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L 12 and 13 estrogens Flashcards

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1
Q

estrogens

A

-Development and maintenance of female
reproductive tissues (ovaries, uterus, breast, vagina)
-Regulation in CNS (temperature, mood)
-Effects in peripheral tissues (bone, cardiovascular, liver)

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2
Q

progesterone

A

-Development and maintenance of female
reproductive tissues (uterus and breast)
-Maintenance of pregnancy
-Effects in other tissues (brain

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3
Q

17 beta estradiol

A

-Most potent estrogen in human
-Binds to the estrogen receptor and alters rate of transcription
-Produced mostly in the ovaries in premenopausal women.
-Synthesized most in the placenta during pregnancy.
-Plasma levels: 5 – 85 ng/dL
-Cyclically varies during the menstrual cycle.
-Mostly bound to sex hormone-binding globulin (SHBG) and albumin and only 2% free in circulation.

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4
Q

gransulosa cells produce

A

estrogen

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5
Q

corpus letum produces both

A

estrogen and progesterone

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6
Q

menstrual cycle

A

early follicular phase, late follicular phase, luteal phase

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7
Q

early follicular phase

A

Estrogen suppresses the production of
FSH.

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8
Q

late follicular phase

A

Estrogen stimulates the surge of LH and FSH –> ovulation and formation of corpus luteum

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9
Q

luteal phase

A

Estrogen and progesterone suppresses
the production of LH and FSH

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10
Q

if pregnancy does not occur

A

-corpus luteum degenerates.
-Production of estrogen and progesterone by corpus luteum declines. –> menstruation

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11
Q

if pregnancy occurs

A

-Fertilized egg/embryo secrets human chorionic gonadotropin (hCG).
-hCG acts like LH to stimulate corpus luteum to produce progesterone during the first trimester.
-Higher progesterone levels support maintenance of endometrium.
-Chromatographic immunoassays of hCG in the urine are used as pregnancy tests.

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12
Q

estrone and estriol are synthesized in the

A

liver and peripheral tissues

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13
Q

types of estrogens

A

-estrogenic activity is shared by large number of chemical substances
-natural estrogen
-synthetic estrogens
-phytoestrogens
-environmental estrogens

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14
Q

natural estrogens

A

-17β‐Estradiol – Most potent
-Estrone – Less potent
-Estriol – Less potent. Dominant form during pregnancy (synthesized in the placenta)

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15
Q

synthetic estrogens

A

drugs with estrogenic activities (steroidal and non-steroidal)

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16
Q

phytoestrogens

A

estrogen-mimetic compounds in plants (flavonoids)

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17
Q

environmental estrogens

A

compounds used in the manufacture of plastics (bisphenol, alkyl-phenols, phthalate products)

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18
Q

metabolism and excretion of estrogens

A

-Metabolized in the liver mostly and excreted to the bile and to the urine.
-Conjugated estrogens in the bile can be hydrolyzed in the intestine and reabsorbed (enterohepatic circulation).
-Orally administered estrogens have a high ratio of hepatic to peripheral effects; can be avoided by using a routes that avoid first-pass liver exposure

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19
Q

physical effects of estrogen on female maturation

A

-Development of the vagina, uterus, and uterine tubes
-Stromal development and ductal growth in the breast
-Accelerated growth phase and the epiphyseal closure
-Growth of axillary and pubic hair
-Alteration in the distribution of body fat to produce female body contours
-Pigmentation in the skin (nipples, areolae, and genital region)

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20
Q

physical effects of estrogen on endometrial effects

A

-Development of endometrial lining during menstrual cycles
-Prolonged exposure leads to hyperplasia of the endometrium and abnormal bleeding.

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21
Q

physiological effects of estrogen on metabolic and cardiovascular effects

A

-Decrease in the rate of resorption of bone
 Estrogen deficiency can lead to osteoporosis.
-Stimulation of synthesis of transcortin and SHBG
-Alteration in the composition of plasma lipids
 Increase in HDL
 Decrease in LDL

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22
Q

physiological effects of estrogen on blood coagulation

Study These Flashcards
A

enhancement of the coagulability of blood

23
Q

physiologial effects of estrogen on CNS

24
Q

clinical uses of estrogen

Study These Flashcards
A

-hormone replacement therapy in postmenopausal women
-osteoporosis
-hormonal contraception
-replacement therapy in patients with hypogonadism

25
hormone replacement therapy in postmenopausal women
-Relief of CNS disturbances – hot flashes, sweating, flushing -Relief of symptoms resulting from urogenital atrophy - vaginal dryness, increased risk of infections -Relief of psychological effects – mood swings, insomnia, depression, nervousness
26
osteoporosis
-For post-menopausal osteoporosis only -Estrogens decrease the rate of bone resorption
27
replacement therapy in patients with primary hypogonadism
-Failure of development of the ovaries -Chromosomal disorders  Turner syndrome – absence of one or all sex chromosomes -Castration (oophorectomy)
28
adverse effects of estrogens
uterine bleeding endometrial carcinoma breast cancer nausea, headaches, fluid retention, weight gain
29
uterine bleeding
-estrogen therapy is a major cause of postmenopausal uterine bleeding. -Endometrial hyperplasia -Estrogen should be given cyclically. -Can be prevented by administration of a progestin in each cycle
30
endometrial carcinoma
concomitant use of progestin reduces risk
31
breast cancer
-Particularly for a long-term use -Addition of a progestin does not have a protective effect.
32
17 alpha alkylated estrogens
-Ethinyl estradiol, Mestranol, Quinestrol -17α-alkylation prevents conversion to estrone. --> enhances oral bioavailability and increases the half life. -3-alkylated ether is quickly dealkylated in vivo.
33
estrogenic esters
-Esterification decreases solubility and slows the absorption. -Slow absorption from the injection site (depot) prolongs the action.--> less frequent injections. -Estradiol valerate, Estradiol cypionate
34
conjugated estrogens
-Usually collected from pregnant mares’ urine (Premarin ®). -Mixture of estrogens  50-60% estrone sulfate  20-30% equilin sulfate  Other estrogenic substances
35
diethylstilbestrol
-Used in 1940 – 1970 to prevent miscarriage. -increased risk of vaginal adenocarcinoma in women exposed in utero. -Used in advanced prostate cancer.
36
chlorotrianisene
-Postpartum breast engorgement -Menopause symptoms -Prostate cancer
37
selective estrogen receptor modulators
-SERM -“Designer estrogens” -Partial estrogen agonists  Block the action of stronger estrogens. -Estrogenic in some tissues and antiestrogenic in others -Mostly nonsteroidal estrogens -Hold promise as the alternative for estrogen replacement therapy.
38
structural basis of SERM actvity
-Ligand binding domain with an agonist (diethyl stilbestrol) bound -Helix 12 conformation allows for coactivator binding. -Ligand binding domain with a selective estrogen receptor modulator (tamoxifen) bound -Helix 12 conformation blocks coactivator binding.
39
tamoxifen
-Prodrug; oxidized in vivo. -Partial estrogen agonist -Antiestrogen actions  Treatment of breast cancer  Prevents breast cancer in high risk women. -Estrogenic actions  Weak estrogen agonist at endometrial cells  increase the risk for thromboembolic events.  Prevents osteoporosis.
40
toremifene
-Structurally similar to tamoxifen -SERM -Used to treat advanced breast cancer
41
ospemifene
-Structurally similar to toremifene -SERM -Estrogenic effects on the vaginal epithelium -Used to treat dyspareunia in post-menopausal women
42
raloxifene
-SERM; partial estrogen agonist -Tissue-specific activities -Bazedoxifene is a recently approved analog with similar activities
43
raloxifene estrogen actions
-Estrogen actions -Prevents osteoporosis in postmenopausal women (approved). - Decreases LDL levels in blood. -increases the risk for blood clots.
44
raloxifene antiestrogen actions
 Decreases the risk for breast cancer (approved).  Does not stimulate endometrial cells.  May cause hot flashes.
45
clomiphene
-SERM; partial estrogen agonist -Increases secretion of FSH and LH by inhibiting negative estradiol feedback. -Used to stimulate ovulation in women with oligomenorrhea or amenorrhea and ovulatory dysfunction (frequently from polycystic ovary syndrome). -Polycystic ovary syndrome (PCOS) -7% of women of reproductive age -Gonadotropin-dependent ovarian hyperandrogenism -Anovulation and infertility
46
fulvestrant
-Selective estrogen receptor downregulator (SERD) -Pure estrogen receptor antagonist for the treatment of breast cancer -Somewhat more effective than SERM in patients who have become resistant to tamoxifen
47
aromatase inhibitors
-Block the biosynthesis of estrogens. -Effective in some patients whose breast cancer has become resistant to tamoxifen. -Ovulation induction (off-label use) -Gynecomastia
48
17α‐alkylated estrogens (too many brand names)
-Ethinyl estradiol -Mestranol -Quinestrol
49
estrogenic esters
-Estradiol valerate (Progynova® ) -Estradiol cypionate (Depo-Estradiol® )
50
conjugates estrogens
Estrone sulfate/equilin sulfate (Premarin ® )
51
nonsteroidal estrogen agonist
-Diethylstilbestrol (Stilphostrol ® ) -Chlorotrianisene (Tace ® )
52
selective estrogen receptor modulators (SERMs)
-Tamoxifen (Nolvadex® , Soltamox ® ) -Toremifene (Fareston ® ) -Ospemifene (Osphena® , Senshio® ) -Raloxifene (Evista® ) -Bazedoxifene (Conbriza® ,Viviant ® ) -Clomiphene (Clomid® )
53
selective estrogen receptor downregulator (SERD)
Fulvestrant (Faslodex®)
54
aromatase inhibitor
-Anastrazole (Arimidex ®) -Letrozole (Femara® ) -Exemestane (Aromasin® )

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