The document discusses the chemistry, nomenclature, and stereochemistry of steroid hormones. It provides details on key steroid hormones like estrogens, progesterone, and testosterone. Estradiol, estrone and estriol are the three main naturally occurring estrogens. Testosterone is the main androgen and progesterone plays an important role in the female menstrual cycle and pregnancy. The structures and activities of these hormones are described. Their uses in medicine and indications are also mentioned.

1. C H E M I S T R Y O F S E X H O R M O N E S

2. N O M E N C L AT U R E
A N D
S T E R E O C H E M I S T R Y
O F S T E R O I D
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

3.  Chemically, these hydrocarbons are cyclopentanoperhydrophenanthrenes; they contain a five-membered
cyclopentane ring plus the three rings of phenanthrene.
 The term “cholestane” refers to a steroid with 27 carbons that includes a side chain of eight carbons at
position 17.
Raj K Prasad (Gold medalist), M.Pharm. (Pharmaceutical Chemistry)

4. Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

5. Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

6. S T E R E O C H E M I S T R Y O F S T E R O I D S
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

7.  The 5α notation is used to denote the configuration of the hydrogen atom
at C5, which is opposite from the C19 angular methyl group, making the
A/B ring juncture trans.
 The compound 5α-cholestane said to have a trans-anti-trans-anti-trans
backbone.
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

8. M E TA B O L I S M O F
S T E R O I D
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

9. Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

10. E S T R O G E N S
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

11. E S T R O G E N S
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

12. S T R U C T U R E –
A C T I V I T Y
R E L AT I O N S H I P S
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

13. • The aromatic A ring and the C3
hydroxyl group are structural
features essential for estrogenic
activity.
• The 17β-hydroxyl, the distance
between the C3 and C17 hydroxyl
groups, and the presence of planar
hydrophobic scaffolding also are
important structural contributors
and help to optimize estrogenic
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

14. •Functionality at the C1
position greatly reduces
activity, and only small
groups can be
accommodated at the 2 and
4 positions.
•Addition of hydroxyl groups
at positions 6, 7, and 11
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

15. •Removal of the oxygen function
from position 3 or 17 or
epimerization of the 17β-hydroxyl
group of estradiol to the α-
configuration results in estrogenic
analogs that are less active.
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

16. O E S T R I O L
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

17. U S E S
 It is used in premenopausal and
menopausal periods, for skin
atrophy.
 It can be used alone or in
combinations with estradiol (Bi-
Est) or with estradiol and estrone
(Tri-Est)
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

18. O E S T R A D I O L
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

19. O E S T R A D I O L
Estradiol, the most potent, represents 10% to
20% of the circulating estrogen.
Estradiol exhibits a high affinity for the ER
and high potency when administered
parenterally.
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

20. The order of bioavailability of the
three naturally occurring steroids is
estradiol > estrone > estriol.
When administered orally, this order
changes to estriol > estradiol >
estrone
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

21. U S E S
 Transdermal estradiol products avoid first-pass
metabolism, allowing estradiol to be as effective as
oral estrogens for treating menopausal symptoms.
 17α-ethynyl estradiol, is the most commonly used
estrogen in oral contraceptives.
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

22. O E S T R I O N E
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

23. O E S T R I O N E
 Oestrone is a follicular hormone necessary for
the development of the female body from the
time of pubescence to menopause.
 Estrone is 10-fold less potent than estradiol
and accounts for 60% to 80% of the circulating
estrogen.
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

24. O E S T R I O N E
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)
 Estrone was the first estrogen to be isolated in
crystalline form from the urine of pregnant
women.
 The two other C18 estrogen steroids, 17β-
estradiol and Estriol, were isolated and
characterized later.

25. U S E S
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)
 It is used for insufficient ovary function, for
postmenopausal, infertility, post mature
pregnancies, weak uterine contractions, and
after gynecological operations.

26. T E S T O S T E R O N E
( 1 7 Β - H Y D R O X Y A N D R O S T - 4 - E N E - 3 - O N E )

27. T E S T O S T E R O N E
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)
 Testosterone was the first androgen to be used clinically for its
anabolic activity.
 It is prepared from various steroids, including sarsasapogenin,
diosgenin, and certain androgens found in stallion urine.
 The male body produces 2.5–10 mg of testosterone daily, mostly
in the early morning.
 The female body also produces androgens, but in a significantly
smaller amount than in males.

28. U S E S
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)
• In applied medicine, testosterone esters
(propionate, cypionate, and enantate) and
a synthetic analog, methyltestosterone,
are widely used.
• Testosterone (esters) are used
medicinally for maturation arrest,
functional problems in the reproductive
system, hypertrophy of the prostate
gland, in abnormal spermatogenesis.

29. N A N D R O L O N E
( 1 7 Β - H Y D R O X Y E S T E R - 4 - E N - 3 - O N E )
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

30. U S E S
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)
 Nandrolone facilitates formation of body muscle mass
and strengthens the process of osseous tissue
development.
 The main indications for using nandrolone, as well as
other anabolic steroids, are abnormal protein
anabolism, asthenia, diseases accompanied by protein
loss, adrenal insufficiency, steroid diabetes.

31. P R O G E S T E R O N E
( P R E G N - 4 - E N - 3 , 2 0 - D I O N E )
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

32. P R O G E S T E R O N E
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)
 Its structure is more similar to the structure of the
male sex hormone testosterone, differing only in the
substituent on C17 (acetyl group instead of a
hydroxyl group).
 Esterification of the hydroxyl group by long-chained
fatty acids, such as caproic acid, leads to the
formation of long-lasting.

33. Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)
 Progesterone is not effective when taken orally due
to intensive metabolism, and therefore it is used by
either parenteral or transvaginal introduction.
P R O G E S T E R O N E

34. U S E S
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)
 Progesterone is used-
 as a contraceptive,
 for amenorrhea,
 for premenopausal syndrome,
 infertility,
 incomplete pregnancies,
 and ovulatory uterine bleeding.

35. D I E T H Y L S T I L B E S T R O L
( T R A N S - Α , Β - D I E T H Y L - 4 , 4 ’ -
S T I L B E N D I O L )
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)

36. D I E T H Y L S T I L B E S T R O L
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)
• Synthetic nonsteroidal molecules such as diethylstilbestrol (DES)
could have the same activity as estradiol or other estrogens. It has
shown the OH-to-OH distance to be actually 12.1 Å in DES and 10.9
Å in estradiol.
• In aqueous solution, estradiol has two water molecules that are
hydrogen bonded to the 17-OH. If one of the two water molecules is
included in the distance measurement, there is a perfect fit with the
two OH groups of DES.

37. Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)
•Because of the safety
concerns associated with
DES, it was completely
removed from the U.S.
market in the late 1990s.
DES is still available as an
estrogen for use in
veterinary medicine.

38. T H A N K
Y O U
Raj
K
Prasad
(Gold
medalist),
M.Pharm.
(Pharmaceutical
Chemistry)