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

Stem definition	Drug id	CAS RN
	87	106685-40-9

Description:

Molecule	Description
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

Molecule

Description

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:

Property	Value	Reference
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:

Date	Agency	Company	Orphan
May 31, 1996	FDA	GALDERMA LABS LP

FDA Adverse Event Reporting System (Female)

MedDRA adverse event term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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 term	Likelihood ratio	Likelihood ratio threshold	Patients taking drug having adverse event	Patients taking drug not having adverse event	Patients not taking drug having adverse event	Patients 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:

Source	Code	Description
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|

Disease	Relation	SNOMED_ID
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 level	Dissociation constant	Type (acidic/basic)
pKa1	3.92	acidic

Orange Book patent data (new drug applications)

Formulation strength	Trade name	Applicant	Application number	Approval date	Type	Dose form	Route	Patent number	Patent expiration date	Patent 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:

Target	Class	Pharos	UniProt	Action	Type	Activity value (-log[M])	Bioact source	MoA source
Retinoic acid receptor beta	Nuclear hormone receptor	P10826	RARB_HUMAN	AGONIST	Ki	7.47	CHEMBL	CHEMBL
Retinoic acid receptor gamma	Nuclear hormone receptor	P13631	RARG_HUMAN	AGONIST	Ki	6.89	CHEMBL	CHEMBL
Glycine receptor subunit alpha-1	Ion channel	P23415	GLRA1_HUMAN		EC50	5.89	CHEMBL
Retinoic acid receptor alpha	Nuclear hormone receptor	P10276	RARA_HUMAN		Ki	5.96	CHEMBL
Aspartate aminotransferase, cytoplasmic	Enzyme	P17174	AATC_HUMAN		IC50	4.66	CHEMBL

External reference:

ID	Source
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:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
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