Adapalene

Adapalene
Clinical data
Trade namesDifferin, others
AHFS/Drugs.comMonograph
MedlinePlusa604001
License data
Pregnancy
category
  • AU: D
Routes of
administration		Topical
Drug classRetinoids
ATC code
Legal status
Legal status
Pharmacokinetic data
BioavailabilityVery low[medical citation needed]
ExcretionBile duct
Identifiers
  • 6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid
CAS Number
PubChem CID
IUPHAR/BPS
DrugBank
ChemSpider
UNII
KEGG
ChEBI
ChEMBL
CompTox Dashboard (EPA)
ECHA InfoCard100.149.379 Edit this at Wikidata
Chemical and physical data
FormulaC28H28O3
Molar mass412.529 g·mol−1
3D model (JSmol)
  • COC1=C(C=C(C=C1)C2=CC3=C(C=C2)C=C(C=C3)C(=O)O)C45CC6CC(C4)CC(C6)C5
  • InChI=InChI=1S/C28H28O3/c1-31-26-7-6-23(21-2-3-22-12-24(27(29)30)5-4-20(22)11-21)13-25(26)28-14-17-8-18(15-28)10-19(9-17)16-28/h2-7,11-13,17-19H,8-10,14-16H2,1H3,(H,29,30) checkY
  • Key:LZCDAPDĜCYOEH-UHFFFAOYSA-N checkY
  (verify)
Adapalene Gel, sold in trade name Differin in China

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.[6] Studies have found adapalene is as effective as other retinoids, while causing less irritation.[7] It also has several advantages over other retinoids. The adapalene molecule is more stable compared to tretinoin and tazarotene, which leads to less concern for photodegradation.[7] It is also chemically more stable compared to the other two retinoids, allowing it to be used in combination with benzoyl peroxide.[7] Due to its effects on keratinocyte proliferation and differentiation, adapalene is superior to tretinoin for the treatment of comedonal acne and is often used as a first-line agent.[8] The Swiss company Galderma sells adapalene under the brand name Differin.

  1. ^ Anvisa (31 March 2023). "RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial" [Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese). Diário Oficial da União (published 4 April 2023). Archived from the original on 3 August 2023. Retrieved 15 August 2023.
  2. ^ "Differin- adapalene gel". DailyMed. 7 December 2022. Retrieved 15 May 2024.
  3. ^ "Differin- adapalene cream". DailyMed. 31 October 2022. Retrieved 15 May 2024.
  4. ^ "Differin- adapalene gel". DailyMed. 27 December 2023. Retrieved 15 May 2024.
  5. ^ "Differin- adapalene lotion". DailyMed. 19 April 2023. Retrieved 15 May 2024.
  6. ^ Rolewski SL (October 2003). "Clinical review: topical retinoids". Dermatology Nursing. 15 (5): 447–50, 459–65. PMID 14619325.
  7. ^ a b c Tolaymat L, Dearborn H, Zito PM (June 2023). "Adapalene". StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing. PMID 29494115.
  8. ^ Asai Y, Baibergenova A, Dutil M, Humphrey S, Hull P, Lynde C, et al. (February 2016). "Management of acne: Canadian clinical practice guideline". CMAJ. 188 (2): 118–126. doi:10.1503/cmaj.140665. PMC 4732962. PMID 26573753.