View source for Alclometasone

{{short description|Chemical compound}}
{{cs1 config|name-list-style=vanc|display-authors=6}}
{{refimprove|date=November 2018}}
{{Drugbox
| Verifiedfields = changed
| Watchedfields = changed
| verifiedrevid = 477316653
| IUPAC_name = (7''R'',8''S'',9''S'',10''R'',11''S'',13''S'',14''S'',16''R'',17''R'')-7-Chloro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,9,11,12,14,15,16-octahydro-6''H''-cyclopenta[''a'']phenanthren-3-one
| image = Alclometasone.svg

<!--Clinical data-->
| tradename = Aclovate
| Drugs.com = {{drugs.com|monograph|aclovate}}
| MedlinePlus = a604021
| pregnancy_US = C
| legal_US = Rx only
| routes_of_administration = Topical

<!--Pharmacokinetic data-->
| bioavailability = 3% systemically (topical)
| metabolism = Hepatic
| onset = Eczema: 5.3 - 13.9 days; Psoriasis: 6.7 - 14.8 days
<ref name=PPA>{{cite web|url=https://www.drugs.com/ppa/alclometasone.html|title=Alclometasone - Professional Patient Advice|website=Drugs.com|access-date=29 December 2017}}</ref>

<!--Identifiers-->
| CAS_number_Ref = {{cascite|correct|??}}
| CAS_number = 67452-97-5
| ATC_prefix = D07
| ATC_suffix = AB10
| ATC_supplemental =  {{ATC|S01|BA10}}
| PubChem = 5311000
| DrugBank_Ref = {{drugbankcite|correct|drugbank}}
 | DrugBank = DB00240
| ChemSpiderID_Ref = {{chemspidercite|correct|chemspider}}
| ChemSpiderID = 4470541
| UNII_Ref = {{fdacite|correct|FDA}}
| UNII = 136H45TB7B
| KEGG_Ref = 
| KEGG = 
| ChEBI_Ref = {{ebicite|correct|EBI}}
| ChEBI = 53776
| ChEMBL_Ref = {{ebicite|changed|EBI}}
| ChEMBL = 1201361

<!--Chemical data-->
| C=22 | H=29 | Cl=1 | O=5 
| smiles = C[C@@H]1C[C@H]2[C@@H]3[C@@H](CC4=CC(=O)C=C[C@@]4([C@H]3[C@H](C[C@@]2([C@]1(C(=O)CO)O)C)O)C)Cl
| StdInChI_Ref = {{stdinchicite|correct|chemspider}}
| StdInChI =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
| StdInChIKey_Ref = {{stdinchicite|correct|chemspider}}
| StdInChIKey = FJXOGVLKCZQRDN-PHCHRAKRSA-N
}}

'''Alclometasone''' is a synthetic [[corticosteroid]] for topical dermatologic use, possessing anti-inflammatory, antipruritic, and vasoconstrictive properties.<ref name=FDA-PI>{{cite web|url=https://www.drugs.com/pro/alclometasone.html|title=Alclometasone - FDA Prescribing Information|website=Drugs.com|access-date=29 December 2017}}</ref><ref name="pmid3574236">{{cite journal | vauthors = ((No authors listed)) | title = Alclometasone--another topical corticosteroid | journal = The Medical Letter on Drugs and Therapeutics | volume = 29 | issue = 738 | pages = 42–43 | date = April 1987 | pmid = 3574236 | doi = | url = }}</ref>

The [[prodrug]] '''alclometasone dipropionate''' was originally marketed under the brand name '''Aclovate''' by [[GlaxoSmithKline]] as a topical cream and ointment. However, generic versions of the drug are available.

==Medical uses==
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

==Pharmacology==
Alclometasone induces the production of lipocortins, formally known as [[annexins]], which inhibit [[phospholipase A2]] – the enzyme responsible for the synthesis of [[arachidonic acid]]. Without the oxidation of arachidonic acid, [[eicosanoids]], such as [[prostaglandins]], [[thromboxanes]], and [[leukotrienes]], can't be produced.

Alclometasone also inhibits the release of pro-inflammatory mediators from leukocytes (e.g., [[cytokines]], [[histamine]], leukotrienes, [[serotonin]]).

==Formulations==
Alclometasone as Aclovate is supplied in:
* Cream; Topical; 0.05%
* Ointment; Topical; 0.05%

==References==
<references />

{{Glucocorticoids}}
{{Glucocorticoidics}}

[[Category:Glucocorticoids]]
[[Category:Organochlorides]]