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About This Item
Empirical Formula (Hill Notation):
C28H28O3
CAS Number:
Molecular Weight:
412.52
NACRES:
NA.24
PubChem Substance ID:
UNSPSC Code:
41116107
MDL number:
Product Name
Adapalene, European Pharmacopoeia (EP) Reference Standard
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)/t17-,18+,19-,28-
SMILES string
COc1ccc(cc1C23C[C@H]4C[C@H](C[C@H](C4)C2)C3)-c5ccc6cc(ccc6c5)C(O)=O
InChI key
LZCDAPDGXCYOEH-AADAIPAGSA-N
grade
pharmaceutical primary standard
API family
adapalene
manufacturer/tradename
EDQM
application(s)
pharmaceutical (small molecule)
format
neat
storage temp.
2-8°C
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Related Categories
Application
Adapalene EP Reference standard, intended for use in laboratory tests only as specifically prescribed in the European Pharmacopoeia.
Biochem/physiol Actions
Retinoic acid analogue that is a RARβ and RARγ agonist (AC50 values are 2.2, 9.3, 22 and > 1000 nM for RARβ, RARγ, RARα and RXRα receptors respectively).
Retinoic acid analogue that is a RARβ and RARγ agonist (AC50 values are 2.2, 9.3, 22 and > 1000 nM for RARβ, RARγ, RARα and RXRα receptors respectively). Inhibits proliferation and induces apoptosis in colorectal cancer cells in vitro. Displays comedolytic activity. Its unique pharmacological properties make it superior to other retinoids for the treatment of acne.
General description
This product is provided as delivered and specified by the issuing Pharmacopoeia. All information provided in support of this product, including SDS and any product information leaflets have been developed and issued under the Authority of the Issuing Pharmacopoeia. For further information and support please go to the website of the issuing Pharmacopoeia.
Other Notes
Sales restrictions may apply.
Packaging
The product is delivered as supplied by the issuing Pharmacopoeia. For the current unit quantity, please visit the EDQM reference substance catalogue.
signalword
Warning
hcodes
Hazard Classifications
Repr. 2
Storage Class
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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[Adapalene--a new retinoid receptor agonist for the treatment of acne vulgaris].
C S Petersen
Ugeskrift for laeger, 160(46), 6668-6671 (1998-11-24)
L E Millikan
International journal of dermatology, 39(10), 784-788 (2000-11-30)
Extensive modification of the retinoic acid molecular skeleton has resulted in the development of adapalene, a more stable, less irritating compound with receptor selectivity. Adapalene selectively targets nuclear retinoic acid receptors found primarily in the epidermis. Pharmacologic and preclinical studies
Cynthia E Irby et al.
The Journal of adolescent health : official publication of the Society for Adolescent Medicine, 43(5), 421-424 (2008-10-14)
Topical retinoids help address the early lesions of acne vulgaris. Consensus guidelines advocate the use of topical retinoids as the primary treatment for most forms of acne vulgaris. However, all topical retinoid preparations may be irritating, and this may contribute
L E Millikan
Journal of the European Academy of Dermatology and Venereology : JEADV, 15 Suppl 3, 19-22 (2002-02-15)
Adapalene, a naphthoic-acid derivative, possesses some of the biological activities of tretinoin but has distinct physicochemical properties and binding properties for selective affinity for retinoic acid receptors. As such, adapalene is less likely to be associated with certain local tolerability
R N Brogden et al.
Drugs, 53(3), 511-519 (1997-03-01)
Adapalene, a naphthoic acid derivative with retinoid-like activity, is used for the topical treatment of mild to moderate acne vulgaris. It binds to retinoic acid receptors found predominantly in the terminal differentiation zone of epidermis and is more active than
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