Compound: ADAPALENE
SMILES: O=C(O)c1cc2c(cc(-c3cc(c(OC)cc3)C45CC6CC(C4)CC(C5)C6)cc2)cc1
InChIKey: LZCDAPDGXCYOEH-UHFFFAOYSA-N
Synonyms: ADAPALENE, 106685-40-9, Differin, Adapaleno, Adapalenum, Adaferin, CD-271, CD 271, Differine, 6-(3-(1-Adamantyl)-4-methoxyphenyl)-2-naphthoic acid, 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoic acid, DTXSID5046481, 1L4806J2QF, 6-(4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-2-naphthalenecarboxylic acid, 6-[3-(adamantan-1-yl)-4-methoxyphenyl]naphthalene-2-carboxylic acid, IDP-126 Component Adapalene, DTXCID3026481, CHEBI:31174, CABTREO COMPONENT ADAPALENE, 2-Naphthalenecarboxylic acid, 6-(4-methoxy-3-tricyclo(3.3.1.1(sup 3,7))dec-1-ylphenyl)-, CD271, Adaplaene, Effaclar, Adapalene Gel, 6-(3-(adamantan-1-yl)-4-methoxyphenyl)naphthalene-2-carboxylic acid, Proactiv MD Kit, 6-(4-Methoxy-3-tricyclo(3.3.1.13,7)dec-1-ylphenyl)-2-naphthalenecarboxylic Acid, Curist Acne Relief, MD Kit, Adaplane 0.1%, Proactiv MD Adapalene, Adapalene Gel 0.1%, RefChem:53995, Adapalene Topical Solution, Adapalene Gel USP, 0.3%, D10AD03, Proactiv MD Adapalene Acne Treatment, 271, CD, Neutrogena Adapalene 0.1% Acne Treatment, 620-513-9, 6-(3-(Adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acid, Adapalenum [INN-Latin], Adapaleno [INN-Spanish], 6-[3-(1-adamantyl)-4-methoxy-phenyl]naphthalene-2-carboxylic acid, C28H28O3, 6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid, MFCD03106112, CHEMBL1265, 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid, NCGC00164617-01, 6-[3-(adamantan-1-yl)-4-methoxyphenyl]-2-naphthoic acid, Adapalen, Differin Gel, 6-(3-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acid, Differin (TN), CAS-106685-40-9, Differin Gel 0.1%, Adapelene, Adapalene [USAN:INN:BAN], UNII-1L4806J2QF, Adapalene CRS, Adapalene; 6-(4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)naphthalene-2-carboxylic acid, Adapalene (Standard), KS-1196, ADAPALENE [INN], ADAPALENE [JAN], ADAPALENE [MI], ADAPALENE [USAN], ADAPALENE [VANDF], ADAPALENE [MART.], ADAPALENE [USP-RS], ADAPALENE [WHO-DD], SCHEMBL2747, Adapalene (JAN/USP/INN), MLS000759463, MLS006010036, orb746767, BIDD:GT0264, Adapalene - Bio-X trade mark, GTPL5429, orb1309802, orb3025950, ADAPALENE [ORANGE BOOK], ADAPALENE [EP MONOGRAPH], Adapalene, >=98% (HPLC), CHEMBL4303650, SCHEMBL26688757, SCHEMBL29356474, SCHEMBL29357372, SCHEMBL29393098, SCHEMBL29688458, EPIDUO COMPONENT ADAPALENE, HY-B0091R, ADAPALENE [USP MONOGRAPH], HMS3264F15, HMS3654F11, HMS3715H16, HMS3754C15, HMS5079F05, HY-B0091, Tox21_112236, BDBM50048280, EBC-27000, MSK159098, s1276, STL453114, Adapalene for peak identification CRS, AKOS005145841, AKOS015895391, Tox21_112236_1, AB13763, AC-1974, CCG-213060, CCG-221237, CS-1789, DB00210, FA17220, NCGC00164617-02, NCGC00164617-04, NCGC00164617-05, BA164138, PD119179, SMR000466349, SMR002529673, SY009767, A2549, NS00010470, SW219282-1, D01112, SBI-0653441.0001, SBI-0653441.0002, AB01274764-01, AB01274764-02, AB01274764_03, AB01274764_04, EN300-19997240, Q352348, SR-01000942194, SR-01000942194-2, BRD-K33127281-001-01-5, BRD-K33127281-001-04-9, BRD-K33127281-001-05-6, F2173-0588, 6-(3-(Adamantan-1-yl)-4-methoxyphenyl)-2-naphthoicacid, Adapalene 100 microg/mL in Acetonitrile:Dimethylsulfoxide, Adapalene, European Pharmacopoeia (EP) Reference Standard, Adapalene, United States Pharmacopeia (USP) Reference Standard, 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthalene-carboxylic acid, 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthalenecarboxylic acid, Adapalene, Pharmaceutical Secondary Standard; Certified Reference Material, 6-[4-methoxy-3-(tricyclo[3.3.1.1~3,7~]dec-1-yl)phenyl]naphthalene-2-carboxylic acid, Adapalene for peak identification, European Pharmacopoeia (EP) Reference Standard, 2-NAPHTHALENECARBOXYLIC ACID, 6-(4-METHOXY-3-TRICYCLO(3.3.1.(SUP 13,7))DEC-1-YLPHENYL)-
Theoretical properties:
molecular_formula: C28H28O3
molecular_weight: 412.5 g/mol
exact_mass: 412.20384475 g/mol
formal_charge: 0
hydrogen_bond_donor_count: 1
hydrogen_bond_acceptor_count: 3
rotatable_bond_count: 4
heavy_atom_count: 31
topological_polar_surface_area: 46.5 Å²
isotope_atom_count: 0
covalently_bonded_unit_count: 1
Physical properties:
solubility: 4.01e-06 g/L
Descriptions:
pubchem: Adapalene is a naphthoic acid that is CD437 in which the phenolic hydroxy group has been converted to its methyl ether. It has a role as a non-steroidal anti-inflammatory drug, a dermatologic drug and an EC 2.7.11.22 (cyclin-dependent kinase) inhibitor. It is a monocarboxylic acid, a naphthoic acid and a member of adamantanes. It is functionally related to a CD437.
chebi: A naphthoic acid that is CD437 in which the phenolic hydroxy group has been converted to its methyl ether.
chembl: ADAPALENE is a small molecule listed in the ChEMBL database and has reached clinical trial phase 4.0.
wikipedia: Adapalene, sold under the brand name Differin among others, 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. Studies have found adapalene is as effective as other retinoids, while causing less irritation. It also has several advantages over other retinoids. The adapalene molecule is more stable compared to tretinoin and tazarotene, which leads to less concern for photodegradation. It is also chemically more stable compared to the other two retinoids, allowing it to be used in combination with benzoyl peroxide. Due to its effects on keratinocyte proliferation and differentiation, adapalene is superior to tretinoin for the treatment of comedonal acne and is often used as a first-line agent. The Swiss company Galderma developed adapalene.