Chemistry:Alclometasone

Short description: Chemical compound

Alclometasone

Clinical data
Trade names	Aclovate
AHFS/Drugs.com	Monograph
MedlinePlus	a604021
Pregnancy category	US: C (Risk not ruled out)
Routes of administration	Topical
ATC code	D07AB10 (WHO) S01BA10 (WHO)
Legal status
Legal status	US: ℞-only
Pharmacokinetic data
Bioavailability	3% systemically (topical)
Metabolism	Hepatic
Onset of action	Eczema: 5.3 - 13.9 days; Psoriasis: 6.7 - 14.8 days
Identifiers
IUPAC name (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 Y
PubChem CID	5311000
DrugBank	DB00240 Y
ChemSpider	4470541 Y
UNII	136H45TB7B
ChEBI	CHEBI:53776 Y
ChEMBL	ChEMBL1201361 N
Chemical and physical data
Formula	C22H29ClO5
Molar mass	408.92 g·mol−1
3D model (JSmol)	Interactive image
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
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 a synthetic corticosteroid for topical dermatologic use, possessing anti-inflammatory, antipruritic, and vasoconstrictive properties.

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%