Tue . 18 Nov 2018

List of corticosteroids

list of corticosteroids, list of corticosteroids medications
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 12-dehydrogenation, 6α-, 9α-, 16α-, and 16β-substitution with a halogen or methyl group, 16α,17α-acetonidation, and 17α- and 21-esterification

Contents

  • 1 Natural
  • 2 Synthetic
    • 21 Progesterone-type
    • 22 Hydrocortisone-type
    • 23 Methasone-type 16-methylated
    • 24 Acetonides and related
    • 25 Others
  • 3 See also
  • 4 References

Natural

Cortisol hydrocortisone, the major endogenous glucocorticoid
  • 11-Dehydrocorticosterone 11-oxocorticosterone, 17-deoxycortisone = 21-hydroxypregn-4-ene-3,11,20-trione
  • 11-Deoxycorticosterone deoxycortone, desoxycortone; 21-hydroxyprogesterone = 21-hydroxypregn-4-ene-3,20-dione
  • 11-Deoxycortisol cortodoxone, cortexolone = 17α,21-dihydroxypregn-4-ene-3,20-dione
  • 11-Ketoprogesterone 11-oxoprogesterone; Ketogestin = pregn-4-ene-3,11,20-trione
  • 11β-Hydroxypregnenolone = 3β,11β-dihydroxypregn-5-en-20-one
  • 11β-Hydroxyprogesterone 21-deoxycorticosterone = 11β-hydroxypregn-4-ene-3,20-dione
  • 11β,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-one
  • 17α-Hydroxyprogesterone = 17α-hydroxypregn-4-ene-3,11,20-trione
  • 18-Hydroxy-11-deoxycorticosterone = 18,21-dihydroxypregn-4-ene-3,20-dione
  • 18-Hydroxycorticosterone = 11β,18,21-trihydroxypregn-4-ene-3,20-dione
  • 18-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-trione
  • 21-Hydroxypregnenolone prebediolone = 3β,21-dihydroxypregn-5-en-20-one
  • Aldosterone = 11β,21-dihydroxypregn-4-ene-3,18,20-trione
  • Corticosterone 17-deoxycortisol = 11β,21-dihydroxypregn-4-ene-3,20-dione
  • Cortisol hydrocortisone = 11β,17α,21-trihydroxypregn-4-ene-3,20-dione
  • Cortisone = 17α,21-dihydroxypregn-4-ene-3,11,20-trione
  • Pregnenolone = pregn-5-en-3β-ol-20-one
  • Progesterone = pregn-4-ene-3,20-dione

Note that the 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-dione
  • Fluorometholone = 6α-methyl-9α-fluoro-11β,17α-dihydroxypregna-1,4-diene-3,20-dione
  • Medrysone hydroxymethylprogesterone = 6α-methyl-11β-hydroxypregn-4-ene-3,20-dione
  • Prebediolone acetate 21-acetoxypregnenolone = 3β,21-dihydroxypregn-5-en-20-one 21-acetate

In 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-trione
  • Cloprednol = 6-chloro-11β,17α,21-trihydroxypregna-1,4,6-triene-3,20-dione
  • Difluprednate = 6α,9α-difluoro-11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione 17α-butyrate 21-acetate
  • Fludrocortisone = 9α-fluoro-11β,17α,21-trihydroxypregn-4-ene-3,20-dione
  • Fluocinolone = 6α,9α-difluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione
  • Fluperolone = 9α-fluoro-11β,17α,21-trihydroxy-21-methylpregna-1,4-diene-3,20-dione
  • Fluprednisolone = 6α-fluoro-11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione
  • Loteprednol = 11β,17α,dihydroxy-21-oxa-21-chloromethylpregna-1,4-diene-3,20-dione
  • Methylprednisolone = 6α-methyl-11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione
  • Prednicarbate = 11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione 17α-ethylcarbonate 21-propionate
  • Prednisolone = 11β,17α,21-trihydroxypregna-1,4-diene-3,20-dione
  • Prednisone = 17α,21-dihydroxypregna-1,4-diene-3,11,20-trione
  • Tixocortol = 11β,17α-dihydroxy-21-sulfanylpregn-4-ene-3,20-dione
  • Triamcinolone = 9α-fluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione

Methasone-type 16-methylated

Dexamethasone, one of the most widely used synthetic glucocorticoids Main article: Methasone
  • Alclometasone = 7α-chloro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione
  • Beclometasone = 9α-chloro-11β,17α,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione
  • Betamethasone = 9α-fluoro-11β,17α,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione
  • Clobetasol = 9α-fluoro-11β,17α-dihydroxy-16β-methyl-21-chloropregna-1,4-diene-3,20-dione
  • Clobetasone = 9α-fluoro-16β-methyl-17α-hydroxy-21-chloropregna-1,4-diene-3,11,20-trione
  • Clocortolone = 6α-fluoro-9α-chloro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione
  • Desoximetasone = 9α-fluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione
  • Dexamethasone = 9α-fluoro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione
  • Diflorasone = 6α,9α-difluoro-11β,17α,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione
  • Difluocortolone = 6α,9α-difluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione
  • Fluclorolone = 6α-fluoro-9α,11β-dichloro-16α,17α,21-trihydroxypregna-1,4-dien-3,20-dione
  • Flumetasone = 6α,9α-difluoro-11β,17α,21-trihydroxy-16α-methylpregna-1,4-diene-3,20-dione
  • Fluocortin = 6α-fluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20,21-trione
  • Fluocortolone = 6α-fluoro-11β,21-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione
  • Fluprednidene = 9α-fluoro-11β,17α,21-trihydroxy-16-methylenepregna-1,4-diene-3,20-dione
  • Fluticasone = 6α,9α-difluoro-11β,17α-dihydroxy-16α-methyl-21-thia-21-fluoromethylpregna-1,4-dien-3,20-dione
  • Fluticasone 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-dione
  • Meprednisone = 16β-methyl-17α,21-dihydroxypregna-1,4-diene-3,11,20-trione
  • Mometasone = 9α,21-dichloro-11β,17α-dihydroxy-16α-methylpregna-1,4-diene-3,20-dione
  • Mometasone 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-dione
  • Prednylidene = 11β,17α,21-trihydroxy-16-methylenepregna-1,4-diene-3,20-dione
  • Rimexolone = 11β-hydroxy-16α,17α,21-trimethylpregna-1,4-dien-3,20-dione
  • Ulobetasol halobetasol = 6α,9α-difluoro-11β,17α-dihydroxy-16β-methyl-21-chloropregna-1,4-diene-3,20-dione

Acetonides and related

  • Amcinonide = 9α-fluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with cyclopentanone, 21-acetate
  • Budesonide = 11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with butyraldehyde
  • Ciclesonide = 11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with R-cyclohexanecarboxaldehyde, 21-isobutyrate
  • Deflazacort = 11β,21-dihydroxy-2'-methyl-5'H-pregna-1,4-dienooxazole-3,20-dione 21-acetate
  • Desonide = 11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with acetone
  • Formocortal 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-acetate
  • Fluclorolone acetonide flucloronide = 6α-fluoro-9α,11β-dichloro-16α,17α,21-trihydroxypregna-1,4-dien-3,20-dione cyclic 16α,17α-acetal with acetone
  • Fludroxycortide flurandrenolone, flurandrenolide = 6α-fluoro-11β,16α,17α,21-tetrahydroxypregn-4-ene-3,20-dione cyclic 16α,17α-acetal with acetone
  • Flunisolide = 6α-fluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with acetone
  • Fluocinolone acetonide = 6α,9α-difluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with acetone
  • Fluocinonide = 6α,9α-difluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with acetone, 21-acetate
  • Halcinonide = 9α-fluoro-11β,16α,17α-trihydroxy-21-chloropregn-4-ene-3,20-dione cyclic 16α,17α-acetal with acetone
  • Triamcinolone acetonide = 9α-fluoro-11β,16α,17α,21-tetrahydroxypregna-1,4-diene-3,20-dione cyclic 16α,17α-acetal with acetone

Others

  • Cortivazol = 6,16α-dimethyl-11β,17α,21-trihydroxy-2'-phenylpyrazolopregna-4,6-dien-20-one 21-acetate
  • RU-28362 = 6-methyl-11β,17β-dihydroxy-17α-1-propynylandrosta-1,4,6-trien-3-one

See also

  • List of steroids
  • List of corticosteroid cyclic ketals
  • List of corticosteroid esters

References

  1. ^ 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:101210/en2015-1087 PMID 26207344 

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List of corticosteroids


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    List of corticosteroids beatiful post thanks!

    29.10.2014


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