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Medicinal Chemistry - Winter > 12 - Sex Hormones > Flashcards

12 - Sex Hormones Flashcards

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1
Q

What are the primary sites of production of sex hormones?

A
  • Ovaries, testes
  • Placenta
  • Adrenal gland
  • Prostate
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2
Q

What are the 3 main types of sex hormones? Which are female and which are male?

A
  • Estrogens (female)
  • Progestagens (female)
  • Androgens (male)
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3
Q

What are synthetic analogs of progestagens called?

A

Progestins

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4
Q

What is the function of hCG (human chorionic gonadotropin)?

A

Sustains luteal phase during pregnancy by stimulating corpus luteum to release progesterone and estradiol, which inhibit the next round of ovulation and menstruation

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5
Q

When is estradiol released? What do it do?

A
  • Released by mature follicle to create proliferative endometrium
  • Triggers release of LH
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6
Q

What is the function of luteinizing hormone?

A

Triggers ovulation and initiates formation of corpus luteum

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7
Q

What is the function of progesterone?

A
  • Stimulates and maintains secretory endometrium
  • When levels subside, menstruation begins
  • Stimulates thickening of cervical secretions to decrease sperm penetration
  • Stimulates breast lactation
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8
Q

Where is estradiol production the highest?

A

Ovaries

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9
Q

Is estradiol production higher during menstruation or during pregnancy? Why?

A

1000x more during pregnancy to inhibit ovulation

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10
Q

What effect does estradiol have on calcium?

A

Inhibits Ca loss from bones by reducing production of bone resorption stimulating protein

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11
Q

Where is progesterone production the highest?

A

Ovaries

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12
Q

Is progesterone production higher during menstruation or during pregnancy?

A

Pregnancy

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13
Q

Where is production of testosterone the highest?

A

Testes

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14
Q

What is testosterone converted into and by what?

A

Converted in 5 alpha-DHT by 5 alpha-reductase

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15
Q

What is the function of testosterone?

A
  • Androgenic effects = dev’t of male sex characteristics

- Anabolic effects = growth of skeletal and cardiac muscle, bone, and RBC’s

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16
Q

What is testosterones effect in women?

A
  • Libido
  • Mood
  • Muscle mass and bone density
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17
Q

Where is production of 5 alpha-DHT (dihydrotestosterone) the highest?

A

Scalp (hair follicles) and prostate

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18
Q

Is testosterone or 5 alpha-DHT more potent?

A

5 alpha-DHT

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19
Q

What can high levels of 5 alpha-DHT lead to?

A

Prostate hypertrophy

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20
Q

What is needed on CYP19 aromatase for it to be able to aromatize?

A

Methyl group on A ring

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21
Q

What is produced when testosterone is aromatized?

A

Estradiol

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22
Q

Are the reduction products of progesterone active or inactive?

A

Inactive

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23
Q

What are progesterones primarily converted into?

A

Corticosterone and hydrocortisone

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24
Q

What is required for a metabolite of testosterone to be active?

A
  • Trans/trans/trans backbone configuration

- Configuration at C-17 must have OH in beta and H in alpha positions

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25
Q

What are estrogenic drugs used for?

A
  • Hormone replacement therapy
  • Birth control
  • Certain types of cancer therapy
26
Q

What are the 3 structural classes of estrogens?

A
  • Steroidal
  • Phytoestrogens
  • Non-steroidal (diethylstilbestrol and derivatives)
27
Q

Which estrogens are useful for hormone replacement therapy?

A

Conjugated

28
Q

What do phytoestrogens contain?

A

Flavone and isoflavone rings

29
Q

What is important about diethylstilbestrol? What it is indicated for?

A
  • One of the most active non-steroidal estrogens

- Indicated for use in therapy for prostate cancer b/c it can suppress testosterone production

30
Q

What are indications for anti-estrogenic drugs?

A

Treatment of breast or uterine tumours w/ estrogen receptors

31
Q

Do anti-estrogenic drugs have steroidal structures? Why?

A

No, have non-steroidal structures b/c steroidal structures are too potent for therapy

32
Q

Do SERMs have agonist or antagonist activity?

A

Both

33
Q

Which structural feature of anastrozole is required to bind to the aromatase enzyme?

A

1,2-4-triazole

34
Q

What type of enzyme is the aromatase enzyme?

A

CYP isozyme

35
Q

What is the most common use of progestins?

A

Birth control (alone or in combination w/ estrogen)

36
Q

What are the 2 frequently used progestins?

A
  • Medroxyprogesterone acetate

- Norethindrone

37
Q

How do estrogen and progestin work as contraceptives?

A
  • By suppressing production of GnRH, LH, and FSH through a negative feedback mechanism => suppression of ovulation
  • Progestins also thicken cervical mucous to reduce sperm penetration
38
Q

All androgens have both ____ and ____ properties

A

Androgenic and anabolic

39
Q

Which hormones are generally used for androgen replacement therapy?

A

Testosterone derivatives w/ enhanced metabolic stability (rather than testosterone precursors)

40
Q

What is the preferred route of administration for testosterone? Why?

A

Transdermal (patch or topical gel) b/c oral testosterone is rapidly metabolized during first pass phase

41
Q

What is important about 17 alpha-alkynyl derivatives of testosterone?

A

Usually give more progestogenic action than androgenic action

42
Q

What is important about 17 alpha-alkyl derivatives of testosterone?

A

Good for oral administration b/c have higher metabolic stability

43
Q

What is important about 17 beta-ester derivatives of testosterone?

A

Good for IM/SC/transdermal administration b/c give “slow release” effects

44
Q

Which drugs are used for endometriosis?

A

Drugs that inhibit endometrial growth, like testosterone derivative danazol

45
Q

What is the mechanism of danazol?

A
  • Exact mechanism unknown
  • Thought to act on pituitary gland and reduce release of FSH and LH, thereby reducing production of estrogen and progesterone
46
Q

What are indications for anti-androgens?

A
  • Hyperandrogenism in males and females

- Benign and cancerous prostate conditions responsive to androgens

47
Q

What are sx of hyperandrogenism?

A
  • Loss of scalp hair but increased growth of body hair
  • Acute acne
  • Premature menopause
48
Q

What is finasteride? What is its indication?

A
  • Selective tight-binding 5 alpha-reductase inhibit

- Used in tx of benign prostatic hyperplasia

49
Q

What do androgen precursors cause?

A

Augmented biosynthesis of both active androgens and estradiol in vivo

50
Q

How can testosterone abuse be tested?

A
  • Will lead to a high ratio of testosterone glucuronide to epitestosterone glucuronide
  • Ratio greater than 4:1 = abuse
51
Q

What are some adverse effects of abusing anabolic steroids?

A
  • Premature stunted growth through early skeletal maturation (only in growing adolescents)
  • Reduced sperm count/shrinking of testes
  • Prostate hypertrophy
52
Q

What are some methods to mask steroid detection in urine?

A
  • Uricosuric agents (excretion of uric acid in urine)
  • Diuretics
  • Epitestosterone
  • Saline injections
53
Q

What are some drugs that structurally resemble estrogens, progestagens, and androgens?

A
  • Estrogenic drugs
  • Anti-estrogenic drugs (non-steroidal and aromatase inhibitors)
  • Progestins
  • Androgenic drugs
  • Anti-androgenic drugs
  • Muscle building and steroids abuse
54
Q

What do dehydrogenase enzymes do to a steroid?

A

Convert OH to =O and vice versa

55
Q

What do ketoreductase enzymes do to a steroid?

A

Convert OH to =O

56
Q

What do hydroxylase enzymes do to a steroid?

A

Convert a carbon w/ 2 hydrogen groups to a carbon w/ an OH group

57
Q

What do isomerase enzymes do to a steroid?

A

Move a double bond

58
Q

What do reductase enzymes do to a steroid?

A

Remove a double bond

59
Q

What do aromatase enzymes do to a steroid?

A

Remove methyl group and add double bonds to a ring to make it aromatic

60
Q

What does a conjugation enzyme do to a steroid?

A

Changes OH to O-R

Medicinal Chemistry - Winter (15 decks)

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