Prednylidene

Prednylidene
Clinical data

ATC code	H02AB11 (WHO)
Identifiers
IUPAC name (11β)-11,17,21-trihydroxy-16-methylenepregna-1,4-diene-3,20-dione
Synonyms	(8S,9S,10R,11S,13S,14S,17R)-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13-dimethyl-16-methylidene-6,7,8,9,11,12,14,15-octahydrocyclopenta[a]phenanthren-3-one
CAS Number	599-33-7^N
PubChem (CID)	20055008
ChemSpider	16735979^Y
UNII	IF8PQP966U^Y
ECHA InfoCard	100.009.060
Chemical and physical data
Formula	C₂₂H₂₈O₅
Molar mass	372.455
3D model (Jmol)	Interactive image
SMILES OCC(=O)[C@@]2(O)C(=C)C[C@H]3[C@@H]4CC\C1=C\C(=O)\C=C/[C@]1(C)[C@H]4[C@@H](O)C[C@]23C
InChI InChI=1S/C22H28O5/c1-12-8-16-15-5-4-13-9-14(24)6-7-20(13,2)19(15)17(25)10-21(16,3)22(12,27)18(26)11-23/h6-7,9,15-17,19,23,25,27H,1,4-5,8,10-11H2,2-3H3/t15-,16-,17-,19+,20-,21-,22-/m0/s1^Y Key:WSVOMANDJDYYEY-CWNVBEKCSA-N^Y
^NY (what is this?) (verify)

Prednylidene is a glucocorticoid^[1] for systemic use.

Substitution at position 16 also leads to more potent corticosteroids. The additional steric bulk introduced by such substituents adjacent to the dihydroxyacetone side chain also protects that moiety against metabolic degradation.

References

↑ Buttgereit F, Brand MD, Burmester GR (July 1999). "Equivalent doses and relative drug potencies for non-genomic glucocorticoid effects: a novel glucocorticoid hierarchy". Biochem. Pharmacol. 58 (2): 363–8. doi:10.1016/S0006-2952(99)00090-8. PMID 10423179.

Glucocorticoids and antiglucocorticoids (H02)

Glucocorticoids

Natural	Cortisone Cortodoxone (cortexolone, 11-deoxycortisol) Desoxycortone (deoxycortone, cortexone, 11-deoxycorticosterone) Hydrocortisone (cortisol)^# Hydrocortisone aceponate Hydrocortisone buteprate Hydrocortisone butyrate

Synthetic	Progesterone-type: Flugestone acetate (flurogestone acetate) Fluorometholone Fluorometholone acetate Medrysone Prebediolone acetate Pregnenolone Pregnenolone acetate Pregnenolone succinate Hydrocortisone-type: Chloroprednisone Cloprednol Difluprednate Fludrocortisone Fluocinolone Fluperolone Fluperolone acetate Fluprednisolone Loteprednol Methylprednisolone Methylprednisolone aceponate Methylprednisolone acetate Methylprednisolone suleptanate Prednicarbate Prednisolone Prednisone Tixocortol Tixocortol pivalate Triamcinolone Methasone-type (16-methylated): Alclometasone Beclometasone Beclometasone dipropionate Betamethasone Betamethasone dipropionate Clobetasol Clobetasol propionate Clobetasone Clocortolone Cortivazol Desoximetasone Dexamethasone Dexamethasone acefurate Dexamethasone isonicotinate Diflorasone Difluocortolone Difluocortolone valerate Fluclorolone Flumetasone Fluocortin Fluocortolone Fluprednidene Fluprednidene acetate Fluticasone Fluticasone propionate Halometasone Meprednisone Mometasone Paramethasone Prednylidene Rimexolone Ulobetasol (halobetasol) Acetonides and related: Amcinonide Budesonide Ciclesonide Deflazacort Desonide Formocortal (fluoroformylone) Fluclorolone acetonide (flucloronide) Fludroxycortide (flurandrenolone, flurandrenolide) Flunisolide Fluocinolone acetonide Fluocinonide Fluticasone furoate Halcinonide Mometasone furoate Triamcinolone acetonide Triamcinolone benetonide Triamcinolone furetonide Triamcinolone hexacetonide

Antiglucocorticoids

SGRMs: Dagrocorat^§
Fosdagrocorat^§
Mapracorat^†

Antagonists: Ketoconazole
Mifepristone

Synthesis modifiers

^#WHO-EM
^‡Withdrawn from market
Clinical trials:
- ^†Phase III
- ^§Never to phase III

See also: Androgens and antiandrogens • Estrogens and antiestrogens • Progestogens and antiprogestogens • Mineralocorticoids and antimineralocorticoids

Glucocorticoid receptor modulators

Agonists	Corticosteroids: 3α,5α-Tetrahydrocorticosterone 5α-Dihydrocorticosterone 11-Deoxycorticosterone (desoxycortone, cortexone) 11-Deoxycortisol (cortodoxone, cortexolone)) 17α-Hydroxyprogesterone 21-Deoxycortisol Acrocinonide Alclometasone Amcinafal Amcinafide Amcinonide Amebucort Amelometasone Amicinonide AZD5423 Beclometasone Beclometasone dipropionate Betamethasone Betamethasone acibutate Betamethasone dipropionate Budesonide Butixocort Chloroprednisone Ciclesonide Cicortonide Ciprocinonide Clobetasol Clobetasol propionate Clobetasone Clocortolone Cloprednol Cloticasone Cormetasone Corticosterone Cortisone Cortisuzol Cortivazol Deflazacort Deprodone Descinolone Desonide Desoximetasone Dexbudesonide Dexamethasone Dexamethasone acefurate Dexamethasone cipecilate Dexamethasone isonicotinate Dichlorisone Diflorasone Difluocortolone Difluocortolone valerate Difluprednate Domoprednate Doxibetasol Drocinonide Etiprednol dicloacetate Fluazacort Fluclorolone Fluclorolone (flucloronide) Fludrocortisone Fludroxycortide Flumoxonide Flumetasone Flunisolide Fluocinolone Fluocinolone acetonide Fluocinonide Fluocortin Fluocortolone Fluorometholone Fluperolone Fluperolone acetate Fluprednidene Fluprednidene acetate Fluprednisolone Fluticasone Fluticasone furoate Fluticasone propionate Formocortal GSK-9027 Halcinonide Halocortolone Halometasone Halopredone Hydrocortamate Hydrocortisone (cortisol) Hydrocortisone aceponate Hydrocortisone buteprate Hydrocortisone-17-butyrate Hydrocortisone-21-butyrate Icometasone enbutate Isoflupredone Isoprednidene Itrocinonide Locicortolone dicibate Loteprednol Mazipredone Meclorisone Medrysone Meprednisone Methylprednisolone Methylprednisolone aceponate Methylprednisolone acetate Methylprednisolone suleptanate Mometasone Mometasone furoate Naflocort Nicocortonide Nivacortol Oxisopred Paramethasone Prebediolone Prebediolone acetate Prednazate Prednazoline Prednicarbate Prednimustine Prednisolamate Prednisolone Prednisolone steaglate Prednisone Prednylidene Pregnenolone Pregnenolone acetate Pregnenolone succinate Procinonide Resocortol Rimexolone Rofleponide RU-28362 Timobesone Tipredane Tixocortol Tixocortol pivalate Tralonide Triamcinolone Triamcinolone acetonide Triamcinolone benetonide Triamcinolone furetonide Triamcinolone hexacetonide Triclonide Ulobetasol (halobetasol) Vamorolone Other steroids: 15β-Hydroxycyproterone acetate 17α-Hydroxyprogesterone Chlormadinone acetate Cyproterone Cyproterone acetate Delmadinone acetate Flugestone Flugestone acetate (flurogestone acetate) Fluoxymesterone Gestodene Medrogestone Medroxyprogesterone acetate Megestrol acetate Metribolone Norgestomet Osaterone acetate Progesterone Promegestone Quingestrone Segesterone acetate (nestorone) Tetrahydrogestrinone

Mixed (SEGRAs)	Dagrocorat Fosdagrocorat Mapracorat

Antagonists	3α-Hydroxytibolone 3β-Hydroxytibolone 7α-Hydroxy-DHEA 17α-Methylprogesterone Aglepristone Asoprisnil C108297 C113176 CORT-108297 Cyproterone acetate Formebolone Guggulsterone Ketoconazole Lilopristone LLY-2707 Miconazole Mifepristone Onapristone ORG-34116 ORG-34517 (SCH-900636) ORG-34850 Pregnenolone 16α-carbonitrile Telapristone Tibolone Toripristone Ulipristal acetate

See also: Androgenics • Estrogenics • Mineralocorticoidics • Progestogenics • Steroid hormone metabolism modulators

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