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Endocrine/Nutrition Exam 2 Crider
Endocrine/Nutrition Exam 2 Crider
23
Pharmacology
Graduate
11/03/2010

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Cards

Term
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stereochemistry differences at these points can make significant changes in biological activity
Definition
steroid backbone
Term
alpha
beta
Definition
if the bond is projecting into the plane of the paper, it is designated ( )
if the bond is projecting out of the plane of the paper, it is designated ( )
Term
[image]
Definition
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numbering of 5-alpha-cholestane
C-27 steroid with no double bonds
Term
estrane
Definition
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the name of this C-18 steroid
Term
androstane
Definition
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the name of this C-19 steroid
Term
pregnane
Definition
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the name of this C-21 steroid
Term
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enzyme catalyzed cleavage of the side chain of cholesterol and the conversion to the C-21 steroid pregnenolone
pregnenolone serves as the precursor of the adrenocorticoids
Definition
conversion of cholesterol to pregnenolone
Term
[image]
Definition
conversion of pregnenolone to cortisol (glucocorticoid)
reaction occurs in the endoplasmic reticulum
Term
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Definition
conversion of pregnenolone to aldosterone
Term
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summary:
1) oxidation of hydrocortisone to cortisone at the 11 position leads to a biologically active compound (but less active than hydrocortisone)
2) action on hydrocortisone by 5beta-reductase leads to an inactive metabolite
3) the 3-keto group of 5beta-dihydrocortisol can be reduced by 3alpha-hydroxysteroid dehydrogenase. This is a reversible reaction and both metabolites are biologically active
Definition
metabolism of hydrocortisone
Term
1) reduction of the 4,5 double bond to the 5alpha and 5beta dihydrosteroids. This leads to a loss of biological activity.
2) reduction of the 3-keto function to either 3alpha or 3beta. this leads to loss of biological function
3) in some cases (cortisone, hydrocortisone), the 11-keto-11beta-OH are metabolically interconvertible
other routes of metabolism include:
6 beta hydroxylase (CYP3A4)
reduction of the C-20 C=O group to 20-OH analogues
Definition
in general, the main routes of metabolites of the glucocorticoids are
Term
[image]
all estrogens have an aromatic ring
Definition
conversion of androstenedione to estrone
Term
hydrocortisone
11beta-OH
21-OH
17alpha-OH
3-C=O
Definition
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Term
progesterone
C-21
Definition
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Term
testosterone
C-19
no aromatic A ring
androgen
Definition
[image]
Term
estradiol
C-18
aromatic A ring
Definition
[image]
Term
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18-aldehyde
no 17alpha-OH
Definition
structure of aldosterone
Term
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cortisol is active form
cortisol increases lipolysis
Definition
there is a correlation between 11beta-HSD in adipose tissue and degree of obesity. why is this?
Term
prevent excessive build up of hydrocortisone (cortisol) and thereby protecting the mineralocorticoid receptors (HC has both mineralocorticoid and glucocorticoid actions) and allowing aldosterone to function normally.
Definition
what is the function of 11beta-HSD2 in the kidneys, colon, and salivary glands?
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Term
introduction of a 1,2 double bond: increases GC activity, stable towards 5beta-reductase
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11beta-OH essential for GC activity
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4,5 double bond, 17alpha-OH, 21-OH present in most clinically used glucocorticoids
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introduction of a 9alpha-F dramatically enhances GC activity
[image]
Definition
SAR of glucocorticoids
Term
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hydrocortisone (GC/MC)
many mineralocorticoids lack 11-OH
9alpha-F increases mineralocorticoid activity
1,2 double bond slight decrease in MC activity
6alpha-methyl decreases MC activity
16alpha-OH, 16alpha-methyl, 16beta-methyl decrease MC activity
Definition
SAR of mineralocorticoids
Term
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[image]
Definition
K sparing diuretics (aldosterone antagonists)
Term
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C-18 of aldosterone acts as a H-bond donor to the C=O of Asn 770
C-21 OH of aldosterone acts as a H-bond acceptor for the N-H of Asn 770
C-21 OH acts as a H-bond donor to the side chain OH of Thr 945
C-3 C=O of aldosterone acts as a H-bond acceptor to the amide N-H group of Gln 776
Definition
key interactions of aldosterone binding to the active site of a mineralocorticoid receptor
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