Adapalene

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Adapalene
Adapalene structure.svg
Adapalene-3D-balls.png
Clinical data
Trade names Differin, Teva, Pimpal, Gallet, Adelene, Adeferin
AHFS/Drugs.com Monograph
MedlinePlus a604001
License data
Pregnancy
category
  • AU: D
  • US: C (Risk not ruled out)
Routes of
administration
Topical
ATC code
Legal status
Legal status
Pharmacokinetic data
Bioavailability Very low
Excretion Biliary
Identifiers
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
ECHA InfoCard 100.149.379
Chemical and physical data
Formula C28H28O3
Molar mass 412.52 g/mol
3D model (JSmol)
  (verify)

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] It is effective against acne conditions where comedones are predominant.

Medical uses[edit]

It is used for the treatment of acne.[2]

Side effects[edit]

There is no evidence that the cream causes problems in the baby if used during pregnancy but this use has not been well studied.[2]

Interactions[edit]

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]

Pharmacology[edit]

Unlike the retinoid 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]

Pharmacokinetics[edit]

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.[6]

Pharmacodynamics[edit]

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.[7]

History[edit]

Adapalene is a research product of Galderma Laboratories, France.[8] Adapalene was approved in 1996 by the U.S. Food and Drug Administration (FDA) for use in the treatment of acne.[9]

Available forms[edit]

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.[10] The 0.1% gel is available as a generic made by Teva.[11][12] It is also available combined with benzoyl peroxide under the brand name Epiduo.[13] 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.[14] It is mostly available in 0.1% w/w gel form.

As of July 8, 2016, Galderma received approval from the U.S. Food and Drug Administration (FDA) for Differin Gel (adapalene gel 0.1%) as an over-the-counter (OTC) treatment for acne.[2]

References[edit]

  1. ^ Rolewski S (2003). "Clinical review: topical retinoids". Dermatol Nurs. 15 (5): 447–50, 459–65. PMID 14619325. 
  2. ^ a b c "FDA approves Differin Gel 0.1% for over-the-counter use to treat acne". July 8, 2016. Retrieved 14 July 2016. 
  3. ^ 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. 
  4. ^ 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. 
  5. ^ 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. 
  6. ^ "DIFFERIN® (adapalene) Cream, 0.1% Label" (PDF). FDA. May 25, 2000. Retrieved 4 Oct 2011. 
  7. ^ Czernielewski J, Michel S, Bouclier M, Baker M, Hensby C (December 2001). "Adapalene biochemistry and the evolution of a new topical retinoid for treatment of acne". J Eur Acad Dermatol Venereol. 15 (s3): 5–12. doi:10.1046/j.0926-9959.2001.00006.x. PMID 11843234. 
  8. ^ US Patent 4717720A, Shroot B, Eustache J, Bernardon J-M, "Benzonaphthalene derivatives and compositions", published 1988-01-05, issued 1988-01-05, assigned to Galderma Research and Development SNC 
  9. ^ "FDA approval of DIFFERIN® (adapalene) Solution, 0.1%". FDA. May 31, 1996. Retrieved 29 May 2017. 
  10. ^ About Differin Archived May 9, 2008, at the Wayback Machine.
  11. ^ "Teva Introduces Adapalene Gel, 0.1%". PharmQD. 4 June 2010. Retrieved 30 Aug 2011. 
  12. ^ Webber, Keith (2 June 2010). "FDA Approval Letter" (PDF). Department of Health and Human Services. Retrieved 30 August 2011. [permanent dead link]
  13. ^ "EPIDUO® (adapalene and benzoyl peroxide) Gel 0.1%/2.5% Approval Letter" (PDF). FDA. Dec 8, 2008. Retrieved 29 May 2017. 
  14. ^ http://www.drugsupdate.com/brand/generic/Adapalene/7099/none/2

External links[edit]