adapalene 🐶 Veterinary Use | Indications/Contra | FAERs-F | FAERs-M | Orange Bk | PK/Tox | Related Drugs | 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
BA (Bioavailability) 0 %

Predicted pharmacokinetic/toxicological properties (PK-AZ):

PropertyDescriptionValueUnitConfidenceSimilarity
kinase-safety-class ACVR2A,ACVR2B,AURKA,AXL,BRAF,BTK,CAMK2B,CAMK2D,CDK5,CDK9,DYRK1B,EGFR,EIF2AK3,ERBB2,FLT3,GRK2,ITK,MAP2K6,MAP3K21,MAPK10,MAPK7,PDK1,PDK2,PDK4,PIK3CA,PIK3CB,PIK3CG,PIM2,PRKDC,SIK2,STK33,TEK,TGFBR1,TTK 34
kinase-selectivity-class EIF2AK3,PDK4 2
pfas-class PFAS structural alert (1 = True, 0 = False) 0

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 779.98 32.16 170 2866 19441 90605970
Erythema 485.92 32.16 206 2830 229040 90396371
Dry skin 449.86 32.16 151 2885 87922 90537489
Skin exfoliation 340.53 32.16 115 2921 67798 90557613
Skin irritation 329.76 32.16 79 2957 13524 90611887
Pain of skin 281.84 32.16 72 2964 16010 90609401
Chemical burn of skin 110.55 32.16 16 3020 160 90625251
Inappropriate schedule of product administration 107.05 32.16 65 2971 149868 90475543
Skin swelling 98.23 32.16 26 3010 6588 90618823
Acne 71.07 32.16 29 3007 28478 90596933
Pruritus 62.06 32.16 83 2953 541442 90083969
Overdose 56.94 32.16 45 2991 157664 90467747
Dermatitis 53.32 32.16 22 3014 22198 90603213
Swelling face 52.18 32.16 33 3003 81319 90544092
Rash macular 49.88 32.16 23 3013 30257 90595154
Rash 40.77 32.16 85 2951 796015 89829396
Rash papular 38.40 32.16 17 3019 20338 90605073
Skin fissures 38.04 32.16 17 3019 20792 90604619
Chemical burn 35.07 32.16 7 3029 508 90624903
Urticaria 32.74 32.16 46 2990 312688 90312723

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 209.18 65.79 42 585 7445 42613263
Erythema 207.78 65.79 72 555 108721 42511987
Dry skin 156.73 65.79 48 579 48290 42572418
Skin exfoliation 112.36 65.79 36 591 41517 42579191
Skin irritation 79.04 65.79 19 608 7555 42613153

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 926.11 39.36 194 2968 21631 110564506
Erythema 611.19 39.36 248 2914 291199 110294938
Dry skin 560.49 39.36 180 2982 107473 110478664
Skin exfoliation 428.75 39.36 140 3022 87511 110498626
Skin irritation 374.78 39.36 88 3074 16231 110569906
Pain of skin 321.71 39.36 81 3081 19948 110566189
Chemical burn of skin 132.72 39.36 19 3143 208 110585929
Inappropriate schedule of product administration 123.27 39.36 75 3087 203562 110382575
Skin swelling 106.68 39.36 28 3134 8052 110578085
Pruritus 81.19 39.36 91 3071 581469 110004668
Acne 77.87 39.36 31 3131 33489 110552648
Dermatitis 69.06 39.36 27 3135 27810 110558327
Rash macular 66.96 39.36 29 3133 38657 110547480
Overdose 63.76 39.36 53 3109 233741 110352396
Acne cystic 61.63 39.36 12 3150 900 110585237
Urticaria 53.30 39.36 55 3107 318802 110267335
Swelling face 50.62 39.36 32 3130 92289 110493848
Rash papular 48.73 39.36 21 3141 27618 110558519
Rash 45.87 39.36 83 3079 820881 109765256
Sensitive skin 44.86 39.36 12 3150 3700 110582437
Hypersensitivity 42.68 39.36 55 3107 403943 110182194

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 D000893 Anti-Inflammatory Agents
MeSH PA D000894 Anti-Inflammatory Agents, Non-Steroidal
MeSH PA D003879 Dermatologic Agents
MeSH PA D018501 Antirheumatic Agents
MeSH PA D018689 Sensory System Agents
MeSH PA D018712 Analgesics, Non-Narcotic
FDA EPC N0000175607 Retinoid
CHEBI has role CHEBI:35475 non-steroidal anti-inflammatory drug
CHEBI has role CHEBI:50177 dermatologic drug
CHEBI has role CHEBI:82665 EC 2.7.11.22 (cyclin-dependent kinase) inhibitor

Related Drugs by ATC class:

D10AD Retinoids for topical use in acne 5 drugs
isotretinoinmotretinideretinoltretinointrifarotene

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% DIFFERIN GALDERMA LABS LP N022502 March 17, 2010 DISCN LOTION TOPICAL 8435502 Sept. 15, 2026 TREATMENT OF ACNE
0.1% DIFFERIN GALDERMA LABS LP N022502 March 17, 2010 DISCN LOTION TOPICAL 8709392 Sept. 15, 2026 TREATMENT OF ACNE
0.1%;2.5% EPIDUO GALDERMA LABS LP N022320 Dec. 8, 2008 DISCN GEL TOPICAL 8071644 July 18, 2027 TREATMENT OF ACNE
0.1%;2.5% EPIDUO GALDERMA LABS LP N022320 Dec. 8, 2008 DISCN GEL TOPICAL 8080537 July 18, 2027 TREATMENT OF ACNE
0.1%;2.5% EPIDUO GALDERMA LABS LP N022320 Dec. 8, 2008 DISCN GEL TOPICAL 8129362 July 18, 2027 TREATMENT OF ACNE
0.1% DIFFERIN GALDERMA LABS LP N022502 March 17, 2010 DISCN LOTION TOPICAL 7998467 May 31, 2028 TREATMENT OF ACNE
0.15%;3.1%;1.2% CABTREO BAUSCH N216632 Oct. 20, 2023 RX GEL TOPICAL 10220049 June 3, 2029 TOPICAL TREATMENT OF ACNE VULGARIS IN ADULT AND PEDIATRIC PATIENTS 12 YEARS OF AGE AND OLDER
0.15%;3.1%;1.2% CABTREO BAUSCH N216632 Oct. 20, 2023 RX GEL TOPICAL 10624918 June 3, 2029 TOPICAL TREATMENT OF ACNE VULGARIS IN ADULT AND PEDIATRIC PATIENTS 12 YEARS OF AGE AND OLDER
0.15%;3.1%;1.2% CABTREO BAUSCH N216632 Oct. 20, 2023 RX GEL TOPICAL 9561208 June 3, 2029 TOPICAL TREATMENT OF ACNE VULGARIS IN ADULT AND PEDIATRIC PATIENTS 12 YEARS OF AGE AND OLDER
0.15%;3.1%;1.2% CABTREO BAUSCH N216632 Oct. 20, 2023 RX GEL TOPICAL 8288434 Aug. 5, 2029 TOPICAL TREATMENT OF ACNE VULGARIS IN ADULT AND PEDIATRIC PATIENTS 12 YEARS OF AGE AND OLDER
0.15%;3.1%;1.2% CABTREO BAUSCH N216632 Oct. 20, 2023 RX GEL TOPICAL 12128059 July 31, 2040 TOPICAL TREATMENT OF ACNE VULGARIS IN ADULT AND PEDIATRIC PATIENTS 12 YEARS OF AGE AND OLDER
0.15%;3.1%;1.2% CABTREO BAUSCH N216632 Oct. 20, 2023 RX GEL TOPICAL 11389467 Dec. 28, 2040 TOPICAL TREATMENT OF ACNE VULGARIS IN ADULT AND PEDIATRIC PATIENTS 12 YEARS OF AGE AND OLDER

Orange Book exclusivity data (new drug applications)

Formulation strengthTrade nameApplicantApplication numberApproval dateTypeDose formRouteExclusivity dateDescription
0.15%;3.1%;1.2% CABTREO BAUSCH N216632 Oct. 20, 2023 RX GEL TOPICAL Oct. 20, 2026 NEW PRODUCT

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
173193 MMSL
4134 MMSL
6162 MMSL
4020981 VANDF
005905 NDDF
108903004 SNOMEDCT_US
386934008 SNOMEDCT_US
1L4806J2QF INXIGHT DRUGS

Pharmaceutical products:

ProductCategoryIngredientsNDCFormQuantityRouteMarketingLabel
Adapalene HUMAN PRESCRIPTION DRUG LABEL 1 0168-0424 CREAM 1 mg TOPICAL ANDA 23 sections
Cabtreo HUMAN PRESCRIPTION DRUG LABEL 3 0187-0006 GEL 1.50 mg TOPICAL NDA 26 sections
Differin Epiduo HUMAN OTC DRUG LABEL 2 0299-4908 GEL 1 mg TOPICAL NDA 15 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 24 sections
DIFFERIN HUMAN PRESCRIPTION DRUG LABEL 1 0299-5918 GEL 3 mg TOPICAL NDA 25 sections
PanOxyl HUMAN OTC DRUG LABEL 1 0316-0143 GEL 1 mg TOPICAL ANDA 15 sections
PanOxyl HUMAN OTC DRUG LABEL 1 0316-0284 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 0363-1401 GEL 1 mg TOPICAL ANDA 14 sections
Adapalene HUMAN OTC DRUG LABEL 1 0363-4110 GEL 1 mg TOPICAL ANDA 14 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 0480-3154 GEL 3 mg TOPICAL ANDA 23 sections
ADAPALENE HUMAN OTC DRUG LABEL 1 0536-1412 GEL 1 mg TOPICAL ANDA 15 sections
Proactiv MD AdapaleneAcne Treatment HUMAN OTC DRUG LABEL 1 11410-958 GEL 0.10 g TOPICAL ANDA 15 sections
ADAPALENE HUMAN OTC DRUG LABEL 1 11822-0062 GEL 1 mg TOPICAL ANDA 15 sections
Adapalene HUMAN OTC DRUG LABEL 1 21130-754 GEL 1 mg TOPICAL ANDA 14 sections
Adapalene Gel USP, 0.3% HUMAN PRESCRIPTION DRUG LABEL 1 21922-051 GEL 3 mg TOPICAL ANDA 25 sections
Adapalene and Benzoyl Peroxide Gel, 0.1%/2.5% HUMAN PRESCRIPTION DRUG LABEL 2 21922-052 GEL 1 mg TOPICAL ANDA 25 sections
Adapalene HUMAN OTC DRUG LABEL 1 30142-725 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 authorized generic 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 HUMAN OTC DRUG LABEL 1 46122-768 GEL 1 mg TOPICAL ANDA 15 sections
ADAPALENE HUMAN PRESCRIPTION DRUG LABEL 1 46708-549 GEL 3 mg TOPICAL ANDA 17 sections
ADAPALENE AND BENZOYL PEROXIDE HUMAN PRESCRIPTION DRUG LABEL 2 46708-662 GEL 3 mg TOPICAL ANDA 22 sections
Adapalene Topical Solution HUMAN PRESCRIPTION DRUG LABEL 1 49908-117 SOLUTION 1 mg TOPICAL ANDA 19 sections