Details of the Active Pharmaceutical Ingredient (API)

General Information of API (ID: D00808)
Name
Adapalene
Synonyms    Click to Show/Hide the Synonyms of This API
ADAPALENE; 106685-40-9; Differin; 6-(3-(Adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acid; Adapaleno; Adapalenum; Adapalenum [INN-Latin]; Adapaleno [INN-Spanish]; CD-271; CD 271; 6-(3-(1-Adamantyl)-4-methoxyphenyl)-2-naphthoic acid; 6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid; 6-[3-(1-adamantyl)-4-methoxy-phenyl]naphthalene-2-carboxylic acid; 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoic acid; UNII-1L4806J2QF; MFCD03106112; CHEMBL1265; 6-(4-Methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-2-naphthalenecarboxylic acid; Adaferin; CHEBI:31174; 1L4806J2QF; NCGC00164617-01; Adapalen; Differine; 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid; 6-[3-(adamantan-1-yl)-4-methoxyphenyl]naphthalene-2-carboxylic acid; DSSTox_CID_26481; DSSTox_RID_81652; DSSTox_GSID_46481; 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthalenecarboxylic acid; Differin Gel; Differin (TN); CAS-106685-40-9; Differin Gel 0.1%; Adapalene [USAN:INN:BAN]; Adapalene/; KS-1196; SCHEMBL2747; Adapalene (JAN/USP/INN); MLS000759463; MLS006010036; BIDD:GT0264; GTPL5429; NAP030; Adapalene, >=98% (HPLC); CHEMBL4303650; DTXSID5046481; AOB6389; HMS3264F15; HMS3654F11; HMS3715H16; BCP02081; EBD19549; HY-B0091; ZINC3784182; Tox21_112236; ABP000590; BDBM50048280; s1276; STL453114; AKOS005145841; AKOS015895391; Tox21_112236_1; AB13763; AC-1974; BCP9000231; CCG-213060; CCG-221237; CS-1789; DB00210; 2-Naphthalenecarboxylic acid, 6-(4-methoxy-3-tricyclo(3.3.1.1(sup 3,7))dec-1-ylphenyl)-; NCGC00164617-02; NCGC00164617-04; NCGC00164617-05; AK-72900; I810; SMR000466349; SMR002529673; SY009767; AB0013899; A2549; FT-0631040; SW219282-1; D01112; S-3513; AB01274764-01; AB01274764-02; AB01274764_03; AB01274764_04; 685A409; A801483; Q352348; SR-01000942194; SR-01000942194-2; 6-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthoicacid; BRD-K33127281-001-01-5; F2173-0588; 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-((3r,5r,7r)-adamantan-1-yl)-4-methoxyphenyl)-2-naphthoic acid; 6-(3-Adamantan-1-yl-4-methoxy-phenyl)-naphthalene-2-carboxylic acid; Adapalene, Pharmaceutical Secondary Standard; Certified Reference Material; 2-Naphthalenecarboxylic acid, 6-(4-methoxy-3-tricyclo[3.3.1.13,7]dec-1-ylphenyl)-; 6-[4-methoxy-3-(tricyclo[3.3.1.1~3,7~]dec-1-yl)phenyl]naphthalene-2-carboxylic acid; 6-[4-methoxy-3-(tricyclo[3.3.1.13,7]dec-1-yl)phenyl]naphthalene-2-carboxylic acid; Adapalene for peak identification, European Pharmacopoeia (EP) Reference Standard
Clinical Status
Approved
PubChem CID
60164
Formula
C28H28O3
Canonical SMILES
COC1=C(C=C(C=C1)C2=CC3=C(C=C2)C=C(C=C3)C(=O)O)C45CC6CC(C4)CC(C6)C5
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
   Click to Show/Hide the Molecular Data (Structure/Property) of This API
Structure
<iframe style="width: 300px; height: 300px;" frameborder="0" src="https://embed.molview.org/v1/?mode=balls&cid=60164"></iframe>
3D MOL 2D MOL
Physicochemical Properties Molecular Weight 412.5 Topological Polar Surface Area 46.5
XlogP 7.7 Complexity 645
Heavy Atom Count 31 Rotatable Bond Count 4
Hydrogen Bond Donor Count 1 Hydrogen Bond Acceptor Count 3
Full List of Drug Formulations (DFMs) Containing This API
          Adapalene 0.3% gel Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Carbopol 980; Edetate Disodium; Methylparaben; Poloxamer 124; Propylene Glycol; Purified Water; Sodium Hydroxide
                   Dosage Form Gel
                   Company Alembic Pharmaceuticals ; Aleor Dermaceuticals Limited
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
methylparaben DIG Info Carbonic anhydrase VII (Ki = 780 nM) [1]
Acrylic acid DIG Info Choline acetylase (IC50 < 200000 nM) [2]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [3]
          Adapalene 0.1% gel Click to Show/Hide the Full List of Formulation(s):          1 Formulation(s)
             Drug Formulation 1 DFM Info click to show the detail info of this DFM
                   All DIGs    Click to Show/Hide the Full List of DIGs in This DFM
Carbomer Homopolymer; Edetate Disodium; Methylparabem; Poloxamer 182; Propylene Glycol; Purified Water; Sodium Hydroxide
                   Dosage Form Gel
                   Company Safeway
                   DIG(s) with
                   Biological Activity
DIG Name DIG Info Representative Biological Activity of This DIG REF
methylparaben DIG Info Carbonic anhydrase VII (Ki = 780 nM) [1]
Propylene glycol DIG Info Albendazole monooxygenase (Inhibition ratio < 20 %) [3]
References
1 Mono-/dihydroxybenzoic acid esters and phenol pyridinium derivatives as inhibitors of the mammalian carbonic anhydrase isoforms I, II, VII, IX, XII and XIV. Bioorg Med Chem. 2013 Mar 15; 21(6):1564-9.
2 Chemistry and biological activities of N,N-dimethylaminoethyl acrylate, a choline acetyltransferase inhibitor. J Med Chem. 1976 Feb; 19(2):300-3.
3 Pharmaceutical excipients inhibit cytochrome P450 activity in cell free systems and after systemic administration. Eur J Pharm Biopharm. 2008 Sep;70(1):279-88.

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