Chem Basis: Steroids 1

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kyleannkelsey
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268417
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Chem Basis: Steroids 1
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2014-03-29 22:44:46
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Chem Basis Steroids
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Chem Basis: Steroids
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Chem Basis: Steroids
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  1. The Steroids are a group of substances of ______________origin.
    both plant and animal
  2. All steroids possess what characteristics?
    • Tetracyclic backbone/skeleton derived from cyclopentanohydrophenathrene
  3. Among the steroids are substances of very considerable medicinal importance such as:
    • Adrenocortical hormones
    • sex hormones
    • vitamin D2
    • cardiac glycosides
    • sterols
    • bile acids.
  4. ________________may be considered the starting point with some of it synthesized in the cortex from acetate.
    Cholesterol
  5. Some cholesterol used in steroid synthesis in the adrenal cortex is derived endogenously from what?
    Acetate
  6. __________________ probably represents the major source of cholesterol for the biosynthesis of the various steroids.
    Exogenous dietary cholesterol
  7. Corticosteroids are classified into two groups, what are they?
    • Adrenocorticoid hormones
    • Sex hormone
  8. What are the Adrenocorticoid hormones?
    • Glucocorticoids
    • Mineralcorticoids
  9. Describe the Hypothalamic/pituitary control of Glucocorticoids:
    • Hypothalamus: CRF (corticotrophin releasing factor)
    • Pituitary: ACTH (adrenocorticotropic hormone)
    • Adrenal cortex: Synthesizes and releases GC
  10. What is the general action of GCs in the peripheral tissues?
    • Production of glucose from non-sugar sources
    • Inhibit the use of glucose in the tissues
    • Promote gluconeogenesis
  11. Describe the physiological control of Mineralcorticoids:
    • Octapeptide angiotensin II
    • Stimulates synthesis of permease called: antiduiretic-induced protein (AIP)
  12. What is the general action of MCs in the peripheral tissues?
    • REtation of Na
    • K and H excretion
    • Maintain blood volume
    • Electrolyte regulation
  13. What group of patients should MCs be avoided in?
    HTN
  14. What group of patients requires supplementation of MCs?
    Addison’s
  15. Describe how Glucocorticoids and mineralocorticoids act on the receptor/cell?
    • Pass through cell membranes into the cytosol and bind to intracellular receptor proteins
    • Form a steroid-receptor complex
    • Translocation to nucleus
    • Initiates transcription
  16. The portion of MC or GC receptors that binds to _____ is highly conserved, and looks the same regardless of receptor type.
    DNA
  17. The domain that binds the ________ is different from one type of steroid to the next.
    Steroid
  18. GC receptors are believed to interact with which face of the glucocorticoid structure?
    Beta
  19. MC receptors are believed to interact with which face of the mineralocorticoid structure?
    Alpha
  20. What general effects are Corticosteroids used for?
    Glucocorticoid effects
  21. ____________ activity of corticosteroids is considered undesirable therapeutically.
    Mineralcorticoid activity
  22. What are the general therapeutic uses of Corticosteroids?
    • Anti-inflammatory agents
    • Immunosuppressants
    • Anti-allergic acitivty
    • Replacement therapy
  23. How do GCs have Anti-inflammatory activity?
    • GCs stimulate the synthesis of Lipocortin, which inhibits phospholipase A2
    • PLA2 cleaves AA from Phospholipids resulting in inflammatory prostaglandins
  24. What diseases are treated by the anti-inflammatory effects of GCs?
    • Rheumatoid arthritis
    • Bursitis
    • Contact dermatitis
    • Autoimmune disease
    • Ulcerative colitis
    • Enteritis
    • Erythema
    • Exfoliative dermatitis
  25. How do GCs inhibit the immune system?
    • Inhibit Interleukin-1 (IL-1)
    • Impacts proliferation of B-lymphocytes
    • Inhibits activation of T-lymphocytes
    • Decreased IL-2 production
    • TNF is decreased
  26. In what group of patients should Immunosuppressant GCs be avoided in?
    Those with an infection
  27. How do GCs prevent allergic activity?
    Inhibit synthesis and release of histamines
  28. Why do GCs need weaning during D/C?
    Hypothalamic-Pituitary-Adrenal axis suppression occurs with use
  29. Under what conditions do you not need to wean patients off of Glucocorticoids?
    Short treatments of 7-10 days
  30. What are the side effects of GC therapies?
    • Increased infection risk
    • Increased BP
    • Salt/water retention
    • Increased K secretion
    • Increased Ca excretion
    • Muscle weakness
    • Osteoporosis
    • Peptic ulcer
    • Cushingoid state
    • Decreased growth
  31. Describe the basic skeleton structure which steroid hormones are derived from:
    • Perhydro (saturated)
    • Tetracyclic (four rings, three cyclohexane and one cyclopentane)
    • Called cyclopentanoperhydrophenanthrene
  32. What is the most stable conformation, chair or boat, of cyclopentanoperhydrophenanthrene?
    Chair
  33. What is a sterol?


    • Cyclopentanoperhydrophenanthrene w/ hydroxyl groups
    • (Cyclopentanoperhydrophenanthrene shown)
  34. What is a sterid?
    • Cyclopentanoperhydrophenanthrene basic hydrocarbon structure
    • (Cyclopentanoperhydrophenanthrene shown)
  35. What is a Steroid?
    • Cyclopentanoperhydrophenanthrene w/ more carbonyl groups
    • (Cyclopentanoperhydrophenanthrene shown)
  36. All steroids have one or two angular methyl groups at what locations?
    • C13 and or C10
    • Numbered: C18 (at C13) and C19 (at C10)
  37. Some steroids have an additional carbon chain attached at what point?
    • 17 Beta
  38. Under what conditions can a steroid have a two carbon chain at 17 Beta?
    • Must have C13 and C10 methyls
  39. What are the two carbons attached at 17 Beta named?
    • C20 and C21
  40. Which is the A ring?

  41. Which is the B ring?

  42. Which is the C ring?

  43. Which is the D ring?
  44. In the corticoids and sex steroids, the A/B ring fusion and the C/D ring fusion are most commonly ______________, making the entire steroid structure very flat.
    • Trans
  45. What is the allo conformation of a steroid?
    • A/B is trans (C/D is also trans)
  46. What is the “Normal” conformation of the steroid?
    • A/B is cis (C/D is still trans)

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