Flumetasone

Flumetasone
Systematic (IUPAC) name

(1R,2S,8S,10S,11S,13R,14R,15S,17S)-1,8-difluoro-14,17-dihydroxy-14-(2-hydroxyacetyl)-2,13,15-trimethyltetracyclo[8.7.0.0^2,7.0^11,15]heptadeca-3,6-dien-5-one
Clinical data
AHFS/Drugs.com	Micromedex Detailed Consumer Information
Routes of administration	Topical
Pharmacokinetic data
Metabolism	Hepatic, CYP3A4-mediated
Identifiers
CAS Number	2135-17-3^Y
ATC code	D07AB03 , D07XB01 (combinations), QH02AB90
PubChem	CID 16490
ChemSpider	15632
UNII	LR3CD8SX89^N
KEGG	D04208^Y
ChEBI	CHEBI:34764
ChEMBL	CHEMBL1201392^N
Synonyms	Flumethasone
Chemical data
Formula	C₂₂H₂₈F₂O₅
Molar mass	410.452 g/mol
SMILES C[C@@H]1C[C@H]2[C@@H]3C[C@@H](C4=CC(=O)C=C[C@@]4([C@]3([C@H](C[C@@]2([C@]1(C(=O)CO)O)C)O)F)C)F
InChI InChI=1S/C22H28F2O5/c1-11-6-13-14-8-16(23)15-7-12(26)4-5-19(15,2)21(14,24)17(27)9-20(13,3)22(11,29)18(28)10-25/h4-5,7,11,13-14,16-17,25,27,29H,6,8-10H2,1-3H3/t11-,13+,14+,16+,17+,19+,20+,21+,22+/m1/s1 Key:WXURHACBFYSXBI-GQKYHHCASA-N
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Flumetasone (INN; or flumethasone) is a corticosteroid for topical use. Trade names include Locacorten, Locorten, and Orsalin. It is available in combination with clioquinol, under the trade name Locacorten-Vioform (in some countries Locorten-Vioform), for the treatment of otitis externa and otomycosis. It is usually formulated as the pivalic acid ester prodrug flumetasone pivalate.

Flumethasone is 420 times as potent as cortisone in an animal model for anti-inflammatory activity.

References

Glucocorticoids and antiglucocorticoids (H02)

Glucocorticoids

Pregnene	Cortisone

Pregnenedione	Hydrocortisone (cortisol)^# (Hydrocortisone aceponate Hydrocortisone buteprate Hydrocortisone butyrate) Budesonide Ciclesonide Deflazacort Medrysone Tixocortol Halogenated at 6: Cloprednol Halogenated, with FG at 16: Halcinonide

Pregnadiene	Rimexolone Halogenated, with FG at 16: Flunisolide Triamcinolone Amcinonide Fluocinolone acetonide (Fluocinonide)

Pregnadienediol	Prednisone (Meprednisone) Halogenated at 9: Fluorometholone Halogenated, with FG at 16: Fluocortolone (Clocortolone Diflucortolone Fluocortin) Desoximetasone

Pregnadienetriol	Prednisolone^# (Methylprednisolone Methylprednisolone aceponate Prednicarbate Prednylidene) Desonide Halogenated: Fluprednisolone (Difluprednate Fluperolone) Halogenated, with FG at 16: Dexamethasone^# Betamethasone (Clobetasol Clobetasone Diflorasone Halometasone Ulobetasol) Beclometasone Paramethasone Alclometasone Fluclorolone acetonide Flumetasone Fluprednidene

Pregnatriene	Cortivazol

Androstene	Halogenated, with FG at 16: Fluticasone (Fluticasone propionate Fluticasone furoate)

Others/unsorted	Halogenated: Loteprednol Halogenated, with FG at 16: Fludroxycortide Formocortal Mometasone furoate Promestriene

Antiglucocorticoids

SGRMs: Dagrocorat^§
Fosdagrocorat^§
Mapracorat^†

Antagonists: Ketoconazole
Mifepristone

Synthesis modifiers

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

Glucocorticoid signaling

Receptor
(ligands)

Agonists	5α-Dihydrocorticosterone 11-Deoxycorticosterone (desoxycortone, cortexone) 11-Deoxycortisol (cortodoxone, cortexolone)) 15β-Hydroxycyproterone acetate 17-Hydroxyprogesterone 21-Deoxycortisol Acrocinonide Alclometasone Amcinafal Amcinafide Amcinonide Amebucort Amelometasone Amicinonide Anecortave AZD5423 Beclometasone Beclometasone dipropionate Betamethasone Betamethasone acibutate Betamethasone dipropionate Budesonide Butixocort Chlormadinone acetate Chloroprednisone Ciclesonide Cicortonide Ciprocinonide Clobetasol Clobetasol propionate Clobetasone Clocortolone Cloprednol Cloticasone Cormetasone Corticosterone Cortisone Cortisuzol Cortivazol Cyproterone Cyproterone acetate 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 Medroxyprogesterone acetate Megestrol acetate Medrysone Meprednisone Methylprednisolone Methylprednisolone aceponate Methylprednisolone suleptanate Mometasone Mometasone furoate Naflocort Nestorone Nicocortonide Nivacortol Oxisopred Paramethasone Prednazate Prednazoline Prednicarbate Prednimustine Prednisolamate Prednisolone Prednisolone steaglate Prednisone Prednylidene Procinonide Progesterone Promestriene Resocortol Rimexolone Rofleponide Tetrahydrocorticosterone Tetrahydrogestrinone Timobesone Tipredane Tixocortol Tixocortol pivalate Tralonide Triamcinolone Triamcinolone acetonide Triamcinolone benetonide Triamcinolone furetonide Triamcinolone hexacetonide Triclonide Ulobetasol (halobetasol)

Mixed (SEGRAs)	Dagrocorat Fosdagrocorat Mapracorat

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

Enzyme

Modulators	See here instead (modulators of 20,22-desmolase, 17α-hydroxylase/17,20-lyase, 3β-HSD, 11β-HSD, 21-hydroxylase, 11β-hydroxylase, and 18-hydroxylase).

Others

Precursors	Cholesterol 22R-Hydroxycholesterol 20α,22R-Dihydroxycholesterol Pregnenolone Pregnenolone sulfate 17-Hydroxypregnenolone Progesterone 17-Hydroxyprogesterone 11-Deoxycorticosterone

Indirect	ACTH (corticotropin) CRH DHEA DHEA sulfate Plasma proteins (albumin, transcortin) Vasopressin

See also: Androgenics • Estrogenics • Mineralocorticoids • Progestogenics

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