ADAPALENE

Details

Stereochemistry	ACHIRAL
Molecular Formula	C28H28O3
Molecular Weight	412.5201
Optical Activity	NONE
Defined Stereocenters	0 / 0
E/Z Centers	0
Charge	0

SHOW SMILES / InChI

Structure Search

SMILES

COC1=C(C=C(C=C1)C2=CC=C3C=C(C=CC3=C2)C(O)=O)C45CC6CC(CC(C6)C4)C5

InChI

InChIKey=LZCDAPDGXCYOEH-UHFFFAOYSA-N

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)

HIDE SMILES / InChI

Molecular Formula	C28H28O3
Molecular Weight	412.5201
Charge	0
Count

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description
Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2000/20748lbl.pdf

Adapalene is a topical retinoid primarily used in the treatment of acne and is used (off-label) to treat keratosis pilaris as well as other skin conditions. Galderma currently markets it under the trade names Differin in some countries, and Adaferin in India. Adapalene acts on retinoid receptors. Biochemical and pharmacological profile studies have demonstrated that adapalene is a modulator of cellular differentiation, keratinization, and inflammatory processes all of which represent important features in the pathology of acne vulgaris. Mechanistically, adapalene binds to specific retinoic acid nuclear receptors but does not bind to the cytosolic receptor protein. Although the exact mode of action of adapalene is unknown, it is suggested that topical adapalene normalizes the differentiation of follicular epithelial cells resulting in decreased microcomedone formation.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Retinoic acid receptor gamma 18 Target ID: CHEMBL2003 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10651997	Agonist 2752
Retinoic acid receptor beta 18 Target ID: CHEMBL2008 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10651997	Agonist 2752

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acne vulgaris 34 Sources: http://www.accessdata.fda.gov/drugsatfda_docs/label/2000/20748lbl.pdf	Primary		Approved 8583	DIFFERIN Approved Use Adapalene gel, 0.1% is indicated for the topical treatment of acne vulgaris. Launch Date 1996

C_max

Value	Dose	Co-administered	Analyte	Population
0.04 ng/mL EXPERIMENT https://www.ncbi.nlm.nih.gov/pubmed/10898827	6.8 mg 1 times / day multiple, topical dose: 6.8 mg route of administration: Topical experiment type: MULTIPLE co-administered:		ADAPALENE plasma	Homo sapiens population: UNHEALTHY age: ADULT sex: UNKNOWN food status: UNKNOWN

Doses

Dose	Population	Adverse events
0.1 % 1 times / day multiple, topical Studied dose Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20415678	unhealthy, 12–26 Health Status: unhealthy Age Group: 12–26 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/20415678	Disc. AE: Irritation skin... AEs leading to discontinuation/dose reduction: Irritation skin (severe, 9.2%) Sources: https://pubmed.ncbi.nlm.nih.gov/20415678
0.3 % 1 times / day multiple, topical Recommended Dose: 0.3 %, 1 times / day Route: topical Route: multiple Dose: 0.3 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/22007702	unhealthy, 45 - 65 Health Status: unhealthy Age Group: 45 - 65 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/22007702	Disc. AE: Irritation skin... AEs leading to discontinuation/dose reduction: Irritation skin (severe, 7.5%) Sources: https://pubmed.ncbi.nlm.nih.gov/22007702
0.3 % 1 times / day multiple, topical Recommended Dose: 0.3 %, 1 times / day Route: topical Route: multiple Dose: 0.3 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021753s004lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021753s004lbl.pdf	Disc. AE: Erythema, Scales... AEs leading to discontinuation/dose reduction: Erythema Scales Application site dryness Stinging Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021753s004lbl.pdf

AEs

AE	Significance	Dose	Population
Irritation skin	severe, 9.2% Disc. AE	0.1 % 1 times / day multiple, topical Studied dose Dose: 0.1 %, 1 times / day Route: topical Route: multiple Dose: 0.1 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/20415678	unhealthy, 12–26 Health Status: unhealthy Age Group: 12–26 Sex: M+F Sources: https://pubmed.ncbi.nlm.nih.gov/20415678
Irritation skin	severe, 7.5% Disc. AE	0.3 % 1 times / day multiple, topical Recommended Dose: 0.3 %, 1 times / day Route: topical Route: multiple Dose: 0.3 %, 1 times / day Sources: https://pubmed.ncbi.nlm.nih.gov/22007702	unhealthy, 45 - 65 Health Status: unhealthy Age Group: 45 - 65 Sex: F Sources: https://pubmed.ncbi.nlm.nih.gov/22007702
Application site dryness	Disc. AE	0.3 % 1 times / day multiple, topical Recommended Dose: 0.3 %, 1 times / day Route: topical Route: multiple Dose: 0.3 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021753s004lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021753s004lbl.pdf
Erythema	Disc. AE	0.3 % 1 times / day multiple, topical Recommended Dose: 0.3 %, 1 times / day Route: topical Route: multiple Dose: 0.3 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021753s004lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021753s004lbl.pdf
Scales	Disc. AE	0.3 % 1 times / day multiple, topical Recommended Dose: 0.3 %, 1 times / day Route: topical Route: multiple Dose: 0.3 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021753s004lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021753s004lbl.pdf
Stinging	Disc. AE	0.3 % 1 times / day multiple, topical Recommended Dose: 0.3 %, 1 times / day Route: topical Route: multiple Dose: 0.3 %, 1 times / day Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021753s004lbl.pdf	unhealthy Health Status: unhealthy Sources: https://www.accessdata.fda.gov/drugsatfda_docs/label/2012/021753s004lbl.pdf

Sourcing

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:31174	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31174
ChemicalBook	CB6771245	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6771245
eMolecules	901333	https://www.emolecules.com/cgi-bin/more?vid=901333
MolPort	MolPort-003-986-211	https://www.molport.com/shop/molecule-link/MolPort-003-986-211
Selleck Chemicals	Adapalene	http://www.selleckchem.com/products/Adapalene.html
ZINC	ZINC000003784182	http://zinc15.docking.org/substances/ZINC000003784182

PubMed

Title	Date	PubMed
The potential risks of nanomaterials: a review carried out for ECETOC.	2006-08-14	16907977
The MORE trial: effectiveness of adapalene gel 0.1% in real-world dermatology practices.	2006-07	16910026
The results of the MORE trial: overview.	2006-07	16910025
Adapalene gel, 0.1%, as maintenance therapy for acne vulgaris: a randomized, controlled, investigator-blind follow-up of a recent combination study.	2006-05	16702497
Treatment of solar lentigines.	2006-05	16631967
Adapalene gel 0.3% for the treatment of acne vulgaris: a multicenter, randomized, double-blind, controlled, phase III trial.	2006-02	16443054
Pseudoacne of the nasal crease in a patient with congenital deafness and pigmentary mosaicism.	2005-12-16	16354272
[Rosacea. Clinical features, pathogenesis and therapy].	2005-09	16133636
Anti-inflammatory effects of tretinoin (all-trans-retinoic acid) 0.1% and adapalene 0.1% in rats.	2005-09	16045694
Comedolytic effect of a novel RARgamma-specific retinoid, ER36009: comparison with retinoic acid in the rhino mouse model.	2005-08-23	16280299
The efficacy and safety of adapalene gel 0.3% in the treatment of acne vulgaris: A randomized, multicenter, investigator-blinded, controlled comparison study versus adapalene gel 0.1% and vehicle.	2005-08	16209161
Acne vulgaris.	2005-06	16135322
Topical retinoids during pregnancy (continued).	2005-06	15981398
Prediction of genotoxicity of chemical compounds by statistical learning methods.	2005-06	15962942
Minimal important difference (MID) of the Dermatology Life Quality Index (DLQI): results from patients with chronic idiopathic urticaria.	2005-05-20	15907211
Mechanism-based treatment of acne vulgaris: the value of combination therapy.	2005-05-19	15898282
Combination therapy with adapalene gel 0.1% and doxycycline for severe acne vulgaris: a multicenter, investigator-blind, randomized, controlled study.	2005-05-14	15891249
Drugs. Adapalene.	2005-05-11	15881906
Cumulative irritation potential of adapalene 0.1% cream and gel compared with tazarotene cream 0.05% and 0.1%.	2005-05	15984630
Cumulative irritation potential of adapalene 0.1% cream and gel compared with tretinoin microsphere 0.04% and 0.1%.	2005-04	15916222
Prescribing patterns for topical retinoids within NAMCS data.	2005-03-22	15776774
Clinical experience results with clindamycin 1% benzoyl peroxide 5% gel (Duac) as monotherapy and in combination.	2005-03-22	15776773
Tazarotene cream versus adapalene cream in the treatment of facial acne vulgaris: a multicenter, double-blind, randomized, parallel-group study.	2005-03-22	15776771
The potential immunomodulatory effects of topical retinoids.	2005-03-01	15748544
Benzoyl peroxide, adapalene, and their combination in the treatment of acne vulgaris.	2005-03	15863861
Adapalene vs. metronidazole gel for the treatment of rosacea.	2005-03	15807740
Milia en plaque.	2005-03	15752313
Mechanisms of the comedolytic and anti-inflammatory properties of topical retinoids.	2005-02-09	15696984
Topical retinoids in inflammatory acne: a retrospective, investigator-blinded, vehicle-controlled, photographic assessment.	2005-02	15811485
Fox fordyce disease in a prepubertal girl.	2005-01-22	15660912
Retinoid therapy for acne. A comparative review.	2005	15675886
Facial tolerability of topical retinoid therapy.	2004-12-31	15624747
A successful maintenance approach in inflammatory acne with adapalene gel 0.1% after an initial treatment in combination with clindamycin topical solution 1% or after monotherapy with clindamycin topical solution 1%.	2004-12	15764049
Comparison of topical retinoids in the treatment of acne.	2004-11-24	15556727
Meta-analysis of topical tazarotene in the treatment of mild to moderate acne.	2004-10	15543714
Topical retinoids in the management of acne: the best path to clear results.	2004-10	15543712
Topical agents used in the management of hyperpigmentation.	2004-08-31	15334278
Phototoxic effects of topical azelaic acid, benzoyl peroxide and adapalene were not detected when applied immediately before UVB to normal skin.	2004-08-21	15319156
Skin tolerability and efficacy of combination therapy with hydrogen peroxide stabilized cream and adapalene gel in comparison with benzoyl peroxide cream and adapalene gel in common acne. A randomized, investigator-masked, controlled trial.	2004-08	15327558
Topical tretinoin or adapalene in acne vulgaris: an overview.	2004-07	15764031
Potentiated anticancer effects on hepatoma cells by the retinoid adapalene.	2004-05-10	15105045
[The clinical observation of treating acne vulgaris with "xiao cuo fang"].	2004-04	15307690
Axillary granular parakeratosis.	2004-01-24	14738100
An unusual late onset closed-comedone naevus: successful therapy with light cautery and a topical retinoid.	2004-01	14754653
Spotlight on adapalene in acne vulgaris.	2004	15554742
Adapalene: a review of its use in the treatment of acne vulgaris.	2004	15212561
Cumulative irritancy potential of adapalene cream 0.1% compared with adapalene gel 0.1% and several tretinoin formulations.	2003-12	14700217
The synthetic retinoid adapalene inhibits proliferation and induces apoptosis in colorectal cancer cells in vitro.	2003-11-10	14506747
Clinical review: topical retinoids.	2003-10	14619325
Single-blind and comparative clinical study of the efficacy and safety of benzoyl peroxide 4% gel (BID) and adapalene 0.1% Gel (QD) in the treatment of acne vulgaris for 11 weeks.	2003-09	14522627

Patents

Sample Use Guides

In Vivo Use Guide

Cream should be applied to affected areas of the skin, once daily at nighttime.

Route of Administration: Topical

In Vitro Use Guide

Explants of normal human skin and explants of acne patients were incubated with adapalene (10(-7) or 10(-6) M) for 24 h. Evaluation of epidermal expression by immunohistochemistry showed a decreased expression of TLR-2 and IL-10 in explants of normal skin and explants of acne with adapalene. On the contrary, adapalene increased CD1d expression in explants of acne patients. Thus, adapalene can modulate the epidermal immune system by increasing the CD1d expression and by decreasing the IL-10 expression by keratinocytes.

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:02:43 GMT 2025` Edited by `admin` on `Mon Mar 31 18:02:43 GMT 2025`
Record UNII	1L4806J2QF
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

ADAPALENE

Official Name

English

EPIDUO COMPONENT ADAPALENE

Preferred Name

English

CD-271

Code

English

IDP-126 Component Adapalene

Code

English

DIFFERIN

Brand Name

English

ADAPALENE [MI]

Common Name

English

CD 271

Code

English

ADAPALENE [MART.]

Common Name

English

ADAPALENE [ORANGE BOOK]

Common Name

English

ADAPALENE [VANDF]

Common Name

English

2-NAPHTHALENECARBOXYLIC ACID, 6-(4-METHOXY-3-TRICYCLO(3.3.1.(SUP 13,7))DEC-1-YLPHENYL)-

Common Name

English

ADAPALENE [USP-RS]

Common Name

English

ADAPALENE [USP MONOGRAPH]

Common Name

English

Adapalene [WHO-DD]

Common Name

English

ADAPALENE [EP MONOGRAPH]

Common Name

English

ADAPALENE [JAN]

Common Name

English

2-NAPHTHALENECARBOXYLIC ACID, 6-(4-METHOXY-3-TRICYCLO(3.3.1.1(SUP 3,7))DEC-1-YLPHENYL)-

Common Name

English

ADAPALENE [USAN]

Common Name

English

6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoic acid

Systematic Name

English

adapalene [INN]

Common Name

English

CABTREO COMPONENT ADAPALENE

Brand Name

English

Classification Tree Code System Code

WHO-VATC

QD10AD53