MEDICINAL CHEMISTRY-II

STEROIDS

Dr. Ganesh D. Barkade

M. Pharm. Ph.D.

Assistant Professor
Department of Pharm. Chemistry,
Dr. Vithalrao Vikhe Patil Foundation’s College of
Pharmacy, Ahilyanagar
STEROIDS

• Steroids are the group of structurally related compounds which are

widely distributed in animals and plants.
• The term steroid is applies to the compounds containing
cyclopentanoperhydrophenanthrene nucleus skeleton.

Hydrogenation Cyclopentane

Cyclopentanoperhydro-
Phenanthrene Perhydrophenanthrene phenanthrene
GENERAL STRUCTURE OF STEROID

Cyclopenta perhydrophenanthrene

Phenanthrene

Cyclopenta Phenanthrene Numbering

NUMBERING OF STEROIDS

• Steroids consist of 4 rings (A,B, C, D).

• A perhydrophenanthrene (Ring A, B & C) is a completely
saturated derivative of phenanthrenes.
• Ring D is five membered cyclopenatane ring.
• The basicskeleton contains 17 carbons & the numbering starts
from ring A of phenanthrene& then followed by B, C and D.
• Additional carbons are present on C13 and C10 & alkyl
substituents on C17 are numbered in sequence.
NOMENCLATURE OF STEROIDS

• Methyl group at position 10 & 13 are angular methyl group.

• The systemic names for steroids are based upon the basic
skeleton with number of carbons.
18 18 20 21
18
12
13 17
11
19 19
16
1 14
10 9
2
8 15

5
3 7
4 6

5α-Estrane (18 C) 5α-Aldrostrane (19 C) 5α-Pregnane (21 C)

NOMENCLATURE OF STEROIDS

Cholestane (27 C)

• Additional 8 carbon chain on C17 of androstane gives cholestane skeleton

with total 27 carbons.
• Basic nucleus of cholesterol. (First identified member of steroid family)
NOMENCLATURE

17β-Estradiol Testosterone
NOMENCLATURE

13

Cortisone
5α-Aldrostrane

• Solid line is β configuration

• Dotted line is α configuration
NOMENCKLATURE

• Stereochemistry of H atom at C-5 is showing incorporated in

the name itself.
• Stereochemistry of other H-atoms is not usually indicated
unless and until it essentially happens to differ from 5α-
cholestane.
CLASSIFICATION
• Sterols: Where R is an aliphatic side chain. They contain usually one or
more hydroxyl groups attached in alicyclic linkage.
• Sex hormones: Where R bears a ketonic or hydroxyl group and mostly
possesses a two carbon side chain.
• Cardiac glycosides: Where R is a lactone ring. The glycosides also contain
sugar linked through oxygen in other parts of the molecule. Normally on
hydrolysis it yields this sugar together with the cardiac aglycone.
• Bile acids: Where R is essentially a five carbon side chain ending with
carboxylic acid moiety.
• Sapogenins: Where R contains oxacyclic ring system.
STEROLS

The term sterols has been

coined from the word
steroidal alcohols.

CHOLESTEROL
 SEX HORMONES

• Generally, hormones are substances that are secreted by the ductless

glands, and only minute amounts are necessary to produce various
physiological reaction in the body.
• Sex hormones belong to the steroid class of compounds and are produced
in the gonads, i. e. testes in the male and ovaries in the female.
• The activity of hormones is monitored and controlled by pituitary gland.
CLASSIFICATION

Sex hormones are usually classified under the following three

categories:

• Androgens (Male hormone): Androsterone, Testosterone

• Oestrogens (Female or Follicular hormones): Oestrone,
Oestriol, Oestradiol, Diethyl Stilbesterol, Hexesterol
• Gestogens (The corpus luteum hormone): Progesterone
TESTOSTERONE

• Testosterone controls the development as well as maintenance

of the male sex organs and is solely responsible for the male
secondary sexual characters.
• It also increases size of the srotum, phallus, seminal vesiscles,
prostate and enhances the sexual activity in adolescent males.
TESTOSTERONE

• Testostereone along with androgens are invariably employed in

the male for replacement therapy in hypogonadism,
eunuchoidism and male climacteric.
• Dose:
 For prolonged treatment, subcutaneously, 600 mg;
 For breast cancer upto 1.5 g; Alternatively 10-30 mg per day
through the buccal administration.
NANDRALONE

• Nandralone is used in treatment of anemias, cachexia,

osteoporosis, breast cancer and for some other indication. It is
not used orally, generally used by injection in muscle.
• Dose: 50 to 100 mg by deep intramuscular injection once a
week.
PROGESTERONES

• It is employed in the treatment of function of uterine bleeding. It is also

used in conjunction with an oestrogen in the treatment of menstrual
disorders, neoplasm of breast and endometrium. Sometimes it also finds
use in habitual and threatened abortion.
• Dose:
 Uterine Bleeding-5-10 mg per day;
 For habitual abortion 5-20 mg twice or thrice per week.
OESTRIOL / ESTRIOL

Oestriol is more potent than oestrone or oestradiol in its

oestrogenic activity when administered orally. It is reported to
posses a selective action on the cervix.
Dose: 250-500 mg/ day
OESTRADIOL / ESTRADIOL

• Oestradiol is found to be the most active of the naturally occurring

oestrogenic hormones produced in the ovarian follicles under the influence
of pituitary. It helps to regulate and subsequent maintenance of female sex
organs, certain functions of the human uterus and above all the secondary
sexual features, and mammary glands.
• Dose: Orally 2 mg/day; IM 1.5 mg 2-3 times weekly
OESTRIONE

• It is mainly used in the replacement therapy in deficiency states.

Eg. Primary amenorrhoea delayed onset of puberty, control and
management of menopausal syndrome, malignant neoplasm of
the prostate.
• Dose: 0.1-5 mg/ Day
DIETHYL STILBESTEROL

• It is synthetic non-steroidal oestrogen having similar actions and used to

those of estradiol. It is used in the treatment of menopausal symptoms and
in secondary amenorhoea due to ovarian insufficiency. It has also been
recommended for the inhibition of lactation, in the palliavative treatment of
malignant neoplasms of the breast, in carcinoma of the prostate and for
postcoital contraception.
• Dose: For menopausal symptoms oral, 0.1-2 mg; for secondary
amenorrhoea, 0.2-0.5 mg for carcinoma of prostate, 3 mg per day.
DRUGS USED IN ERECTILE
DYSFUNCTION
Silenafil
Dose: 5-20 mg 3
times per day

• It was synthesized for the management of hypertension and angina pectoris.

• By increasing cycli nucleotide level, it relaxes the arterial wall, leading to
decreased pulmonary arterial resistance and pressure, As a result of
selective distribution PDE5 within the arterial smooth muscle of lungs and
penis. It is used in management of erectile dysfunction.
Tadalafil
• Tadalafil is apotent PDE5 inhibitor.
• It is used in management of erectile
dysfunction.
• Dose: 2.5 mg/ day
ORAL CONTRACEPTIVES
ORAL CONTRACEPTIVES

• Oral contraceptives (OCP’s) are also called as birth control

pills.
• These are the medications taken by mouth for the purpose of
birth control.
• Examples: Combined oral contraceptive pill contains
estrogen and progestin
MIFEPRESTONE
• Mefeprestone is a synthetic
steroid and also known as RU-
486. It is a medication mainly
used in combination with
mesoprostol to bring about an
abortion during pregnancy.
•
MIFEPRESTONE

• Mefeprestone is an antiprogestin that block the action of

progesterone a hormone necessary to maintain pregnancy.
• By blocking the action of progesterone, mefeprestone alter the
endometrium (The uterine lining), induces bleeding and causes
uterine lining to shed.
• Mefeprestone used in combination with misoprostol to end an
early pregnancy.
NORGESTRIL
• Norgestril is a form of
progestin hormone that
prevent pregnancy.
• It is a hormone that prevent
pregnancy by making vaginal
fluid thicker to help prevent the
sperm from reaching an eggs
and prevent the attachment of
fertilized egg from binding to
uterine wall.
LEVONORGESTRIL
• Levonorgestril is a synthetic
estrane steroid and a
derivative of testosterone. It is
used in contraception and
hormone therapy.
• It prevent fertilization by
inhibiting the ovulation and
thickening the cervical mucus.
CORTICOSTEROIDS
 CORTICOSTEROIDS

• Any of a group of steroid hormone produced in the cortex of

adrenal gland.
• There are two types: Glucocorticoids and Mineralocorticoids
CORTISONE
• Major corticosterods
• Cortisone is a steroid hormone
that naturally reduces swelling
and suppresses the immune
system, used medicinally to treat
a wide range of inflammatory,
allergic, and autoimmune
conditions like arthritis, asthma,
and lupus.
HYDROCORTISONE
• Hydrocortisone is a
corticosteroid (cortisone-like
medicine or steroid). It works on
the immune system to help
relieve swelling, redness, itching,
and allergic reactions.
PREDNISOLONE
• Prednisolone is a corticosteroid
(cortisone-like medicine or
steroid). It works on the immune
system to help relieve swelling,
redness, itching, and allergic
reactions. This medicine is
available only with your doctor's
prescription.
BETAMETHASONE • Betamethasone topical is used to
treat the itching, redness, dryness,
crusting, scaling, inflammation, and
discomfort of various skin conditions,
including psoriasis (a skin disease in
which red, scaly patches form on
some areas of the body) and eczema
(a skin disease that causes the skin
to be dry and itchy and to sometimes
develop red, scaly rashes).
DEXAMETHASONE
• Dexamethasone provides relief for
inflamed areas of the body. It is
used to treat a number of different
conditions, such as inflammation
(swelling), severe allergies, adrenal
problems, arthritis, asthma, blood
or bone marrow problems, kidney
problems, skin conditions, and
flare-ups of multiple sclerosis.
THYROID AND ANTITHYROID
DRUGS
L-THYROXIN

• Levothyroxine is used in adults and children to treat hyperthyr

(underactive thyroid - a condition where the thyroid gland does not
produce enough thyroid hormone).
• Levothyroxine is also used in adults along with surgery and
radioactive iodine therapy to treat a certain type of thyroid cancer.
L-THYRONINE

• L-Thyronine" can refer to a specific chemical compound that is the de-

iodinated backbone of thyroid hormones, but it is more commonly used
to refer to liothyronine, which is 3,3',5-Triiodo-L-thyronine (T3).
Liothyronine (T3) is the active thyroid hormone that regulates metabolic
processes, and it is used medically as a replacement therapy for
hypothyroidism and in thyroid cancer treatment.
PROPYLTHIOURACIL

• Propylthiouracil is used to treat Graves' disease and hyperthyroidism, a

condition where the thyroid gland produces too much thyroid hormone. It
is also used before thyroid surgery or radioactive iodine treatment in
patients who have already been treated with other medicines (e.g.,
methimazole) that did not work well.
METHIMAZOLE
• Methimazole is used to treat
hyperthyroidism, a condition where
the thyroid gland produces too much
thyroid hormone. It is also used before
thyroid surgery or radioactive iodine
treatment. Methimazole is
an antithyroid medicine. It works by
making it harder for the body to make
thyroid hormone.
THANK YOU !!