Details
Stereochemistry | ACHIRAL |
Molecular Formula | C28H28O3 |
Molecular Weight | 412.5212 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
COc1ccc(cc1C23CC4CC(CC(C4)C2)C3)-c5ccc6cc(ccc6c5)C(=O)O
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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Adapalene in the treatment of African patients. | 2001 |
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A comparison of adapalene gel 0.1% vs. tretinoin gel 0.025% in the treatment of acne vulgaris in China. | 2001 |
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Adapalene gel 0.1% for topical treatment of acne vulgaris in African patients. | 2001 Oct |
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Epithelial malignancies in organ transplant patients: clinical presentation and new methods of treatment. | 2002 |
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A multicenter, double-blind, randomized comparison study of the efficacy and tolerability of once-daily tazarotene 0.1% gel and adapalene 0.1% gel for the treatment of facial acne vulgaris. | 2002 Feb |
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Randomised, controlled trial of the efficacy and safety of adapalene gel 0.1% and tretinoin cream 0.05% in patients with acne vulgaris. | 2002 Jul-Aug |
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Perioral dermatitis successfully treated with topical adapalene. | 2002 Mar |
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Potential anti-inflammatory effects of topical retinoids and retinoid analogues. | 2002 May-Jun |
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Optimizing treatment with topical tazarotene. | 2003 |
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The rationale for using a topical retinoid for inflammatory acne. | 2003 |
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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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Management of acne. | 2003 Jan |
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Assessment of adapalene gel for the treatment of actinic keratoses and lentigines: a randomized trial. | 2003 Jul |
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Axillary granular parakeratosis. | 2003 Jul-Aug |
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13-cis-retinoic acid competitively inhibits 3 alpha-hydroxysteroid oxidation by retinol dehydrogenase RoDH-4: a mechanism for its anti-androgenic effects in sebaceous glands? | 2003 Mar 28 |
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Retinoids: fascinating up-and-coming scenario. | 2003 May |
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Clinical review: topical retinoids. | 2003 Oct |
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Cumulative irritancy comparison of adapalene gel 0.1% versus other retinoid products when applied in combination with topical antimicrobial agents. | 2003 Sep |
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Is combined oral and topical therapy better than oral therapy alone in patients with moderate to moderately severe acne vulgaris? A comparison of the efficacy and safety of lymecycline plus adapalene gel 0.1%, versus lymecycline plus gel vehicle. | 2003 Sep |
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A review of the use of combination therapies for the treatment of acne vulgaris. | 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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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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An unusual late onset closed-comedone naevus: successful therapy with light cautery and a topical retinoid. | 2004 Jan |
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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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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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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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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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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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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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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
Created by
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NDF-RT |
N0000175607
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N0000007700
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NCI_THESAURUS |
C804
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NDF-RT |
N0000007700
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WHO-ATC |
D10AD03
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NDF-RT |
N0000007700
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NDF-RT |
N0000007700
Created by
admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
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WHO-VATC |
QD10AD03
Created by
admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
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WHO-ATC |
D10AD53
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admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
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NDF-RT |
N0000007700
Created by
admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
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Code System | Code | Type | Description | ||
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ADAPALENE
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SUB05261MIG
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CHEMBL1265
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6675
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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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1011709
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106685-40-9
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5429
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60164
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Adapalene
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106685-40-9
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ACTIVE MOIETY