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Adapalene

Systematic (IUPAC) name
6-[3-(1-adamantyl)-4-methoxy-phenyl] naphthalene-2-carboxylic acid
Identifiers
CAS number	106685-40-9
ATC code	D10AD03
PubChem	60164
DrugBank	APRD00780
ChemSpider	54244
Chemical data
Formula	C28H28O3
Mol. mass	412.52 g/mol
SMILES	eMolecules & PubChem
Pharmacokinetic data
Bioavailability	Very low
Metabolism	?
Half life	?
Excretion	Biliary
Therapeutic considerations
Pregnancy cat.	C
Legal status	POM(UK) ℞-only(US)
Routes	Topical
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Adapalene is a third-generation topical retinoid primarily used in the treatment of mild-moderate acne and is also used (off-label) to treat keratosis pilaris as well as other skin conditions.^[1] Adapalene is marketed by Galderma under the trade names Differin in some countries, and Adaferin in India. In the United States, Adapalene is marketed as Differin and Epiduo. Epiduo also contains benzoyl peroxide. (Patient Drug Information, uptodate.com, August 2009).

Contents 1 Indications 2 History 3 Dosage 4 Available forms 5 Pharmacology 5.1 Drug interactions 5.2 Pharmacodynamics 5.3 Pharmacokinetics 6 References 7 External links

[edit] Indications

Adapalene is indicated for the topical treatment of acne vulgaris. It is possibly more effective than tretinoin 0.025% gel in the treatment of acne vulgaris.

[edit] History

Adapalene was approved in 1996 by the U.S. Food and Drug Administration (FDA) for use in the treatment of acne.

[edit] Dosage

Adapalene is applied once daily, after washing and before retiring. In some circumstances, when a patient complains of skin irritation, the application may be decreased to once every other day until the irritation ceases.

[edit] Available forms

In the United States, adapalene is available under the brand name Differin in three different preparations: 0.1% cream, 0.1% gel, and 0.3% gel.^[2] In Europe, only the 0.1% cream and 0.1% gel are available. In Pakistan, adapalene is available under the brand names Clear by Saffron Pharmaceuticals and Gallet by Pharma Health Pakistan, both of these are in the form of 0.1% cream.

[edit] Pharmacology

[edit] Drug interactions

Adapalene has been shown to enhance the efficacy of topical clindamycin, although adverse effects are also increased.^[3] Application of adapalene gel to the skin 3–5 minutes before application of clindamycin enhances penetration of clindamycin into the skin, which may enhance the overall efficacy of the treatment as compared to clindamycin alone.^[4]

Unlike tretinoin (Retin-A), adapalene has also been shown to retain its efficacy when applied at the same time as benzoyl peroxide due to its more stable chemical structure.^[5]

[edit] Pharmacodynamics

Adapalene in small concentrations is a moderator of cellular differentiation, keratinization, and inflammatory processes. It has both exfoliating and anti-inflammatory effects. The exact mode of action of adapalene is unknown.

[edit] Pharmacokinetics

Adapalene is applied topically to the skin, and its absorption into the blood through this medium is very low. Only trace amounts of adapalene have been found in the plasma of chronically treated patients.

[edit] References

[edit] External links

• Differin product insert
• Adapalene General Information, Patient Information, Contraindications and Interactions
• [www.epiduo.com/Includes/PDF/BriefSummary.pdf Epiduo Prescribing Information]

v • d • e Acne-treating agents (D10) Antibacterial agents Azelaic acid • Benzoyl peroxide • Blue light therapy • Tea tree oil Keratolytic agents Glycolic acid • Salicylic acid • Sulfur • Benzoyl peroxide Anti-inflammatory agents Aspirin • Ibuprofen • Red light therapy Antibiotics Clindamycin • Dapsone • Erythromycin • Sulfacetamide • Minocycline • Tetracyclines Hormonal Antiandrogens • Contraceptives Retinoids Adapalene • Isotretinoin • Tazarotene • Tretinoin Combination drugs ZIANA • Duac • BenzaClin • PLEXION • Epiduo