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Introduction
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)
Estrogens
One hydroxyl group
attached to the D
ring. The di refers
both to this
hydroxyl & the one
on the A ring.
Ovarian Hormones
Natural Estrogenic
Estradiol,
Conjugated
Estrogen,
Estrone,
Ethinyl
estradiol
Hormones
Structure Activity
Relationships:
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:
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:
Estrone
IUPAC
name:
3-hydroxy-13methyl6,7,8,9,11,12,13,14,15,16decahydrocyclopenta[a]phenanth
ren- 17- one
Molecular Formula: C18H22O2
Structure:
Ethinyl Estradiol
IUPAC name: (17)-19-Norpregna1,3,5(10)-trien-20-yne-3,17-diol
Molecular Formula: C20H24O2
Structure:
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:
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:
Tamoxifen (Silicone
Derivatives)
IUPAC
name:
2-[4-(1,2diphenylbut-1-enyl)phenoxy]-N,Ndimethylethanamine
Molecular Formula: C26H29NO
Structure:
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:
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:
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:
E. Sex Hormones
E.2 Androgenic Hormones
- Testoterone, Stanozolol
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:
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:
Generic Name
Brand name
Manufacturer
Estradiol
Vagifem
Novo Nordisk
Conjugated Estrogen
Premarin
Pfizer
Estrone
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