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100 Cards in this Set

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Absorption of adrenal steroids (like cortisol)
100%, very good even topically/ocular
Protein binding of adrenal steroids (like cortisol) (3)
1)bind to Transcortin or CBG MOSTLY
2)also bind to albumin to a minor degree
3)normally 95% bound, 5% free
CBG and synthetic steroids
CBG has less affinity for synthetic steroids (like dexamethasone), resulting in increased potency
Side effects of adrenal steroids incidence
100% in long term therapy
2 categories of adrenal steroids side effects
1)adrenal insufficiency during withdrawal
2)drug induced Cushing's Syndrome
Adrenal insufficiency during withdrawal
b)what will happen
a)use of glucocorticoids for several months will turn off ACTH secretion
b)zona reticularis and faciculata will atrophy
Adrenal insufficiency during withdrawal (to prevent) (3)
1)withdraw drug slowly
2)ACTH 2 weeks before withdrawal
3)alternate day therapy reduces atrophy
Drug induced "Cushing's syndrome" mechanism
Too much glucocorticoids will result in Cushings syndrome
Cushing's syndrome results in (7)
1)elevated blood glucose
2)peptic ulceration
6)depressed immune cells (lymphocytes, eosinophils, neutrophils)
7)poor healing, increased infexns
2 broad categories of therapeutic uses of adrenal steroids
1)adrenal insufficiency
2)treatment of nonendocrine disorders
3 adrenal insufficiency types
1)primary adrenal insufficiency
2)secondary adrenal insufficiency
3)congenital adrenal hyperplasia
Primary adrenal insufficiency
decreased glucocorticoid and mineralocorticoid secretion
Secondary adrenal insufficiency (4)
1)anterior pituitary or hypothalamic insufficiency
2)corisol secretion decreased
3)aldosterone secretion nearly normal
4)glucocorticoids LOW, mineralcorticoids OK
Congential Adrenal Hyperplasia (3)
1)excessive testosterone produced to compensate for low glucocort and low mineralocort
2)90% of patients lack 21 Beta hydroxylase
3)10% of patients lack 11 Beta hydroxylase
What happens in patients who lack 21 beta hydroxylase (2)
1)deficiency of glucocorts and mineralcorts
2)adrenal hyperplasia
What happens in patients who lack 11 beta hydroxylase (2)
1)glucocorts deficient
2)mineralocorts OK
Treatment of nonendocrine disorders w/ adrenal steroids (what disorders (4))
2)allergic rxns
3)ocular inflammation
Types of arthritis treated w/ adrenal steroids (2)
1)rheumatoid arthritis
2)osteoarthritis (via intrajoint injection to limit SE's)
Adrenal steroids treat what allergic rxns (5 and are ideal for which)
1)Contact dermatitis***
2)severe bronchial asthma
3)serum sickness
4)insect bites
5)organ transplant
Concern w/ ocular inflammation and adrenal steroids?
must be certain that inflammation is NOT associated w/ an infection b/c steroids stop infection symptoms while infection progresses faster
Other misc diseases treated by adrenal steroids (4)
1)nephrotic syndrome
2)ulcerative colitis
3)lymphatic/neoplastic disorders
4)cerebral edema
Precautions w/ adrenal steroids
1)cause psychotic state
Contraindications w/ adrenal steroids (5)
1)peptic ulcers
4)HTN (b/c of mineralocorts)
5)infection (will mask signs of)
Glucorticoid synthesis inhibitors drug
1)aminoglutethidine (cytadren)
b)treats... (2)
a)inhibits enzymes involved in steroid biosyn from cholesterol so inhibits glucocorts, mineralocorts, estrogens, adrogens
b1)adrenal hypersecretion (Cushing's syndrome)
b2)medical adrenalectomy in ppl w/ breast cancer
Prototype of glucocorticoid synthesis inhibition
aminoglutethidine (cytadren)
Adrenal Steroid inhibitors catergories (2)
1)glucocorticoid synthesis inhibitors
2)mineralocorticoid receptor antagonist
Mineralocorticoid receptor antagonist drug
spironolactone (aldactone)
Spironolactone properties (4)
1)structure similar to aldosterone and testosterone
2)acts as receptor antagonist
3)used as a short acting K-sparing diuretic
4)treat hirsuitism in women via testosterone inhibition
1)Common gonadal steroids such as estradiol and testosterone are produced by the adrenal cortex
2)Treatment w/ dexamethasone would cause a rapid increase in the level of lymphocytes and neutrophils in the circulation
3)Synthetic glucocorticoids (triamcinolone) have a much lower affinity for CBG than endogenous glucocorticoid (cortisone)
1)Cortisol treatment would be expected to increase the body's resistance to infection
2)Aminoglutethidine (cytadren) is used to treat Cushing's syndrome
Production of prostaglandin is got from where?
modify prostaglandin A2 obtained from Sea Whip Coral
_____ is template for semi-synthetic prostaglandin
Are prostagladins in plants?
NO, just fatty acid precursor arachidonic acid
Where are prostaglandins found (types of organisms)(3)
3)sea whip (marine organism)
3 things seen in all natural prostaglandins
1)carbon's 12-13, Beta attachment
2)carbon's 7-8, alpha attachment
3)15-OH in alpha config
Subclasses of PG determined by...
substituents on C9 and C11 of CYCLOPENTANE ring
3 basic things that make a prostaglandin a PG
1)C1 is COOH
2)C20 is methyl
3)cyclopentane ring
# of saturations that can be seen in PG and where
1, 2, or 3

in the side chains off of the cyclopentane
How saturations affect nomenclature
1)If 1 unsaturation it is not specified b/c there is ALWAYS and unsaturation at 13-14
2)If 2 unsaturations just one will be mentioned in the name b/c the 13-14 is understood to ALWAYS be there
Prostaglandin w/ 3 unsaturations

5-6, 17-18, (these will only be seen in the name b/c the unsaturation @ 13-14 is ALWAYS there)
What is this and name it?
Eicosanoids are synthesized from ____ and they are gotten from _____
arachidonic acid

cell membrane phospholipids
(4) are produced from arachidonic acid via COX
(1) is produced from arachidonic acid but NOT via COX
Affect of COX on arachidonic acid
uses peroxide to form a cyclopentane ring (forms PGG2)
Once you get PGG2 from arachidonic acid via COX what then...
you get PGH2, the intermediate to prostaglandins, thromboxanes, prostacyclins
Is COX1/2 found in plants?
Blockage of COX1 can lead to...
Only difference b/w COX1/2 in the AS
COX1- isoleucine @ 523
COX2- valine @ 523
Enzyme used to get PGE2
PG endoperoxide E isomerase
Enzyme used to get PGF2alpha
PG endoperoxide reductase
Enzyme used to get PGD2
Leukotrienes are technically....
open chain FA's
Why are PG's unstable?
B/c they are easily metabolized
4 ways that PG's are metabolized (and which is the main way)
1)oxidation of the allylic hydroxyl @ C15 to a ketone
2)reduction of the unsaturated bond b/w C13-14
3)Beta oxidation to nor-PG***
4)omega oxidation of the alkyl side chain
What is done in synthetic PG's to make them more stable?
Add groups at C16 and C15 to prevent breakdown
What is a semisynthetic PG?
start w/ a natural PG and modify it
If you add a group to C15 on a PG what is special about it?
it will be in beta configuation b/c the OH there always takes the alpha config
What do all steroids begin with?
____ is a steroid that if shaken in water froths like soap
CPPP is the beginning of... (9)
1)cardiac glycoside steroids
6)bile acids
7)steroid alkaloids
9)adrenal cortex hormone
Most natural steroids are...

Bile acids and cardiac glycoside steroids are...

Androgens, testosterone, glucocorticoids are...
Delta4 steroids
Cholesterol is a ____ steroid?
Delta5 steroid
Only natural steroids that are 5beta (2)
bile acids
cardiac glycoside steroids
What makes a steroid a delta4/5 steroid
double bond @ C15
ALL CLASSES of steroids are 5alpha except... (2)
bile acids
cardiac glycosides
Estranes have ____ carbons
Androstanes have ___ carbons
Pregnanes have ____ carbons
HMG-coA is composed of...
3 acetates
Cholesterol biosynthesis steps (4)
1)AcoA + acetoacetyl-coA yields HMG-coA
2)HMG-coA is reduced to the alcohol mevalonic acid via HMG-coA reductase splitting off a coA
3)mevalonic acid is activated to a pyrophosphate by ATP
4)Then STEROIDS, TERPINE OR RUBBER can be produced
____(3) can be produced by activated pyrophosphate
The activated pyrophosphate is converted to what before cholesterol is made
Squalene via farnesyl pyrophosphate
Difference b/w plants and animals in production of cholesterol
Diversion to glucocorticoids or mineralocorticoids is where from cholesterol (2)
1)pregnenolone to glucocorticoids via 17alpha hydroxylase
2)pregnenolone to mineralocorticoids via 3beta deH
How is pregnenolone produced from cholesterol
side chain cleavage
Pregnenolone to cortisol via...
17alpha hydroxylation
Pregnenolone to progesterone, aldosterone via...
isomerization of 5-6 double bond to 4-5 double bond
Adrenocorticoid metabolism of hydrocortisone/cortisone (2 and 2 enzymes)
1)To Urocortisone/Urocortisol which are inactive
2)3alpha,11beta-one's via loss of 17-ketol side chain

1)5alpha/beta reductase
5alpha/beta reductase mechanism of adrenocorticoid metabolism
makes compounds to 5alpha or 5beta structures
deH mechanism of adrenocorticoid metabolism
makes compounds alpha/beta and loss of 17ketol side chain
affect intermediary metabolism and are associated w/ inhibition of the inflammatory process (low salt retention)
High salt retention
2 types of adrenocorticoids
Pathologic conditions related to the adrenal cortex and adrenocorticoids? (3)
Mineralocorticoid structural features (and which is most defining)
1)keto group @ C3
2)unsaturation @ C4-5
3)C11 will have nothing, O or OH
4)C17 lacks alphaOH****
Glucocoricoid structural features (cortisol group) AND which is most defining (6)
1)keto group @ C3
2)unsaturation @ C4-5
3)keto or OH @ C11
4)Beta-ketol side chain @ C17
5)alpha-OH @ C17****
6)alpha-F @ C9
Glucocorticoids (cortisol group), things can be put where to affect fxn and an ex
@ C9, putting an alpha-F there increases glucorticoid activity
Glucocorticoids (prednisolone group) structural features (4)
1)modifications of cortisol structure to reduce Na retention
2)Add 2x bond @ C1-2
3)Add OH, CH3 @ C16
4)F @ C6 or C9 in alpha config
Glucocorticoids (prednisolone group), what increases glucocorticoid activity
Add double bond @ C1-2
Substituents which significantly INCR anti-inflammatory and glucocorticoid activity (2)
Substituents which significantly DECR mineralocorticoid activity (3)
1)16alpha hydroxy
2)16alpha/beta methyl
3)16alpha/beta ketals
Substituents which significantly INCR BOTH glucocorticoid and mineralocorticoid activity (4)
1)9alpha fluoro
2)9alpha chloro
3)2alpha methyl
The ___ of hydrocortisone is of major importance to receptor binding; ____ may be reduced to hydrocortisone for this purpose

cortisone reduced to hydrocortisone
Why does 9alpha chloro or fluoro increase activity? (3)
1)electronic withdrawing inductive effect on the 11beta-OH
2)makes it more acidic
3)therefore binds better to receptors
Way to increase glucocorticoid potency w/o adding a group?
delta1 double bond (C1-2), b/c of resultant change in the A ring
A steroid will end in ____ if it is to be used topically
Goal of modifying drugs in the adrenocorticoid (cortisol group)
search for compounds w/ high glucocorticoid and low mineralocorticoid activity