Lecture 13 - chemistry of potency of steroids Flashcards
what are adrenoreceptors used in treatment of?
stress response, immune response, regulation of inflammatory response, carbohydrate metabolism, protein catabolism, control of blood electrolyte levels and behaviour.
where are the alpha and beta in the steroid nomenclature
substituents above the plane are beta
substituents below the plane are alpha
what is the steroid backbone primary up of?
four cyclic rings and two methyl groups
what has an impact on overall molecular shape?
ring geometry
what is cortisol?
the primary stress hormone
what does cortisol do in the bloodstream?
increases sugars (glucose) in the bloodstream, enhances your brain’s use of glucose and increases the availability of substances that repair tissues. Cortisol also curbs functions that would be nonessential or harmful in a fight-or-flight situation.
what are the three classes of adrenocorticosteroids?
glucocorticoids, mineralocorticoids and sex hormones
what do glucorticoids do?
regulate carbohydrate, lipid and protein metabolism. used for the treatment of rheumatoid diseases, symptomatic relief forms them and allergic reaction and topical application for dermatologic disorders and cancer therapy (by preventing phospholipid release amongst other mechanisms)
what do mineralocorticoids do?
salt balance and water retention
what do sex hormones do?
steroid hormones that interact with vertebrae androgen or oestrogen receptors
what are natural and synthetic glucocorticoids?
natural: hydrocortisone, cortisone
synthetic : prednisolone, beclomethasone, dexamethasone, flucilonone, budesonide, betamethasone, fluticasone
what do glucocorticoids require in their structure?
all biologically active adrenocorticosteroids require a 3-keto group and 4,5 unsaturation
Glucocorticoid activity can be increased by introducing a double bond between C1 and C2 (anti-inflammatory effect enhances)
e.g.
cortisone→ prednisone,
hydrocortisone → prednisolone
An α-hydroxyl group at C17 is found in glucocorticoids but not mineralocorticoids
Glucocorticoid activity can be increased by introducing an 11 β-hydroxyl (OH) group
what are requirements for mineralocorticoid structure?
The 3-keto group and 4,5 unsaturation as all adrenocorticoids
Hydroxyl group on 21st position on ring D for mineralocorticoid activity
what are requirements for sex hormones structure?
Natural sex steroids are made by the gonads, by adrenal glands, or by conversion from other sex steroids
C20 & C21 are usually absent
what are adsorption and distribution considerations?
Requires significant lipophilicity to reach target receptors in cell nuclei (although transport mechanisms exist too)
Hydrophilic molecules are more readily absorbed in the lung
