U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

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 of ADAPALENE

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)

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

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
Adapalene biochemistry and the evolution of a new topical retinoid for treatment of acne.
2001
The integral role of topical and oral retinoids in the early treatment of acne.
2001
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
Synthesis, high-performance liquid chromatography-nuclear magnetic resonance characterization and pharmacokinetics in mice of CD271 glucuronide.
2001 Jun 5
A comparative trial of two retinoids commonly used in the treatment of acne vulgaris.
2001 Sep
Developments in topical retinoid therapy for acne.
2001 Sep
Retinoids--which dermatological indications will benefit in the near future?
2001 Sep-Oct
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
Efficacy and cutaneous safety of adapalene in black patients versus white patients with acne vulgaris.
2002 Oct
Assessment of adapalene gel for the treatment of actinic keratoses and lentigines: a randomized trial.
2003 Jul
Clinical review: topical retinoids.
2003 Oct
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
Adapalene: a review of its use in the treatment of acne vulgaris.
2004
Topical tretinoin or adapalene in acne vulgaris: an overview.
2004 Jul
Facial tolerability of topical retinoid therapy.
2004 Nov-Dec
Comparison of topical retinoids in the treatment of acne.
2004 Sep-Oct
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
Acne vulgaris.
2005 Jun
Prediction of genotoxicity of chemical compounds by statistical learning methods.
2005 Jun
Minimal important difference (MID) of the Dermatology Life Quality Index (DLQI): results from patients with chronic idiopathic urticaria.
2005 May 20
Mechanism-based treatment of acne vulgaris: the value of combination therapy.
2005 May-Jun
The potential risks of nanomaterials: a review carried out for ECETOC.
2006 Aug 14
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 Dec 16 17:35:49 UTC 2022
Edited
by admin
on Fri Dec 16 17:35:49 UTC 2022
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
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 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 Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
NDF-RT N0000175607
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
NDF-RT N0000007700
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
NCI_THESAURUS C804
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
NDF-RT N0000007700
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
WHO-ATC D10AD03
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
NDF-RT N0000007700
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
NDF-RT N0000007700
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
WHO-VATC QD10AD03
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
WHO-ATC D10AD53
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
NDF-RT N0000007700
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
Code System Code Type Description
WIKIPEDIA
ADAPALENE
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
PRIMARY
DAILYMED
1L4806J2QF
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
PRIMARY
EVMPD
SUB05261MIG
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
PRIMARY
ChEMBL
CHEMBL1265
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
PRIMARY
RS_ITEM_NUM
1011709
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
PRIMARY
CHEBI
31174
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
PRIMARY
INN
6675
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
PRIMARY
DRUG BANK
DB00210
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
PRIMARY
MESH
C063610
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
PRIMARY
MERCK INDEX
M1408
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
PRIMARY Merck Index
NCI_THESAURUS
C28989
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
PRIMARY
RXCUI
60223
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
PRIMARY RxNorm
DRUG CENTRAL
87
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
PRIMARY
FDA UNII
1L4806J2QF
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
PRIMARY
CAS
106685-40-9
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
PRIMARY
IUPHAR
5429
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
PRIMARY
USAN
DD-46
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
PRIMARY
PUBCHEM
60164
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
PRIMARY
LACTMED
Adapalene
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
PRIMARY
EPA CompTox
DTXSID5046481
Created by admin on Fri Dec 16 17:35:49 UTC 2022 , Edited by admin on Fri Dec 16 17:35:49 UTC 2022
PRIMARY
Related Record Type Details
BASIS OF STRENGTH->SUBSTANCE
ASSAY (HPLC)
EP
Related Record Type Details
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
USP
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
IMPURITY -> PARENT
CHROMATOGRAPHIC PURITY (HPLC/UV)
EP
Related Record Type Details
ACTIVE MOIETY