ADAPALENE

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)

HIDE SMILES / InChI

Molecular Formula	C28H28O3
Molecular Weight	412.5201
Charge	0
Count	MOL RATIO 1 MOL RATIO (average)

Stereochemistry	ACHIRAL
Additional Stereochemistry	No
Defined Stereocenters	0 / 0
E/Z Centers	0
Optical Activity	NONE

Description

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.

Originator

Approval Year

Targets

Primary Target	Pharmacology	Condition	Potency
Retinoic acid receptor gamma 18	Agonist 2,678
Retinoic acid receptor beta 18	Agonist 2,678

Conditions

Condition	Modality	Targets	Highest Phase	Product
Acne vulgaris 34	Primary		Approved 8,429	DIFFERIN

C_max

C_max

Value	Dose	Co-administered	Analyte	Population
0.04 ng/mL	6.8 mg 1 times / day multiple, topical		ADAPALENE plasma	Homo sapiens

Doses

Show entries

Dose	Population	Adverse events
0.1 % 1 times / day multiple, topical Studied dose	unhealthy, 12–26 n = 87	Disc. AE: Irritation skin...
0.3 % 1 times / day multiple, topical Recommended	unhealthy, 45 - 65 n = 40	Disc. AE: Irritation skin...
0.3 % 1 times / day multiple, topical Recommended	unhealthy	Disc. AE: Erythema, Scales...

Showing 1 to 3 of 3 entries

Previous1Next

AEs

Show entries

AE	Significance	Dose	Population
Irritation skin	severe, 9.2% Disc. AE	0.1 % 1 times / day multiple, topical Studied dose	unhealthy, 12–26 n = 87
Irritation skin	severe, 7.5% Disc. AE	0.3 % 1 times / day multiple, topical Recommended	unhealthy, 45 - 65 n = 40
Application site dryness	Disc. AE	0.3 % 1 times / day multiple, topical Recommended	unhealthy
Erythema	Disc. AE	0.3 % 1 times / day multiple, topical Recommended	unhealthy
Scales	Disc. AE	0.3 % 1 times / day multiple, topical Recommended	unhealthy

Showing 1 to 5 of 6 entries

Previous1 2Next

Sourcing

Sourcing

Show entries

Vendor/Aggregator	ID	URL
ChEBI	CHEBI:31174	https://www.ebi.ac.uk/chebi/searchId.do?chebiId=CHEBI:31174
ChemicalBook	CB6771245	https://www.chemicalbook.com/ChemicalProductProperty_EN_CB6771245
MolPort	MolPort-003-986-211	https://www.molport.com/shop/molecule-link/MolPort-003-986-211
Selleck Chemicals	Adapalene	http://www.selleckchem.com/products/Adapalene.html
ZINC	ZINC000003784182	http://zinc15.docking.org/substances/ZINC000003784182

Showing 1 to 5 of 6 entries

Previous1 2Next

PubMed

Show entries

Title	Date	PubMed
Adapalene in the treatment of African patients.	2001	11843232
A comparison of adapalene gel 0.1% vs. tretinoin gel 0.025% in the treatment of acne vulgaris in China.	2001	11843231
New photographic techniques for clinical evaluation of acne.	2001	11843228
Lipid analysis of follicular casts from cyanoacrylate strips as a new method for studying therapeutic effects of antiacne agents.	2001 Jul	11453902
Randomized facial tolerability studies comparing gel formulations of retinoids used to treat acne vulgaris.	2001 Jun	11499328

Showing 1 to 5 of 29 entries

Previous1 2 3 4 5 6Next

Patents

Sample Use Guides

In Vivo Use Guide

Cream should be applied to affected areas of the skin, once daily at nighttime.

Route of Administration: Topical

In Vitro Use Guide

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
Record UNII	1L4806J2QF
Record Status	`Validated (UNII)`
Record Version

Show entries

Name

Type

Language

ADAPALENE

Official Name

English

CD-271

Code

English

IDP-126 Component Adapalene

Code

English

DIFFERIN

Brand Name

English

ADAPALENE [MI]

Common Name

English

Showing 1 to 5 of 22 entries

Previous1 2 3 4 5Next

Show entries

Classification Tree

Code System

Code

Retinoids for topical use in acne

WHO-VATC

QD10AD53

Established Pharmacologic Class

NDF-RT

N0000175607

Carotenoids

NDF-RT

N0000007700

Differentiation Inducer

NCI_THESAURUS

C804

Carotenoids

NDF-RT

N0000007700

Showing 1 to 5 of 11 entries

Previous1 2 3Next

Show entries

Code System

Code

Type

Description

WIKIPEDIA

ADAPALENE

PRIMARY

DAILYMED

1L4806J2QF

PRIMARY

EVMPD

SUB05261MIG

PRIMARY

ChEMBL

CHEMBL1265

PRIMARY

RS_ITEM_NUM

1011709

PRIMARY

Showing 1 to 5 of 21 entries

Previous1 2 3 4 5Next

Show entries

Related Record

Type

Details


					1L4806J2QF

ADAPALENE

BASIS OF STRENGTH->SUBSTANCE

Interaction Type:

ASSAY (HPLC)

Qualification:

EP

Amount:

RELATIONSHIP_AMOUNT [98 to 102] WEIGHT PERCENT (limits)

Showing 1 to 1 of 1 entries

Previous1Next

Show entries

Related Record

Type

Details


					LV4PI5YV3S

4,4'-DIMETHOXY-3,3'-DI(ADAMANT-1-YL)BIPHENYL

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

[<0.2] PERCENT PEAK AREA (limits)


					LV4PI5YV3S

4,4'-DIMETHOXY-3,3'-DI(ADAMANT-1-YL)BIPHENYL

IMPURITY -> PARENT

Comments:

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

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

[<0.2] PERCENT PEAK AREA (limits)


					W05XV3TPP3

ADAPALENE METHYL ESTER

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

[<0.1] PERCENT PEAK AREA (limits)


					A0P25CKJ7S

O-ADAMANTYLANISOLE

IMPURITY -> PARENT

Comments:

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;

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

EP

Amount:

[<0.15] PERCENT PEAK AREA (limits)


					47YX2K4GR3

2-BROMO-6-METHOXYCARBONYLNAPHTHALENE

IMPURITY -> PARENT

Interaction Type:

CHROMATOGRAPHIC PURITY (HPLC/UV)

Qualification:

USP

Amount:

[<0.1] PERCENT PEAK AREA (limits)

Showing 1 to 5 of 7 entries

Previous1 2Next

Show entries

Related Record

Type

Details


					1L4806J2QF

ADAPALENE

ACTIVE MOIETY

Amount:

Showing 1 to 1 of 1 entries

Previous1Next

SMILES

InChI

Originator

Approval Year

Targets

Conditions

Cmax

Doses

AEs

Sourcing

PubMed

Patents

Sample Use Guides

C_max