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)
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 |
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 |
---|---|---|---|
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 |
---|---|---|---|
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 |
---|---|---|
Adapalene biochemistry and the evolution of a new topical retinoid for treatment of acne. | 2001 |
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The integral role of topical and oral retinoids in the early treatment of acne. | 2001 |
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Are 2 combined antimicrobial mechanisms better than 1 for the treatment of acne vulgaris? Clinical and antimicrobial results of a topical combination product containing 1% clindamycin and 5% benzoyl peroxide. Introduction. | 2001 Feb |
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Synthesis, high-performance liquid chromatography-nuclear magnetic resonance characterization and pharmacokinetics in mice of CD271 glucuronide. | 2001 Jun 5 |
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A comparative trial of two retinoids commonly used in the treatment of acne vulgaris. | 2001 Sep |
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Developments in topical retinoid therapy for acne. | 2001 Sep |
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Retinoids--which dermatological indications will benefit in the near future? | 2001 Sep-Oct |
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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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Efficacy and cutaneous safety of adapalene in black patients versus white patients with acne vulgaris. | 2002 Oct |
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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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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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Adapalene: a review of its use in the treatment of acne vulgaris. | 2004 |
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Topical tretinoin or adapalene in acne vulgaris: an overview. | 2004 Jul |
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Facial tolerability of topical retinoid therapy. | 2004 Nov-Dec |
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Comparison of topical retinoids in the treatment of acne. | 2004 Sep-Oct |
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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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Acne vulgaris. | 2005 Jun |
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Prediction of genotoxicity of chemical compounds by statistical learning methods. | 2005 Jun |
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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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The potential risks of nanomaterials: a review carried out for ECETOC. | 2006 Aug 14 |
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The results of the MORE trial: overview. | 2006 Jul |
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.
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 16 17:35:49 UTC 2022
by
admin
on
Fri Dec 16 17:35:49 UTC 2022
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Record UNII |
1L4806J2QF
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Record Status |
Validated (UNII)
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Record Version |
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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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NDF-RT |
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
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WHO-VATC |
QD10AD03
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WHO-ATC |
D10AD53
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NDF-RT |
N0000007700
Created by
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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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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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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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Related Record | Type | Details | ||
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BASIS OF STRENGTH->SUBSTANCE |
ASSAY (HPLC)
EP
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Related Record | Type | Details | ||
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
correction factors: for the calculation of content, multiply the peak areas of the following impurities by the corresponding correction factor: impurity A = 0.7; impurity C = 7; impurity D = 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
correction factors: for the calculation of content, multiply the peak areas of the following impurities by the corresponding correction factor: impurity A = 0.7; impurity C = 7; impurity D = 1.4;
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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IMPURITY -> PARENT |
correction factors: for the calculation of content, multiply the peak areas of the following impurities by the corresponding correction factor: impurity A = 0.7; impurity C = 7; impurity D = 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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IMPURITY -> PARENT |
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
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Related Record | Type | Details | ||
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ACTIVE MOIETY |
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