4728
T3D4673
Adapalene
Adapalene is a topical retinoid primarily used in the treatment of acne and is also used (off-label) to treat keratosis pilaris as well as other skin conditions. It is currently marketed by Galderma under the trade names Differin in some countries, and Adaferin in India.
106685-40-9
60164
C28H28O3
White powder.
4.01e-06 g/L
Absorption of adapalene through human skin is low. Only trace amounts (<0.25 ng/mL) of parent substance have been found in the plasma of acne patients following chronic topical application of adapalene in controlled clinical trials
Mechanistically, adapalene binds to specific retinoic acid nuclear receptors (gamma and beta) and retinoid X 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 may normalize the differentiation of follicular epithelial cells resulting in decreased microcomedone formation.
Metabolized mainly by O-demethylation, hydroxylation and conjugation, and excretion is primarily by the biliary route.
Route of Elimination: Excretion appears to be primarily by the biliary route.
The acute oral toxicity of adapalene in mice and rats is greater than 10 mL/kg
No indication of carcinogenicity to humans (not listed by IARC).
For the topical treatment of comedo, papular and pustular acne (acne vulgaris) of the face, chest or back.
Chronic ingestion of the drug may lead to the same side effects as those associated with excessive oral intake of Vitamin A.
2014-09-11T02:04:16Z
2014-12-24T20:26:54Z
http://en.wikipedia.org/wiki/Adapalene
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DB00210
true
COC1=C(C=C(C=C1)C1=CC=C2C=C(C=CC2=C1)C(O)=O)C12CC3CC(CC(C3)C1)C2
C28H28O3
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)
InChIKey=LZCDAPDGXCYOEH-UHFFFAOYSA-N
412.5201
412.203844762
Exogenous
Solid
8.6
HMDB14355
CHEMBL1265
54244
<p>Graziano Castaldi, Pietro Allegrini, Gabriele Razzetti, Mauro Ercoli, “Process for the preparation of adapalene.” U.S. Patent US20060229465, issued October 12, 2006.</p>