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Thera VI > 20 Steroid Hormones: Medicinal Chemistry Duncan > Flashcards

20 Steroid Hormones: Medicinal Chemistry Duncan Flashcards

1
Q

How many carbons are in the basic steroid structure?

A

17

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2
Q

Which position is this carbon in?

A

1

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3
Q

Which position is this carbon in?

A

5

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4
Q

Which position is this carbon in?

A

6

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5
Q

Which position is this carbon in?

A

10

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6
Q

Which position is this carbon in?

A

11

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7
Q

Which position is this carbon in?

A

14

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8
Q

Which position is this carbon in?

A

15

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9
Q

Which position is this carbon in?

A

17

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10
Q

Which position is this carbon in?

A

21

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11
Q

Which position is this carbon in?

A

19

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12
Q

Which position is this carbon in?

A

18

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13
Q

Which position is this carbon in?

A

20

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14
Q

Beta or Alpha?

A

Alpha

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15
Q

Beta or Alpha?

A

Beta

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16
Q

Which form is this structure in?

A

Allo Form

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17
Q

Which form is this structure in?

A

Normal form

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18
Q

Which form is commonly found in the human body?

A

Allo form

19
Q

Cis or Trans?

A

Trans (up/down)

20
Q

Cis or Trans?

A

Trans (up/down)

21
Q

Cis or Trans?

A

Cis (down/down)

22
Q

What is the double bond nomenclature?

A

Delta symbol or “-ene-“

23
Q

What are the three main classes of steroid hormones?

A

Estranes, Androstanes, Pregnanes (glucocorticoids/Progestins)

24
Q

How many carbons are found in main Androstane structure?

A

19

25
Q

How many carbons are found in main Estrane structure?

A

18

26
Q

How many carbons are found in main Pregnane (Glucocorticoids/Progestins) structure?

A

21

27
Q

What class of steroid is this?

A

Androstane (Androgen)

28
Q

What class of steroid is this?

A

Estrane (Estrogen)

29
Q

What class of steroid is this?

A

Pregnane (Adrenocorticosteroid). Requires the -OH group on the 21 carbon to be in the adrenocorticoid family

30
Q

What class of steroid is this?

A

Pregnane (Progesterone)

31
Q

What is the first thing to be named in a structure?

A

The side chains

32
Q

What is the second thing to be named in a structure?

A

Structural class

33
Q

What is the third thing to be named in a structure?

A

The double bonds and ketos

34
Q

What is the chief precursor for all the steroid hormones?

A

Cholesterol

35
Q

What is the rate limiting step is the production of cholesterol?

A

The formation of mevalonic acid catalyzed by HMG-CoA reductase (target of statins)

36
Q

What needs to happen for Pregnenolone to make Progesterone?

A

The double bond is in the wrong place (C5=C6), needs to be moved to C4=C5

37
Q

What are the main things that need to happen to Pregnenolone for it to have high ACH activity?

A

Needs the double bond to be moved to C4=C5 and REQUIRES the addition of C17 OH group (missing in corticosterone)

38
Q

How does the biosynthesis of Androgens and Estrogens occur?

A

Pregnenolone (made from cholesterol) and/or progesterone are converted first to androgenic compounds. These can be further converted into the estrogens. Note: Tissues making lots of estrogens must first make lots of androgens, since these are the starting material (tissues that synthesize large amounts of androgens can have a small amount of estrogens “leak out”)

39
Q

What needs to happen in the basic steps of steroid catabolism?

A

Steroids are hydrophobic in large part. To aid in their excretion, they need to be rendered more water soluble. Thus, a major late step in catabolism is linking hydrophilic molecules such as glucuronic acid or sulfate

40
Q

What happens in the catabolism of ACSs?

A

Removal of C4=C5 double bond, then the C3 =O; and also the C17-beta side chain (-COCH2OH)

41
Q

What happens in the catabolism of Estrogens?

A

Converted to either estriol (addition of C16 -OH) or a C2 methoxy, C17 keto metabolite

42
Q

What happens in the catabolism of Androgens (i.e. testosterone)?

A

C4=C5 double bond and the C3 keto are reduced. 17 hydroxy is reveresed

43
Q

How can the use of tests determine if someone is taking exogenous testosterone?

A

There is typically a 1:1 ratio of testosterone to its metabolite epitestosterone in the urine. Using exogenous testosterone-generating steroids increases testosterone, but has not effect on epitestosterone. A ratio of T:epi of greater than 1 is indicative of steroid use, a ratio of > 4:1 is taken as evidence of abuse, illegal

Thera VI (27 decks)

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