Adapalene

Structural formula
General
Non-proprietary name	Adapalene
other names	6- [3- (1-Adamantyl) -4-methoxyphenyl] -naphthalene-2-carboxylic acid
Molecular formula	C 28 H 28 O 3
External identifiers / databases
EC number	620-513-9
ECHA InfoCard	100.149.379
PubChem	60164
ChemSpider	54244
DrugBank	DB00210
Wikidata	Q352348
Drug information
ATC code	D10 AD03 , D10 AD53
Drug class	polyaromatic retinoid
properties
Molar mass	412.52 g · mol -1
Physical state	firmly
Melting point	314 ° C
safety instructions
	Please note the exemption from the labeling requirement for drugs, medical devices, cosmetics, food and animal feed
GHS labeling of hazardous substances	no GHS pictograms
	no GHS pictograms
H and P phrases	H: no H-phrases
	P: no P-phrases
	As far as possible and customary, SI units are used. Unless otherwise noted, the data given apply to standard conditions .

Adapalene is a synthetic naphthoic acid - derivative and retinoids assigned to third-generation (polyaromatic retinoids).

operation area

Adapalen is used topically in acne therapy . It is approved as a drug in Europe, Australia, and North America; Gel and cream preparations are offered. For improved efficacy in acne vulgaris one was gel formulation in combination with benzoyl peroxide developed.

Effects

Adapalen has a comedolytic and anti-inflammatory effect . Clinical studies have shown a faster onset of action compared to tretinoin, while at the same time being better tolerated. This is a particularly high affinity to the retinoid - receptors in the duct of the sebaceous gland follicle explained.

Side effects

Reddening of the skin, a feeling of warmth, dehydration and itching can occur.

Interactions

A combination with the common antibiotics used in acne treatment, especially erythromycin and clindamycin , has so far not shown any interactions . In contrast to other retinoids, adapalene is photostable, non- phototoxic and also non-photosensitizing.

pregnancy and breast feeding period

Systemic absorption of significant amounts of active ingredient through the skin is not to be expected. However, it is not recommended to use it during pregnancy and breastfeeding , as the safety has not yet been adequately investigated.

Trade names

Monopreparations

Differin (D, A, CH), Dipalen (D)

Combination preparations

Epiduo (D, A, CH)

Individual evidence

↑ Entry on adapalene. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.
↑ ^a ^b Adapalene data sheet from Sigma-Aldrich , accessed on May 12, 2011 ( PDF ).

↑ DM Thiboutot, J. Weiss, A. Bucko, L. Eichenfield, T. Jones, S. Clark, Y. Liu, M. Graeber, S. Kang; Adapalene-BPO Study Group: Adapalene-benzoyl peroxide, a fixed-dose combination for the treatment of acne vulgaris: results of a multicenter, randomized double-blind, controlled study. In: J Am Acad Dermatol. 57 (5), Nov 2007, pp. 791-799. Epub 2007 Jul 26. PMID 17655969 .

↑ Entry on adapalene. In: Römpp Online . Georg Thieme Verlag, accessed on February 3, 2019.

↑ ROTE LISTE 2017, Verlag Rote Liste Service GmbH, Frankfurt am Main, ISBN 978-3-946057-10-9 , p. 158.

[1] Entry on adapalene. In: Römpp Online . Georg Thieme Verlag, accessed on December 28, 2014.

[Sigma-2] Adapalene data sheet from Sigma-Aldrich , accessed on May 12, 2011 ( PDF ).

[3] DM Thiboutot, J. Weiss, A. Bucko, L. Eichenfield, T. Jones, S. Clark, Y. Liu, M. Graeber, S. Kang; Adapalene-BPO Study Group: Adapalene-benzoyl peroxide, a fixed-dose combination for the treatment of acne vulgaris: results of a multicenter, randomized double-blind, controlled study. In: J Am Acad Dermatol. 57 (5), Nov 2007, pp. 791-799. Epub 2007 Jul 26. PMID 17655969 .

[4] Entry on adapalene. In: Römpp Online . Georg Thieme Verlag, accessed on February 3, 2019.

[ROTE_LISTE-5] ROTE LISTE 2017, Verlag Rote Liste Service GmbH, Frankfurt am Main, ISBN 978-3-946057-10-9 , p. 158.