Mnpc Iii Exam 1- Estrogens

Front 1

4 things that estrogens do in the body

Back 1

influence menstrual cycle by their varied secretional rates during cycle

maintain secondary sex characteristics

induces estrus (heat)

minor mineralcorticoid activity

Front 2

estrogen effect on lipids (2)

Back 2

increases lipoprotein and TG levels

decreases circulating cholesterol (LDL down, HDL up)

Front 3

estrogen and tumors

Back 3

involved in some tumor growth

Front 4

core of estrogen- how many Cs
whats it called

Back 4

18 carbons- estrane

Front 5

6 therapeutic uses for estrogen (not including BC)

Back 5

estrogen deficiencies- like
ovarian failure
menopause sx
dysmenorrhea (painful period)
prostate cancer/post menopausal cancer
hirsutism (too much hair on body)

Front 6

locations that produce estrogen (4)

Back 6

large amts made in the ovaries
small amts from adrenal cortex
small amts from testes
placenta = main production site during pregnancy

Front 7

estrogen is made from what (2)

Back 7

biologically they are produced from testosterone
and androstenedione

Front 8

FSH- what does it do

synthed and secreted from where

Back 8

Regulates the synthesis of
estrogens. FSH is a hormone synthesized and secreted by gonadotropes in
the anterior pituitary gland.

Front 9

estrogen signalling cascade (3)

Back 9

hypothalamus releases GnRH-->pituitary releases FSH
which stimulates production of estrogens

Front 10

4 steps of estradiol synthesis (must know og precursor)

Back 10

17a-hydroxyprogesterone-->androstenedione-->testosterone -->estradiol

Front 11

aromatase

Back 11

enzyme that converts 19-hydroxy-1,2-dehydro testosterone to estradiol (makes aromatic ring)

Front 12

testosterone 19-hydroxylase

Back 12

converts testosterone to 19-hydroxytestosterone

Front 13

how is estrone made?

Back 13

Androstenedione is oxidized to estrone (know stupid pathway)

Front 14

1,2 dehydrogenase

Back 14

enzyme that makes a second dbl bond in estrone/estrogen ring (from 19-hydroxytestosterone)

Front 15

what distinguishes NATURAL sex hormones (estrogen) from synthetic

Back 15

natural has aromatic ring

Front 16

first isolated estrogen
potency

Back 16

estrone
2nd most potent

Front 17

estradiol- potency
made where?

Back 17

most potent (3x more potent than estrone)
made in ovaries

NOTE: HAS 2 OH
ESTRIOL HAS 3 HERP DERP

Front 18

3 estrogens made in body

Back 18

estrone
estradiol
estriol

Front 19

estriol- potency
made where
found in large amounts where (and why)

Back 19

relatively weak estrogen (1/60 of estrone)
major estrogen found in human peepee because
it is the most polar due to 3 OHs
made by placenta

Front 20

metabolism of estrogen pathway

Back 20

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Front 21

2 conjugated estrogens (from metabolism i guess)

Back 21

estrogen glucuronide
estrone 3-sulfate

Front 22

essential SAR on estrogen (3)
and 1 SAR that is not essential but there anyway

Back 22

steroid nucleus- not required for hormone activity
critical distance between C-3 and C-17= 14A
aromatic ring (ring A)
phenolic hydroxyl group at C3

Front 23

C-17 esterification of hydroxyl group - can do what 4 things to drug?

Back 23

making less polar compounds
longer acting
can be delivered IM
to make prodrugs

Front 24

adding alkyl group to C-17 OH- what can this do? (4)
common group that is also stuck onto C-17

Back 24

stabilize drug to metabolic degradation
epimerization is prevented
oxidation to ketone is prevented
improves oral efficiency (idk why...less polar?)
ethynyl group is very common

Front 25

2 mods you can do to estrogen to improve function/SAR

Back 25

C-17 hydroxyl esterification
C-17 OH alkyl group