Medicinal chemistry of steroids pdf

Indeed, steroids interact with enzymes and receptors in a strikingly specific manner. Chemistry and Biological Activity of Steroids aims to provide an updated overview of recent advances in the medicinal chemistry of steroids. Novel synthetic methods in the steroids field, including steroi Novel synthetic methods in the steroids field, including steroid biotransformations, new steroids able to tackle steroid receptors, and steroid enzymes with clinical relevance, are critically reviewed in this book.

Furthermore, the diverse physiopathological roles of oxysterols and their therapeutic value are also discussed. By Svetlana N. Morozkina and Alexander G. This is made possible by the EU reverse charge method. These cookies will be stored in your browser only with your consent. You also have the option to opt-out of these cookies. But opting out of some of these cookies may affect your browsing experience. Necessary Necessary. Necessary cookies are absolutely essential for the website to function properly.

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Shah Pharmacy College 22 Progesterone Shah Pharmacy College 23 Shah Pharmacy College 24 Glucocorticoids with moderate-to-low salt retention Betamethasone DexamethasoneMethylprednisolone 3.

Shah Pharmacy College 26 Shah Pharmacy College 28 Shah Pharmacy College 29 Shah Pharmacy College 30 Shah Pharmacy College 31 It is used to replace aldosterone where the adrenal cortex is destroyed Addison's disease. Fludrocortisone is also the drug of choice in most patients with autonomic neuropathy, in whom volume expansion is easier to achieve than a sustained increase in vasoconstrictor tone. Shah Pharmacy College 32 Contraction of ring A to norcortisol yields and inactive compound.

The introduction of unsaturation a double bond at C-1 leads to enhanced anti-inflammatory activity ex. Whereas the addition of —OH group leads to the compound becoming inactive. C-3 spirofused thiazolidine derivative 1 was found to be active and this derivative considerably reduced the thinning of the skin, generally found in corticosteroids. Ring A can be fused with a pyrazole ring. Compound 2 has times the potency of cortisol, but also lacks mineralocorticoid activity.

Modification in Ring B i. Introduction of 8 9 double in prednisolone affords compound with lower anti-inflammatory activity. Removal of the C angular —CH3 group reduces anti-inflammatory activity. Shah Pharmacy College 35 Anti-inflammatory potency of corticosteroids drastically influenced by the substituents at C-9 position. Modification of Ring C i. The C oxygen group is not essential for anti-inflammatory activity. It can be replaced by groups like —Cl, which can be converted to the hydroxyl group in vivo.

Modification in ring D i. Shah Pharmacy College 36 Modification in the side chain at C i. Acetonide derivatives across the 17, diol arrangement resulted in more potent analogues compared to free diols. Hydroxyethanone side chain attached at C in the classical corticosteroid is not essential for activity. Tipredane, a thioketal is a potent topical anti- inflammatory drug.

Shah Pharmacy College 37 Tipredane may also form acetonide derivatives, which are more potent than the corresponding 16, dihydroxy derivatives. At C introduction of chloro, methyl groups increase activity. Ketals and esters yield compounds with improved potency. Retaining of anti-inflammatory activity of corticosteroids observed upon ketalization of the C carbonyl group with ethylene glycol.

Replacement of the C carbon by sulphur fluticasone afforded thioesters, also useful clinically. The C —OH group can be esterified to afford lipophilic compounds that are meant for respiratory use. Introduction of activating groups at C, conversion of —CH2OH group to a —CH3 group medrysone yields clinically useful ophthalmic anti-inflammatory compound with relatively little effect on intraocular pressure.

Shah Pharmacy College 38 Fluticasone Medrysone Androgen, commonly referred to as male sex hormones or anabolic steroids, in particular, testosterone, are produced by male sex glands in the male body. Shah Pharmacy College 39 Shah Pharmacy College 40 It is converted by hydroxylation to the active dihydrotestosterone.

Growth of bone is promoted, but the rate of closure of the epiphyses is also hastened, causing short stature in cases of precocious puberty or of androgen overdose in the course of treating hypo gonadal children. Shah Pharmacy College 41 Shah Pharmacy College 42 Shah Pharmacy College 43 For a substance to have activity, it must contain the androstane skeleton.

Oxygen at C-3 and C are not essential for the androgenic activity. There should not be chain constriction or extension because it leads to finished the activity. Shah Pharmacy College 44 Introduction of 3-hydroxy group and 3-keto group enhance the activity.

Hydroxy group at C position has no androgenic or anabolic activity. Halogen substitution produces compounds with decreased activity except when placed at C-4 or C-9 position. Halogen introduction will decrease the activity except the C-4 and C Introduction of double bond at C-1 position increases the anabolic activity for example — methandrostenolone is more active than methyltestosterone.

Replacement of carbon atom at C-2 position by oxygen e.