Adapalene

• CAT Number: A000191
• CAS Number: 106685-40-9
• Molecular Formula: C28H28O3
• Molecular Weight: 412.5
• Purity: ≥95%
• Synonyms: 106685-40-9; Differin; Adapalenum; Adapaleno; 6-(3-(Adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acid
• Target: RARβ and RARγ agonist
• Storage: -20°C
• 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)
• InChIKey: LZCDAPDGXCYOEH-UHFFFAOYSA-N
• SMILES: COC1=C(C=C(C=C1)C2=CC3=C(C=C2)C=C(C=C3)C(=O)O)C45CC6CC(C4)CC(C6)C5

Adapalene is a retinoic acid analog that is a RARβ and RARγ agonist. It inhibits proliferation and induces apoptosis in colorectal cancer cells in vitro and displays comedolytic activity.

Reference

1: Myhill T, Coulson W, Nixon P, Royal S, McCormack T, Kerrouche N. Use of
Supplementary Patient Education Material Increases Treatment Adherence and
Satisfaction Among Acne Patients Receiving Adapalene 0.1%/Benzoyl Peroxide 2.5%
Gel in Primary Care Clinics: A Multicenter, Randomized, Controlled Clinical
Study. Dermatol Ther (Heidelb). 2017 Oct 12. doi: 10.1007/s13555-017-0203-4.
[Epub ahead of print] PubMed PMID: 29027127.

2: Maiti R, Sirka CS, Ashique Rahman MA, Srinivasan A, Parida S, Hota D. Efficacy
and Safety of Tazarotene 0.1% Plus Clindamycin 1% Gel Versus Adapalene 0.1% Plus
Clindamycin 1% Gel in Facial Acne Vulgaris: A Randomized, Controlled Clinical
Trial. Clin Drug Investig. 2017 Nov;37(11):1083-1091. doi:
10.1007/s40261-017-0568-2. PubMed PMID: 28913735.

3: Stein Gold L, Werschler WP, Mohawk J. Adapalene/Benzoyl Peroxide Gel
0.3%/2.5%: Effective Acne Therapy Regardless of Age or Gender. J Drugs Dermatol.
2017 Jun 1;16(6):582-589. PubMed PMID: 28686776.

4: Alexis AF, Cook-Bolden FE, York JP. Adapalene/Benzoyl Peroxide Gel 0.3%/2.5%:
A Safe and Effective Acne Therapy in All Skin Phototypes. J Drugs Dermatol. 2017
Jun 1;16(6):574-581. PubMed PMID: 28686775.

5: Sallam MA, Marín Boscá MT. Mechanistic Analysis of Human Skin Distribution and
Follicular Targeting of Adapalene-Loaded Biodegradable Nanospheres With an
Insight Into Hydrogel Matrix Influence, In Vitro Skin Irritation, and In Vivo
Tolerability. J Pharm Sci. 2017 Oct;106(10):3140-3149. doi:
10.1016/j.xphs.2017.05.038. Epub 2017 Jun 8. PubMed PMID: 28603018.

6: Bouloc A, Roo E, Imko-Walczuk B, Moga A, Chadoutaud B, Dréno B. A skincare
combined with combination of adapalene and benzoyl peroxide provides a
significant adjunctive efficacy and local tolerance benefit in adult women with
mild acne. J Eur Acad Dermatol Venereol. 2017 Oct;31(10):1727-1731. doi:
10.1111/jdv.14379. Epub 2017 Jul 7. PubMed PMID: 28573779.

7: Osman-Ponchet H, Sevin K, Gaborit A, Wagner N, Poncet M. Fixed-Combination
Gels of Adapalene and Benzoyl Peroxide Provide Optimal Percutaneous Absorption
Compared to Monad Formulations of These Compounds: Results from Two In Vitro
Studies. Dermatol Ther (Heidelb). 2017 Mar;7(1):123-131. doi:
10.1007/s13555-016-0159-9. Epub 2016 Nov 30. PubMed PMID: 27900658; PubMed
Central PMCID: PMC5336428.

8: Dreno B, Tan J, Rivier M, Martel P, Bissonnette R. Adapalene 0.1%/benzoyl
peroxide 2.5% gel reduces the risk of atrophic scar formation in moderate
inflammatory acne: a split-face randomized controlled trial. J Eur Acad Dermatol
Venereol. 2017 Apr;31(4):737-742. doi: 10.1111/jdv.14026. Epub 2016 Dec 7. PubMed
PMID: 27790756.

9: Kim SY, Ochsendorf FR. New developments in acne treatment: role of combination
adapalene-benzoylperoxide. Ther Clin Risk Manag. 2016 Oct 3;12:1497-1506.
eCollection 2016. Review. PubMed PMID: 27757036; PubMed Central PMCID:
PMC5055040.

10: Ramezanli T, Zhang Z, Michniak-Kohn BB. ‬‬‬‬‬‬‬‬Development and
characterization of polymeric nanoparticle-based formulation of adapalene for
topical acne therapy‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬‬. Nanomedicine. 2017
Jan;13(1):143-152. doi: 10.1016/j.nano.2016.08.008. Epub 2016 Aug 24. PubMed
PMID: 27565687.