adapalene Indications/Contra | FAERs-F | FAERs-M | Orange Bk | BioActivity |

Stem definitionDrug idCAS RN
87 106685-40-9

Description:

MoleculeDescription

Molfile Inchi Smiles

Synonyms:

  • adapalene
  • differin
A naphthalene derivative that has specificity for RETINOIC ACID RECEPTORS. It is used as a DERMATOLOGIC AGENT for the treatment of ACNE.
  • Molecular weight: 412.53
  • Formula: C28H28O3
  • CLOGP: 9.15
  • LIPINSKI: 1
  • HAC: 3
  • HDO: 1
  • TPSA: 46.53
  • ALOGS: -8.01
  • ROTB: 4

  • Status: OFP

  • Legend:
    OFP - off patent
    OFM - off market
    ONP - on patent

Drug dosage:

None

ADMET properties:

PropertyValueReference
MRTD (Maximum Recommended Therapeutic Daily Dose) 0.21 ┬ÁM/kg/day Contrera JF, Matthews EJ, Kruhlak NL, Benz RD
BDDCS (Biopharmaceutical Drug Disposition Classification System) 2 Benet LZ, Broccatelli F, Oprea TI

Approvals:

DateAgencyCompanyOrphan
May 31, 1996 FDA GALDERMA LABS LP

FDA Adverse Event Reporting System (Female)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event
Skin burning sensation 690.77 189.74 102 326 1854 2355803
Erythema 660.37 189.74 143 285 25016 2332641
Dry skin 486.68 189.74 90 338 6562 2351095
Acne 403.83 189.74 69 359 3107 2354550
Skin exfoliation 387.95 189.74 73 355 5717 2351940
Pain of skin 256.49 189.74 42 386 1406 2356251
Skin irritation 251.17 189.74 41 387 1344 2356313

FDA Adverse Event Reporting System (Male)

MedDRA adverse event termLikelihood ratioLikelihood ratio thresholdPatients taking drug having adverse eventPatients taking drug not having adverse eventPatients not taking drug having adverse eventPatients not taking drug not having adverse event

Pharmacologic Action:

SourceCodeDescription
ATC D10AD03 DERMATOLOGICALS
ANTI-ACNE PREPARATIONS
ANTI-ACNE PREPARATIONS FOR TOPICAL USE
Retinoids for topical use in acne
ATC D10AD53 DERMATOLOGICALS
ANTI-ACNE PREPARATIONS
ANTI-ACNE PREPARATIONS FOR TOPICAL USE
Retinoids for topical use in acne
FDA EPC N0000175607 Retinoid
FDA CS M0018962 Retinoids
MeSH PA D000700 Analgesics
MeSH PA D018712 Analgesics, Non-Narcotic
MeSH PA D000893 Anti-Inflammatory Agents
MeSH PA D000894 Anti-Inflammatory Agents, Non-Steroidal
MeSH PA D018501 Antirheumatic Agents
MeSH PA D003879 Dermatologic Agents
MeSH PA D018373 Peripheral Nervous System Agents
MeSH PA D018689 Sensory System Agents
CHEBI has role CHEBI:50177 dermatologic drug
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drug

Drug Use (View source of the data)

DiseaseRelationSNOMED_IDDOID
Acne vulgaris indication 88616000
Photosensitivity contraindication 90128006
Erythroderma contraindication 399992009
Inflammatory dermatosis contraindication 703938007

Acid dissociation constants calculated using MoKa v3.0.0

Dissociation levelDissociation constantType (acidic/basic)
pKa1 3.92 acidic

Orange Book patent data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRoutePatent numberPatent expiration datePatent use
0.1% EPIDUO GALDERMA LABS LP N022320 Dec. 8, 2008 RX GEL TOPICAL 8105618 Dec. 23, 2022 TREATMENT OF ACNE
0.1% EPIDUO GALDERMA LABS LP N022320 Dec. 8, 2008 RX GEL TOPICAL 8809305 Dec. 23, 2022 TREATMENT OF ACNE
0.1% EPIDUO GALDERMA LABS LP N022320 Dec. 8, 2008 RX GEL TOPICAL 8936800 Dec. 23, 2022 TREATMENT OF ACNE
0.3% EPIDUO FORTE GALDERMA LABS N207917 July 15, 2015 RX GEL TOPICAL 8445543 Dec. 23, 2022 TREATMENT OF ACNE
0.3% EPIDUO FORTE GALDERMA LABS N207917 July 15, 2015 RX GEL TOPICAL 8785420 Dec. 23, 2022 TREATMENT OF ACNE
0.3% EPIDUO FORTE GALDERMA LABS N207917 July 15, 2015 RX GEL TOPICAL 8809305 Dec. 23, 2022 TREATMENT OF ACNE
0.3% EPIDUO FORTE GALDERMA LABS N207917 July 15, 2015 RX GEL TOPICAL 8936800 Dec. 23, 2022 TREATMENT OF ACNE
0.3% EPIDUO FORTE GALDERMA LABS N207917 July 15, 2015 RX GEL TOPICAL 9814690 Dec. 23, 2022 TREATMENT OF ACNE
0.3% DIFFERIN GALDERMA LABS LP N021753 June 19, 2007 RX GEL TOPICAL 7834060 March 12, 2023 TREATMENT OF ACNE
0.3% DIFFERIN GALDERMA LABS LP N021753 June 19, 2007 RX GEL TOPICAL 7868044 March 12, 2023 TREATMENT OF ACNE
0.3% DIFFERIN GALDERMA LABS LP N021753 June 19, 2007 RX GEL TOPICAL 8703820 March 12, 2023 TREATMENT OF ACNE
0.3% EPIDUO FORTE GALDERMA LABS N207917 July 15, 2015 RX GEL TOPICAL 8703820 March 12, 2023 TREATMENT OF ACNE
0.3% EPIDUO FORTE GALDERMA LABS N207917 July 15, 2015 RX GEL TOPICAL 8729127 March 12, 2023 TREATMENT OF ACNE
0.3% EPIDUO FORTE GALDERMA LABS N207917 July 15, 2015 RX GEL TOPICAL 9381179 March 12, 2023 TREATMENT OF ACNE
0.3% EPIDUO FORTE GALDERMA LABS N207917 July 15, 2015 RX GEL TOPICAL 9387187 March 12, 2023 TREATMENT OF ACNE
0.1% EPIDUO GALDERMA LABS LP N022320 Dec. 8, 2008 RX GEL TOPICAL 7964202 Sept. 1, 2024 TREATMENT OF ACNE
0.3% DIFFERIN GALDERMA LABS LP N021753 June 19, 2007 RX GEL TOPICAL 7579377 Feb. 23, 2025 TOPICAL TREATMENT OF ACNE VULGARIS
0.1% DIFFERIN GALDERMA LABS LP N022502 March 17, 2010 RX LOTION TOPICAL 8435502 Sept. 15, 2026 TREATMENT OF ACNE
0.1% DIFFERIN GALDERMA LABS LP N022502 March 17, 2010 RX LOTION TOPICAL 8709392 Sept. 15, 2026 TREATMENT OF ACNE
0.1% EPIDUO GALDERMA LABS LP N022320 Dec. 8, 2008 RX GEL TOPICAL 8445543 July 12, 2027 TREATMENT OF ACNE
0.1% EPIDUO GALDERMA LABS LP N022320 Dec. 8, 2008 RX GEL TOPICAL 8071644 July 18, 2027 TREATMENT OF ACNE
0.1% EPIDUO GALDERMA LABS LP N022320 Dec. 8, 2008 RX GEL TOPICAL 8080537 July 18, 2027 TREATMENT OF ACNE
0.1% EPIDUO GALDERMA LABS LP N022320 Dec. 8, 2008 RX GEL TOPICAL 8129362 July 18, 2027 TREATMENT OF ACNE
0.1% DIFFERIN GALDERMA LABS LP N022502 March 17, 2010 RX LOTION TOPICAL 7998467 May 31, 2028 TREATMENT OF ACNE

Orange Book exclusivity data (new drug applications)

None

Bioactivity Summary:

TargetClassPharosUniProtActionTypeActivity value
(-log[M])
Mechanism
action
Bioact sourceMoA source
Retinoic acid receptor gamma Nuclear hormone receptor AGONIST Ki 6.89 CHEMBL CHEMBL
Retinoic acid receptor beta Nuclear hormone receptor AGONIST Ki 7.47 CHEMBL CHEMBL
Retinoic acid receptor alpha Nuclear hormone receptor Ki 5.96 CHEMBL
Glycine receptor subunit alpha-1 Ion channel EC50 5.89 CHEMBL

External reference:

IDSource
D000068816 MESH_DESCRIPTOR_UI
4020981 VUID
N0000148452 NUI
C0165631 UMLSCUI
D01112 KEGG_DRUG
1L4806J2QF UNII
6675 INN_ID
108903004 SNOMEDCT_US
4020981 VANDF
173193 MMSL
005905 NDDF
4134 MMSL
60223 RXNORM
386934008 SNOMEDCT_US
CHEMBL1265 ChEMBL_ID
DB00210 DRUGBANK_ID
CHEBI:31174 CHEBI
5429 IUPHAR_LIGAND_ID
60164 PUBCHEM_CID

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Adapalene HUMAN PRESCRIPTION DRUG LABEL 1 0093-6301 GEL 1 mg TOPICAL ANDA 11 sections
Adapalene HUMAN PRESCRIPTION DRUG LABEL 1 0168-0424 CREAM 1 mg TOPICAL ANDA 12 sections
Differin HUMAN OTC DRUG LABEL 1 0299-4910 GEL 1 mg TOPICAL NDA 12 sections
epiduo forte HUMAN PRESCRIPTION DRUG LABEL 2 0299-5906 GEL 3 mg TOPICAL NDA 16 sections
EPIDUO HUMAN PRESCRIPTION DRUG LABEL 2 0299-5908 GEL 1 mg TOPICAL NDA 15 sections
Differin HUMAN PRESCRIPTION DRUG LABEL 1 0299-5912 LOTION 0.10 g TOPICAL NDA 15 sections
Differin HUMAN PRESCRIPTION DRUG LABEL 1 0299-5915 CREAM 1 mg TOPICAL NDA 11 sections
DIFFERIN HUMAN PRESCRIPTION DRUG LABEL 1 0299-5918 GEL 3 mg TOPICAL NDA 16 sections
adapalene HUMAN PRESCRIPTION DRUG LABEL 1 0472-0126 GEL 3 mg TOPICAL ANDA 17 sections
Adapalene and Benzoyl Peroxide HUMAN PRESCRIPTION DRUG LABEL 2 0472-0310 GEL 1 mg TOPICAL ANDA 16 sections
Adapalene Topical Solution HUMAN PRESCRIPTION DRUG LABEL 1 0682-0053 SWAB 1 mg TOPICAL ANDA 12 sections
Adapalene HUMAN PRESCRIPTION DRUG LABEL 1 0781-7142 GEL 3 mg TOPICAL ANDA 17 sections
Adapalene and Benzoyl Peroxide HUMAN PRESCRIPTION DRUG LABEL 2 0781-7182 GEL 1 mg TOPICAL ANDA 16 sections
Proactiv MD Adapalene HUMAN OTC DRUG LABEL 1 11410-956 GEL 0.10 g TOPICAL NDA AUTHORIZED GENERIC 10 sections
Adapalene HUMAN OTC DRUG LABEL 1 21130-708 GEL 1 mg TOPICAL ANDA 9 sections
Adapalene HUMAN OTC DRUG LABEL 1 41250-288 GEL 1 mg TOPICAL ANDA 9 sections
Adapalene HUMAN PRESCRIPTION DRUG LABEL 1 42546-720 GEL 45 g TOPICAL ANDA 12 sections
Adapalene HUMAN PRESCRIPTION DRUG LABEL 1 45802-453 CREAM 0.10 g TOPICAL NDA 13 sections
adapalene and benzoyl peroxide HUMAN PRESCRIPTION DRUG LABEL 2 45802-846 GEL 0.10 g TOPICAL ANDA 16 sections
Adapalene HUMAN PRESCRIPTION DRUG LABEL 1 49908-118 SWAB 1 mg TOPICAL ANDA 12 sections
Adapalene HUMAN OTC DRUG LABEL 1 49967-354 GEL 1 mg TOPICAL ANDA 9 sections
Adapalene HUMAN PRESCRIPTION DRUG LABEL 1 50090-2004 GEL 1 mg TOPICAL ANDA 12 sections
ADAPALENE and BENZOYL PEROXIDE HUMAN PRESCRIPTION DRUG LABEL 2 51672-1364 GEL 1 mg TOPICAL ANDA 17 sections
Adapalene HUMAN PRESCRIPTION DRUG LABEL 1 51672-1377 GEL 3 mg TOPICAL ANDA 18 sections
Adapalene and Benzoyl Peroxide HUMAN PRESCRIPTION DRUG LABEL 2 51672-1384 GEL 3 mg TOPICAL ANDA 17 sections
DIFFERIN HUMAN PRESCRIPTION DRUG LABEL 1 54868-5030 GEL 1 mg TOPICAL NDA 11 sections
Differin HUMAN PRESCRIPTION DRUG LABEL 1 54868-5271 CREAM 1 mg TOPICAL NDA 11 sections
DIFFERIN HUMAN PRESCRIPTION DRUG LABEL 1 54868-5958 GEL 3 mg TOPICAL NDA 16 sections
EPIDUO HUMAN PRESCRIPTION DRUG LABEL 2 54868-5991 GEL 1 mg TOPICAL NDA 15 sections
Differin HUMAN PRESCRIPTION DRUG LABEL 1 54868-6114 LOTION 1 mg TOPICAL NDA 15 sections