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

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 808.28 40.51 176 2786 10516 46672584
Erythema 524.76 40.51 228 2734 142592 46540508
Dry skin 476.82 40.51 153 2809 40863 46642237
Acne 467.11 40.51 128 2834 19791 46663309
Skin exfoliation 378.72 40.51 122 2840 32816 46650284
Skin irritation 344.21 40.51 82 2880 7205 46675895
Pain of skin 303.57 40.51 75 2887 7667 46675433
Chemical burn of skin 123.46 40.51 18 2944 92 46683008
Inappropriate schedule of product administration 121.77 40.51 66 2896 64947 46618153
Skin swelling 117.44 40.51 27 2935 2013 46681087
Swelling face 113.85 40.51 59 2903 53000 46630100
Pruritus 83.57 40.51 89 2873 242263 46440837
Hypersensitivity 56.64 40.51 58 2904 150263 46532837
Rash 56.29 40.51 89 2873 356423 46326677
Dermatitis 49.26 40.51 22 2940 14186 46668914
Rash macular 48.77 40.51 24 2938 19236 46663864
Rash papular 48.03 40.51 21 2941 12877 46670223
Underdose 45.47 40.51 23 2939 19535 46663565
Skin fissures 43.92 40.51 17 2945 7663 46675437
Overdose 43.25 40.51 42 2920 101937 46581163

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
Skin burning sensation 255.57 77.27 48 659 3732 29948039
Erythema 232.53 77.27 81 626 77370 29874401
Dry skin 170.45 77.27 48 659 22406 29929365
Acne 138.00 77.27 34 673 9402 29942369
Skin exfoliation 103.60 77.27 33 674 23139 29928632
Skin irritation 102.79 77.27 23 684 4169 29947602
Pain of skin 88.87 77.27 20 687 3713 29948058

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 CS M0018962 Retinoids
FDA EPC N0000175607 Retinoid
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:35475 non-steroidal anti-inflammatory drugs
CHEBI has role CHEBI:50177 dermatological agent
CHEBI has role CHEBI:82665 ndk inhibitors

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)

None

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
1L4806J2QF UNII
4020981 VUID
N0000148452 NUI
D01112 KEGG_DRUG
C0165631 UMLSCUI
CHEBI:31174 CHEBI
CHEMBL1265 ChEMBL_ID
60164 PUBCHEM_CID
DB00210 DRUGBANK_ID
D000068816 MESH_DESCRIPTOR_UI
6675 INN_ID
5429 IUPHAR_LIGAND_ID
153184 RXNORM
173193 MMSL
4134 MMSL
6162 MMSL
005905 NDDF
108903004 SNOMEDCT_US
386934008 SNOMEDCT_US
4020981 VANDF

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Adapalene HUMAN PRESCRIPTION DRUG LABEL 1 0093-6301 GEL 1 mg TOPICAL ANDA 20 sections
Adapalene HUMAN PRESCRIPTION DRUG LABEL 1 0168-0424 CREAM 1 mg TOPICAL ANDA 23 sections
Differin HUMAN OTC DRUG LABEL 1 0299-4910 GEL 1 mg TOPICAL NDA 14 sections
epiduo forte HUMAN PRESCRIPTION DRUG LABEL 2 0299-5906 GEL 3 mg TOPICAL NDA 25 sections
EPIDUO HUMAN PRESCRIPTION DRUG LABEL 2 0299-5908 GEL 1 mg TOPICAL NDA 24 sections
Differin HUMAN PRESCRIPTION DRUG LABEL 1 0299-5912 LOTION 0.10 g TOPICAL NDA 24 sections
Differin HUMAN PRESCRIPTION DRUG LABEL 1 0299-5915 CREAM 1 mg TOPICAL NDA 21 sections
DIFFERIN HUMAN PRESCRIPTION DRUG LABEL 1 0299-5918 GEL 3 mg TOPICAL NDA 25 sections
Adapalene HUMAN OTC DRUG LABEL 1 0363-0888 GEL 1 mg TOPICAL ANDA 14 sections
adapalene HUMAN PRESCRIPTION DRUG LABEL 1 0472-0126 GEL 3 mg TOPICAL ANDA 18 sections
Adapalene HUMAN PRESCRIPTION DRUG LABEL 1 0781-7142 GEL 3 mg TOPICAL ANDA 25 sections
Adapalene and Benzoyl Peroxide HUMAN PRESCRIPTION DRUG LABEL 2 0781-7182 GEL 1 mg TOPICAL ANDA 25 sections
Proactiv MD Adapalene Acne Treatment HUMAN OTC DRUG LABEL 1 11410-956 GEL 0.10 g TOPICAL NDA AUTHORIZED GENERIC 15 sections
Adapalene HUMAN OTC DRUG LABEL 1 11673-888 GEL 1 mg TOPICAL ANDA 14 sections
Adapalene HUMAN OTC DRUG LABEL 1 21130-708 GEL 1 mg TOPICAL ANDA 14 sections
Adapalene HUMAN OTC DRUG LABEL 1 36800-088 GEL 1 mg TOPICAL ANDA 14 sections
Adapalene HUMAN OTC DRUG LABEL 1 41250-288 GEL 1 mg TOPICAL ANDA 14 sections
Adapalene HUMAN PRESCRIPTION DRUG LABEL 1 42546-720 GEL 45 g TOPICAL ANDA 20 sections
Adapalene HUMAN PRESCRIPTION DRUG LABEL 1 45802-453 CREAM 0.10 g TOPICAL NDA 24 sections
adapalene and benzoyl peroxide HUMAN PRESCRIPTION DRUG LABEL 2 45802-846 GEL 0.10 g TOPICAL ANDA 25 sections
Adapalene HUMAN PRESCRIPTION DRUG LABEL 1 49908-118 SWAB 1 mg TOPICAL ANDA 20 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 19 sections
ADAPALENE and BENZOYL PEROXIDE HUMAN PRESCRIPTION DRUG LABEL 2 51672-1364 GEL 1 mg TOPICAL ANDA 27 sections
Adapalene HUMAN PRESCRIPTION DRUG LABEL 1 51672-1377 GEL 3 mg TOPICAL ANDA 28 sections
Adapalene and Benzoyl Peroxide HUMAN PRESCRIPTION DRUG LABEL 2 51672-1384 GEL 3 mg TOPICAL ANDA 28 sections
DIFFERIN HUMAN PRESCRIPTION DRUG LABEL 1 54868-5030 GEL 1 mg TOPICAL NDA 21 sections
Differin HUMAN PRESCRIPTION DRUG LABEL 1 54868-5271 CREAM 1 mg TOPICAL NDA 12 sections
DIFFERIN HUMAN PRESCRIPTION DRUG LABEL 1 54868-5958 GEL 3 mg TOPICAL NDA 25 sections
EPIDUO HUMAN PRESCRIPTION DRUG LABEL 2 54868-5991 GEL 1 mg TOPICAL NDA 24 sections