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

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	690.77	189.74	102	326	1854	2355803
Erythema	660.37	189.74	143	285	25016	2332641
Dry skin	486.68	189.74	90	338	6562	2351095
Acne	403.83	189.74	69	359	3107	2354550
Skin exfoliation	387.95	189.74	73	355	5717	2351940
Pain of skin	256.49	189.74	42	386	1406	2356251
Skin irritation	251.17	189.74	41	387	1344	2356313

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

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 EPC	N0000175607	Retinoid
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
CHEBI has role	CHEBI:50177	dermatologic drug
CHEBI has role	CHEBI:35475	non-steroidal anti-inflammatory drug

Drug Use (View source of the data)

Disease	Relation	SNOMED_ID
Acne vulgaris	indication	88616000
Photosensitivity	contraindication	90128006
Erythroderma	contraindication	399992009
Inflammatory dermatosis	contraindication	703938007

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
0.1%	EPIDUO	GALDERMA LABS LP	N022320	Dec. 8, 2008	RX	GEL	TOPICAL	8105618	Dec. 23, 2022	TREATMENT OF ACNE
0.1%	EPIDUO	GALDERMA LABS LP	N022320	Dec. 8, 2008	RX	GEL	TOPICAL	8809305	Dec. 23, 2022	TREATMENT OF ACNE
0.1%	EPIDUO	GALDERMA LABS LP	N022320	Dec. 8, 2008	RX	GEL	TOPICAL	8936800	Dec. 23, 2022	TREATMENT OF ACNE
0.3%	EPIDUO FORTE	GALDERMA LABS	N207917	July 15, 2015	RX	GEL	TOPICAL	8445543	Dec. 23, 2022	TREATMENT OF ACNE
0.3%	EPIDUO FORTE	GALDERMA LABS	N207917	July 15, 2015	RX	GEL	TOPICAL	8785420	Dec. 23, 2022	TREATMENT OF ACNE
0.3%	EPIDUO FORTE	GALDERMA LABS	N207917	July 15, 2015	RX	GEL	TOPICAL	8809305	Dec. 23, 2022	TREATMENT OF ACNE
0.3%	EPIDUO FORTE	GALDERMA LABS	N207917	July 15, 2015	RX	GEL	TOPICAL	8936800	Dec. 23, 2022	TREATMENT OF ACNE
0.3%	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%	EPIDUO FORTE	GALDERMA LABS	N207917	July 15, 2015	RX	GEL	TOPICAL	8703820	March 12, 2023	TREATMENT OF ACNE
0.3%	EPIDUO FORTE	GALDERMA LABS	N207917	July 15, 2015	RX	GEL	TOPICAL	8729127	March 12, 2023	TREATMENT OF ACNE
0.3%	EPIDUO FORTE	GALDERMA LABS	N207917	July 15, 2015	RX	GEL	TOPICAL	9381179	March 12, 2023	TREATMENT OF ACNE
0.3%	EPIDUO FORTE	GALDERMA LABS	N207917	July 15, 2015	RX	GEL	TOPICAL	9387187	March 12, 2023	TREATMENT OF ACNE
0.1%	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%	EPIDUO	GALDERMA LABS LP	N022320	Dec. 8, 2008	RX	GEL	TOPICAL	8445543	July 12, 2027	TREATMENT OF ACNE
0.1%	EPIDUO	GALDERMA LABS LP	N022320	Dec. 8, 2008	RX	GEL	TOPICAL	8071644	July 18, 2027	TREATMENT OF ACNE
0.1%	EPIDUO	GALDERMA LABS LP	N022320	Dec. 8, 2008	RX	GEL	TOPICAL	8080537	July 18, 2027	TREATMENT OF ACNE
0.1%	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 gamma	Nuclear hormone receptor	P13631	RARG_HUMAN	AGONIST	Ki	6.89	CHEMBL	CHEMBL
Retinoic acid receptor beta	Nuclear hormone receptor	P10826	RARB_HUMAN	AGONIST	Ki	7.47	CHEMBL	CHEMBL
Retinoic acid receptor alpha	Nuclear hormone receptor	P10276	RARA_HUMAN		Ki	5.96	CHEMBL
Glycine receptor subunit alpha-1	Ion channel	P23415	GLRA1_HUMAN		EC50	5.89	CHEMBL

External reference:

ID	Source
D000068816	MESH_DESCRIPTOR_UI
4020981	VUID
N0000148452	NUI
C0165631	UMLSCUI
D01112	KEGG_DRUG
1L4806J2QF	UNII
6675	INN_ID
108903004	SNOMEDCT_US
4020981	VANDF
173193	MMSL
005905	NDDF
4134	MMSL
60223	RXNORM
386934008	SNOMEDCT_US
CHEMBL1265	ChEMBL_ID
DB00210	DRUGBANK_ID
CHEBI:31174	CHEBI
5429	IUPHAR_LIGAND_ID
60164	PUBCHEM_CID

Pharmaceutical products:

Product	Category	Ingredients	NDC	Form	Quantity	Route	Marketing	Label
Adapalene	HUMAN PRESCRIPTION DRUG LABEL	1	0093-6301	GEL	1 mg	TOPICAL	ANDA	11 sections
Adapalene	HUMAN PRESCRIPTION DRUG LABEL	1	0168-0424	CREAM	1 mg	TOPICAL	ANDA	12 sections
Differin	HUMAN OTC DRUG LABEL	1	0299-4910	GEL	1 mg	TOPICAL	NDA	12 sections
epiduo forte	HUMAN PRESCRIPTION DRUG LABEL	2	0299-5906	GEL	3 mg	TOPICAL	NDA	16 sections
EPIDUO	HUMAN PRESCRIPTION DRUG LABEL	2	0299-5908	GEL	1 mg	TOPICAL	NDA	15 sections
Differin	HUMAN PRESCRIPTION DRUG LABEL	1	0299-5912	LOTION	0.10 g	TOPICAL	NDA	15 sections
Differin	HUMAN PRESCRIPTION DRUG LABEL	1	0299-5915	CREAM	1 mg	TOPICAL	NDA	11 sections
DIFFERIN	HUMAN PRESCRIPTION DRUG LABEL	1	0299-5918	GEL	3 mg	TOPICAL	NDA	16 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	0472-0310	GEL	1 mg	TOPICAL	ANDA	16 sections
Adapalene Topical Solution	HUMAN PRESCRIPTION DRUG LABEL	1	0682-0053	SWAB	1 mg	TOPICAL	ANDA	12 sections
Adapalene	HUMAN PRESCRIPTION DRUG LABEL	1	0781-7142	GEL	3 mg	TOPICAL	ANDA	17 sections
Adapalene and Benzoyl Peroxide	HUMAN PRESCRIPTION DRUG LABEL	2	0781-7182	GEL	1 mg	TOPICAL	ANDA	16 sections
Proactiv MD Adapalene	HUMAN OTC DRUG LABEL	1	11410-956	GEL	0.10 g	TOPICAL	NDA AUTHORIZED GENERIC	10 sections
Adapalene	HUMAN OTC DRUG LABEL	1	21130-708	GEL	1 mg	TOPICAL	ANDA	9 sections
Adapalene	HUMAN OTC DRUG LABEL	1	41250-288	GEL	1 mg	TOPICAL	ANDA	9 sections
Adapalene	HUMAN PRESCRIPTION DRUG LABEL	1	42546-720	GEL	45 g	TOPICAL	ANDA	12 sections
Adapalene	HUMAN PRESCRIPTION DRUG LABEL	1	45802-453	CREAM	0.10 g	TOPICAL	NDA	13 sections
adapalene and benzoyl peroxide	HUMAN PRESCRIPTION DRUG LABEL	2	45802-846	GEL	0.10 g	TOPICAL	ANDA	16 sections
Adapalene	HUMAN PRESCRIPTION DRUG LABEL	1	49908-118	SWAB	1 mg	TOPICAL	ANDA	12 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	12 sections
ADAPALENE and BENZOYL PEROXIDE	HUMAN PRESCRIPTION DRUG LABEL	2	51672-1364	GEL	1 mg	TOPICAL	ANDA	17 sections
Adapalene	HUMAN PRESCRIPTION DRUG LABEL	1	51672-1377	GEL	3 mg	TOPICAL	ANDA	18 sections
Adapalene and Benzoyl Peroxide	HUMAN PRESCRIPTION DRUG LABEL	2	51672-1384	GEL	3 mg	TOPICAL	ANDA	17 sections
DIFFERIN	HUMAN PRESCRIPTION DRUG LABEL	1	54868-5030	GEL	1 mg	TOPICAL	NDA	11 sections
Differin	HUMAN PRESCRIPTION DRUG LABEL	1	54868-5271	CREAM	1 mg	TOPICAL	NDA	11 sections
DIFFERIN	HUMAN PRESCRIPTION DRUG LABEL	1	54868-5958	GEL	3 mg	TOPICAL	NDA	16 sections
EPIDUO	HUMAN PRESCRIPTION DRUG LABEL	2	54868-5991	GEL	1 mg	TOPICAL	NDA	15 sections
Differin	HUMAN PRESCRIPTION DRUG LABEL	1	54868-6114	LOTION	1 mg	TOPICAL	NDA	15 sections