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Identification
NameAdapalene
Accession NumberDB00210  (APRD00780)
TypeSmall Molecule
GroupsApproved
DescriptionAdapalene is a topical retinoid primarily used in the treatment of acne and is also used (off-label) to treat keratosis pilaris as well as other skin conditions. It is currently marketed by Galderma under the trade names Differin in some countries, and Adaferin in India. [Wikipedia]
Structure
Thumb
Synonyms
6-(3-(1-Adamantyl)-4-methoxyphenyl)-2-naphthoic acid
Adaferin
Adapaleno
Adapalenum
Differine
External Identifiers Not Available
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Adapalenelotion.1 g/100mLtopicalOwen Laboratories, Inc.2010-03-31Not applicableUs
Adapalenecream.1 g/100gtopicalPerrigo New York Inc2010-10-26Not applicableUs
Adapalenegel3 mg/gtopicalOwen Laboratories, Inc.2009-09-15Not applicableUs
Adapalenegel1 mg/gtopicalTaro Pharmaceuticals U.S.A., Inc.1996-05-31Not applicableUs
Adapalenegel3 mg/gtopicalPrasco Laboratories2014-01-01Not applicableUs
Differincream1 mg/gtopicalPhysicians Total Care, Inc.2005-04-19Not applicableUs
Differingel1 mg/gtopicalGalderma Laboratories, L.P.1996-05-31Not applicableUs
Differingel3 mg/gtopicalPhysicians Total Care, Inc.2008-10-24Not applicableUs
Differinlotion.1 g/100mLtopicalGalderma Laboratories, L.P.2010-03-31Not applicableUs
Differinlotion1 mg/gtopicalPhysicians Total Care, Inc.2010-04-27Not applicableUs
Differincream1 mg/gtopicalGALDERMA LABORATORIES, L.P2009-11-24Not applicableUs
Differinlotion0.1 %topicalGalderma Canada IncNot applicableNot applicableCanada
Differingel1 mg/gtopicalPhysicians Total Care, Inc.2004-07-07Not applicableUs
Differingel3 mg/gtopicalGalderma Laboratories, L.P.2009-09-15Not applicableUs
Differincream0.1 %topicalGalderma Canada Inc1998-01-08Not applicableCanada
Differin - Gel Top 0.1%gel0.1 %topicalGalderma Canada Inc1996-12-31Not applicableCanada
Differin - Liq Top 0.1%liquid0.1 %topicalGalderma Canada Inc2001-08-082003-07-08Canada
Differin Xpgel0.3 %topicalGalderma Canada Inc2007-07-19Not applicableCanada
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Adapaleneswab1 mg/mLtopicalCall Inc. (Dba Rochester Pharmaceuticals)2016-01-05Not applicableUs
Adapalenegel1 mg/gtopicalTeva Pharmaceuticals USA Inc2010-06-02Not applicableUs
Adapalenegel1 mg/gtopicalPhysicians Total Care, Inc.2010-07-09Not applicableUs
Adapalenegel45 g/gtopicalPru Gen, Inc.2016-03-04Not applicableUs
Adapalenecream1 mg/gtopicalE. Fougera & Co. a division of Fougera Pharmaceuticals Inc.2010-06-30Not applicableUs
Adapalenecream1 mg/gtopicalPhysicians Total Caer, Inc.2010-10-01Not applicableUs
Adapalenegel3 mg/gtopicalActavis Pharma, Inc.2014-10-27Not applicableUs
Adapalenegel1 mg/gtopicalGlenmark Pharmaceuticals Inc., Usa2010-07-01Not applicableUs
Adapalenegel3 mg/gtopicalSandoz Inc.2014-04-28Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International Brands
NameCompany
AdaferinNot Available
Brand mixtures
NameLabellerIngredients
EpiduoGalderma Laboratories, L.P.
Epiduo ForteGalderma Laboratories, L.P.
TactupumpGalderma Canada Inc
Tactupump ForteGalderma Canada Inc
SaltsNot Available
Categories
UNII1L4806J2QF
CAS number106685-40-9
WeightAverage: 412.5201
Monoisotopic: 412.203844762
Chemical FormulaC28H28O3
InChI KeyInChIKey=LZCDAPDGXCYOEH-UHFFFAOYSA-N
InChI
InChI=1S/C28H28O3/c1-31-26-7-6-23(21-2-3-22-12-24(27(29)30)5-4-20(22)11-21)13-25(26)28-14-17-8-18(15-28)10-19(9-17)16-28/h2-7,11-13,17-19H,8-10,14-16H2,1H3,(H,29,30)
IUPAC Name
6-[3-(adamantan-1-yl)-4-methoxyphenyl]naphthalene-2-carboxylic acid
SMILES
COC1=C(C=C(C=C1)C1=CC2=C(C=C1)C=C(C=C2)C(O)=O)C12CC3CC(CC(C3)C1)C2
Taxonomy
DescriptionThis compound belongs to the class of organic compounds known as retinoids. These are oxygenated derivatives of 3,7-dimethyl-1-(2,6,6-trimethylcyclohex-1-enyl)nona-1,3,5,7-tetraene and derivatives thereof.
KingdomOrganic compounds
Super ClassLipids and lipid-like molecules
ClassPrenol lipids
Sub ClassRetinoids
Direct ParentRetinoids
Alternative Parents
Substituents
  • Adapalene
  • Phenylnaphthalene
  • 2-naphthalenecarboxylic acid or derivatives
  • 2-naphthalenecarboxylic acid
  • Naphthalene
  • Methoxybenzene
  • Phenol ether
  • Benzoyl
  • Anisole
  • Alkyl aryl ether
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Ether
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationFor the topical treatment of comedo, papular and pustular acne (acne vulgaris) of the face, chest or back.
PharmacodynamicsAdapalene is a chemically stable retinoid-like compound. Biochemical and pharmacological profile studies have demonstrated that adapalene is a modulator of cellular differentiation, keratinization, and inflammatory processes all of which represent important features in the pathology of acne vulgaris.
Mechanism of actionMechanistically, adapalene binds to specific retinoic acid nuclear receptors (gamma and beta) and retinoid X receptors but does not bind to the cytosolic receptor protein. Although the exact mode of action of adapalene is unknown, it is suggested that topical adapalene may normalize the differentiation of follicular epithelial cells resulting in decreased microcomedone formation.
Related Articles
AbsorptionAbsorption of adapalene through human skin is low. Only trace amounts (<0.25 ng/mL) of parent substance have been found in the plasma of acne patients following chronic topical application of adapalene in controlled clinical trials
Volume of distributionNot Available
Protein bindingNot Available
Metabolism

Metabolized mainly by O-demethylation, hydroxylation and conjugation, and excretion is primarily by the biliary route.

Route of eliminationExcretion appears to be primarily by the biliary route.
Half lifeNot Available
ClearanceNot Available
ToxicityThe acute oral toxicity of adapalene in mice and rats is greater than 10 mL/kg. Chronic ingestion of the drug may lead to the same side effects as those associated with excessive oral intake of Vitamin A.
Affected organisms
  • Humans and other mammals
PathwaysNot Available
SNP Mediated EffectsNot Available
SNP Mediated Adverse Drug ReactionsNot Available
ADMET
Predicted ADMET features
PropertyValueProbability
Human Intestinal Absorption+1.0
Blood Brain Barrier+0.7061
Caco-2 permeable+0.8439
P-glycoprotein substrateNon-substrate0.5408
P-glycoprotein inhibitor INon-inhibitor0.8074
P-glycoprotein inhibitor IIInhibitor0.5
Renal organic cation transporterNon-inhibitor0.8646
CYP450 2C9 substrateNon-substrate0.7171
CYP450 2D6 substrateNon-substrate0.8925
CYP450 3A4 substrateNon-substrate0.5116
CYP450 1A2 substrateNon-inhibitor0.7812
CYP450 2C9 inhibitorInhibitor0.7758
CYP450 2D6 inhibitorNon-inhibitor0.9466
CYP450 2C19 inhibitorNon-inhibitor0.653
CYP450 3A4 inhibitorNon-inhibitor0.8246
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.8509
Ames testNon AMES toxic0.8575
CarcinogenicityNon-carcinogens0.8707
BiodegradationNot ready biodegradable0.9715
Rat acute toxicity2.6913 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9774
hERG inhibition (predictor II)Non-inhibitor0.8855
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Nycomed us inc
  • Galderma laboratories lp
  • Glenmark generics inc usa
  • Pliva hrvatska doo
  • Galderma research and development inc
  • Galderma Laboratories
Packagers
Dosage forms
FormRouteStrength
Creamtopical.1 g/100g
Creamtopical1 mg/g
Geltopical1 mg/g
Geltopical45 g/g
Swabtopical1 mg/mL
Creamtopical0.1 %
Geltopical3 mg/g
Lotiontopical.1 g/100mL
Lotiontopical0.1 %
Lotiontopical1 mg/g
Geltopical0.1 %
Liquidtopical0.1 %
Geltopical0.3 %
Geltopical
Prices
Unit descriptionCostUnit
Differin 0.1% Cream 45 gm Tube227.13USD tube
Differin 0.1% Gel 45 gm Tube227.13USD tube
Differin 0.3% Gel 45 gm Tube219.65USD tube
Differin 0.1% cream4.85USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US4717720 No1993-05-312010-05-31Us
US7579377 No2005-02-232025-02-23Us
US7737181 No2004-08-292024-08-29Us
US7820186 No2005-11-232025-11-23Us
US7834060 No2003-03-122023-03-12Us
US7838558 No2003-03-122023-03-12Us
US7868044 No2003-03-122023-03-12Us
US7964202 No2004-09-012024-09-01Us
US7998467 No2008-05-312028-05-31Us
US8071644 No2007-07-182027-07-18Us
US8080537 No2007-07-182027-07-18Us
US8105618 No2002-12-232022-12-23Us
US8129362 No2007-07-182027-07-18Us
US8241649 No2002-12-232022-12-23Us
US8435502 No2006-09-152026-09-15Us
US8445543 No2007-07-122027-07-12Us
US8703820 No2003-03-122023-03-12Us
US8709392 No2006-09-152026-09-15Us
US8729127 No2003-03-122023-03-12Us
US8785420 No2002-12-232022-12-23Us
US8809305 No2002-12-232022-12-23Us
US8909305 No2002-12-232022-12-23Us
US8936800 No2002-12-232022-12-23Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
water solubilityPractically InsolubleNot Available
logP8.6Not Available
Predicted Properties
PropertyValueSource
Water Solubility4.01e-06 mg/mLALOGPS
logP6.06ALOGPS
logP6.46ChemAxon
logS-8ALOGPS
pKa (Strongest Acidic)3.99ChemAxon
pKa (Strongest Basic)-4.8ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count3ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area46.53 Å2ChemAxon
Rotatable Bond Count4ChemAxon
Refractivity122.07 m3·mol-1ChemAxon
Polarizability47.65 Å3ChemAxon
Number of Rings6ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
Spectra
Spectrum TypeDescriptionSplash Key
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, PositiveNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 10V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 20V, NegativeNot Available
Predicted LC-MS/MSPredicted LC-MS/MS Spectrum - 40V, NegativeNot Available
References
Synthesis Reference

Graziano Castaldi, Pietro Allegrini, Gabriele Razzetti, Mauro Ercoli, “Process for the preparation of adapalene.” U.S. Patent US20060229465, issued October 12, 2006.

US20060229465
General References
  1. Rolewski SL: Clinical review: topical retinoids. Dermatol Nurs. 2003 Oct;15(5):447-50, 459-65. [PubMed:14619325 ]
External Links
ATC CodesD10AD03D10AD53
AHFS Codes
  • 84:92.00
PDB EntriesNot Available
FDA labelDownload (25.9 KB)
MSDSDownload (57.1 KB)
Interactions
Drug Interactions
Drug
AbciximabAdapalene may increase the anticoagulant activities of Abciximab.
AcebutololAdapalene may decrease the antihypertensive activities of Acebutolol.
AceclofenacThe risk or severity of adverse effects can be increased when Adapalene is combined with Aceclofenac.
AcenocoumarolAdapalene may increase the anticoagulant activities of Acenocoumarol.
Acetylsalicylic acidThe risk or severity of adverse effects can be increased when Adapalene is combined with Acetylsalicylic acid.
Alendronic acidThe risk or severity of adverse effects can be increased when Adapalene is combined with Alendronic acid.
AliskirenAdapalene may decrease the antihypertensive activities of Aliskiren.
AlprenololAdapalene may decrease the antihypertensive activities of Alprenolol.
AlprostadilThe therapeutic efficacy of Alprostadil can be decreased when used in combination with Adapalene.
AmikacinAdapalene may decrease the excretion rate of Amikacin which could result in a lower serum level and potentially a reduction in efficacy.
AmilorideAdapalene may decrease the antihypertensive activities of Amiloride.
AncrodAdapalene may increase the anticoagulant activities of Ancrod.
AntipyrineThe risk or severity of adverse effects can be increased when Adapalene is combined with Antipyrine.
Antithrombin III humanAdapalene may increase the anticoagulant activities of Antithrombin III human.
ApixabanAdapalene may increase the anticoagulant activities of Apixaban.
ApremilastThe risk or severity of adverse effects can be increased when Adapalene is combined with Apremilast.
ArdeparinAdapalene may increase the anticoagulant activities of Ardeparin.
ArgatrobanAdapalene may increase the anticoagulant activities of Argatroban.
ArotinololAdapalene may decrease the antihypertensive activities of Arotinolol.
AtenololAdapalene may decrease the antihypertensive activities of Atenolol.
AzapropazoneThe risk or severity of adverse effects can be increased when Adapalene is combined with Azapropazone.
AzelastineThe risk or severity of adverse effects can be increased when Adapalene is combined with Azelastine.
Azilsartan medoxomilThe risk or severity of adverse effects can be increased when Azilsartan medoxomil is combined with Adapalene.
BalsalazideAdapalene may increase the nephrotoxic activities of Balsalazide.
BalsalazideThe risk or severity of adverse effects can be increased when Balsalazide is combined with Adapalene.
BecaplerminAdapalene may increase the anticoagulant activities of Becaplermin.
BefunololAdapalene may decrease the antihypertensive activities of Befunolol.
BenazeprilThe risk or severity of adverse effects can be increased when Benazepril is combined with Adapalene.
BendroflumethiazideThe therapeutic efficacy of Bendroflumethiazide can be decreased when used in combination with Adapalene.
BenoxaprofenThe risk or severity of adverse effects can be increased when Adapalene is combined with Benoxaprofen.
BetaxololAdapalene may decrease the antihypertensive activities of Betaxolol.
BevantololAdapalene may decrease the antihypertensive activities of Bevantolol.
BimatoprostThe therapeutic efficacy of Bimatoprost can be decreased when used in combination with Adapalene.
BisoprololAdapalene may decrease the antihypertensive activities of Bisoprolol.
BivalirudinAdapalene may increase the anticoagulant activities of Bivalirudin.
BopindololAdapalene may decrease the antihypertensive activities of Bopindolol.
BromfenacThe risk or severity of adverse effects can be increased when Adapalene is combined with Bromfenac.
BufuralolAdapalene may decrease the antihypertensive activities of Bufuralol.
BumetanideAdapalene may decrease the diuretic activities of Bumetanide.
BupranololAdapalene may decrease the antihypertensive activities of Bupranolol.
CandesartanThe risk or severity of adverse effects can be increased when Candesartan is combined with Adapalene.
CandoxatrilThe risk or severity of adverse effects can be increased when Candoxatril is combined with Adapalene.
CaptoprilThe risk or severity of adverse effects can be increased when Captopril is combined with Adapalene.
Carboprost TromethamineThe therapeutic efficacy of Carboprost Tromethamine can be decreased when used in combination with Adapalene.
CarprofenThe risk or severity of adverse effects can be increased when Adapalene is combined with Carprofen.
CarteololAdapalene may decrease the antihypertensive activities of Carteolol.
CarvedilolAdapalene may decrease the antihypertensive activities of Carvedilol.
CastanospermineThe risk or severity of adverse effects can be increased when Adapalene is combined with Castanospermine.
CelecoxibThe risk or severity of adverse effects can be increased when Adapalene is combined with Celecoxib.
CeliprololAdapalene may decrease the antihypertensive activities of Celiprolol.
CertoparinAdapalene may increase the anticoagulant activities of Certoparin.
ChloroquineThe risk or severity of adverse effects can be increased when Adapalene is combined with Chloroquine.
ChlorothiazideThe therapeutic efficacy of Chlorothiazide can be decreased when used in combination with Adapalene.
ChlorthalidoneThe therapeutic efficacy of Chlorthalidone can be decreased when used in combination with Adapalene.
CholestyramineCholestyramine can cause a decrease in the absorption of Adapalene resulting in a reduced serum concentration and potentially a decrease in efficacy.
CilazaprilThe risk or severity of adverse effects can be increased when Cilazapril is combined with Adapalene.
Citric AcidAdapalene may increase the anticoagulant activities of Citric Acid.
ClodronateThe risk or severity of adverse effects can be increased when Adapalene is combined with Clodronate.
ClonixinThe risk or severity of adverse effects can be increased when Adapalene is combined with Clonixin.
CloprostenolThe therapeutic efficacy of Cloprostenol can be decreased when used in combination with Adapalene.
ColesevelamColesevelam can cause a decrease in the absorption of Adapalene resulting in a reduced serum concentration and potentially a decrease in efficacy.
ColestipolColestipol can cause a decrease in the absorption of Adapalene resulting in a reduced serum concentration and potentially a decrease in efficacy.
CyclosporineAdapalene may increase the nephrotoxic activities of Cyclosporine.
D-LimoneneThe risk or severity of adverse effects can be increased when Adapalene is combined with D-Limonene.
Dabigatran etexilateAdapalene may increase the anticoagulant activities of Dabigatran etexilate.
DalteparinAdapalene may increase the anticoagulant activities of Dalteparin.
DanaparoidAdapalene may increase the anticoagulant activities of Danaparoid.
DaunorubicinAdapalene may decrease the excretion rate of Daunorubicin which could result in a lower serum level and potentially a reduction in efficacy.
DeferasiroxThe risk or severity of adverse effects can be increased when Adapalene is combined with Deferasirox.
DesirudinAdapalene may increase the anticoagulant activities of Desirudin.
DesmopressinThe risk or severity of adverse effects can be increased when Adapalene is combined with Desmopressin.
DexketoprofenThe risk or severity of adverse effects can be increased when Dexketoprofen is combined with Adapalene.
DextranAdapalene may increase the anticoagulant activities of Dextran.
Dextran 40Adapalene may increase the anticoagulant activities of Dextran 40.
Dextran 70Adapalene may increase the anticoagulant activities of Dextran 70.
Dextran 75Adapalene may increase the anticoagulant activities of Dextran 75.
DiclofenacThe risk or severity of adverse effects can be increased when Adapalene is combined with Diclofenac.
DicoumarolAdapalene may increase the anticoagulant activities of Dicoumarol.
DiflunisalThe risk or severity of adverse effects can be increased when Adapalene is combined with Diflunisal.
DigoxinThe serum concentration of Digoxin can be increased when it is combined with Adapalene.
DihydrostreptomycinAdapalene may decrease the excretion rate of Dihydrostreptomycin which could result in a lower serum level and potentially a reduction in efficacy.
DinoprostoneThe therapeutic efficacy of Dinoprostone can be decreased when used in combination with Adapalene.
DoxorubicinAdapalene may decrease the excretion rate of Doxorubicin which could result in a lower serum level and potentially a reduction in efficacy.
DrospirenoneAdapalene may increase the hyperkalemic activities of Drospirenone.
DroxicamThe risk or severity of adverse effects can be increased when Adapalene is combined with Droxicam.
Edetic AcidAdapalene may increase the anticoagulant activities of Edetic Acid.
EdoxabanAdapalene may increase the anticoagulant activities of Edoxaban.
EnalaprilThe risk or severity of adverse effects can be increased when Enalapril is combined with Adapalene.
EnalaprilatThe risk or severity of adverse effects can be increased when Enalaprilat is combined with Adapalene.
EnoxaparinAdapalene may increase the anticoagulant activities of Enoxaparin.
EpirizoleThe risk or severity of adverse effects can be increased when Adapalene is combined with Epirizole.
EpirubicinAdapalene may decrease the excretion rate of Epirubicin which could result in a lower serum level and potentially a reduction in efficacy.
EplerenoneAdapalene may decrease the antihypertensive activities of Eplerenone.
EpoprostenolThe therapeutic efficacy of Epoprostenol can be decreased when used in combination with Adapalene.
EprosartanThe risk or severity of adverse effects can be increased when Eprosartan is combined with Adapalene.
EsmololAdapalene may decrease the antihypertensive activities of Esmolol.
Etacrynic acidAdapalene may decrease the diuretic activities of Etacrynic acid.
EtanerceptThe risk or severity of adverse effects can be increased when Etanercept is combined with Adapalene.
Ethyl biscoumacetateAdapalene may increase the anticoagulant activities of Ethyl biscoumacetate.
Etidronic acidThe risk or severity of adverse effects can be increased when Adapalene is combined with Etidronic acid.
EtodolacThe risk or severity of adverse effects can be increased when Adapalene is combined with Etodolac.
EtofenamateThe risk or severity of adverse effects can be increased when Adapalene is combined with Etofenamate.
EtoricoxibThe risk or severity of adverse effects can be increased when Adapalene is combined with Etoricoxib.
Evening primrose oilThe risk or severity of adverse effects can be increased when Adapalene is combined with Evening primrose oil.
exisulindThe risk or severity of adverse effects can be increased when Adapalene is combined with exisulind.
FenbufenThe risk or severity of adverse effects can be increased when Adapalene is combined with Fenbufen.
FenoprofenThe risk or severity of adverse effects can be increased when Adapalene is combined with Fenoprofen.
FloctafenineThe risk or severity of adverse effects can be increased when Floctafenine is combined with Adapalene.
FlunixinThe risk or severity of adverse effects can be increased when Adapalene is combined with Flunixin.
FlurbiprofenThe risk or severity of adverse effects can be increased when Adapalene is combined with Flurbiprofen.
Folic AcidThe therapeutic efficacy of Folic Acid can be decreased when used in combination with Adapalene.
Fondaparinux sodiumAdapalene may increase the anticoagulant activities of Fondaparinux sodium.
ForasartanThe risk or severity of adverse effects can be increased when Forasartan is combined with Adapalene.
FosinoprilThe risk or severity of adverse effects can be increased when Fosinopril is combined with Adapalene.
FramycetinAdapalene may decrease the excretion rate of Framycetin which could result in a lower serum level and potentially a reduction in efficacy.
FurosemideAdapalene may decrease the diuretic activities of Furosemide.
GemeprostThe therapeutic efficacy of Gemeprost can be decreased when used in combination with Adapalene.
GentamicinAdapalene may decrease the excretion rate of Gentamicin which could result in a lower serum level and potentially a reduction in efficacy.
HaloperidolThe risk or severity of adverse effects can be increased when Adapalene is combined with Haloperidol.
HeparinAdapalene may increase the anticoagulant activities of Heparin.
HirulogAdapalene may increase the anticoagulant activities of Hirulog.
HMPL-004The risk or severity of adverse effects can be increased when Adapalene is combined with HMPL-004.
HydralazineAdapalene may decrease the antihypertensive activities of Hydralazine.
HydrochlorothiazideThe therapeutic efficacy of Hydrochlorothiazide can be decreased when used in combination with Adapalene.
HydroflumethiazideThe therapeutic efficacy of Hydroflumethiazide can be decreased when used in combination with Adapalene.
Hygromycin BAdapalene may decrease the excretion rate of Hygromycin B which could result in a lower serum level and potentially a reduction in efficacy.
IbandronateThe risk or severity of adverse effects can be increased when Adapalene is combined with Ibandronate.
IbuprofenThe risk or severity of adverse effects can be increased when Adapalene is combined with Ibuprofen.
IbuproxamThe risk or severity of adverse effects can be increased when Adapalene is combined with Ibuproxam.
IcatibantThe risk or severity of adverse effects can be increased when Adapalene is combined with Icatibant.
IdarubicinAdapalene may decrease the excretion rate of Idarubicin which could result in a lower serum level and potentially a reduction in efficacy.
IloprostThe therapeutic efficacy of Iloprost can be decreased when used in combination with Adapalene.
IndapamideThe therapeutic efficacy of Indapamide can be decreased when used in combination with Adapalene.
IndenololAdapalene may decrease the antihypertensive activities of Indenolol.
IndomethacinThe risk or severity of adverse effects can be increased when Adapalene is combined with Indomethacin.
IndoprofenThe risk or severity of adverse effects can be increased when Adapalene is combined with Indoprofen.
IrbesartanThe risk or severity of adverse effects can be increased when Irbesartan is combined with Adapalene.
IsoxicamThe risk or severity of adverse effects can be increased when Adapalene is combined with Isoxicam.
KanamycinAdapalene may decrease the excretion rate of Kanamycin which could result in a lower serum level and potentially a reduction in efficacy.
KebuzoneThe risk or severity of adverse effects can be increased when Adapalene is combined with Kebuzone.
KetoprofenThe risk or severity of adverse effects can be increased when Adapalene is combined with Ketoprofen.
KetorolacThe risk or severity of adverse effects can be increased when Ketorolac is combined with Adapalene.
LabetalolAdapalene may decrease the antihypertensive activities of Labetalol.
LeflunomideThe risk or severity of adverse effects can be increased when Adapalene is combined with Leflunomide.
LepirudinAdapalene may increase the anticoagulant activities of Lepirudin.
LevobunololAdapalene may decrease the antihypertensive activities of Levobunolol.
LisinoprilThe risk or severity of adverse effects can be increased when Lisinopril is combined with Adapalene.
LithiumThe serum concentration of Lithium can be increased when it is combined with Adapalene.
LornoxicamThe risk or severity of adverse effects can be increased when Adapalene is combined with Lornoxicam.
LosartanThe risk or severity of adverse effects can be increased when Losartan is combined with Adapalene.
LoxoprofenThe risk or severity of adverse effects can be increased when Adapalene is combined with Loxoprofen.
LubiprostoneThe therapeutic efficacy of Lubiprostone can be decreased when used in combination with Adapalene.
LumiracoxibThe risk or severity of adverse effects can be increased when Adapalene is combined with Lumiracoxib.
Magnesium salicylateThe risk or severity of adverse effects can be increased when Adapalene is combined with Magnesium salicylate.
MasoprocolThe risk or severity of adverse effects can be increased when Masoprocol is combined with Adapalene.
Meclofenamic acidThe risk or severity of adverse effects can be increased when Adapalene is combined with Meclofenamic acid.
Mefenamic acidThe risk or severity of adverse effects can be increased when Adapalene is combined with Mefenamic acid.
MeloxicamThe risk or severity of adverse effects can be increased when Adapalene is combined with Meloxicam.
MesalazineAdapalene may increase the nephrotoxic activities of Mesalazine.
MesalazineThe risk or severity of adverse effects can be increased when Mesalazine is combined with Adapalene.
MetamizoleThe risk or severity of adverse effects can be increased when Adapalene is combined with Metamizole.
MethotrexateThe serum concentration of Methotrexate can be increased when it is combined with Adapalene.
MethyclothiazideThe therapeutic efficacy of Methyclothiazide can be decreased when used in combination with Adapalene.
MetipranololAdapalene may decrease the antihypertensive activities of Metipranolol.
MetolazoneThe therapeutic efficacy of Metolazone can be decreased when used in combination with Adapalene.
MetoprololAdapalene may decrease the antihypertensive activities of Metoprolol.
MetrizamideAdapalene may decrease the excretion rate of Metrizamide which could result in a lower serum level and potentially a reduction in efficacy.
MisoprostolThe therapeutic efficacy of Misoprostol can be decreased when used in combination with Adapalene.
MoexiprilThe risk or severity of adverse effects can be increased when Moexipril is combined with Adapalene.
MorniflumateThe risk or severity of adverse effects can be increased when Morniflumate is combined with Adapalene.
Mycophenolate mofetilThe risk or severity of adverse effects can be increased when Adapalene is combined with Mycophenolate mofetil.
Mycophenolic acidThe risk or severity of adverse effects can be increased when Adapalene is combined with Mycophenolic acid.
NabumetoneThe risk or severity of adverse effects can be increased when Adapalene is combined with Nabumetone.
NadololAdapalene may decrease the antihypertensive activities of Nadolol.
NadroparinAdapalene may increase the anticoagulant activities of Nadroparin.
NaftifineThe risk or severity of adverse effects can be increased when Adapalene is combined with Naftifine.
NaproxenThe risk or severity of adverse effects can be increased when Adapalene is combined with Naproxen.
NCX 4016The risk or severity of adverse effects can be increased when Adapalene is combined with NCX 4016.
NeomycinAdapalene may decrease the excretion rate of Neomycin which could result in a lower serum level and potentially a reduction in efficacy.
NepafenacThe risk or severity of adverse effects can be increased when Adapalene is combined with Nepafenac.
NetilmicinAdapalene may decrease the excretion rate of Netilmicin which could result in a lower serum level and potentially a reduction in efficacy.
Niflumic AcidThe risk or severity of adverse effects can be increased when Adapalene is combined with Niflumic Acid.
NimesulideThe risk or severity of adverse effects can be increased when Adapalene is combined with Nimesulide.
OlmesartanThe risk or severity of adverse effects can be increased when Olmesartan is combined with Adapalene.
OlopatadineThe risk or severity of adverse effects can be increased when Adapalene is combined with Olopatadine.
OlsalazineAdapalene may increase the nephrotoxic activities of Olsalazine.
OlsalazineThe risk or severity of adverse effects can be increased when Olsalazine is combined with Adapalene.
Omacetaxine mepesuccinateThe risk or severity of adverse effects can be increased when Adapalene is combined with Omacetaxine mepesuccinate.
OmapatrilatThe risk or severity of adverse effects can be increased when Omapatrilat is combined with Adapalene.
OrgoteinThe risk or severity of adverse effects can be increased when Adapalene is combined with Orgotein.
OtamixabanAdapalene may increase the anticoagulant activities of Otamixaban.
OxaprozinThe risk or severity of adverse effects can be increased when Adapalene is combined with Oxaprozin.
OxprenololAdapalene may decrease the antihypertensive activities of Oxprenolol.
OxyphenbutazoneThe risk or severity of adverse effects can be increased when Adapalene is combined with Oxyphenbutazone.
PamidronateThe risk or severity of adverse effects can be increased when Adapalene is combined with Pamidronate.
ParecoxibThe risk or severity of adverse effects can be increased when Adapalene is combined with Parecoxib.
ParomomycinAdapalene may decrease the excretion rate of Paromomycin which could result in a lower serum level and potentially a reduction in efficacy.
PenbutololAdapalene may decrease the antihypertensive activities of Penbutolol.
Pentosan PolysulfateAdapalene may increase the anticoagulant activities of Pentosan Polysulfate.
PerindoprilThe risk or severity of adverse effects can be increased when Perindopril is combined with Adapalene.
PhenindioneAdapalene may increase the anticoagulant activities of Phenindione.
PhenprocoumonAdapalene may increase the anticoagulant activities of Phenprocoumon.
PhenylbutazoneThe risk or severity of adverse effects can be increased when Adapalene is combined with Phenylbutazone.
PimecrolimusThe risk or severity of adverse effects can be increased when Adapalene is combined with Pimecrolimus.
PindololAdapalene may decrease the antihypertensive activities of Pindolol.
PiretanideAdapalene may decrease the diuretic activities of Piretanide.
PirfenidoneThe risk or severity of adverse effects can be increased when Adapalene is combined with Pirfenidone.
PiroxicamThe risk or severity of adverse effects can be increased when Adapalene is combined with Piroxicam.
PlicamycinAdapalene may decrease the excretion rate of Plicamycin which could result in a lower serum level and potentially a reduction in efficacy.
PolythiazideThe therapeutic efficacy of Polythiazide can be decreased when used in combination with Adapalene.
PractololAdapalene may decrease the antihypertensive activities of Practolol.
PralatrexateThe serum concentration of Pralatrexate can be increased when it is combined with Adapalene.
ProbenecidThe serum concentration of Adapalene can be increased when it is combined with Probenecid.
PropacetamolThe risk or severity of adverse effects can be increased when Adapalene is combined with Propacetamol.
PropranololAdapalene may decrease the antihypertensive activities of Propranolol.
Prostaglandin D2The therapeutic efficacy of Prostaglandin D2 can be decreased when used in combination with Adapalene.
Protein CAdapalene may increase the anticoagulant activities of Protein C.
ProtocatechualdehydeAdapalene may increase the anticoagulant activities of Protocatechualdehyde.
PTC299The risk or severity of adverse effects can be increased when Adapalene is combined with PTC299.
PuromycinAdapalene may decrease the excretion rate of Puromycin which could result in a lower serum level and potentially a reduction in efficacy.
QuinaprilThe risk or severity of adverse effects can be increased when Quinapril is combined with Adapalene.
QuinethazoneThe therapeutic efficacy of Quinethazone can be decreased when used in combination with Adapalene.
RamiprilThe risk or severity of adverse effects can be increased when Ramipril is combined with Adapalene.
RescinnamineThe risk or severity of adverse effects can be increased when Rescinnamine is combined with Adapalene.
ResveratrolThe risk or severity of adverse effects can be increased when Adapalene is combined with Resveratrol.
ReviparinAdapalene may increase the anticoagulant activities of Reviparin.
RibostamycinAdapalene may decrease the excretion rate of Ribostamycin which could result in a lower serum level and potentially a reduction in efficacy.
RisedronateThe risk or severity of adverse effects can be increased when Adapalene is combined with Risedronate.
RivaroxabanAdapalene may increase the anticoagulant activities of Rivaroxaban.
RofecoxibThe risk or severity of adverse effects can be increased when Adapalene is combined with Rofecoxib.
SalicylamideThe risk or severity of adverse effects can be increased when Adapalene is combined with Salicylamide.
Salicylic acidThe risk or severity of adverse effects can be increased when Adapalene is combined with Salicylic acid.
SalsalateThe risk or severity of adverse effects can be increased when Adapalene is combined with Salsalate.
SaprisartanThe risk or severity of adverse effects can be increased when Saprisartan is combined with Adapalene.
SaralasinThe risk or severity of adverse effects can be increased when Saralasin is combined with Adapalene.
SeratrodastThe risk or severity of adverse effects can be increased when Adapalene is combined with Seratrodast.
SotalolAdapalene may decrease the antihypertensive activities of Sotalol.
SpectinomycinAdapalene may decrease the excretion rate of Spectinomycin which could result in a lower serum level and potentially a reduction in efficacy.
SpiraprilThe risk or severity of adverse effects can be increased when Spirapril is combined with Adapalene.
SpironolactoneAdapalene may decrease the antihypertensive activities of Spironolactone.
SRT501The risk or severity of adverse effects can be increased when Adapalene is combined with SRT501.
StreptomycinAdapalene may decrease the excretion rate of Streptomycin which could result in a lower serum level and potentially a reduction in efficacy.
StreptozocinAdapalene may decrease the excretion rate of Streptozocin which could result in a lower serum level and potentially a reduction in efficacy.
SulfasalazineAdapalene may increase the nephrotoxic activities of Sulfasalazine.
SulfasalazineThe risk or severity of adverse effects can be increased when Sulfasalazine is combined with Adapalene.
SulindacThe risk or severity of adverse effects can be increased when Adapalene is combined with Sulindac.
SulodexideAdapalene may increase the anticoagulant activities of Sulodexide.
SuprofenThe risk or severity of adverse effects can be increased when Adapalene is combined with Suprofen.
TacrolimusAdapalene may increase the nephrotoxic activities of Tacrolimus.
TalniflumateThe risk or severity of adverse effects can be increased when Talniflumate is combined with Adapalene.
TasosartanThe risk or severity of adverse effects can be increased when Tasosartan is combined with Adapalene.
Technetium Tc-99m MedronateThe risk or severity of adverse effects can be increased when Adapalene is combined with Technetium Tc-99m Medronate.
TelmisartanThe risk or severity of adverse effects can be increased when Telmisartan is combined with Adapalene.
TemocaprilThe risk or severity of adverse effects can be increased when Temocapril is combined with Adapalene.
TenofovirThe risk or severity of adverse effects can be increased when Adapalene is combined with Tenofovir.
TenoxicamThe risk or severity of adverse effects can be increased when Adapalene is combined with Tenoxicam.
TepoxalinThe risk or severity of adverse effects can be increased when Adapalene is combined with Tepoxalin.
TeriflunomideThe risk or severity of adverse effects can be increased when Adapalene is combined with Teriflunomide.
Tiaprofenic acidThe risk or severity of adverse effects can be increased when Adapalene is combined with Tiaprofenic acid.
TiludronateThe risk or severity of adverse effects can be increased when Adapalene is combined with Tiludronate.
TimololAdapalene may decrease the antihypertensive activities of Timolol.
TobramycinAdapalene may decrease the excretion rate of Tobramycin which could result in a lower serum level and potentially a reduction in efficacy.
Tolfenamic AcidThe risk or severity of adverse effects can be increased when Adapalene is combined with Tolfenamic Acid.
TolmetinThe risk or severity of adverse effects can be increased when Adapalene is combined with Tolmetin.
TorasemideAdapalene may decrease the diuretic activities of Torasemide.
TrandolaprilThe risk or severity of adverse effects can be increased when Trandolapril is combined with Adapalene.
TranilastThe risk or severity of adverse effects can be increased when Adapalene is combined with Tranilast.
TravoprostThe therapeutic efficacy of Travoprost can be decreased when used in combination with Adapalene.
TreprostinilThe risk or severity of adverse effects can be increased when Treprostinil is combined with Adapalene.
TriamtereneAdapalene may decrease the antihypertensive activities of Triamterene.
TrichlormethiazideThe therapeutic efficacy of Trichlormethiazide can be decreased when used in combination with Adapalene.
Trisalicylate-cholineThe risk or severity of adverse effects can be increased when Adapalene is combined with Trisalicylate-choline.
ValdecoxibThe risk or severity of adverse effects can be increased when Adapalene is combined with Valdecoxib.
ValsartanThe risk or severity of adverse effects can be increased when Valsartan is combined with Adapalene.
VancomycinThe serum concentration of Vancomycin can be increased when it is combined with Adapalene.
WarfarinAdapalene may increase the anticoagulant activities of Warfarin.
XimelagatranAdapalene may increase the anticoagulant activities of Ximelagatran.
ZaltoprofenThe risk or severity of adverse effects can be increased when Adapalene is combined with Zaltoprofen.
ZileutonThe risk or severity of adverse effects can be increased when Adapalene is combined with Zileuton.
Zoledronic acidThe risk or severity of adverse effects can be increased when Adapalene is combined with Zoledronic acid.
ZomepiracThe risk or severity of adverse effects can be increased when Adapalene is combined with Zomepirac.
Food InteractionsNot Available

Targets

Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, acts m...
Gene Name:
RARG
Uniprot ID:
P13631
Molecular Weight:
50341.405 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Berman HM, Westbrook J, Feng Z, Gilliland G, Bhat TN, Weissig H, Shindyalov IN, Bourne PE: The Protein Data Bank. Nucleic Acids Res. 2000 Jan 1;28(1):235-42. [PubMed:10592235 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence or presence of ho...
Gene Name:
RARB
Uniprot ID:
P10826
Molecular Weight:
50488.63 Da
References
  1. Shroot B, Michel S: Pharmacology and chemistry of adapalene. J Am Acad Dermatol. 1997 Jun;36(6 Pt 2):S96-103. [PubMed:9204085 ]
  2. Shroot B, Michel S, Allec J, Chatelus A, Wagner N: A new concept of drug delivery for acne. Dermatology. 1998;196(1):165-70. [PubMed:9557255 ]
  3. Michel S, Jomard A, Demarchez M: Pharmacology of adapalene. Br J Dermatol. 1998 Oct;139 Suppl 52:3-7. [PubMed:9990413 ]
  4. Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [PubMed:11752352 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. The high affinity ligand for RXR...
Gene Name:
RXRG
Uniprot ID:
P48443
Molecular Weight:
50870.72 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Kim MJ, Ciletti N, Michel S, Reichert U, Rosenfield RL: The role of specific retinoid receptors in sebocyte growth and differentiation in culture. J Invest Dermatol. 2000 Feb;114(2):349-53. [PubMed:10651997 ]
Kind
Protein
Organism
Human
Pharmacological action
yes
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5 (By similarity). Specifically bin...
Gene Name:
RXRB
Uniprot ID:
P28702
Molecular Weight:
56921.38 Da
References
  1. Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [PubMed:17139284 ]
  2. Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [PubMed:17016423 ]
  3. Kim MJ, Ciletti N, Michel S, Reichert U, Rosenfield RL: The role of specific retinoid receptors in sebocyte growth and differentiation in culture. J Invest Dermatol. 2000 Feb;114(2):349-53. [PubMed:10651997 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
agonist
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RXR/RAR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. In the absence of ligand, the RX...
Gene Name:
RARA
Uniprot ID:
P10276
Molecular Weight:
50770.805 Da
References
  1. Shroot B, Michel S: Pharmacology and chemistry of adapalene. J Am Acad Dermatol. 1997 Jun;36(6 Pt 2):S96-103. [PubMed:9204085 ]
  2. Griffiths CE, Ancian P, Humphries J, Poncet M, Rizova E, Michel S, Clucas A: Adapalene 0.1% gel and adapalene 0.1% cream stimulate retinoic acid receptor mediated gene transcription without significant irritative effects in the skin of healthy human volunteers. Br J Dermatol. 1998 Oct;139 Suppl 52:12-6. [PubMed:9990415 ]
  3. Michel S, Jomard A, Demarchez M: Pharmacology of adapalene. Br J Dermatol. 1998 Oct;139 Suppl 52:3-7. [PubMed:9990413 ]
  4. Shroot B, Michel S, Allec J, Chatelus A, Wagner N: A new concept of drug delivery for acne. Dermatology. 1998;196(1):165-70. [PubMed:9557255 ]
  5. Kim MJ, Ciletti N, Michel S, Reichert U, Rosenfield RL: The role of specific retinoid receptors in sebocyte growth and differentiation in culture. J Invest Dermatol. 2000 Feb;114(2):349-53. [PubMed:10651997 ]
Kind
Protein
Organism
Human
Pharmacological action
no
Actions
other/unknown
General Function:
Zinc ion binding
Specific Function:
Receptor for retinoic acid. Retinoic acid receptors bind as heterodimers to their target response elements in response to their ligands, all-trans or 9-cis retinoic acid, and regulate gene expression in various biological processes. The RAR/RXR heterodimers bind to the retinoic acid response elements (RARE) composed of tandem 5'-AGGTCA-3' sites known as DR1-DR5. The high affinity ligand for RXR...
Gene Name:
RXRA
Uniprot ID:
P19793
Molecular Weight:
50810.835 Da
References
  1. Bernard BA: Adapalene, a new chemical entity with retinoid activity. Skin Pharmacol. 1993;6 Suppl 1:61-9. [PubMed:8142113 ]
  2. Kim MJ, Ciletti N, Michel S, Reichert U, Rosenfield RL: The role of specific retinoid receptors in sebocyte growth and differentiation in culture. J Invest Dermatol. 2000 Feb;114(2):349-53. [PubMed:10651997 ]
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Drug created on June 13, 2005 07:24 / Updated on September 30, 2016 02:27