Alclometasone

Chemical compound
  • D07AB10 (WHO) S01BA10 (WHO)
Legal statusLegal status
  • US: ℞-only
Pharmacokinetic dataBioavailability3% systemically (topical)MetabolismHepaticOnset of actionEczema: 5.3 - 13.9 days; Psoriasis: 6.7 - 14.8 days [1]Identifiers
  • (7R,8S,9S,10R,11S,13S,14S,16R,17R)-7-Chloro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-7,8,9,11,12,14,15,16-octahydro-6H-cyclopenta[a]phenanthren-3-one
CAS Number
  • 67452-97-5 checkY
PubChem CID
  • 5311000
DrugBank
  • DB00240 checkY
ChemSpider
  • 4470541 checkY
UNII
  • 136H45TB7B
ChEBI
  • CHEBI:53776 checkY
ChEMBL
  • ChEMBL1201361 ☒N
Chemical and physical dataFormulaC22H29ClO5Molar mass408.92 g·mol−13D model (JSmol)
  • Interactive image
  • 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
  • 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 checkY
  • Key:FJXOGVLKCZQRDN-PHCHRAKRSA-N checkY
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Alclometasone is a synthetic corticosteroid for topical dermatologic use, possessing anti-inflammatory, antipruritic, and vasoconstrictive properties.[2]

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:

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:

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

  1. ^ "Alclometasone - Professional Patient Advice". Drugs.com. Retrieved 29 December 2017.
  2. ^ "Alclometasone - FDA Prescribing Information". Drugs.com. Retrieved 29 December 2017.
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Glucocorticoids and antiglucocorticoids
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List of corticosteroids