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
SMILES
COC1=C(C=C(C=C1)C2=CC3=C(C=C2)C=C(C=C3)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)
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.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL2003 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10651997 |
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Target ID: CHEMBL2008 Sources: https://www.ncbi.nlm.nih.gov/pubmed/10651997 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | DIFFERIN Approved UseAdapalene gel, 0.1% is indicated for the topical treatment of acne vulgaris. Launch Date8.3350081E11 |
Cmax
Value | Dose | Co-administered | Analyte | Population |
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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 |
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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: Page: p.1364 |
unhealthy, 12–26 n = 87 Health Status: unhealthy Condition: Acne Age Group: 12–26 Sex: M+F Population Size: 87 Sources: Page: p.1364 |
Disc. AE: Irritation skin... AEs leading to discontinuation/dose reduction: Irritation skin (severe, 9.2%) Sources: Page: p.1364 |
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: Page: p.59 |
unhealthy, 45 - 65 n = 40 Health Status: unhealthy Condition: Cutaneous photoaging Age Group: 45 - 65 Sex: F Population Size: 40 Sources: Page: p.59 |
Disc. AE: Irritation skin... AEs leading to discontinuation/dose reduction: Irritation skin (severe, 7.5%) Sources: Page: p.59 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acne Sources: Page: p.1 |
Disc. AE: Erythema, Scales... AEs leading to discontinuation/dose reduction: Erythema Sources: Page: p.1Scales Application site dryness Stinging |
AEs
AE | Significance | Dose | Population |
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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: Page: p.1364 |
unhealthy, 12–26 n = 87 Health Status: unhealthy Condition: Acne Age Group: 12–26 Sex: M+F Population Size: 87 Sources: Page: p.1364 |
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: Page: p.59 |
unhealthy, 45 - 65 n = 40 Health Status: unhealthy Condition: Cutaneous photoaging Age Group: 45 - 65 Sex: F Population Size: 40 Sources: Page: p.59 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acne Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acne Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acne Sources: Page: p.1 |
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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Acne Sources: Page: p.1 |
PubMed
Title | Date | PubMed |
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Cumulative irritancy potential of adapalene cream 0.1% compared with adapalene gel 0.1% and several tretinoin formulations. | 2003 Dec |
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Axillary granular parakeratosis. | 2003 Jul-Aug |
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The synthetic retinoid adapalene inhibits proliferation and induces apoptosis in colorectal cancer cells in vitro. | 2003 Nov 10 |
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Clinical review: topical retinoids. | 2003 Oct |
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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 Sep |
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Spotlight on adapalene in acne vulgaris. | 2004 |
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Adapalene: a review of its use in the treatment of acne vulgaris. | 2004 |
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[The clinical observation of treating acne vulgaris with "xiao cuo fang"]. | 2004 Apr |
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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 Aug |
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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 Dec |
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An unusual late onset closed-comedone naevus: successful therapy with light cautery and a topical retinoid. | 2004 Jan |
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Topical tretinoin or adapalene in acne vulgaris: an overview. | 2004 Jul |
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Phototoxic effects of topical azelaic acid, benzoyl peroxide and adapalene were not detected when applied immediately before UVB to normal skin. | 2004 Jul-Aug |
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Topical agents used in the management of hyperpigmentation. | 2004 Jun-Jul |
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Potentiated anticancer effects on hepatoma cells by the retinoid adapalene. | 2004 May 10 |
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Facial tolerability of topical retinoid therapy. | 2004 Nov-Dec |
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Meta-analysis of topical tazarotene in the treatment of mild to moderate acne. | 2004 Oct |
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Topical retinoids in the management of acne: the best path to clear results. | 2004 Oct |
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Comparison of topical retinoids in the treatment of acne. | 2004 Sep-Oct |
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Retinoid therapy for acne. A comparative review. | 2005 |
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Cumulative irritation potential of adapalene 0.1% cream and gel compared with tretinoin microsphere 0.04% and 0.1%. | 2005 Apr |
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Drugs. Adapalene. | 2005 Apr 26-May 2 |
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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 Aug |
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Topical retinoids in inflammatory acne: a retrospective, investigator-blinded, vehicle-controlled, photographic assessment. | 2005 Feb |
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Mechanisms of the comedolytic and anti-inflammatory properties of topical retinoids. | 2005 Jan-Feb |
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Fox fordyce disease in a prepubertal girl. | 2005 Jan-Feb |
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Acne vulgaris. | 2005 Jun |
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Topical retinoids during pregnancy (continued). | 2005 Jun |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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Benzoyl peroxide, adapalene, and their combination in the treatment of acne vulgaris. | 2005 Mar |
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Adapalene vs. metronidazole gel for the treatment of rosacea. | 2005 Mar |
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Milia en plaque. | 2005 Mar |
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The potential immunomodulatory effects of topical retinoids. | 2005 Mar 1 |
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Prescribing patterns for topical retinoids within NAMCS data. | 2005 Mar-Apr |
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Clinical experience results with clindamycin 1% benzoyl peroxide 5% gel (Duac) as monotherapy and in combination. | 2005 Mar-Apr |
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Tazarotene cream versus adapalene cream in the treatment of facial acne vulgaris: a multicenter, double-blind, randomized, parallel-group study. | 2005 Mar-Apr |
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Cumulative irritation potential of adapalene 0.1% cream and gel compared with tazarotene cream 0.05% and 0.1%. | 2005 May |
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Minimal important difference (MID) of the Dermatology Life Quality Index (DLQI): results from patients with chronic idiopathic urticaria. | 2005 May 20 |
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Mechanism-based treatment of acne vulgaris: the value of combination therapy. | 2005 May-Jun |
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Combination therapy with adapalene gel 0.1% and doxycycline for severe acne vulgaris: a multicenter, investigator-blind, randomized, controlled study. | 2005 May-Jun |
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Pseudoacne of the nasal crease in a patient with congenital deafness and pigmentary mosaicism. | 2005 Nov-Dec |
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Comedolytic effect of a novel RARgamma-specific retinoid, ER36009: comparison with retinoic acid in the rhino mouse model. | 2005 Nov-Dec |
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[Rosacea. Clinical features, pathogenesis and therapy]. | 2005 Sep |
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Anti-inflammatory effects of tretinoin (all-trans-retinoic acid) 0.1% and adapalene 0.1% in rats. | 2005 Sep |
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The potential risks of nanomaterials: a review carried out for ECETOC. | 2006 Aug 14 |
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Adapalene gel 0.3% for the treatment of acne vulgaris: a multicenter, randomized, double-blind, controlled, phase III trial. | 2006 Feb |
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The MORE trial: effectiveness of adapalene gel 0.1% in real-world dermatology practices. | 2006 Jul |
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The results of the MORE trial: overview. | 2006 Jul |
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Adapalene gel, 0.1%, as maintenance therapy for acne vulgaris: a randomized, controlled, investigator-blind follow-up of a recent combination study. | 2006 May |
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Treatment of solar lentigines. | 2006 May |
Sample Use Guides
Cream should be applied to affected areas of the skin, once daily at nighttime.
Route of Administration:
Topical
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/17518990
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.
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Classification Tree | Code System | Code | ||
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WHO-VATC |
QD10AD53
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NDF-RT |
N0000175607
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N0000007700
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NCI_THESAURUS |
C804
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N0000007700
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WHO-ATC |
D10AD03
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N0000007700
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N0000007700
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QD10AD03
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D10AD53
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NDF-RT |
N0000007700
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Code System | Code | Type | Description | ||
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ADAPALENE
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1L4806J2QF
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SUB05261MIG
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CHEMBL1265
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1011709
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31174
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DB00210
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C063610
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m1408
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C28989
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60223
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87
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100000087680
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1L4806J2QF
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106685-40-9
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5429
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DD-46
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60164
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Adapalene
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DTXSID5046481
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ACTIVE MOIETY