Adapalene

Adapalene
Clinical data
Trade names	Differin, others
AHFS/Drugs.com	Monograph
MedlinePlus	a604001
License data	US DailyMed: Adapalene;
Pregnancy; category	AU: D; ;
Routes of; administration	Topical
Drug class	Retinoids
ATC code	D10AD03 (WHO) ;
Legal status
Legal status	AU: S4 (Prescription only) / S3; BR: Class C2 (Retinoids); CA: ℞-only; UK: POM (Prescription only); US: OTC / Rx-only;
Pharmacokinetic data
Bioavailability	Very low[medical citation needed]
Excretion	Bile duct
Identifiers
	IUPAC name 6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid;
CAS Number	106685-40-9 ;
PubChem CID	60164;
IUPHAR/BPS	5429;
DrugBank	DB00210 ;
ChemSpider	54244 ;
UNII	1L4806J2QF;
KEGG	D01112 ;
ChEBI	CHEBI:31174 ;
ChEMBL	ChEMBL1265 ;
CompTox Dashboard (EPA)	DTXSID5046481 ;
ECHA InfoCard	100.149.379
Chemical and physical data
Formula	C28H28O3
Molar mass	412.529 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES 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=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) ; Key:LZCDAPDĜCYOEH-UHFFFAOYSA-N ;
	(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.^[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.

^ 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.
^ "Differin- adapalene gel". DailyMed. 7 December 2022. Retrieved 15 May 2024.
^ "Differin- adapalene cream". DailyMed. 31 October 2022. Retrieved 15 May 2024.
^ "Differin- adapalene gel". DailyMed. 27 December 2023. Retrieved 15 May 2024.
^ "Differin- adapalene lotion". DailyMed. 19 April 2023. Retrieved 15 May 2024.
^ Rolewski SL (October 2003). "Clinical review: topical retinoids". Dermatology Nursing. 15 (5): 447–50, 459–65. PMID 14619325.
^ ^a ^b ^c Tolaymat L, Dearborn H, Zito PM (June 2023). "Adapalene". StatPearls [Internet]. Treasure Island (FL): StatPearls Publishing. PMID 29494115.
^ 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.

[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.

[Differin_cream_FDA_label-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.

[Tolaymat-7] 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.

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