosed light-resistant containers.
Uses :
4. For replacement therapy in adrenocortical failure or hypopituitarism (low production of hydrocortisone or aldosterone)
5. To treat asthma or other respiratory tract diseases.
6. To treat allergic and anaphylactic reactions
7. To treat disease of connective tissues e. g. rheumatic diseases rheumatoid arthritis, osteoarthritis etc.
8. To treat collagen diseases e.g. Lupus erythematosus.
9. To treat dermatological diseases.
10. To treat Addison's disease
11. To treat chronic lymphatic leukemia
12. To prevent hypercalcaemia.
Official preparation:
1. Cortisone Acetate, B.P., I.P.
2. Cortisone Injection, B.P., I.P.
3. Cortisone Tablet, B.P., I.P.

Brand names : Cortin, Otek,Cotaryl-H

Hydrocortisone

Properties:

4. Hydrocortisone is a main glucocortisone which occurs ns a white or almost white, odourless, crystalline powder, tasteless at first but followed by a
persistent bitter taste.

5. It is practically iinsoluble in water but soluble in alcohol and acetone.

6. Alcoholic solution for use in preparing injections are sterilized by filtration.

7. It should be stored in a well tight closed container and protected from light.

Uses :

8. It is the main glucocorticoid secreted by the adrenal cortex.

9. It is used in pharmacological doses for their anti - inflammatory and immunosuppressant glucocorticoid properties.

10. It is also used in allergic condition such as bronchial asthma, and allergic skin reaction.

11. It is also useful in the treatment of rheumatoid arthritis.

 Official Preparation

•Hydrocortisone B.P., I.P.

•Hydrocortisone Ointment B.P.

•Hydrocortisone and Cloquinol Ointment B.P. Hydrocortisone Acetate B.P., I.P.

•Hydrocortisone Acetate and Cloquinol Cream, B.P. Hydrocortisone Acetate Injection, B.P.,I.P.

•Hydrocortisone Acetate Ointment B.P.

•Hydrocortisone Eye Ointment, B.P.

•Hydrocortisone Sodium Phosphate, B.P.

•Hydrocortisone Sodium Phosphate Injection, B.P. Hydrocortisone Sodium Succinate, B.P.

•Hydrocortisone Sodium Succinate Injection B.P.

Brand names: Cort-S, Nebacortril, Tetracortil
 Prednisolone
Properties:
1) Prednisolone is a synthetic glucocorticoid which occurs as an odourless, white or almost white crystalline hygroscopic
powder with a bitter taste.
2) It is insoluble in water and soluble in alcohol and acetone. A solution in doxan is dextrorotatory.
3) It should be stored in a well tight closed container and protected from light.
Uses :
1. It is also used for replacement therapy in adrenocortical failure or hypopituitarism (low production of hydrocortisone or
aldosterone)
2. To treat asthma or other respiratory tract diseases.
3. To treat diseases of liver e. g. hepatic necrosis, acute hepatic failure.
4. To treat diseases of Gastrointestinal tract - ulcerative colitis, inflammatory bowel disease.
5. To treat diseases of Kidney e. g. glomerulo-nephritis.
6. To treat diseases of Eye e. g. inflammation of eye.
7. To treat blood disorder and malignancies e.g. haemolytic ,anemia, thrombocytopenic purpurea.
8. To manage leukemias and lymphomas in conjunction with antineoplastic agents.
Official Preparation :
Prednisolone, B.P., I.P.
Prednisolone Tablet, B.P., I.P.
Prednisolone Acetate, I. P.
Prednisolone Pivalate, B.P.
Prednisolone Pivalate Injection, B.P.
Prednisolone Sodium Phosphate, B.P.
Prednisolone Sodium Phosphate Injection, B.P
Brand names : Histocortin, Prednisol, Prenidsol-N
 Betamethasone
Properties:
1. Betamethasone is a glucocorticoid which occurs as a white to creamy white odourless, crystalline powder with a bitter
taste.
2. It is practically insoluble in water and soluble in alcohol.
3. It should be stored in a well tight closed container and protected from light.
Uses :
a)Topically it is used:
1.To control all forms of eczema.
2.To treat severe acute photosensitive reaction including sunburn.
3.To treat certain forms of psoriasis.
4.To treat acute contact dermatis and allergic skin reaction.
5.To treat leukoderma (defective skin pigmentation).
b)By inhalation : it is used to control asthma.
c)It is also used to treat disease of connective tissue, (anti-inflammatory effect) like rheumatoid arthritis.
 Official Preparation :
•Betamethasone, B.P., I.P.
•Betamethasone Tablet, B.P., I.P.
•Betamethasone Sodium Phosphate, B.P., I.P.

•Betamethasone Sodium Phosphate Injection, B.P., I.P.

•Betamethasone Sodium Phosphate Tablet B.P., I.P.

•Betamethasone Valerate, B.P., I.P.

•Betamethasone Valerate Cream, B.P.

•Betamethasone Valerate Lotion, B.P.

•Betamethasone Valerate Ointment, B.P.

•Betamethasone Valerate scalp Application, B.P.

Brand names: Betnesol, Betacortrill,Betnovate
List of questions:

1. Define steroids .draw the basic steroidal nucleus with numbering.

2. Write a note on sex hormone. Or Name the hormone which are derivatives of androstane, estrange and pregnane.

3. State what are androstane. Give their functions.

4.State what are estrange. Give their functions.

5.State what are pregnane. Give their functions.

6. What are adrenocortical hormones and explain it.

7. Discuss in short about cortisone.

8.Give the properties, uses and official preparations and popular brand name of:

a) Testosterone b) Estradiol c) Progesterone d) Hydrocortisone e) Betamethasone f) Cortisone

g) Prednisolone