Adapalene

For research use only. Not for therapeutic Use.

  • CAT Number: A000191
  • CAS Number: 106685-40-9
  • Molecular Formula: C28H28O3
  • Molecular Weight: 412.50
  • Purity: ≥95%
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Adapalene(Cat No.:A000191)is a third-generation topical retinoid commonly used to treat acne. By modulating cellular differentiation, keratinization, and inflammatory processes, adapalene prevents clogged pores and reduces acne lesions. It binds selectively to retinoic acid receptors, promoting skin cell turnover and reducing inflammation, making it effective against both comedonal and inflammatory acne. Known for its stability and reduced skin irritation compared to other retinoids, adapalene is favored in dermatology. Its anti-inflammatory and comedolytic effects also make it valuable for research into other skin conditions, such as photoaging and hyperpigmentation.


Catalog Number A000191
CAS Number 106685-40-9
Synonyms

106685-40-9; Differin; Adapalenum; Adapaleno; 6-(3-(Adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acid

Molecular Formula C28H28O3
Purity ≥95%
Target RARβ and RARγ agonist
Storage -20°C
IUPAC Name 6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid
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)
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
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.
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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.
<br>

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.

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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.
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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.

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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.
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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.
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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.
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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.
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10: Ramezanli T, Zhang Z, Michniak-Kohn BB. &#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;Development and
characterization of polymeric nanoparticle-based formulation of adapalene for
topical acne therapy&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;&#8236;. Nanomedicine. 2017
Jan;13(1):143-152. doi: 10.1016/j.nano.2016.08.008. Epub 2016 Aug 24. PubMed
PMID: 27565687.

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