Alclometasone

Alclometasone
Systematic (IUPAC) name

[7-chloro-11-hydroxy-10,13,16-trimethyl-3-oxo-17-(2-propanoyloxyacetyl)-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-17-yl] propanoate
Clinical data
Trade names	Aclovate
AHFS/Drugs.com	monograph
MedlinePlus	a604021
Routes of administration	topical
Legal status	Rx Only (US)
Identifiers
CAS Number	66734-13-2^Y
ATC code	D07AB10 (WHO) S01BA10
PubChem	CID 5311000
DrugBank	DB00240^Y
ChemSpider	4470541^Y
UNII	136H45TB7B^Y
KEGG	D01820^Y
ChEBI	CHEBI:53776^Y
ChEMBL	CHEMBL1201361^N
Chemical data
Formula	C₂₈H₃₇ClO₇
Molar mass	521.042 g/mol
SMILES O=C\1\C=C/[C@]4(/C(=C/1)C[C@@H](Cl)[C@@H]2[C@@H]4[C@@H](O)C[C@@]3([C@@](O)(C(=O)CO)[C@@H](C[C@@H]23)C)C)C
InChI InChI=1S/C22H29ClO5/c1-11-6-14-18-15(23)8-12-7-13(25)4-5-20(12,2)19(18)16(26)9-21(14,3)22(11,28)17(27)10-24/h4-5,7,11,14-16,18-19,24,26,28H,6,8-10H2,1-3H3/t11-,14+,15-,16+,18-,19+,20+,21+,22+/m1/s1^Y Key:FJXOGVLKCZQRDN-PHCHRAKRSA-N^Y
^NY (what is this?) (verify)

Alclometasone is synthetic glucocorticoid steroid for topical use in dermatology as anti-inflammatory, antipruritic, antiallergic, antiproliferative and vasoconstrictive agent.

The prodrug alclometasone dipropionate is marketed as Aclovate by GlaxoSmithKline.

Pharmacology

Alclometasone inhibits phospholipase A2 by inducing production of lipocortins; inhibits synthesis of arachidonic acid, prostaglandins and leukotrienes acid, reduce release of cytokines from lymphocytes and others mediators of inflammation (incl. histamine).

Indications

Alclometasone cream and ointment are indicated for the relief of corticosteroid-responsive dermatoses, including:

atopic dermatitis
eczema
psoriasis
allergic dermatitis
contact dermatitis
actinic dermatitis
kiss-type allergy
skin itch

Alclometasone may be used on sensitive skin sites (face, skinfolds); in pediatric patients 1 year or older and in geriatric patients.

Contraindications

hypersensitivity to alclometasone or any of ingredients in pharmaceutical forms
cutaneous tuberculosis
chicken pox
perioral dermatitis
acne
rosacea
open wounds
trophic ulcers
viral infection of skin
skin manifestations of syphilis

Side effects

Adverse reactions (sometimes, less than 1-2% cases) include:

burning
itching
erythema
skin reddening
xerodermia
skin irritation
acne
hypopigmentation
prickly heat
folliculitis
white atrophy
hypertrichosis
reinfection of skin

How supplied

Alclometasone as Aclovate is supplied in:

Cream; Topical; 0.05%
Ointment; Topical; 0.05%

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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