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List of corticosteroids

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.

Steroid ring system.

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.

Note that the glucocorticoid activity of progesterone and 17α-hydroxyprogesterone is very weak (>100-fold less than that of cortisol).[1]

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.
  • 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-dieno[17,16-d]oxazole-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'-phenyl[3,2-c]pyrazolopregna-4,6-dien-20-one 21-acetate
  • RU-28362 = 6-methyl-11β,17β-dihydroxy-17α-(1-propynyl)androsta-1,4,6-trien-3-one

See also

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:10.1210/en.2015-1087. PMID 26207344.

list, corticosteroids, this, list, corticosteroids, glucocorticoids, mineralocorticoids, derivatives, cortisol, hydrocortisone, most, esters, these, corticosteroids, included, this, list, esters, here, instead, steroid, ring, system, most, common, structural, . 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 Steroid ring system The most common structural modifications in synthetic corticosteroids include 1 2 dehydrogenation 6a 9a 16a and 16b substitution with a halogen or methyl group 16a 17a acetonidation and 17a and 21 esterification Contents 1 Natural 2 Synthetic 2 1 Progesterone type 2 2 Hydrocortisone type 2 3 Methasone type 16 methylated 2 4 Acetonides and related 2 5 Others 3 See also 4 ReferencesNatural Edit 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 17a 21 dihydroxypregn 4 ene 3 20 dione 11 Ketoprogesterone 11 oxoprogesterone Ketogestin pregn 4 ene 3 11 20 trione 11b Hydroxypregnenolone 3b 11b dihydroxypregn 5 en 20 one 1 11b Hydroxyprogesterone 21 deoxycorticosterone 11b hydroxypregn 4 ene 3 20 dione 11b 17a 21 Trihydroxypregnenolone 3b 11b 17a 21 tetrahydroxypregn 5 en 20 one 2 17a 21 Dihydroxypregnenolone 3b 17a 21 trihydroxypregn 5 en 20 one 3 17a Hydroxypregnenolone 3b 17a dihydroxypregn 5 en 20 one 17a Hydroxyprogesterone 17a hydroxypregn 4 ene 3 11 20 trione 18 Hydroxy 11 deoxycorticosterone 18 21 dihydroxypregn 4 ene 3 20 dione 4 18 Hydroxycorticosterone 11b 18 21 trihydroxypregn 4 ene 3 20 dione 18 Hydroxyprogesterone 18 hydroxypregn 4 ene 3 20 dione 5 21 Deoxycortisol 11b 17a dihydroxypregn 4 ene 3 20 dione 21 Deoxycortisone 17a hydroxypregn 4 ene 3 11 20 trione 21 Hydroxypregnenolone prebediolone 3b 21 dihydroxypregn 5 en 20 one Aldosterone 11b 21 dihydroxypregn 4 ene 3 18 20 trione Corticosterone 17 deoxycortisol 11b 21 dihydroxypregn 4 ene 3 20 dione Cortisol hydrocortisone 11b 17a 21 trihydroxypregn 4 ene 3 20 dione Cortisone 17a 21 dihydroxypregn 4 ene 3 11 20 trione Pregnenolone pregn 5 en 3b ol 20 one Progesterone pregn 4 ene 3 20 dioneNote that the glucocorticoid activity of progesterone and 17a hydroxyprogesterone is very weak gt 100 fold less than that of cortisol 1 The above list includes precursors and intermediates in corticosteroid biosynthesis Synthetic EditProgesterone type Edit Flugestone flurogestone 9a fluoro 11b 17a dihydroxypregn 4 ene 3 20 dione Fluorometholone 6a methyl 9a fluoro 11b 17a dihydroxypregna 1 4 diene 3 20 dione Medrysone hydroxymethylprogesterone 6a methyl 11b hydroxypregn 4 ene 3 20 dione Prebediolone acetate 21 acetoxypregnenolone 3b 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 Edit Chloroprednisone 6a chloro 17a 21 dihydroxypregna 1 4 diene 3 11 20 trione Cloprednol 6 chloro 11b 17a 21 trihydroxypregna 1 4 6 triene 3 20 dione Difluprednate 6a 9a difluoro 11b 17a 21 trihydroxypregna 1 4 diene 3 20 dione 17a butyrate 21 acetate Fludrocortisone 9a fluoro 11b 17a 21 trihydroxypregn 4 ene 3 20 dione Fluocinolone 6a 9a difluoro 11b 16a 17a 21 tetrahydroxypregna 1 4 diene 3 20 dione Fluperolone 9a fluoro 11b 17a 21 trihydroxy 21 methylpregna 1 4 diene 3 20 dione Fluprednisolone 6a fluoro 11b 17a 21 trihydroxypregna 1 4 diene 3 20 dione Loteprednol 11b 17a dihydroxy 21 oxa 21 chloromethylpregna 1 4 diene 3 20 dione Methylprednisolone 6a methyl 11b 17a 21 trihydroxypregna 1 4 diene 3 20 dione Prednicarbate 11b 17a 21 trihydroxypregna 1 4 diene 3 20 dione 17a ethylcarbonate 21 propionate Prednisolone 11b 17a 21 trihydroxypregna 1 4 diene 3 20 dione Prednisone 17a 21 dihydroxypregna 1 4 diene 3 11 20 trione Tixocortol 11b 17a dihydroxy 21 sulfanylpregn 4 ene 3 20 dione Triamcinolone 9a fluoro 11b 16a 17a 21 tetrahydroxypregna 1 4 diene 3 20 dioneMethasone type 16 methylated Edit Dexamethasone one of the most widely used synthetic glucocorticoids Main article Methasone Alclometasone 7a chloro 11b 17a 21 trihydroxy 16a methylpregna 1 4 diene 3 20 dione Beclometasone 9a chloro 11b 17a 21 trihydroxy 16b methylpregna 1 4 diene 3 20 dione Betamethasone 9a fluoro 11b 17a 21 trihydroxy 16b methylpregna 1 4 diene 3 20 dione Clobetasol 9a fluoro 11b 17a dihydroxy 16b methyl 21 chloropregna 1 4 diene 3 20 dione Clobetasone 9a fluoro 16b methyl 17a hydroxy 21 chloropregna 1 4 diene 3 11 20 trione Clocortolone 6a fluoro 9a chloro 11b 21 dihydroxy 16a methylpregna 1 4 diene 3 20 dione Desoximetasone 9a fluoro 11b 21 dihydroxy 16a methylpregna 1 4 diene 3 20 dione Dexamethasone 9a fluoro 11b 17a 21 trihydroxy 16a methylpregna 1 4 diene 3 20 dione Diflorasone 6a 9a difluoro 11b 17a 21 trihydroxy 16b methylpregna 1 4 diene 3 20 dione Difluocortolone 6a 9a difluoro 11b 21 dihydroxy 16a methylpregna 1 4 diene 3 20 dione Fluclorolone 6a fluoro 9a 11b dichloro 16a 17a 21 trihydroxypregna 1 4 dien 3 20 dione Flumetasone 6a 9a difluoro 11b 17a 21 trihydroxy 16a methylpregna 1 4 diene 3 20 dione Fluocortin 6a fluoro 11b 21 dihydroxy 16a methylpregna 1 4 diene 3 20 21 trione Fluocortolone 6a fluoro 11b 21 dihydroxy 16a methylpregna 1 4 diene 3 20 dione Fluprednidene 9a fluoro 11b 17a 21 trihydroxy 16 methylenepregna 1 4 diene 3 20 dione Fluticasone 6a 9a difluoro 11b 17a dihydroxy 16a methyl 21 thia 21 fluoromethylpregna 1 4 dien 3 20 dione Fluticasone furoate 6a 9a difluoro 11b 17a dihydroxy 16a methyl 21 thia 21 fluoromethylpregna 1 4 dien 3 20 dione 17a 2 furoate Halometasone 2 chloro 6a 9a difluoro 11b 17a 21 trihydroxy 16a methylpregna 1 4 diene 3 20 dione Meprednisone 16b methyl 17a 21 dihydroxypregna 1 4 diene 3 11 20 trione Mometasone 9a 21 dichloro 11b 17a dihydroxy 16a methylpregna 1 4 diene 3 20 dione Mometasone furoate 9a 21 dichloro 11b 17a dihydroxy 16a methylpregna 1 4 diene 3 20 dione 17a 2 furoate Paramethasone 6a fluoro 11b 17a 21 trihydroxy 16a methylpregna 1 4 diene 3 20 dione Prednylidene 11b 17a 21 trihydroxy 16 methylenepregna 1 4 diene 3 20 dione Rimexolone 11b hydroxy 16a 17a 21 trimethylpregna 1 4 dien 3 20 dione Ulobetasol halobetasol 6a 9a difluoro 11b 17a dihydroxy 16b methyl 21 chloropregna 1 4 diene 3 20 dioneAcetonides and related Edit Amcinonide 9a fluoro 11b 16a 17a 21 tetrahydroxypregna 1 4 diene 3 20 dione cyclic 16a 17a acetal with cyclopentanone 21 acetate Budesonide 11b 16a 17a 21 tetrahydroxypregna 1 4 diene 3 20 dione cyclic 16a 17a acetal with butyraldehyde Ciclesonide 11b 16a 17a 21 tetrahydroxypregna 1 4 diene 3 20 dione cyclic 16a 17a acetal with R cyclohexanecarboxaldehyde 21 isobutyrate Deflazacort 11b 21 dihydroxy 2 methyl 5 H pregna 1 4 dieno 17 16 d oxazole 3 20 dione 21 acetate Desonide 11b 16a 17a 21 tetrahydroxypregna 1 4 diene 3 20 dione cyclic 16a 17a acetal with acetone Formocortal fluoroformylone 3 2 chloroethoxy 9a fluoro 11b 16a 17a 21 tetrahydroxy 20 oxopregna 3 5 diene 6 carboxaldehyde cyclic 16a 17a acetal with acetone 21 acetate Fluclorolone acetonide flucloronide 6a fluoro 9a 11b dichloro 16a 17a 21 trihydroxypregna 1 4 dien 3 20 dione cyclic 16a 17a acetal with acetone Fludroxycortide flurandrenolone flurandrenolide 6a fluoro 11b 16a 17a 21 tetrahydroxypregn 4 ene 3 20 dione cyclic 16a 17a acetal with acetone Flunisolide 6a fluoro 11b 16a 17a 21 tetrahydroxypregna 1 4 diene 3 20 dione cyclic 16a 17a acetal with acetone Fluocinolone acetonide 6a 9a difluoro 11b 16a 17a 21 tetrahydroxypregna 1 4 diene 3 20 dione cyclic 16a 17a acetal with acetone Fluocinonide 6a 9a difluoro 11b 16a 17a 21 tetrahydroxypregna 1 4 diene 3 20 dione cyclic 16a 17a acetal with acetone 21 acetate Halcinonide 9a fluoro 11b 16a 17a trihydroxy 21 chloropregn 4 ene 3 20 dione cyclic 16a 17a acetal with acetone Triamcinolone acetonide 9a fluoro 11b 16a 17a 21 tetrahydroxypregna 1 4 diene 3 20 dione cyclic 16a 17a acetal with acetoneOthers Edit Cortivazol 6 16a dimethyl 11b 17a 21 trihydroxy 2 phenyl 3 2 c pyrazolopregna 4 6 dien 20 one 21 acetate RU 28362 6 methyl 11b 17b dihydroxy 17a 1 propynyl androsta 1 4 6 trien 3 oneSee also EditList of steroids List of corticosteroid cyclic ketals List of corticosteroid estersReferences Edit 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 Retrieved from https en wikipedia org w index php title List of corticosteroids amp oldid 1080156486, wikipedia, wiki, book, books, library,

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