Adapalene

Adapalene
Systematic (IUPAC) name
6-[3-(1-adamantyl)-4-methoxy-phenyl] naphthalene-2-carboxylic acid
Clinical data
Trade names Differin, Teva, Pimpal, Gallet, Adelene, Adeferin
AHFS/Drugs.com monograph
MedlinePlus a604001
Licence data US FDA:link
  • AU: D
  • US: C (Risk not ruled out)
Topical
Pharmacokinetic data
Bioavailability Very low
Excretion Biliary
Identifiers
106685-40-9 Yes
D10AD03
PubChem CID 60164
DrugBank DB00210 Yes
ChemSpider 54244 Yes
UNII 1L4806J2QF Yes
KEGG D01112 Yes
ChEBI CHEBI:31174 Yes
ChEMBL CHEMBL1265 Yes
Chemical data
Formula C28H28O3
412.52 g/mol
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Adapalene is a second-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] It is effective against acne conditions where comedones are predominant.

History

Adapalene is a research product of Galderma Laboratories, France. Adapalene was approved in 1996 by the U.S. Food and Drug Administration (FDA) for use in the treatment of acne. Generics are now available in US and India

Mechanism of action

Unlike tretinoin, adapalene inhibits keratinocyte differentiation. This inhibition of keratinocyte differentiation and proliferation is responsible for adapalene’s comedolytic effect. It has both exfoliating and anti-inflammatory effects. In an in vivo study, adapalene’s ability to reduce comedo formation was demonstrated by a 50–60% reduction in comedo counts compared with vehicle.

Available forms

Tube of generic adapalene

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] The 0.1% gel is available as a generic made by Teva.[3][4] It is also available combined with benzoyl peroxide under the brand name Epiduo.[5] In Europe, only the 0.1% cream and 0.1% gel are available. Adapalene is currently marketed by Galderma under the trade names Differin in some countries, and Adaferin in India.[6] It is mostly available in 0.1% w /w gel form.

Pharmacology

Drug interactions

Adapalene has been shown to enhance the efficacy of topical clindamycin, although adverse effects are also increased.[7] 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.[8]

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.[9]

Pharmacokinetics

Absorption of adapalene through the skin is low. A study with six acne patients treated once daily for five days with two grams of adapalene cream applied to 1000 cm² of skin found no quantifiable amounts, or less than 0.35 ng/mL of the drug, in the patients' blood plasma.[10]

References

  1. ↑ Rolewski S (2003). "Clinical review: topical retinoids". Dermatol Nurs 15 (5): 447–50, 459–65. PMID 14619325.
  2. ↑ About Differin
  3. ↑ "Teva Introduces Adapalene Gel, 0.1%". PharmQD. 4 June 2010. Retrieved 30 Aug 2011.
  4. ↑ Webber, Keith (2 June 2010). "FDA Approval Letter" (PDF). Department of Health and Human Services. Retrieved 30 August 2011.
  5. ↑ http://www.webmd.com/news/20090106/fda-oks-new-acne-gel-epiduo
  6. ↑ http://www.drugsupdate.com/brand/generic/Adapalene/7099/none/2
  7. ↑ 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:10.1067/S0190-9622(03)01152-6. PMID 12963897.
  8. ↑ 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:10.4103/0378-6323.34010. PMID 17921613.
  9. ↑ 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:10.1046/j.1365-2133.1998.1390s2008.x. PMID 9990414.
  10. ↑ "DIFFERIN® (adapalene) Cream, 0.1% Label" (PDF). FDA. May 25, 2000. Retrieved 4 Oct 2011.

External links