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]
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Therapeutic Class

Dermatologic Agents

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: CHEBI:31174
CAS Number: 106685-40-9
DrugBank ID: DB00210
TTD ID: D0JC9N
ACDINA ID: D00808

Combinatorial Drugs (CBD)

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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]

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Molecular Interaction Atlas (MIA)

MIA Detail

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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]
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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
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⏷ 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.".