Chem Basis: Steroids 5

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    What would you expect this drug would be used for?
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    • Topical See diminished MC ability and Cl at C21
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    What is this drug?
    Hydrocortisone
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    Name this drug:
    Delta 4-11B,17a,21-trihydroxy-3,20-pregnenedione
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    Does this drug have mineralo or Gluco corticoid activity?
    Both
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    What are the Mineralocorticoid promoting features of this molecule?
    • The 17B-ketol (or 17B glycoloyl) group
    • The Delta 4-3-one A ring
    • The D ring, which forms hydrophobic bonds at the receptor
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    What are the Glucocorticoid promoting features of this molecule?
    • 17B-ketol (or 17B-glycoloyl) group
    • The Delta4-3-one A ring
    • The 11B- and 17a-OH groups, which act synergistically to promote glucocorticoid action.
    • The 11B-OH group H-bonds w/ receptor
    • The D ring, which forms hydrophobic bonds with the receptor
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    What is the Therapeutic use of this compound?
    • Anti-inflammatory through GC activity
    • MC activity is seen in chronic use but is undesired
    • (Hydrocortisone)
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     In what forms is this drug marketed?
    • C21 OH and ester prodrug
    • Oral Suspension and topical
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    The ester form of Hydrocortisone (shown: Hydrocortisone buteprate) is used in what way?
    Exclusively topical
  10. What are the kinetic characteristics of Hydrophilic Hydrocortisone prodrugs: Sodium succinate and phosphate?
    • Decreased log P, rapid OOA and short DOA
    • Poor topical agents
  11. Hydrocortisone prodrugs: Sodium succinate and phosphate are given by what routes?
    • Sodium succinate: IM or IV
    • Sodium phosphate: IM, IV or SQ
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    What is this drug?
    Cortisone
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    Is this drug active, why or why not?
    • No
    • The 11-keto needs to be reduced back to an 11B-OH
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    How do these two drugs compare in terms of activity?
    • Same MC
    • Almost same GC, Hydrocortisone (right) has slightly higher
    • Reason: 11B-keto on Cortisone (Right) converts readily to Hydrocortisone
    • (Left: cortisone, Right: Hydrocortisone)
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    Which patient population may not be able to derive much benefit from this drug because it is an ester prodrug?
    • Hepatic disease patients, because they cannot metabolize it to an active C21-OH
    • (Cortisone)
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    What is this molecule?
    • Adrenosterone
    • The inactive metabolite of Hydrocotisone produced from C17 oxidation of the 17-keto, 5B-OH and 3a-OH
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    What is this structure?
    Prednisolone
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    Name this structure:
    • Delta 1,4-11B, 17a, 21-trihydroxypregnadiene-3,20-dione (Delta1-hydrocortisone)
    • (prednisolone)
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    Why does this drug have a longer DOA than hydrocortisone?
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    • Double bond between C1 and 2
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    Why does this drug have increased GC activity compared to hydrocortisone?
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    • Double bond between C1 and 2
    • Flattens the ring to promote GC activity
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     Why does this drug have reduced MC activity compared to hydrocortisone?
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    • Double bond between C1 and 2
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    How does this drug compare to hydrocortisone in terms of MC and GC activity
    • GC: 4x that of hydrocortisone
    • MC: 0.6x that of hydrocortisone
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    The C21 acetate form of this drug is used by what route and why?
    • Topically due to its increased lipophilicity
    • Few systemic side effects even with chronic use
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    The C21 t-Butylacetate form of this drug is used by what route and why?
    • Topically due to its increased lipophilicity
    • Few systemic side effects even with chronic use
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    What s this drug?
    Aldosterone
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    Name this drug:
    Delta 4-11B, 21-dihydroxy-3,18,20-pregnenetrione
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    What form is this drug marketed in?
    • None, it is endogenous and not marketed as a drug
    • (Aldosterone)
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    What group on this molecule gives it 1000x greater MC activity than Hydrocortisone?
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    • C13 Formyl group
    • (Aldosterone)
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    What group on this drug allows for some GC activity?
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    • 11B-OH
    • (Aldosterone)
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    What is this drug?
    Fludrocortisone
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     Name this compound:
    • Delta 4-9a-fluoro-11B, 17a,21-trihydroxypregnene-3,20-dione-21-acetate
    • (9a-fluorohydrocortisone)
    • (Fludrocortisone)
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    What aspect of this molecule imparts 800 fold greater MC activity and 10 fold greater GC activity than Hydrocortisone?
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    • 9a-Flouro group
    • 9a-Flouro decreases 11B-OH density, enhancing H-binding with the GC receptor
    • 17a-OH enhances GC activity
    • (Fludrocortisone)
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    Does this drug have primarily MC or GC activity?
    • MC
    • (Fludrocortisone)
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    Does this drug have primarily MC or GC activity?
    • MC
    • (Aldosterone)
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     What is the Therapeutic use of this drug?
    • Replacement therapy in:
    • Pprimary and secondary adrenal insufficiency (Addison's disease)
    • Salt-losing adrenogenital syndrome
    • (Fludrocortisone)
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    What effect does the C21 acetate promotes?
    • Prolonged DOA appropriate for chronic therapy
    • (Fludrocortisone)
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    Why is this drug not used topically as an anti-inflammatory?
    • High MC activity
    • Even though it is highly lipophilic, even a little system penetration could cause issues, like fluid retention
    • (Fludrocortisone)
  38. Why are Steroids utilized in post transplant protocols?
    They are effective immunosuppressants
  39. Do steroids have anti-allergic activity?
    Yes
  40. Is the MC or GC active steroids used for replacement therapy in the treatment of chronic adrenal insufficiency (Addison’s disease)?
    Both
  41. Other than Addison’s disease, what other situations may warrant steroid replacement therapy?
    Stressful situations such as surgery, infections, trauma and following withdrawal after prolonged therapy due to the manifestation of an adrenal crisis
  42. When is Intravenous Steroid therapy is indicate?
    • Emergency situations such as:
    • Aadrenal crisis
    • Atatus asthmatics
    • Hypovolemic shock
    • Acute exacerbation/flares of rheumatoid arthritis
  43. A patient has received an IV steroid for an emergency situation, how would they be treated post stabilization?
    Switched to oral therapy
  44. Patients with compliance problems should receive what type of Steroid?
    Lipophilic depo preparations.

Card Set Information

Author:
kyleannkelsey
ID:
268543
Filename:
Chem Basis: Steroids 5
Updated:
2014-03-31 02:04:21
Tags:
Chem Basis Steroids
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Chem Basis: Steroids 5
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Chem Basis: Steroids 5
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