adapalene ๐Ÿถ Veterinary Use | 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 ยตM/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 811.56 34.40 171 2648 12563 63473640
Erythema 513.59 34.40 215 2604 175536 63310667
Dry skin 460.80 34.40 148 2671 56739 63429464
Skin exfoliation 360.24 34.40 115 2704 42987 63443216
Skin irritation 328.71 34.40 78 2741 9663 63476540
Pain of skin 279.96 34.40 71 2748 11563 63474640
Chemical burn of skin 132.87 34.40 17 2802 40 63486163
Inappropriate schedule of product administration 109.52 34.40 64 2755 103901 63382302
Skin swelling 107.69 34.40 26 2793 3433 63482770
Swelling face 77.28 34.40 43 2776 63432 63422771
Pruritus 70.24 34.40 83 2736 361370 63124833
Acne 65.52 34.40 28 2791 23265 63462938
Overdose 58.29 34.40 45 2774 115033 63371170
Dermatitis 49.72 34.40 21 2798 16937 63469266
Rash macular 49.40 34.40 23 2796 23341 63462862
Skin fissures 46.86 34.40 18 2801 11370 63474833
Rash papular 44.55 34.40 19 2800 15683 63470520
Rash 42.43 34.40 83 2736 560788 62925415
Urticaria 40.48 34.40 43 2776 165759 63320444
Underdose 37.23 34.40 20 2799 27436 63458767
Chemical burn 34.44 34.40 7 2812 418 63485785

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 227.34 75.48 43 582 4600 34951706
Erythema 224.24 75.48 76 549 88704 34867602
Dry skin 168.11 75.48 48 577 31239 34925067
Skin exfoliation 120.17 75.48 36 589 27396 34928910
Skin irritation 81.14 75.48 19 606 5558 34950748

FDA Adverse Event Reporting System (Geriatric)

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 976.16 45.35 195 2797 13077 79728319
Erythema 627.87 45.35 253 2739 223037 79518359
Dry skin 589.76 45.35 179 2813 67816 79673580
Skin exfoliation 455.45 45.35 140 2852 54960 79686436
Skin irritation 378.34 45.35 87 2905 11153 79730243
Pain of skin 320.25 45.35 80 2912 14533 79726863
Chemical burn of skin 147.07 45.35 20 2972 106 79741290
Inappropriate schedule of product administration 131.02 45.35 74 2918 133554 79607842
Skin swelling 118.59 45.35 28 2964 3986 79737410
Pruritus 88.19 45.35 90 2902 394558 79346838
Acne 69.22 45.35 29 2963 27161 79714235
Rash macular 67.52 45.35 29 2963 28870 79712526
Swelling face 65.76 45.35 38 2954 71174 79670222
Dermatitis 65.42 45.35 26 2966 21295 79720101
Urticaria 64.05 45.35 54 2938 185147 79556249
Acne cystic 63.63 45.35 12 2980 576 79740820
Overdose 62.24 45.35 53 2939 184153 79557243
Rash papular 54.52 45.35 23 2969 21893 79719503
Hypersensitivity 51.58 45.35 56 2936 262183 79479213
Rash 50.68 45.35 83 2909 578275 79163121
Sensitive skin 50.34 45.35 12 2980 1775 79739621
Skin fissures 47.39 45.35 18 2974 13055 79728341

FDA Adverse Event Reporting System (Pediatric)

None

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
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
FDA EPC N0000175607 Retinoid
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory agent
CHEBI has role CHEBI:50177 dermatologic agent
CHEBI has role CHEBI:82665 EC 2.7.11.22 (cyclin-dependent kinase) inhibitors

Drug Use | Suggest Off label Use Form| |View source of the data|

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




๐Ÿถ Veterinary Drug Use

None

๐Ÿถ Veterinary products

None

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
0.3% 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%;2.5% EPIDUO FORTE GALDERMA LABS N207917 July 15, 2015 RX GEL TOPICAL 8703820 March 12, 2023 TREATMENT OF ACNE
0.3%;2.5% EPIDUO FORTE GALDERMA LABS N207917 July 15, 2015 RX GEL TOPICAL 8729127 March 12, 2023 TREATMENT OF ACNE
0.3%;2.5% EPIDUO FORTE GALDERMA LABS N207917 July 15, 2015 RX GEL TOPICAL 9381179 March 12, 2023 TREATMENT OF ACNE
0.3%;2.5% EPIDUO FORTE GALDERMA LABS N207917 July 15, 2015 RX GEL TOPICAL 9387187 March 12, 2023 TREATMENT OF ACNE
0.1%;2.5% 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%;2.5% EPIDUO GALDERMA LABS LP N022320 Dec. 8, 2008 RX GEL TOPICAL 8445543 July 12, 2027 TREATMENT OF ACNE
0.1%;2.5% EPIDUO GALDERMA LABS LP N022320 Dec. 8, 2008 RX GEL TOPICAL 8071644 July 18, 2027 TREATMENT OF ACNE
0.1%;2.5% EPIDUO GALDERMA LABS LP N022320 Dec. 8, 2008 RX GEL TOPICAL 8080537 July 18, 2027 TREATMENT OF ACNE
0.1%;2.5% 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 beta Nuclear hormone receptor AGONIST Ki 7.47 CHEMBL CHEMBL
Retinoic acid receptor gamma Nuclear hormone receptor AGONIST Ki 6.89 CHEMBL CHEMBL
Glycine receptor subunit alpha-1 Ion channel EC50 5.89 CHEMBL
Retinoic acid receptor alpha Nuclear hormone receptor Ki 5.96 CHEMBL
Aspartate aminotransferase, cytoplasmic Enzyme IC50 4.66 CHEMBL

External reference:

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

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
adapalene and benzoyl peroxide HUMAN PRESCRIPTION DRUG LABEL 2 0093-6303 GEL 3 mg TOPICAL NDA authorized generic 25 sections
adapalene and benzoyl peroxide HUMAN PRESCRIPTION DRUG LABEL 2 0093-6303 GEL 3 mg TOPICAL NDA authorized generic 25 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
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 26 sections
epiduo forte HUMAN PRESCRIPTION DRUG LABEL 2 0299-5906 GEL 3 mg TOPICAL NDA 26 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 26 sections
Differin HUMAN PRESCRIPTION DRUG LABEL 1 0299-5912 LOTION 0.10 g TOPICAL NDA 26 sections
Differin HUMAN PRESCRIPTION DRUG LABEL 1 0299-5912 LOTION 0.10 g TOPICAL NDA 26 sections
Differin HUMAN PRESCRIPTION DRUG LABEL 1 0299-5915 CREAM 1 mg TOPICAL NDA 21 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 27 sections
DIFFERIN HUMAN PRESCRIPTION DRUG LABEL 1 0299-5918 GEL 3 mg TOPICAL NDA 27 sections
DIFFERIN HUMAN PRESCRIPTION DRUG LABEL 1 0299-5918 GEL 3 mg TOPICAL NDA 27 sections
PanOxyl HUMAN OTC DRUG LABEL 1 0316-0143 GEL 1 mg TOPICAL ANDA 15 sections
Adapalene HUMAN OTC DRUG LABEL 1 0363-0888 GEL 1 mg TOPICAL ANDA 14 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 0472-0126 GEL 3 mg TOPICAL ANDA 18 sections
Adapalene and benzoyl peroxide HUMAN PRESCRIPTION DRUG LABEL 2 0480-3154 GEL 3 mg TOPICAL ANDA 23 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
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 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 21130-708 GEL 1 mg TOPICAL ANDA 14 sections