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Sex Hormones

Drona, Mheriz and Espolong, Princess

Introduction

Hormones are powerful chemical substances


manufactured by the endocrine glands (thyroid,
the adrenals,and the pituitary) and secreted
directly into the bloodstream

The most important sex hormones are


testosterone (one of a group of hormones called
androgens) and estrogens and progesterone.

E. Sex Hormones
E1. Ovarian Hormones
e.1.1 Natural Estrogenic Hormones and Derivatives
-Estradiol, Conjugated Estrogen, Estrone, Ethinyl
estradiol
e.1.2 Synthetic Estrogen
-Chlorotrianesene, Diesthylstilbestrol (DES)
e.1.3 Antiestrogen
-Clomiphene, Tamoxifen (Silicone Derivatives)

Sex Hormones Systems


in Female

The ovaries produce two important


hormones, estrogen and progesterone

Estrogen: bringing about many of the


changes of puberty ( growth of uterus &
vagina, enlarging pelvis, stimulating breast)

Progesterone: thickening the lining of the


uterus each month, decreasing the
contractility of the uterine smooth muscle

Estrogens
One hydroxyl group
attached to the D
ring. The di refers
both to this
hydroxyl & the one
on the A ring.

The ketone (=o) group


attached to the D ring.

Two hydroxy (OH) groups


attached to the
D ring.

Ovarian Hormones
Natural Estrogenic
Estradiol,
Conjugated
Estrogen,
Estrone,
Ethinyl
estradiol
Hormones

Structure Activity
Relationships:

Aromatic ring with C-3-OH is essential for activity.


Steroidal structures is not essential for activity.
Alkylation of the aromatic ring decrease the activity.
The 17-hydroxyl with constant distance from 3-OH is
essential for activity.
The group between the two hydroxyl must be
hydrophobic.
Unsaturation of ring B decreases the activity.
17- and 16 position when modified enhance the activity.

Estradiol
IUPAC name: (17)-estra-1,3,5(10)Use/s: Estradiol is used to treat
triene-3,17-diol
symptoms of menopause such as
Molecular Formula: C18H24O2
hot flashes, and vaginal dryness,
Structure:
burning, and irritation.
Commercially Available Product:

Brand Name: Vagifem (Estradiol)


Manufacturer: Novo Nordisk

Conjugated Estrogen
IUPAC name: 13-methyl-17-oxo-3sulfonatooxy-7,8,9,11,12,14,15,16octahydro-6H-cyclopenta[a]
phenanthrene
Molecular Formula: C18H21NaO5S
Structure:

Use/s: medicine that contains a mixture


of estrogen hormones. It is used to treat
moderate to severe hot flashes, changes
in and around the vagina, and other
symptoms of menopause or low amounts
of estrogen (hypoestrogenism).
Commercially Available Product:

Brand name: Premarin


Manufacturer: Pfizer

Estrone
IUPAC
name:
3-hydroxy-13methyl6,7,8,9,11,12,13,14,15,16decahydrocyclopenta[a]phenanth
ren- 17- one
Molecular Formula: C18H22O2
Structure:

Use/s: Treatment for Hot Flashes


Hypogonadism,
Menopause,
Menorrhagia, Prostatic Neoplasms,
Painful sexual intercourse
& Primary Ovarian Insufficiency.
Prevention of Osteoporosis and
postmenopausal.
Commercially Available Product:

Brand name: Estragyn Vaginal


Cream (Estrone)
Manufacturer: Clint Pharmaceutical
Inc

Ethinyl Estradiol
IUPAC name: (17)-19-Norpregna1,3,5(10)-trien-20-yne-3,17-diol
Molecular Formula: C20H24O2
Structure:

Use/s: mainly used in various


hormonal contraceptives -usually in combination with a
progestin.
Commercially Available Product:

Brand name: Nordette


( Levonorgestrel +
Ethinylestradiol)
Manufacturer: Pfizer

Synthetic Estrogen
Chlorotrianesene, Diethylstilbestrol (DES)
Synthetic estrogens are used as part of some
oral contraceptives, in estrogen replacement
therapy for postmenopausal women, and in
hormone replacement therapy for trans
women.

Chlorotrianisene
Use/s: Chlorotrianisene is a form of
IUPAC
name:
1,1,1''-(2estrogen. Chlorotrianisene is used
Chloroethene-1,1,2-triyl)tris(4to treat symptoms of menopause,
methoxybenzene);
11-chloro- deficiencies in ovary function
(including underdevelopment of
4,13-dimethoxy-12-(pfemale sexual characteristics and
methoxyphenyl)stilbene
some types of infertility), and
Molecular Formula: C23H21ClO3
prostate cancer.
Structure:
Commercially Available Products:

Brand name: Tace (Chlorotrianisene)


Manufacturer: Aventis
Pharmaceuticals

Diethylstilbestrol (DES)
IUPAC name: 4,4'-(3E)-hex-3-ene3,4-diyldiphenol;
(E)-11,12Diethyl-4,13-stilbenediol
Molfecular Formula: C18H20O2
Structure:

Use/s:
It
was
prescribed
to
pregnant women between 1940
and 1971 to prevent miscarriage,
premature labor, and related
complications of pregnancy.
Commercially Available Product:
Brand name: Stilbetin
(Diethylstilbestrol)
Manufacturer:
Bristol Myers-Squibb

Antiestrogen
Clomiphene, Tamoxifen (Silicone Derivatives)
A substance that blocks the production or
utilization of estrogens, or inhibits their effects.
Estrogens are the family of hormones that
promote the development and maintenance of
female sex characteristics

Clomiphene
IUPAC name: 2-(4-(2-chloro-1,2diphenylethenyl)
phenoxy)-N,N-diethyl-ethanamine
Molecular Formula: C26H28ClNO
Structure:

Use/s: to induce ovulation (egg


production) in women who do not
produce ova (eggs) but wish to
become
pregnant
(infertility).
Ovulatory stimulants.
Commercially Available Product:

Brand name: Comipen (Clomiphene


citrate)
Manufacturer: Pacific
Pharmaceuticals Ltd.

Tamoxifen (Silicone
Derivatives)
IUPAC
name:
2-[4-(1,2diphenylbut-1-enyl)phenoxy]-N,Ndimethylethanamine
Molecular Formula: C26H29NO
Structure:

Use/s: used to treat some types of


breast cancer in men and women.
It is also used to lower a woman's
chance of developing breast cancer
Commercially Available Product:

Brand name: Soltamox (Tamoxifen)


Manufcaturer: Cytogen

E. Sex Hormones
E1.4 Progestin
e.1.4.1 Naturally Occuring Progestin
-Progesterone
e.1.4.2 Synthetic Progestin
e.1.4.2.1 Progesterone derivatives
- Methyl Progesterone
e.1.4.2.2 19-nor Progestins
-Norethisterone ethinyl estradiol

Progestin
Naturally Occuring
Progesterone
Progestin

Progesterone
IUPACname:
17-acetyl-10,13dimethyl
1,2,6,7,8,9,11,12,14,15,16,17
dodecahydrocyclopenta[a]phenan
thren-3-one
Molecular Formula: C21H30O2
Structure:

Use/s: used to causemenstrual


periodsin women who have not yet
reached menopause but are not
having periods due to a lack of
progesterone in the body.
Commercially Available Product:

Brand name: Utrogestan


Manufacturer: BESINS
MANUFACTURING BELGIUM

Progestin
Synthetic Progestin
Progesterone Derivatives, 19-nor Progestins

Progesterone
Derivatives

Medroxyprogesterone
IUPACname:
17-acetyl-17-hydroxy-6,10,13trimethyl2,6,7,8,9,11,12,14,15,16decahydro-1Hcyclopenta[a]phenanthren-3-one
Molecular Formula: C22H32O3
Structure:

Use/s: helps regulate ovulation (the


release of an egg from an ovary)
and menstrual periods.
Medroxyprogesterone is used to
treat conditions such as absent or
irregular menstrual periods, or
abnormal uterinebleeding.
Commercially Available Product:

Brand name: Povera


Manufacturer: Pharmacia Corp

19-nor Progestins

asteroidalprogestinand closeanalogueof
thesex hormoneprogesterone, lacking only
the C19 methyl group of that molecule.

Norethisterone ethinyl
estradiol
IUPAC name: 17-ethynylestra-4en-17-ol-3-one
Molecular Formula: C20H26O2
Structure:

Use/s: a contraceptive, NET can be


used to treatpremenstrual
syndrome,dysmenorrhea,menorrh
agia
irregular
menstruation,menopausal
symptoms (in combination with
anestrogen), or to postpone
aperiod.
Commercially Available Product:

Brand name: Alyacen

E. Sex Hormones
E.2 Androgenic Hormones
- Testoterone, Stanozolol

Sex Hormones Systems


in Male

The important hormone produced by testes is


testosterone

Has an important functions ins stimulating


and maintaining the secondary sex
characteristics ( beard growth), maintaining
the genitals and their sperm- producing
capability and stimulating the growth of bone
and muscle.

Androgenic Hormones
Testoterone, Stanozolol

Testosterone
IUPACname:
17-hydroxy-10,13-dimethyl1,2,6,7,8,9,11,12,14,15,16,17dodecahydrocyclopenta[a]phenan
thren-3-one
Molecular Formula: C19H28O2
Structure:

Use/s: used in men and boys to


treat conditions caused by a lack of
this hormone, such as delayed
puberty, impotence, or other
hormonal imbalances and also
used in women to treatbreast
cancerthat has spread to other
parts of the body.
Commercially Available Product:
Brand name: Histerone
Manufacturer: Hauck Roswell

Stanozolol

Stanozolol
IUPACname:
1,10a,12a-Trimethyl1,2,3,3a,3b,4,5,5a,6,7,10,10a,10b
,11,12,12ahexadecahydrocyclopenta[5,6]na
phtho[1,2-f]indazol-1-ol
Molecular Formula: C21H32N2O
Structure:

Use/s: used in the treatment of


hereditary angioedema, which
causes episodes of swelling of the
face, extremities, genitals, bowel
wall, and throat.
Commercially Available Product:

Brand name: Winstrol


Manufacturer: Zambon Group

Generic Name

Brand name

Manufacturer

Estradiol

Vagifem

Novo Nordisk

Conjugated Estrogen

Premarin

Pfizer

Estrone

Estragyn Vaginal Cream

Clint Pharmaceutical Inc

Ethinyl estradiol

Nordette
( Levonorgestrel +
Ethinylestradiol)

Pfizer

Chlorotrianesene

Tace

Aventis Pharmaceuticals

Ovarian Hormones

Diethylstilbestrol
Clomiphene

Stilbetin
Comipen

Bristol Myers-Squibb
Pacific Pharmaceuticals
Ltd.

Tamoxifen

Soltamox

Cytogen

Progesterone

Utrogestan

BESINS MANUFACTURING
BELGIUM

Medroxyprogesterone
Norethisterone ethinyl
estradiol

Povera

Pharmacia Corp

Alyacen

Glenmark Pharmaceuticals
Inc.

Testosterone

Histerone

Hauck Roswell

Stanazolol

Winstrol

Zambon Group

Androgenic Hormones