Details of the Drug

General Information of Drug (ID: DMX2358)

Drug Name
Adapalene
Synonyms
Adaferin; Adapaleno; Adapalenum; Differin; Differine; CD 271; CD271; Adaferin (TN); Adapaleno [INN-Spanish]; Adapalenum [INN-Latin]; CD-271; Differin (TN); Differin, Adapalene; KS-1196; Adapalene [USAN:BAN:INN]; Adapalene (JAN/USAN/INN); 6-(3-(1-Adamantyl)-4-methoxyphenyl)-2-naphthoic acid; 6-(3-adamantan-1-yl-4-methoxyphenyl)naphthalene-2-carboxylic acid; 6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid; 6-[3-(adamantan-1-yl)-4-methoxyphenyl]-2-naphthoic acid
Indication
Disease Entry ICD 11 Status REF
Acne vulgaris ED80 Approved [1]
Therapeutic Class
Dermatologic Agents
ATC Code
D10AD03: Adapalene
D10AD: Retinoids for topical use in acne
D10A: ANTI-ACNE PREPARATIONS FOR TOPICAL USE
D10: ANTI-ACNE PREPARATIONS
D: DERMATOLOGICALS
Drug Type
Small molecular drug
Structure
3D MOL 2D MOL
#Ro5 Violations (Lipinski): 1 Molecular Weight (mw) 412.5
Logarithm of the Partition Coefficient (xlogp) 7.7
Rotatable Bond Count (rotbonds) 4
Hydrogen Bond Donor Count (hbonddonor) 1
Hydrogen Bond Acceptor Count (hbondacc) 3
ADMET Property
BDDCS Class
Biopharmaceutics Drug Disposition Classification System (BDDCS) Class 2: low solubility and high permeability [2]
MRTD
The Maximum Recommended Therapeutic Dose (MRTD) of drug that ensured maximising efficacy and moderate side effect is 0.2078 micromolar/kg/day [3]
Chemical Identifiers
Formula
C28H28O3
IUPAC Name
6-[3-(1-adamantyl)-4-methoxyphenyl]naphthalene-2-carboxylic acid
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
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
Cross-matching ID
PubChem CID
60164
ChEBI ID
CHEMBL1265
CAS Number
106685-40-9
TTD ID
D0JC9N
ACDINA ID
D00808
Drug-Molecule Activity Atlas (DMA)NEW Click to Jump to the Detailed DMA Information of This Drug
Drug ADMET Endpoint Profile (DAE)NEW Click to Jump to the Detailed DAE Information of This Drug
Combinatorial Drugs (CBD) Click to Jump to the Detailed CBD Information of This Drug

Molecular Interaction Atlas of This Drug


Drug Therapeutic Target (DTT)
DTT Name DTT ID UniProt ID MOA REF
Retinoic acid receptor (RAR) TTOD7B3 NOUNIPROTAC Binder [4]
Molecular Interaction Atlas (MIA) Jump to Detail Molecular Interaction Atlas of This Drug

Drug-Drug Interaction (DDI) Information of This Drug

Coadministration of a Drug Treating the Disease Different from Adapalene (Comorbidity)
DDI Drug Name DDI Drug ID Severity Mechanism Comorbidity REF
Porfimer Sodium DM7ZWNY Moderate Increased risk of photosensitivity reactions by the combination of Adapalene and Porfimer Sodium. Lung cancer [2C25] [5]
Methoxsalen DME8FZ9 Moderate Increased risk of photosensitivity reactions by the combination of Adapalene and Methoxsalen. Mycosis fungoides [2B01] [6]
Verteporfin DMIY6DB Moderate Increased risk of photosensitivity reactions by the combination of Adapalene and Verteporfin. Psoriasis [EA90] [7]

Drug Inactive Ingredient(s) (DIG) and Formulation(s) of This Drug

DIG
DIG Name DIG ID PubChem CID Functional Classification
Acrylic acid E00132 6581 Other agent
methylparaben E00149 7456 Antimicrobial preservative
Edetate disodium E00186 8759 Complexing agent
Propylene glycol E00040 1030 Antimicrobial preservative; Humectant; Plasticizing agent; Solvent
Sodium hydroxide E00234 14798 Alkalizing agent
Water E00035 962 Solvent
⏷ Show the Full List of 6 Pharmaceutical Excipients of This Drug
Pharmaceutical Formulation
Formulation Name Drug Dosage Dosage Form Route
Adapalene 0.3% gel 0.30% Gel Topical
Adapalene 0.1% gel 0.10% Gel Topical
Jump to Detail Pharmaceutical Formulation Page of This Drug

References

1 URL: http://www.guidetopharmacology.org Nucleic Acids Res. 2015 Oct 12. pii: gkv1037. The IUPHAR/BPS Guide to PHARMACOLOGY in 2016: towards curated quantitative interactions between 1300 protein targets and 6000 ligands. (Ligand id: 5429).
2 BDDCS applied to over 900 drugs
3 Estimating the safe starting dose in phase I clinical trials and no observed effect level based on QSAR modeling of the human maximum recommended daily dose
4 A review of adapalene in the treatment of acne vulgaris. J Adolesc Health. 2008 Nov;43(5):421-4.
5 Blakely KM, Drucker AM, Rosen CF "Drug-induced photosensitivity-an update: Culprit drugs, prevention and management." Drug Saf 42 (2019): 827-47. [PMID: 30888626]
6 Cerner Multum, Inc. "Australian Product Information.".
7 Cerner Multum, Inc. "UK Summary of Product Characteristics.".