16α-Methyl-11-oxoprednisolone

16α-Methyl-11-oxoprednisolone, also known as dexamethasone impurity J, is a synthetic glucocorticoid corticosteroid which was reported in 1979 and was never marketed.[1][2]

16α-Methyl-11-oxoprednisolone
Clinical data

Other names	Dexamethasone impurity J; 17α,21-Dihydroxy-16α-methylpregna-1,4-diene-3,11,20-trione
Drug class	Corticosteroid; Glucocorticoid
Identifiers
IUPAC name (8S,9S,10R,13S,14S,16R,17R)-17-Hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,12,14,15,16-octahydrocyclopenta[a]phenanthrene-3,11-dione
CAS Number	2036-77-3
PubChem CID	68141632
ChemSpider	48063904
Chemical and physical data
Formula	C₂₂H₂₈O₅
Molar mass	372.461 g/mol g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4([C@H]3C(=O)C[C@@]2([C@]1(C(=O)CO)O)C)C
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/h6-7,9,12,15-16,19,23,27H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,19-,20+,21+,22+/m1/s1 Key:PIDANAQULIKBQS-VUOZLLHNSA-N

References

Lutsky BN, Berkenkopf J, Fernandez X, Monahan M, Shue HJ, Tiberi RL, Green MJ (1979). "A novel class of potent topical antiinflammatory agents: 17-benzoylated, 7 alpha-halogeno substituted corticosteroids". Arzneimittelforschung. 29 (11): 1662–7. PMID 543873.
https://www.trc-canada.com/product-detail/?CatNum=M295350

Glucocorticoid receptor modulators

Agonists	Cortisol-like and related (16-unsubstituted): 3α,5α-Tetrahydrocorticosterone 5α-Dihydrocorticosterone 9α-Fluorocortisone (alfluorone) 11-Dehydrocorticosterone (11-oxocorticosterone, 17-deoxycortisone) 11-Dehydrocorticosterone acetate 11-Deoxycorticosterone (desoxycortone, deoxycortone, desoxycorticosterone) Desoxycortone esters 11-Deoxycortisol (cortodoxone, cortexolone) Cortifen (cortiphen, kortifen) Cortodoxone acetate 21-Deoxycortisol Δ⁷-Prednisolone Δ⁷-Prednisolone 21-acetate Amebucort Chloroprednisone Chloroprednisone acetate Cloprednol Cloprednol acetate Corticosterone Corticosterone acetate Corticosterone benzoate Cortisol (hydrocortisone) Benzodrocortisone (hydrocortisone benzoate) Hydrocortamate (hydrocortisone diethylaminoacetate) Hydrocortisone esters Cortisone Cortisone acetate Deprodone Deprodone propionate Dichlorisone Dichlorisone acetate Dichlorisone diacetate Difluprednate Endrisone (endrysone) Etiprednol Etiprednol dicloacetate (etiprednol dichloroacetate) Fludrocortisone (fludrocortone) Fludrocortisone acetate Fluorometholone Fluorometholone acetate Fluperolone Fluperolone acetate Fluprednisolone Fluprednisolone esters Halopredone Halopredone acetate (halopredone diacetate) Isoflupredone (9α-fluoroprednisolone) Isoflupredone acetate Loteprednol Mazipredone (depersolone) Medrysone Methylprednisolone Methylprednisolone esters Prebediolone Prebediolone acetate Prednisolone Prednazate Prednazoline Prednicarbate (prednisolone ethylcarbonate propionate) Prednimustine Prednisolamate (prednisolone diethylaminoacetate) Prednisolone esters Prednisone Prednisone esters Pregnenolone Pregnenolone acetate Pregnenolone succinate (pregnenolone hemisuccinate) Resocortol Tipredane Tixocortol Butixocort (tixocortol butyrate) Butixocort propionate Tixocortol pivalate Methasones and related (16-substituted): 16α-Methyl-11-oxoprednisolone Alclometasone Alclometasone dipropionate Amelometasone Beclometasone (beclomethasone) Beclometasone esters Betamethasone (betametasone) Betamethasone esters Cortobenzolone (betamethasone salicylate) Ciclometasone (ciclomethasone, cyclomethasone) Clobetasol Clobetasol propionate Clobetasone Clobetasone butyrate Clocortolone Clocortolone esters Cloticasone Cloticasone propionate Cormetasone (cormethasone) Cormetasone acetate Descinolone Desoximetasone (desoxymethasone) Dexamethasone (dexametasone) Dexamethasone esters Diflorasone Diflorasone diacetate Diflucortolone Diflucortolone pivalate Diflucortolone valerate Dimesone Dimesone acetate Doxibetasol (doxybetasol) Fluclorolone Flumetasone (flumethasone) Flumetasone acetate Flumetasone pivalate Fluocinolone Fluocortin Fluocortin butyl (fluocortin butylate) Fluocortolone Fluocortolone esters Fluprednidene (fluprednylidene) Fluprednidene acetate Fluticasone Fluticasone furoate Fluticasone propionate Halocortolone Halometasone Icometasone Icometasone enbutate (icometasone butyrate acetate) Isoprednidene Locicortolone (locicortone) Locicortolone dicibate (locicortone dicibate) Meclorisone Meclorisone dibutyrate Meprednisone (methylprednisone) Meprednisone acetate Meprednisone hydrogen succinate (methylprednisone hemisuccinate) Mometasone Mometasone furoate Paramethasone Paramethasone acetate Paramethasone disodium phosphate Paramethasone phosphate Prednylidene Prednylidene diethylaminoacetate Rimexolone Ticabesone Ticabesone propionate Timobesone Timobesone acetate Triamcinolone Triamcinolone diacetate Ulobetasol (halobetasol) Ulobetasol propionate Vamorolone Cyclic ketals (16,17-cyclized): Acrocinonide (triamcinolone acroleinide) Amcinafal (triamcinolone pentanonide) Amcinafide (triamcinolone acetophenide) Amcinonide (triamcinolone acetate cyclopentanonide) Budesonide Ciclesonide Cicortonide Deflazacort (azacort) Descinolone acetonide Desonide (hydroxyprednisolone acetonide) Desonide disodium phosphate Desonide pivalate Dexbudesonide Drocinonide Drocinonide phosphate Fluazacort Fluclorolone acetonide (flucloronide) Fludroxycortide (flurandrenolone, flurandrenolide) Flumoxonide Flunisolide Flunisolide acetate Fluocinolone acetonide Ciprocinonide (fluocinolone acetonide cyclopropylcarboxylate) Fluocinonide (fluocinolide, fluocinolone acetonide acetate) Procinonide (fluocinolone acetonide propionate) Formocortal Halcinonide Itrocinonide Rofleponide Rofleponide palmitate Tralonide Triamcinolone acetonide Flupamesone (triamcinolone acetonide metembonate) Triamcinolone acetonide esters Triamcinolone aminobenzal benzamidoisobutyrate (TBI-PAB) Triclonide Others/atypical (other expanded steroid ring systems, homosteroids, and non-pregnane steroids): Cortisuzol Cortivazol Domoprednate Naflocort Nicocortonide Nicocortonide acetate Nivacortol (nivazol) Oxisopred RU-26988 RU-28362 Non-corticosteroids with some glucocorticoid activity: 15β-Hydroxycyproterone acetate 17α-Hydroxyprogesterone Bromoketoprogesterone Chlormadinone acetate Cyproterone Cyproterone acetate Danazol Delmadinone acetate Desogestrel DU-41165 Etonogestrel Flugestone Flugestone acetate (flurogestone acetate) Fluoromedroxyprogesterone acetate Fluoxymesterone Gestodene Medrogestone Medroxyprogesterone acetate Megestrol acetate Metribolone Norgestomet Osaterone acetate Progesterone Promegestone RU-2309 Quingestrone Segesterone acetate (nestorone) Tetrahydrogestrinone Nonsteroidal glucocorticoids: AZD-5423 GSK-9027
Mixed (SEGRMs)	Dagrocorat Fosdagrocorat Mapracorat
Antagonists	7α-Hydroxy-DHEA 17α-Methylprogesterone Aglepristone Asoprisnil Asoprisnil ecamate C108297 C113176 CORT-108297 Cyproterone acetate Exicorilant (CORT-125281) Guggulsterone Ketoconazole Lilopristone LLY-2707 Metapristone (RU-42633) Miconazole Mifepristone (RU-486) Miricorilant (CORT-118335) Onapristone ORG-34116 ORG-34517 (SCH-900636) ORG-34850 Pregnenolone 16α-carbonitrile Relacorilant (CORT-125134) RTI 3021–012 RTI 3021–022 Telapristone Tibolone Toripristone Ulipristal acetate
Others	Antisense oligonucleotides: IONIS-GCCR_Rx (ISIS-426115)

See also: Receptor/signaling modulators; Glucocorticoids and antiglucocorticoids; Mineralocorticoid receptor modulators; List of corticosteroids

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