Steroid ring system.This is a list of corticosteroids (glucocorticoids and mineralocorticoids ) or derivatives of cortisol (hydrocortisone ). Most esters of these corticosteroids are not included in this list; for esters, see here instead.
The most common structural modifications in synthetic corticosteroids include 1(2)-dehydrogenation , 6α-, 9α-, 16α-, and 16β-substitution (with a halogen or methyl group ), 16α,17α-acetonidation , and 17α- and 21-esterification .
Natural
Cortisol (hydrocortisone ), the major endogenous glucocorticoid.11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone) = 21-hydroxypregn-4-ene-3,11,20-trione11-Deoxycorticosterone (deoxycortone, desoxycortone; 21-hydroxyprogesterone) = 21-hydroxypregn-4-ene-3,20-dione11-Deoxycortisol (cortodoxone, cortexolone) = 17α,21-dihydroxypregn-4-ene-3,20-dione11-Ketoprogesterone (11-oxoprogesterone; Ketogestin) = pregn-4-ene-3,11,20-trione11β-Hydroxypregnenolone = 3β,11β-dihydroxypregn-5-en-20-one 11β-Hydroxyprogesterone (21-deoxycorticosterone) = 11β-hydroxypregn-4-ene-3,20-dione11β,17α,21-Trihydroxypregnenolone = 3β,11β,17α,21-tetrahydroxypregn-5-en-20-one 17α,21-Dihydroxypregnenolone = 3β,17α,21-trihydroxypregn-5-en-20-one 17α-Hydroxypregnenolone = 3β,17α-dihydroxypregn-5-en-20-one17α-Hydroxyprogesterone = 17α-hydroxypregn-4-ene-3,11,20-trione18-Hydroxy-11-deoxycorticosterone = 18,21-dihydroxypregn-4-ene-3,20-dione 18-Hydroxycorticosterone = 11β,18,21-trihydroxypregn-4-ene-3,20-dione18-Hydroxyprogesterone = 18-hydroxypregn-4-ene-3,20-dione 21-Deoxycortisol = 11β,17α-dihydroxypregn-4-ene-3,20-dione,21-Deoxycortisone = 17α-hydroxypregn-4-ene-3,11,20-trione21-Hydroxypregnenolone (prebediolone) = 3β,21-dihydroxypregn-5-en-20-oneAldosterone = 11β,21-dihydroxypregn-4-ene-3,18,20-trioneCorticosterone (17-deoxycortisol) = 11β,21-dihydroxypregn-4-ene-3,20-dioneCortisol (hydrocortisone) = 11β,17α,21-trihydroxypregn-4-ene-3,20-dioneCortisone = 17α,21-dihydroxypregn-4-ene-3,11,20-trionePregnenolone = pregn-5-en-3β-ol-20-oneProgesterone = pregn-4-ene-3,20-dioneThe glucocorticoid activity of progesterone and 17α-hydroxyprogesterone is very weak (>100-fold less than that of cortisol).
The above list includes precursors and intermediates in corticosteroid biosynthesis .
Synthetic
Progesterone-type
Flugestone (flurogestone) = 9α-fluoro-11β,17α-dihydroxypregn-4-ene-3,20-dioneFluorometholone = 6α-methyl-9α-fluoro-11β,17α-dihydroxypregna-1,4-diene-3,20-dioneMedrysone (hydroxymethylprogesterone) = 6α-methyl-11β-hydroxypregn-4-ene-3,20-dionePrebediolone acetate (21-acetoxypregnenolone) = 3β,21-dihydroxypregn-5-en-20-one 21-acetateIn addition to the above, various progesterone derivative progestins such as chlormadinone acetate , cyproterone acetate , medrogestone , medroxyprogesterone acetate , megestrol acetate , and segesterone acetate possess weak glucocorticoid activity which can manifest clinically at high dosages.
Hydrocortisone-type
Chloroprednisone = 6α-chloro-17α,21-dihydroxypregna-1,4-diene-3,11,20-trioneCloprednol = 6-chloro-11β,17α,21-trihydroxypregna-1,4,6-triene-3,20-dioneDifluprednate = 6α,9α-difluoro-11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione 17α-butyrate 21-acetateFludrocortisone = 9α-fluoro-11β,17α,21-trihydroxypregn-4-ene-3,20-dioneFluocinolone = 6α,9α-difluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dioneFluperolone = 9α-fluoro-11β,17α,21-trihydroxy-21-methylpregna-1,4-diene-3,20-dioneFluprednisolone = 6α-fluoro-11β,17α,21-trihydroxypregna-1,4-diene-3,20-dioneLoteprednol = 11β,17α,dihydroxy-21-oxa-21-chloromethylpregna-1,4-diene-3,20-dioneMethylprednisolone = 6α-methyl-11β,17α,21-trihydroxypregna-1,4-diene-3,20-dionePrednicarbate = 11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione 17α-ethylcarbonate 21-propionatePrednisolone = 11β,17α,21-trihydroxypregna-1,4-diene-3,20-dionePrednisone = 17α,21-dihydroxypregna-1,4-diene-3,11,20-trioneTixocortol = 11β,17α-dihydroxy-21-sulfanylpregn-4-ene-3,20-dioneTriamcinolone = 9α-fluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dioneMethasone-type (16-methylated)
Dexamethasone , one of the most widely used synthetic glucocorticoids.Methasone
Alclometasone = 7α-chloro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dioneBeclometasone = 9α-chloro-11β,17α,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dioneBetamethasone = 9α-fluoro-11β,17α,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dioneClobetasol = 9α-fluoro-11β,17α-dihydroxy-16β-methyl-21-chloropregna-1,4-diene-3,20-dioneClobetasone = 9α-fluoro-16β-methyl-17α-hydroxy-21-chloropregna-1,4-diene-3,11,20-trioneClocortolone = 6α-fluoro-9α-chloro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dioneDesoximetasone = 9α-fluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dioneDexamethasone = 9α-fluoro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dioneDiflorasone = 6α,9α-difluoro-11β,17α,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dioneDifluocortolone = 6α,9α-difluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dioneFluclorolone = 6α-fluoro-9α,11β-dichloro-16α,17α,21-trihydroxypregna-1,4-dien-3,20-dioneFlumetasone = 6α,9α-difluoro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dioneFluocortin = 6α-fluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20,21-trioneFluocortolone = 6α-fluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dioneFluprednidene = 9α-fluoro-11β,17α,21-trihydroxy-16-methylenepregna-1,4-diene-3,20-dioneFluticasone = 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-21-thia-21-fluoromethylpregna-1,4-dien-3,20-dioneFluticasone furoate = 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-21-thia-21-fluoromethylpregna-1,4-dien-3,20-dione 17α-(2-furoate)Halometasone = 2-chloro-6α,9α-difluoro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dioneMeprednisone = 16β-methyl-17α,21-dihydroxypregna-1,4-diene-3,11,20-trioneMometasone = 9α,21-dichloro-11β,17α-dihydroxy-16α-methylpregna-1,4-diene-3,20-dioneMometasone furoate = 9α,21-dichloro-11β,17α-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione 17α-(2-furoate)Paramethasone = 6α-fluoro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dionePrednylidene = 11β,17α,21-trihydroxy-16-methylenepregna-1,4-diene-3,20-dioneRimexolone = 11β-hydroxy-16α,17α,21-trimethylpregna-1,4-dien-3,20-dioneUlobetasol (halobetasol) = 6α,9α-difluoro-11β,17α-dihydroxy-16β-methyl-21-chloropregna-1,4-diene-3,20-dioneAcetonides and related
Amcinonide = 9α-fluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with cyclopentanone, 21-acetateBudesonide = 11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with butyraldehydeCiclesonide = 11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with (R)-cyclohexanecarboxaldehyde, 21-isobutyrateDeflazacort = 11β,21-dihydroxy-2'-methyl-5'H-pregna-1,4-dienooxazole-3,20-dione 21-acetateDesonide = 11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with acetoneFormocortal (fluoroformylone) = 3-(2-chloroethoxy)-9α-fluoro-11β,16α,17α,21-tetrahydroxy-20-oxopregna-3,5-diene-6-carboxaldehyde cyclic 16α,17α-acetal with acetone, 21-acetateFluclorolone acetonide (flucloronide) = 6α-fluoro-9α,11β-dichloro-16α,17α,21-trihydroxypregna-1,4-dien-3,20-dione cyclic 16α,17α-acetal with acetoneFludroxycortide (flurandrenolone, flurandrenolide) = 6α-fluoro-11β,16α,17α,21-tetrahydroxypregn-4-ene-3,20-dione cyclic 16α,17α-acetal with acetoneFlunisolide = 6α-fluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with acetoneFluocinolone acetonide = 6α,9α-difluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with acetoneFluocinonide = 6α,9α-difluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with acetone, 21-acetateHalcinonide = 9α-fluoro-11β,16α,17α-trihydroxy-21-chloropregn-4-ene-3,20-dione cyclic 16α,17α-acetal with acetoneTriamcinolone acetonide = 9α-fluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with acetoneOthers
Cortivazol = 6,16α-dimethyl-11β,17α,21-trihydroxy-2'-phenylpyrazolopregna-4,6-dien-20-one 21-acetateRU-28362 = 6-methyl-11β,17β-dihydroxy-17α-(1-propynyl)androsta-1,4,6-trien-3-oneSee also
References
Pijnenburg-Kleizen KJ, Engels M, Mooij CF, Griffin A, Krone N, Span PN, van Herwaarden AE, Sweep FC, Claahsen-van der Grinten HL (2015). "Adrenal Steroid Metabolites Accumulating in Congenital Adrenal Hyperplasia Lead to Transactivation of the Glucocorticoid Receptor" . Endocrinology . 156 (10): 3504–10. doi :10.1210/en.2015-1087 . PMID 26207344 .
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