Adapalene
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| 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 | |
| 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).
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[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
- ^ Rolewski S (2003). "Clinical review: topical retinoids". Dermatol Nurs 15 (5): 447–50, 459–65. PMID 14619325. http://www.medscape.com/viewarticle/464026.
- ^ About Differin
- ^ Wolf JE, Kaplan D, Kraus SJ, et al. (2003). "Efficacy and tolerability of combined topical treatment of acne vulgaris with adapalene and clindamycin: a multicenter, randomized, investigator-blinded study". J Am Acad Dermatol 49 (3 Suppl): S211–7. doi:. PMID 12963897.
- ^ Jain GK, Ahmed FJ (2007). "Adapalene pretreatment increases follicular penetration of clindamycin: in vitro and in vivo studies". Indian J Dermatol Venereol Leprol 73 (5): 326–9. doi:. PMID 17921613. Free full text
- ^ Martin B, Meunier C, Montels D, Watts O (October 1998). "Chemical stability of adapalene and tretinoin when combined with benzoyl peroxide in presence and in absence of visible light and ultraviolet radiation". Br J Dermatol 139 Suppl 52: 8–11. doi:. PMID 9990414.
[edit] External links
- Differin product insert
- Adapalene General Information, Patient Information, Contraindications and Interactions
- [www.epiduo.com/Includes/PDF/BriefSummary.pdf Epiduo Prescribing Information]
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