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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
Structure of ADAPALENE

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)

HIDE SMILES / InChI

Molecular Formula C28H28O3
Molecular Weight 412.5212
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

Targets

Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
DIFFERIN

Approved Use

Adapalene gel, 0.1% is indicated for the topical treatment of acne vulgaris.

Launch Date

8.3350081E11
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
0.04 ng/mL
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

Doses

DosePopulationAdverse 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: 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
Scales
Application site dryness
Stinging
Sources: Page: p.1
AEs

AEs

AESignificanceDosePopulation
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

PubMed

TitleDatePubMed
The role of specific retinoid receptors in sebocyte growth and differentiation in culture.
2000 Feb
Adapalene biochemistry and the evolution of a new topical retinoid for treatment of acne.
2001
Comparison of the cumulative irritation potential of adapalene gel and cream with that of erythromycin/tretinoin solution and gel and erythromycin/isotretinoin gel.
2001 Feb
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
Acral Darier's disease successfully treated with adapalene.
2001 Jan-Feb
Lipid analysis of follicular casts from cyanoacrylate strips as a new method for studying therapeutic effects of antiacne agents.
2001 Jul
Comparison of treatment of acne vulgaris with alternate-day applications of tazarotene 0.1% gel and once-daily applications of adapalene 0.1% gel: a randomized trial.
2001 Jun
Synthesis, high-performance liquid chromatography-nuclear magnetic resonance characterization and pharmacokinetics in mice of CD271 glucuronide.
2001 Jun 5
Adapalene gel 0.1% for topical treatment of acne vulgaris in African patients.
2001 Oct
Adapalene gel 0.1% is effective and well tolerated in acne patients in a dermatology practice setting.
2001 Oct
Polarized light photography and videomicroscopy greatly enhance the capability of estimating the therapeuic response to a topical retinoid (adapalene) in acne vulgaris.
2001 Oct
The modern age of acne therapy: a review of current treatment options.
2001 Sep-Oct
Perioral dermatitis successfully treated with topical adapalene.
2002 Mar
Comparison of the effects of tretinoin, adapalene and collagenase in an experimental model of wound healing.
2002 Mar-Apr
Prospective study of depressive symptoms and quality of life in acne vulgaris patients treated with isotretinoin compared to antibiotic and topical therapy.
2002 Nov
Topical adapalene gel 0.1% vs. isotretinoin gel 0.05% in the treatment of acne vulgaris: a randomized open-label clinical trial.
2002 Sep
Current concepts of the pathogenesis of acne: implications for drug treatment.
2003
Optimizing treatment with topical tazarotene.
2003
Management of acne.
2003 Jan
Assessment of adapalene gel for the treatment of actinic keratoses and lentigines: a randomized trial.
2003 Jul
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
Retinoids: fascinating up-and-coming scenario.
2003 May
The synthetic retinoid adapalene inhibits proliferation and induces apoptosis in colorectal cancer cells in vitro.
2003 Nov 10
Clinical review: topical retinoids.
2003 Oct
Cumulative irritancy comparison of adapalene gel 0.1% versus other retinoid products when applied in combination with topical antimicrobial agents.
2003 Sep
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
Efficacy and tolerability of combined topical treatment of acne vulgaris with adapalene and clindamycin: a multicenter, randomized, investigator-blinded study.
2003 Sep
A review of the use of combination therapies for the treatment of acne vulgaris.
2003 Sep
Adapalene: a review of its use in the treatment of acne vulgaris.
2004
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
Topical tretinoin or adapalene in acne vulgaris: an overview.
2004 Jul
Topical agents used in the management of hyperpigmentation.
2004 Jun-Jul
Drugs. Adapalene.
2005 Apr 26-May 2
Topical retinoids in inflammatory acne: a retrospective, investigator-blinded, vehicle-controlled, photographic assessment.
2005 Feb
Fox fordyce disease in a prepubertal girl.
2005 Jan-Feb
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Benzoyl peroxide, adapalene, and their combination in the treatment of acne vulgaris.
2005 Mar
Adapalene vs. metronidazole gel for the treatment of rosacea.
2005 Mar
Milia en plaque.
2005 Mar
Prescribing patterns for topical retinoids within NAMCS data.
2005 Mar-Apr
Tazarotene cream versus adapalene cream in the treatment of facial acne vulgaris: a multicenter, double-blind, randomized, parallel-group study.
2005 Mar-Apr
Mechanism-based treatment of acne vulgaris: the value of combination therapy.
2005 May-Jun
The MORE trial: effectiveness of adapalene gel 0.1% in real-world dermatology practices.
2006 Jul
The results of the MORE trial: overview.
2006 Jul
Patents

Sample Use Guides

Cream should be applied to affected areas of the skin, once daily at nighttime.
Route of Administration: Topical
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 Fri Jun 25 21:11:53 UTC 2021
Edited
by admin
on Fri Jun 25 21:11:53 UTC 2021
Record UNII
1L4806J2QF
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
ADAPALENE
EP   INN   JAN   MART.   MI   ORANGE BOOK   USAN   USP-RS   VANDF   WHO-DD  
INN   USAN  
Official Name English
CD-271
Code English
ADAPALENE [WHO-DD]
Common Name 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 COMPONENT OF EPIDUO
Common Name English
EPIDUO COMPONENT ADAPALENE
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
Classification Tree Code System Code
WHO-VATC QD10AD53
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
NDF-RT N0000175607
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
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
NCI_THESAURUS C804
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
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
WHO-ATC D10AD03
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
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
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
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
WHO-ATC D10AD53
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
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
Code System Code Type Description
WIKIPEDIA
ADAPALENE
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
PRIMARY
EVMPD
SUB05261MIG
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
PRIMARY
ChEMBL
CHEMBL1265
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
PRIMARY
INN
6675
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
PRIMARY
DRUG BANK
DB00210
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
PRIMARY
MESH
C063610
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
PRIMARY
MERCK INDEX
M1408
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
PRIMARY Merck Index
NCI_THESAURUS
C28989
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
PRIMARY
RXCUI
60223
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
PRIMARY RxNorm
DRUG CENTRAL
87
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
PRIMARY
FDA UNII
1L4806J2QF
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
PRIMARY
USP_CATALOG
1011709
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
PRIMARY USP-RS
CAS
106685-40-9
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
PRIMARY
IUPHAR
5429
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
PRIMARY
PUBCHEM
60164
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
PRIMARY
LACTMED
Adapalene
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
PRIMARY
EPA CompTox
106685-40-9
Created by admin on Fri Jun 25 21:11:53 UTC 2021 , Edited by admin on Fri Jun 25 21:11:53 UTC 2021
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
Related Record Type Details
IMPURITY -> PARENT
correction factor: for the calculation of content, multiply the peak area of impurity A by 0.7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
correction factor: for the calculation of content, multiply the peak area of impurity C by 7
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
correction factor: for the calculation of content, multiply the peak area of impurity D by 1.4
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
Ph.Eur.; USP
Related Record Type Details
ACTIVE MOIETY