adapalene 🐶 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 µM/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 824.00 39.41 170 2362 10015 50592577
Erythema 510.39 39.41 210 2322 146204 50456388
Dry skin 475.43 39.41 146 2386 43045 50559547
Skin exfoliation 370.88 39.41 114 2418 33498 50569094
Skin irritation 332.21 39.41 77 2455 7650 50594942
Pain of skin 288.12 39.41 69 2463 7878 50594714
Chemical burn of skin 130.84 39.41 17 2515 40 50602552
Inappropriate schedule of product administration 121.72 39.41 63 2469 71768 50530824
Skin swelling 116.90 39.41 26 2506 2126 50600466
Swelling face 80.08 39.41 43 2489 52552 50550040
Pruritus 68.22 39.41 77 2455 283491 50319101
Overdose 59.28 39.41 45 2487 99682 50502910
Acne 53.83 39.41 24 2508 19571 50583021
Rash macular 51.01 39.41 23 2509 19254 50583338
Rash papular 46.40 39.41 19 2513 12585 50590007
Skin fissures 45.86 39.41 17 2515 8651 50593941
Dermatitis 44.15 39.41 19 2513 14232 50588360
Rash 41.08 39.41 76 2456 437395 50165197
Underdose 40.71 39.41 20 2512 20258 50582334
Urticaria 39.50 39.41 40 2492 129521 50473071

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 232.26 77.08 43 554 3630 29570300
Erythema 227.40 77.08 76 521 75530 29498400
Dry skin 162.41 77.08 45 552 23262 29550668
Skin exfoliation 113.93 77.08 34 563 22611 29551319
Skin irritation 83.08 77.08 19 578 4442 29569488

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 988.83 47.62 194 2569 10389 64485580
Erythema 629.04 47.62 250 2513 186820 64309149
Dry skin 603.69 47.62 176 2587 50985 64444984
Skin exfoliation 461.40 47.62 139 2624 44746 64451223
Skin irritation 378.94 47.62 86 2677 9108 64486861
Pain of skin 333.07 47.62 78 2685 9469 64486500
Chemical burn of skin 145.24 47.62 20 2743 101 64495868
Inappropriate schedule of product administration 144.69 47.62 73 2690 92213 64403756
Skin swelling 125.28 47.62 28 2735 2738 64493231
Pruritus 84.59 47.62 84 2679 312316 64183653
Rash macular 69.39 47.62 29 2734 23656 64472313
Swelling face 67.65 47.62 38 2725 59128 64436841
Acne cystic 64.16 47.62 12 2751 481 64495488
Acne 63.41 47.62 27 2736 23054 64472915
Dermatitis 62.81 47.62 25 2738 18004 64477965
Overdose 62.78 47.62 53 2710 159513 64336456
Urticaria 62.24 47.62 51 2712 147266 64348703
Hypersensitivity 57.06 47.62 55 2708 196397 64299572
Sensitive skin 55.37 47.62 12 2751 1015 64494954
Rash papular 53.65 47.62 22 2741 17091 64478878
Rash 52.66 47.62 80 2683 458469 64037500
Skin fissures 49.24 47.62 18 2745 10288 64485681

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




🐶 Veterinary Drug Use

None

🐶 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
0.1%;2.5% EPIDUO GALDERMA LABS LP N022320 Dec. 8, 2008 RX GEL TOPICAL 8105618 Dec. 23, 2022 TREATMENT OF ACNE
0.1%;2.5% EPIDUO GALDERMA LABS LP N022320 Dec. 8, 2008 RX GEL TOPICAL 8809305 Dec. 23, 2022 TREATMENT OF ACNE
0.1%;2.5% EPIDUO GALDERMA LABS LP N022320 Dec. 8, 2008 RX GEL TOPICAL 8936800 Dec. 23, 2022 TREATMENT OF ACNE
0.3%;2.5% EPIDUO FORTE GALDERMA LABS N207917 July 15, 2015 RX GEL TOPICAL 8445543 Dec. 23, 2022 TREATMENT OF ACNE
0.3%;2.5% EPIDUO FORTE GALDERMA LABS N207917 July 15, 2015 RX GEL TOPICAL 8785420 Dec. 23, 2022 TREATMENT OF ACNE
0.3%;2.5% EPIDUO FORTE GALDERMA LABS N207917 July 15, 2015 RX GEL TOPICAL 8809305 Dec. 23, 2022 TREATMENT OF ACNE
0.3%;2.5% EPIDUO FORTE GALDERMA LABS N207917 July 15, 2015 RX GEL TOPICAL 8936800 Dec. 23, 2022 TREATMENT OF ACNE
0.3%;2.5% 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%;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)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
0.3%;2.5% ADAPALENE AND BENZOYL PEROXIDE TARO A209148 Oct. 17, 2018 RX GEL TOPICAL May 30, 2022 PATENT CHALLENGE

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

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
173193 MMSL
4134 MMSL
6162 MMSL
005905 NDDF
4020981 VANDF
108903004 SNOMEDCT_US
386934008 SNOMEDCT_US

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
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
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 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 AND BENZOYL PEROXIDE HUMAN PRESCRIPTION DRUG LABEL 2 45802-853 GEL 3 mg TOPICAL ANDA 24 sections
Adapalene Topical Solution HUMAN PRESCRIPTION DRUG LABEL 1 49908-117 SOLUTION 1 mg TOPICAL ANDA 19 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
Effaclar HUMAN OTC DRUG LABEL 1 49967-591 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