Adapalene

Names

[ Name ]:
Adapalene

[Synonym ]:
Adapalene
CD-271
Adapalenum
Differin
6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoic Acid
6-(3-(Adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acid
2-Naphthalenecarboxylic acid, 6-(4-methoxy-3-tricyclo[3.3.1.1]dec-1-ylphenyl)-
6-[3-(Adamantan-1-yl)-4-methoxyphenyl]-2-naphthoic acid
Adapaleno
Adaferin
MFCD03106112
Differine
6-(4-methoxy-3-tricyclo[3.3.1.1]dec-1-ylphenyl)naphthalene-2-carboxylic acid
6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid
6-[4-methoxy-3-(tricyclo[3.3.1.1]dec-1-yl)phenyl]naphthalene-2-carboxylic acid

Biological Activity

[Description]:

Adapalene(CD-271; Differin), a synthetic retinoid, is a retinoic acid receptor agonist (RAR).Target: Retinoic acid receptor agonist (RAR)Adapalene is a third-generation topical retinoid primarily used in the treatment of mild-moderate acne and is also used (off-label) to treat keratosis pilaris as well as other skin conditions. Adapalene is possibly more effective than tretinoin 0.025% gel in the treatment of acne vulgaris [1].Thirty-six rats of either sex were divided into six groups (two control groups, and an etodolac, indomethacin, tretinoin and adapalene group) of six animals each. Each group was given different drugs or chemicals. The inhibitory activities of the drugs were determined on carrageenan-induced rat-paw oedema. The inhibition rate (53.48%) in the tretinoin group was found to be higher thanadapalene and controls (P < 0.05). Adapalene was found to have an inhibition rate of 10.28%, and when compared with the other groups, was found to have no statistically significant anti-inflammatory activity [2].

[Related Catalog]:

Signaling Pathways >> Metabolic Enzyme/Protease >> RAR/RXR

Research Areas >> Inflammation/Immunology

[References]

[1]. Ellis CN, et al. Comparison of adapalene 0.1% solution and tretinoin 0.025% gel in the topical treatment of acne vulgaris. Br J Dermatol. 1998 Oct;139 Suppl 52:41-7.

[2]. Akdeniz N, et al. Anti-inflammatory effects of tretinoin (all-trans-retinoic acid) 0.1% and adapalene 0.1% in rats. Clin Exp Dermatol. 2005 Sep;30(5):570-2.

[Related Small Molecules]

Retinoic acid | AM580 | Tamibarotene | Palovarotene | Fenretinide | TTNPB | Magnolol | AGN 194310 | AGN 193109 | CD437 | AR-7 | Tazarotene | UVI 3003 | Tarenflurbil | AGN 195183

Chemical & Physical Properties

[ Density]:
1.2±0.1 g/cm3

[ Boiling Point ]:
606.3±55.0 °C at 760 mmHg

[ Melting Point ]:
319-322ºC

[ Molecular Formula ]:
C₂₈H₂₈O₃

[ Molecular Weight ]:
412.520

[ Flash Point ]:
205.9±25.0 °C

[ Exact Mass ]:
412.203857

[ PSA ]:
46.53000

[ LogP ]:
8.04

[ Vapour Pressure ]:
0.0±1.8 mmHg at 25°C

[ Index of Refraction ]:
1.655

[ Storage condition ]:
Store at +4°C

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Statements ]:
H413

[ RIDADR ]:
NONH for all modes of transport

[ HS Code ]:
2918990090

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Customs

[ HS Code ]: 2918990090

[ Summary ]:
2918990090. other carboxylic acids with additional oxygen function and their anhydrides, halides, peroxides and peroxyacids; their halogenated, sulphonated, nitrated or nitrosated derivatives. VAT:17.0%. Tax rebate rate:13.0%. . MFN tariff:6.5%. General tariff:30.0%

Articles

Comparison of rheological properties, follicular penetration, drug release, and permeation behavior of a novel topical drug delivery system and a conventional cream.

Eur. J. Pharm. Biopharm. 88(3) , 614-24, (2015)

A novel adapalene-loaded solid lipid microparticle (SLMA) dispersion as a topical drug delivery system (TDDS) for follicular penetration has been introduced. The objective of the present study was to ...

Impaired aldehyde dehydrogenase 1 subfamily member 2A-dependent retinoic acid signaling is related with a mesenchymal-like phenotype and an unfavorable prognosis of head and neck squamous cell carcinoma.

Mol. Cancer 14(1) , 204, (2015)

An inverse correlation between expression of the aldehyde dehydrogenase 1 subfamily A2 (ALDH1A2) and gene promoter methylation has been identified as a common feature of oropharyngeal squamous cell ca...

Origins of the breast milk-derived cells; an endeavor to find the cell sources.

Cell Biol. Int. 39(5) , 611-8, (2015)

Fresh human breast milk consists of a heterogeneous population of cells that may offer a non-invasive source of cells for therapeutic proposes. The aims of this study were to characterize the breast m...