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Fluocortolone

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From Wikipedia, the free encyclopedia

Chemical compound

Not to be confused withFluclorolone orFluocortin.

Pharmaceutical compound

Fluocortolone
Clinical data

Other names	(6S,8S,9R,10S,11S,13S,14S,16R,17S)-6-fluoro-11-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,9,11,12,14,15,16,17-decahydrocyclopenta[a]phenanthren-3-one
Routes of administration	Ointment, suppositories
ATC code	C05AA08 (WHO) D07AC05 (WHO)H02AB03 (WHO)
Identifiers
IUPAC name (1S,2R,8S,10S,11S,13R,14S,15S,17S)-8-fluoro-17-hydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^2,7.0^11,15]heptadeca-3,6-dien-5-one
CAS Number	152-97-6^N
PubChemCID	9053
DrugBank	DB08971^N
ChemSpider	8701^Y
UNII	65VXC1MH0J
KEGG	D04218^Y
ChEMBL	ChEMBL251634^Y
CompTox Dashboard(EPA)	DTXSID00861835
ECHA InfoCard	100.005.284
Chemical and physical data
Formula	C₂₂H₂₉FO₄
Molar mass	376.468 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES O=C\1\C=C/[C@]4(/C(=C/1)[C@@H](F)C[C@@H]2[C@@H]4[C@@H](O)C[C@@]3([C@@H](C(=O)CO)[C@@H](C[C@@H]23)C)C)C
InChI InChI=1S/C22H29FO4/c1-11-6-14-13-8-16(23)15-7-12(25)4-5-21(15,2)20(13)17(26)9-22(14,3)19(11)18(27)10-24/h4-5,7,11,13-14,16-17,19-20,24,26H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19-,20-,21+,22+/m1/s1^Y Key:GAKMQHDJQHZUTJ-ULHLPKEOSA-N^Y
^NY (what is this?) (verify)

Fluocortolone is aglucocorticoid^[1] used in the treatment of several conditions, includinghemorrhoids.

It is similar tofluocortin, but with one lesscarbonyl group.

References

[edit]

^Munro DD, Wilson HT, Rhodes EL (November 1967)."Comparison of betamethasone 17-valerate ointment with fluocortolone and fluocortolone caproate ointment".British Medical Journal.4 (5574):275–6.doi:10.1136/bmj.4.5574.275.PMC 1748932.PMID 6054003.

Glucocorticoids andantiglucocorticoids (D07,H02)

Glucocorticoids

Natural

Synthetic

Cortisol-like and related (16-unsubstituted):Chloroprednisone
Cloprednol
Difluprednate
Fludrocortisone
Flugestone acetate (flurogestone acetate)
Fluocinolone
Fluorometholone
- Fluorometholone acetate
Fluperolone
- Fluperolone acetate
Fluprednisolone
- Fluprednisolone esters
Loteprednol (+tobramycin)
Medrysone
Methylprednisolone
- Methylprednisolone esters
Methylprednisolone aceponate
Prednicarbate
Prednisolone^#
Prednisone
Tixocortol
- Tixocortol pivalate

Methasones and related (16-substituted):Alclometasone
Beclometasone
- Beclometasone esters
Betamethasone^#
- Betamethasone esters
Clobetasol
- Clobetasol propionate
Clobetasone
Clocortolone
- Clocortolone esters
Cortivazol
Desoximetasone
Dexamethasone^#
- Dexamethasone esters
Diflorasone
Diflucortolone
- Diflucortolone valerate
Fluclorolone
Flumetasone
Fluocortin
Fluocortolone
- Fluocortolone esters
Fluprednidene acetate
Fluticasone
- Fluticasone furoate
- Fluticasone propionate
Halometasone
Meprednisone
Mometasone
- Mometasone furoate
Paramethasone
Prednylidene
Rimexolone
Triamcinolone
Ulobetasol (halobetasol)

Antiglucocorticoids

Synthesis modifiers

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

See also: Glucocorticoid receptor modulators; Mineralocorticoids and antimineralocorticoids; List of corticosteroids

Vasoprotectives (C05)

Antihemorrhoidals for topical use

corticosteroids	Hydrocortisone Prednisolone Betamethasone Fluorometholone Fluocortolone Dexamethasone Fluocinolone acetonide Fluocinonide
local anesthetics	Lidocaine Tetracaine Benzocaine Dibucaine Procaine Oxetacaine Pramocaine
other	Tribenoside

Antivaricose therapy

heparins orheparinoids for topical use	Organo-heparinoid Sodium apolate Heparin Pentosan polysulfate
sclerosing agents for local injection	Monoethanolamine oleate Polidocanol Inverted sugar syrup Sodium tetradecyl sulfate Phenol
other	Calcium dobesilate

Capillary stabilising agents

bioflavonoids	Rutoside Monoxerutin Diosmin Troxerutin Hidrosmin
other	Tribenoside Etamsylate

Glucocorticoid receptor modulators

GRTooltip Glucocorticoid receptor

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 (SEGRMsTooltip Selective glucocorticoid receptor agonists)	Dagrocorat Fosdagrocorat Mapracorat
Antagonists	7α-Hydroxy-DHEA 17α-Methylprogesterone Aglepristone Asoprisnil Asoprisnil ecamate C108297 C113176 CORT-108297 Cyproterone acetate Dazucorilant 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 Zavacorilant
Others	Antisense oligonucleotides:IONIS-GCCR_Rx (ISIS-426115)