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Identification
NameBexarotene
Accession NumberDB00307  (APRD00114)
TypeSmall Molecule
GroupsApproved, Investigational
Description

Bexarotene (Targretin) is an antineoplastic agent indicated by the FDA for Cutaneous T cell lymphoma. It has been used off-label for lung cancer, breast cancer, and Kaposi’s sarcoma. [Wikipedia]

Structure
Thumb
Synonyms
4-[1-(3,5,5,8,8-pentamethyltetralin-2-yl)ethenyl]benzoic acid
4-[1-(5,6,7,8,-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphtalenyl)ethenyl]benzoic acid
Bexaroten
Bexarotène
Bexarotene
Bexaroteno
Bexarotenum
P-(1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)vinyl)benzoic acid
p-[1-(5,6,7,8,-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)vinyl]benzoic acid
Targretyn
Targrexin
External Identifiers
  • LG 100069
  • LGD 1069
Approved Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Bexarotenecapsule, liquid filled75 mg/1oralOceanside Pharmaceuticals1999-12-29Not applicableUs
Targretingel1 g/100gtopicalValeant Pharmaceuticals North America LLC2000-06-28Not applicableUs
Targretingel1 g/100gtopicalEisai Inc.2000-06-28Not applicableUs
Targretincapsule, liquid filled75 mg/1oralEisai Inc.1999-12-29Not applicableUs
Targretincapsule, liquid filled75 mg/1oralValeant Pharmaceuticals North America LLC1999-12-29Not applicableUs
Approved Generic Prescription Products
NameDosageStrengthRouteLabellerMarketing StartMarketing End
Bexarotenecapsule, liquid filled75 mg/1oralMylan Pharmaceuticals Inc.2015-07-09Not applicableUs
Bexarotenecapsule, liquid filled75 mg/1oralMylan Institutional Inc.2016-04-15Not applicableUs
Approved Over the Counter ProductsNot Available
Unapproved/Other Products Not Available
International BrandsNot Available
Brand mixturesNot Available
SaltsNot Available
Categories
UNIIA61RXM4375
CAS number153559-49-0
WeightAverage: 348.4779
Monoisotopic: 348.20893014
Chemical FormulaC24H28O2
InChI KeyInChIKey=NAVMQTYZDKMPEU-UHFFFAOYSA-N
InChI
InChI=1S/C24H28O2/c1-15-13-20-21(24(5,6)12-11-23(20,3)4)14-19(15)16(2)17-7-9-18(10-8-17)22(25)26/h7-10,13-14H,2,11-12H2,1,3-6H3,(H,25,26)
IUPAC Name
4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoic acid
SMILES
CC1=CC2=C(C=C1C(=C)C1=CC=C(C=C1)C(O)=O)C(C)(C)CCC2(C)C
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
  • Bexarotene
  • Bisabolane sesquiterpenoid
  • Sesquiterpenoid
  • Tetralin
  • Phenylpropene
  • Benzoic acid
  • Benzoic acid or derivatives
  • Styrene
  • Benzoyl
  • Benzenoid
  • Monocyclic benzene moiety
  • Monocarboxylic acid or derivatives
  • Carboxylic acid
  • Carboxylic acid derivative
  • Hydrocarbon derivative
  • Organooxygen compound
  • Carbonyl group
  • Aromatic homopolycyclic compound
Molecular FrameworkAromatic homopolycyclic compounds
External Descriptors
Pharmacology
IndicationUsed orally for the treatment of skin manifestations of cutaneous T-cell lymphoma (CTCL) in patients who are refractory to at least one prior systemic therapy. Also used topically for the treatment of skin lesions in early (stage IA and IB) CTCL in patients who experience refractory or persistent disease with the use of other therapies or are intolerant of other therapies.
PharmacodynamicsBexarotene is a member of a subclass of retinoids that selectively activate retinoid X receptors (RXRs). These retinoid receptors have biologic activity distinct from that of retinoic acid receptors (RARs). Bexarotene is indicated for the treatment of cutaneous manifestations of cutaneous T-cell lymphoma in patients who are refractory to at least one prior systemic therapy. Bexarotene selectively binds and activates retinoid X receptor subtypes (RXRα, RXRβ, RXRγ). RXRs can form heterodimers with various receptor partners such as retinoic acid receptors (RARs), vitamin D receptor, thyroid receptor, and peroxisome proliferator activator receptors (PPARs). Once activated, these receptors function as transcription factors that regulate the expression of genes that control cellular differentiation and proliferation. Bexarotene inhibits the growth in vitro of some tumor cell lines of hematopoietic and squamous cell origin. It also induces tumor regression in vivo in some animal models.
Mechanism of actionBexarotene selectively binds with and activates retinoid X receptor subtypes. There are three subtypes in total: RXRα, RXRβ, RXRγ. The exact mechanism of action of bexarotene in the treatment of CTCL is unknown but the drug has activity in all clinical stages of CTCL.
Related Articles
AbsorptionNot Available
Volume of distributionNot Available
Protein binding>99%
MetabolismNot Available
Route of eliminationUrinary elimination of bexarotene and its known metabolites is a minor excretory pathway (<1% of administered dose).
Half life7 hours
ClearanceNot Available
ToxicityNot Available
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+0.9954
Blood Brain Barrier+0.9022
Caco-2 permeable+0.794
P-glycoprotein substrateSubstrate0.6283
P-glycoprotein inhibitor INon-inhibitor0.5369
P-glycoprotein inhibitor IINon-inhibitor0.7182
Renal organic cation transporterNon-inhibitor0.8496
CYP450 2C9 substrateNon-substrate0.7722
CYP450 2D6 substrateNon-substrate0.9116
CYP450 3A4 substrateSubstrate0.6786
CYP450 1A2 substrateNon-inhibitor0.8171
CYP450 2C9 inhibitorNon-inhibitor0.8724
CYP450 2D6 inhibitorInhibitor0.5589
CYP450 2C19 inhibitorInhibitor0.8351
CYP450 3A4 inhibitorNon-inhibitor0.8138
CYP450 inhibitory promiscuityLow CYP Inhibitory Promiscuity0.6458
Ames testNon AMES toxic0.8592
CarcinogenicityNon-carcinogens0.7898
BiodegradationNot ready biodegradable0.933
Rat acute toxicity2.2119 LD50, mol/kg Not applicable
hERG inhibition (predictor I)Weak inhibitor0.9703
hERG inhibition (predictor II)Non-inhibitor0.9034
ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397 )
Pharmacoeconomics
Manufacturers
  • Eisai inc
Packagers
Dosage forms
FormRouteStrength
Capsule, liquid filledoral75 mg/1
Geltopical1 g/100g
Prices
Unit descriptionCostUnit
Targretin 75 mg capsule38.0USD capsule
Targretin 75 mg softgel36.54USD softget capsule
Targretin 1% gel30.08USD g
DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.
Patents
Patent NumberPediatric ExtensionApprovedExpires (estimated)
US5780676 No1995-07-142015-07-14Us
US5962731 No1996-10-052016-10-05Us
US6043279 No1995-04-222012-04-22Us
Properties
StateSolid
Experimental Properties
PropertyValueSource
logP6.9Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.000149 mg/mLALOGPS
logP6.86ALOGPS
logP6.94ChemAxon
logS-6.4ALOGPS
pKa (Strongest Acidic)4.07ChemAxon
Physiological Charge-1ChemAxon
Hydrogen Acceptor Count2ChemAxon
Hydrogen Donor Count1ChemAxon
Polar Surface Area37.3 Å2ChemAxon
Rotatable Bond Count3ChemAxon
Refractivity117.12 m3·mol-1ChemAxon
Polarizability40.89 Å3ChemAxon
Number of Rings3ChemAxon
Bioavailability1ChemAxon
Rule of FiveYesChemAxon
Ghose FilterYesChemAxon
Veber's RuleYesChemAxon
MDDR-like RuleYesChemAxon
Spectra
Mass Spec (NIST)Not Available
SpectraNot Available
References
Synthesis Reference

DrugSyn.org

US5466861
General References
  1. Gniadecki R, Assaf C, Bagot M, Dummer R, Duvic M, Knobler R, Ranki A, Schwandt P, Whittaker S: The optimal use of bexarotene in cutaneous T-cell lymphoma. Br J Dermatol. 2007 Sep;157(3):433-40. Epub 2007 Jun 6. [PubMed:17553039 ]
  2. Dragnev KH, Petty WJ, Shah SJ, Lewis LD, Black CC, Memoli V, Nugent WC, Hermann T, Negro-Vilar A, Rigas JR, Dmitrovsky E: A proof-of-principle clinical trial of bexarotene in patients with non-small cell lung cancer. Clin Cancer Res. 2007 Mar 15;13(6):1794-800. [PubMed:17363535 ]
  3. Smit JW, Stokkel MP, Pereira AM, Romijn JA, Visser TJ: Bexarotene-induced hypothyroidism: bexarotene stimulates the peripheral metabolism of thyroid hormones. J Clin Endocrinol Metab. 2007 Jul;92(7):2496-9. Epub 2007 Apr 17. [PubMed:17440015 ]
  4. Lowe MN, Plosker GL: Bexarotene. Am J Clin Dermatol. 2000 Jul-Aug;1(4):245-50; discussion 251-2. [PubMed:11702369 ]
  5. Yen WC, Prudente RY, Corpuz MR, Negro-Vilar A, Lamph WW: A selective retinoid X receptor agonist bexarotene (LGD1069, targretin) inhibits angiogenesis and metastasis in solid tumours. Br J Cancer. 2006 Mar 13;94(5):654-60. [PubMed:16495926 ]
  6. Farol LT, Hymes KB: Bexarotene: a clinical review. Expert Rev Anticancer Ther. 2004 Apr;4(2):180-8. [PubMed:15056048 ]
External Links
ATC CodesL01XX25
AHFS CodesNot Available
PDB EntriesNot Available
FDA labelDownload (40.2 KB)
MSDSNot Available
Interactions
Drug Interactions
Drug
AbirateroneThe serum concentration of Abiraterone can be decreased when it is combined with Bexarotene.
AlfuzosinThe serum concentration of Alfuzosin can be decreased when it is combined with Bexarotene.
AlprazolamThe serum concentration of Alprazolam can be decreased when it is combined with Bexarotene.
AminophyllineThe serum concentration of Aminophylline can be decreased when it is combined with Bexarotene.
AmiodaroneThe serum concentration of Amiodarone can be decreased when it is combined with Bexarotene.
AmlodipineThe serum concentration of Amlodipine can be decreased when it is combined with Bexarotene.
ApixabanThe serum concentration of Apixaban can be decreased when it is combined with Bexarotene.
ApremilastThe serum concentration of Apremilast can be decreased when it is combined with Bexarotene.
AprepitantThe serum concentration of Aprepitant can be decreased when it is combined with Bexarotene.
AripiprazoleThe serum concentration of Aripiprazole can be decreased when it is combined with Bexarotene.
ArmodafinilThe serum concentration of Armodafinil can be decreased when it is combined with Bexarotene.
ArtemetherThe serum concentration of Artemether can be decreased when it is combined with Bexarotene.
AtazanavirThe serum concentration of Atazanavir can be decreased when it is combined with Bexarotene.
AtorvastatinThe serum concentration of Atorvastatin can be decreased when it is combined with Bexarotene.
AvanafilThe serum concentration of Avanafil can be decreased when it is combined with Bexarotene.
AxitinibThe serum concentration of Axitinib can be decreased when it is combined with Bexarotene.
BedaquilineThe serum concentration of Bedaquiline can be decreased when it is combined with Bexarotene.
BenzphetamineThe serum concentration of Benzphetamine can be decreased when it is combined with Bexarotene.
BiotinThe serum concentration of Biotin can be decreased when it is combined with Bexarotene.
BisoprololThe serum concentration of Bisoprolol can be decreased when it is combined with Bexarotene.
BoceprevirThe serum concentration of Boceprevir can be decreased when it is combined with Bexarotene.
BortezomibThe serum concentration of Bortezomib can be decreased when it is combined with Bexarotene.
BosutinibThe serum concentration of Bosutinib can be decreased when it is combined with Bexarotene.
BrexpiprazoleThe serum concentration of Brexpiprazole can be decreased when it is combined with Bexarotene.
BuprenorphineThe serum concentration of Buprenorphine can be decreased when it is combined with Bexarotene.
BuspironeThe serum concentration of Buspirone can be decreased when it is combined with Bexarotene.
CabazitaxelThe serum concentration of Cabazitaxel can be decreased when it is combined with Bexarotene.
CabozantinibThe serum concentration of Cabozantinib can be decreased when it is combined with Bexarotene.
CalcitriolThe serum concentration of Calcitriol can be decreased when it is combined with Bexarotene.
CarbamazepineThe serum concentration of Carbamazepine can be decreased when it is combined with Bexarotene.
CarboplatinThe serum concentration of Bexarotene can be increased when it is combined with Carboplatin.
CeritinibThe serum concentration of Ceritinib can be decreased when it is combined with Bexarotene.
ChlordiazepoxideThe serum concentration of Chlordiazepoxide can be decreased when it is combined with Bexarotene.
ChloroquineThe serum concentration of Chloroquine can be decreased when it is combined with Bexarotene.
ChlorotrianiseneThe serum concentration of Chlorotrianisene can be decreased when it is combined with Bexarotene.
CilostazolThe serum concentration of Cilostazol can be decreased when it is combined with Bexarotene.
CitalopramThe serum concentration of Citalopram can be decreased when it is combined with Bexarotene.
ClarithromycinThe serum concentration of the active metabolites of Clarithromycin can be increased when Clarithromycin is used in combination with Bexarotene.
ClidiniumThe serum concentration of Clidinium can be decreased when it is combined with Bexarotene.
ClonazepamThe serum concentration of Clonazepam can be decreased when it is combined with Bexarotene.
ClorazepateThe serum concentration of Clorazepate can be decreased when it is combined with Bexarotene.
ClozapineThe risk or severity of adverse effects can be increased when Bexarotene is combined with Clozapine.
CobicistatThe serum concentration of Cobicistat can be decreased when it is combined with Bexarotene.
CobimetinibThe serum concentration of Cobimetinib can be decreased when it is combined with Bexarotene.
ConivaptanThe serum concentration of Conivaptan can be decreased when it is combined with Bexarotene.
CrizotinibThe serum concentration of Crizotinib can be decreased when it is combined with Bexarotene.
CyclosporineThe serum concentration of Cyclosporine can be decreased when it is combined with Bexarotene.
Cyproterone acetateThe serum concentration of Cyproterone acetate can be decreased when it is combined with Bexarotene.
DaclatasvirThe serum concentration of Daclatasvir can be decreased when it is combined with Bexarotene.
DantroleneThe serum concentration of Dantrolene can be decreased when it is combined with Bexarotene.
DapsoneThe serum concentration of Dapsone can be decreased when it is combined with Bexarotene.
DarifenacinThe serum concentration of Darifenacin can be decreased when it is combined with Bexarotene.
DarunavirThe serum concentration of Darunavir can be decreased when it is combined with Bexarotene.
DasatinibThe serum concentration of Dasatinib can be decreased when it is combined with Bexarotene.
DelavirdineThe serum concentration of Delavirdine can be decreased when it is combined with Bexarotene.
DesogestrelThe serum concentration of Desogestrel can be decreased when it is combined with Bexarotene.
DexamethasoneThe serum concentration of Dexamethasone can be decreased when it is combined with Bexarotene.
DiazepamThe serum concentration of Diazepam can be decreased when it is combined with Bexarotene.
DienogestThe serum concentration of Dienogest can be decreased when it is combined with Bexarotene.
DiltiazemThe serum concentration of Diltiazem can be decreased when it is combined with Bexarotene.
DisopyramideThe serum concentration of Disopyramide can be decreased when it is combined with Bexarotene.
DocetaxelThe serum concentration of Docetaxel can be decreased when it is combined with Bexarotene.
DoxazosinThe serum concentration of Doxazosin can be decreased when it is combined with Bexarotene.
DoxorubicinThe serum concentration of Doxorubicin can be decreased when it is combined with Bexarotene.
DronedaroneThe serum concentration of Dronedarone can be decreased when it is combined with Bexarotene.
DrospirenoneThe serum concentration of Drospirenone can be decreased when it is combined with Bexarotene.
EfavirenzThe serum concentration of Efavirenz can be decreased when it is combined with Bexarotene.
EliglustatThe serum concentration of Eliglustat can be decreased when it is combined with Bexarotene.
ElvitegravirThe serum concentration of Elvitegravir can be decreased when it is combined with Bexarotene.
EnzalutamideThe serum concentration of Enzalutamide can be decreased when it is combined with Bexarotene.
EplerenoneThe serum concentration of Eplerenone can be decreased when it is combined with Bexarotene.
ErlotinibThe serum concentration of Erlotinib can be decreased when it is combined with Bexarotene.
ErythromycinThe serum concentration of Erythromycin can be decreased when it is combined with Bexarotene.
EscitalopramThe serum concentration of Escitalopram can be decreased when it is combined with Bexarotene.
EstradiolThe serum concentration of Estradiol can be decreased when it is combined with Bexarotene.
Estrone sulfateThe serum concentration of Estropipate can be decreased when it is combined with Bexarotene.
EszopicloneThe serum concentration of Eszopiclone can be decreased when it is combined with Bexarotene.
Ethinyl EstradiolThe serum concentration of Ethinyl Estradiol can be decreased when it is combined with Bexarotene.
EthosuximideThe serum concentration of Ethosuximide can be decreased when it is combined with Bexarotene.
Ethynodiol diacetateThe serum concentration of Ethynodiol can be decreased when it is combined with Bexarotene.
EtonogestrelThe serum concentration of Etonogestrel can be decreased when it is combined with Bexarotene.
EtoposideThe serum concentration of Etoposide can be decreased when it is combined with Bexarotene.
EtravirineThe serum concentration of Etravirine can be decreased when it is combined with Bexarotene.
EverolimusThe serum concentration of Everolimus can be decreased when it is combined with Bexarotene.
ExemestaneThe serum concentration of Exemestane can be decreased when it is combined with Bexarotene.
FelbamateThe serum concentration of Felbamate can be decreased when it is combined with Bexarotene.
FelodipineThe serum concentration of Felodipine can be decreased when it is combined with Bexarotene.
FentanylThe serum concentration of Fentanyl can be decreased when it is combined with Bexarotene.
FesoterodineThe serum concentration of Fesoterodine can be decreased when it is combined with Bexarotene.
FlibanserinThe serum concentration of Flibanserin can be decreased when it is combined with Bexarotene.
FlunisolideThe serum concentration of Flunisolide can be decreased when it is combined with Bexarotene.
FlurazepamThe serum concentration of Flurazepam can be decreased when it is combined with Bexarotene.
FlutamideThe serum concentration of Flutamide can be decreased when it is combined with Bexarotene.
FosamprenavirThe serum concentration of Fosamprenavir can be decreased when it is combined with Bexarotene.
FosaprepitantThe serum concentration of Fosaprepitant can be decreased when it is combined with Bexarotene.
GefitinibThe serum concentration of Gefitinib can be decreased when it is combined with Bexarotene.
GemfibrozilThe serum concentration of Bexarotene can be increased when it is combined with Gemfibrozil.
GuanfacineThe serum concentration of Guanfacine can be decreased when it is combined with Bexarotene.
HaloperidolThe serum concentration of Haloperidol can be decreased when it is combined with Bexarotene.
HydrocodoneThe serum concentration of Hydrocodone can be decreased when it is combined with Bexarotene.
Hydroxyprogesterone caproateThe serum concentration of Hydroxyprogesterone caproate can be decreased when it is combined with Bexarotene.
IbrutinibThe serum concentration of Ibrutinib can be decreased when it is combined with Bexarotene.
IdelalisibThe serum concentration of Idelalisib can be decreased when it is combined with Bexarotene.
IfosfamideThe serum concentration of the active metabolites of Ifosfamide can be reduced when Ifosfamide is used in combination with Bexarotene resulting in a loss in efficacy.
ImatinibThe serum concentration of Imatinib can be decreased when it is combined with Bexarotene.
IndinavirThe serum concentration of Indinavir can be decreased when it is combined with Bexarotene.
IrinotecanThe serum concentration of Irinotecan can be decreased when it is combined with Bexarotene.
IsavuconazoniumThe serum concentration of Isavuconazonium can be decreased when it is combined with Bexarotene.
IsosorbideThe serum concentration of Isosorbide can be decreased when it is combined with Bexarotene.
Isosorbide DinitrateThe serum concentration of Isosorbide Dinitrate can be decreased when it is combined with Bexarotene.
Isosorbide MononitrateThe serum concentration of Isosorbide Mononitrate can be decreased when it is combined with Bexarotene.
IsradipineThe serum concentration of Isradipine can be decreased when it is combined with Bexarotene.
ItraconazoleThe serum concentration of Itraconazole can be decreased when it is combined with Bexarotene.
IvabradineThe serum concentration of Ivabradine can be decreased when it is combined with Bexarotene.
IvacaftorThe serum concentration of Ivacaftor can be decreased when it is combined with Bexarotene.
IxabepiloneThe serum concentration of Ixabepilone can be decreased when it is combined with Bexarotene.
IxazomibThe serum concentration of Ixazomib can be decreased when it is combined with Bexarotene.
KetoconazoleThe serum concentration of Ketoconazole can be decreased when it is combined with Bexarotene.
LansoprazoleThe serum concentration of Lansoprazole can be decreased when it is combined with Bexarotene.
LapatinibThe serum concentration of Lapatinib can be decreased when it is combined with Bexarotene.
LevonorgestrelThe serum concentration of Levonorgestrel can be decreased when it is combined with Bexarotene.
LidocaineThe serum concentration of Lidocaine can be decreased when it is combined with Bexarotene.
LomitapideThe serum concentration of Lomitapide can be decreased when it is combined with Bexarotene.
LopinavirThe serum concentration of Lopinavir can be decreased when it is combined with Bexarotene.
LosartanThe serum concentration of Losartan can be decreased when it is combined with Bexarotene.
LovastatinThe serum concentration of Lovastatin can be decreased when it is combined with Bexarotene.
LumefantrineThe serum concentration of Lumefantrine can be decreased when it is combined with Bexarotene.
LurasidoneThe serum concentration of Lurasidone can be decreased when it is combined with Bexarotene.
MacitentanThe serum concentration of MACITENTAN can be decreased when it is combined with Bexarotene.
MaravirocThe serum concentration of Maraviroc can be decreased when it is combined with Bexarotene.
Medroxyprogesterone AcetateThe serum concentration of Medroxyprogesterone Acetate can be decreased when it is combined with Bexarotene.
MefloquineThe serum concentration of Mefloquine can be decreased when it is combined with Bexarotene.
MestranolThe serum concentration of Mestranol can be decreased when it is combined with Bexarotene.
MetamizoleThe risk or severity of adverse effects can be increased when Metamizole is combined with Bexarotene.
MethadoneThe serum concentration of Methadone can be decreased when it is combined with Bexarotene.
MidazolamThe serum concentration of Midazolam can be decreased when it is combined with Bexarotene.
MifepristoneThe serum concentration of Mifepristone can be decreased when it is combined with Bexarotene.
MirtazapineThe serum concentration of Mirtazapine can be decreased when it is combined with Bexarotene.
ModafinilThe serum concentration of Modafinil can be decreased when it is combined with Bexarotene.
NaloxegolThe serum concentration of Naloxegol can be decreased when it is combined with Bexarotene.
NateglinideThe serum concentration of Nateglinide can be decreased when it is combined with Bexarotene.
NefazodoneThe serum concentration of Nefazodone can be decreased when it is combined with Bexarotene.
NelfinavirThe serum concentration of Nelfinavir can be decreased when it is combined with Bexarotene.
NetupitantThe serum concentration of Netupitant can be decreased when it is combined with Bexarotene.
NevirapineThe serum concentration of Nevirapine can be decreased when it is combined with Bexarotene.
NicardipineThe serum concentration of Nicardipine can be decreased when it is combined with Bexarotene.
NifedipineThe serum concentration of Nifedipine can be decreased when it is combined with Bexarotene.
NilotinibThe serum concentration of Nilotinib can be decreased when it is combined with Bexarotene.
NimodipineThe serum concentration of Nimodipine can be decreased when it is combined with Bexarotene.
NisoldipineThe serum concentration of Nisoldipine can be decreased when it is combined with Bexarotene.
NorethisteroneThe serum concentration of Norethindrone can be decreased when it is combined with Bexarotene.
NorgestimateThe serum concentration of Norgestimate can be decreased when it is combined with Bexarotene.
OlaparibThe serum concentration of Olaparib can be decreased when it is combined with Bexarotene.
OndansetronThe serum concentration of Ondansetron can be decreased when it is combined with Bexarotene.
OspemifeneThe serum concentration of Ospemifene can be decreased when it is combined with Bexarotene.
OxycodoneThe serum concentration of Oxycodone can be decreased when it is combined with Bexarotene.
OxytetracyclineThe risk or severity of adverse effects can be increased when Oxytetracycline is combined with Bexarotene.
PaclitaxelThe serum concentration of Bexarotene can be increased when it is combined with Paclitaxel.
PalbociclibThe serum concentration of Palbociclib can be decreased when it is combined with Bexarotene.
PalonosetronThe serum concentration of Palonosetron can be decreased when it is combined with Bexarotene.
PanobinostatThe serum concentration of Panobinostat can be decreased when it is combined with Bexarotene.
PazopanibThe serum concentration of Pazopanib can be decreased when it is combined with Bexarotene.
PerampanelThe serum concentration of Perampanel can be decreased when it is combined with Bexarotene.
PimozideThe serum concentration of Pimozide can be decreased when it is combined with Bexarotene.
PipotiazineThe serum concentration of Pipotiazine can be decreased when it is combined with Bexarotene.
PorfimerBexarotene may increase the photosensitizing activities of Porfimer.
PraziquantelThe serum concentration of Praziquantel can be decreased when it is combined with Bexarotene.
PrimaquineThe serum concentration of Primaquine can be decreased when it is combined with Bexarotene.
ProgesteroneThe serum concentration of Progesterone can be decreased when it is combined with Bexarotene.
QuetiapineThe serum concentration of Quetiapine can be decreased when it is combined with Bexarotene.
QuinidineThe serum concentration of Quinidine can be decreased when it is combined with Bexarotene.
QuinineThe serum concentration of Quinine can be decreased when it is combined with Bexarotene.
RabeprazoleThe serum concentration of Rabeprazole can be decreased when it is combined with Bexarotene.
RanolazineThe serum concentration of Ranolazine can be decreased when it is combined with Bexarotene.
RegorafenibThe serum concentration of Regorafenib can be decreased when it is combined with Bexarotene.
RepaglinideThe serum concentration of Repaglinide can be decreased when it is combined with Bexarotene.
RifabutinThe serum concentration of Rifabutin can be decreased when it is combined with Bexarotene.
RilpivirineThe serum concentration of Rilpivirine can be decreased when it is combined with Bexarotene.
RiociguatThe serum concentration of Riociguat can be decreased when it is combined with Bexarotene.
RitonavirThe serum concentration of Ritonavir can be decreased when it is combined with Bexarotene.
RivaroxabanThe serum concentration of Rivaroxaban can be decreased when it is combined with Bexarotene.
RoflumilastThe serum concentration of Roflumilast can be decreased when it is combined with Bexarotene.
RolapitantThe serum concentration of Rolapitant can be decreased when it is combined with Bexarotene.
RuxolitinibThe serum concentration of Ruxolitinib can be decreased when it is combined with Bexarotene.
SaquinavirThe serum concentration of Saquinavir can be decreased when it is combined with Bexarotene.
SaxagliptinThe serum concentration of Saxagliptin can be decreased when it is combined with Bexarotene.
SildenafilThe serum concentration of Sildenafil can be decreased when it is combined with Bexarotene.
SilodosinThe serum concentration of Silodosin can be decreased when it is combined with Bexarotene.
SimeprevirThe serum concentration of Simeprevir can be decreased when it is combined with Bexarotene.
SimvastatinThe serum concentration of Simvastatin can be decreased when it is combined with Bexarotene.
SirolimusThe serum concentration of Sirolimus can be decreased when it is combined with Bexarotene.
SolifenacinThe serum concentration of Solifenacin can be decreased when it is combined with Bexarotene.
SonidegibThe serum concentration of Sonidegib can be decreased when it is combined with Bexarotene.
SpiramycinThe serum concentration of Spiramycin can be decreased when it is combined with Bexarotene.
StiripentolThe serum concentration of Stiripentol can be decreased when it is combined with Bexarotene.
SulfamethoxazoleThe serum concentration of Sulfamethoxazole can be decreased when it is combined with Bexarotene.
SulfisoxazoleThe serum concentration of Sulfisoxazole can be decreased when it is combined with Bexarotene.
SunitinibThe serum concentration of Sunitinib can be decreased when it is combined with Bexarotene.
SuvorexantThe serum concentration of Suvorexant can be decreased when it is combined with Bexarotene.
TacrolimusThe serum concentration of Tacrolimus can be decreased when it is combined with Bexarotene.
TamoxifenThe serum concentration of Tamoxifen can be decreased when it is combined with Bexarotene.
TamsulosinThe serum concentration of Tamsulosin can be decreased when it is combined with Bexarotene.
TasimelteonThe serum concentration of Tasimelteon can be decreased when it is combined with Bexarotene.
TelaprevirThe serum concentration of Telaprevir can be decreased when it is combined with Bexarotene.
TelithromycinThe serum concentration of Telithromycin can be decreased when it is combined with Bexarotene.
TemsirolimusThe serum concentration of Temsirolimus can be decreased when it is combined with Bexarotene.
TeniposideThe serum concentration of Teniposide can be decreased when it is combined with Bexarotene.
TetracyclineThe serum concentration of Tetracycline can be decreased when it is combined with Bexarotene.
TheophyllineThe serum concentration of Theophylline can be decreased when it is combined with Bexarotene.
TiagabineThe serum concentration of Tiagabine can be decreased when it is combined with Bexarotene.
TicagrelorThe serum concentration of Ticagrelor can be decreased when it is combined with Bexarotene.
TiclopidineThe serum concentration of Ticlopidine can be decreased when it is combined with Bexarotene.
TipranavirThe serum concentration of Tipranavir can be decreased when it is combined with Bexarotene.
TofacitinibThe serum concentration of Tofacitinib can be decreased when it is combined with Bexarotene.
TolterodineThe serum concentration of Tolterodine can be decreased when it is combined with Bexarotene.
TolvaptanThe serum concentration of Tolvaptan can be decreased when it is combined with Bexarotene.
ToremifeneThe serum concentration of Toremifene can be decreased when it is combined with Bexarotene.
TrabectedinThe serum concentration of Trabectedin can be decreased when it is combined with Bexarotene.
TramadolThe serum concentration of Tramadol can be decreased when it is combined with Bexarotene.
TrazodoneThe serum concentration of Trazodone can be decreased when it is combined with Bexarotene.
TriazolamThe serum concentration of Triazolam can be decreased when it is combined with Bexarotene.
TrimethoprimThe serum concentration of Trimethoprim can be decreased when it is combined with Bexarotene.
TrimipramineThe serum concentration of Trimipramine can be decreased when it is combined with Bexarotene.
UlipristalThe serum concentration of Ulipristal can be decreased when it is combined with Bexarotene.
VandetanibThe serum concentration of Vandetanib can be decreased when it is combined with Bexarotene.
VemurafenibThe serum concentration of Vemurafenib can be decreased when it is combined with Bexarotene.
VenlafaxineThe serum concentration of Venlafaxine can be decreased when it is combined with Bexarotene.
VerapamilThe serum concentration of Verapamil can be decreased when it is combined with Bexarotene.
VerteporfinBexarotene may increase the photosensitizing activities of Verteporfin.
VilazodoneThe serum concentration of Vilazodone can be decreased when it is combined with Bexarotene.
VinblastineThe serum concentration of Vinblastine can be decreased when it is combined with Bexarotene.
VincristineThe serum concentration of Vincristine can be decreased when it is combined with Bexarotene.
VinorelbineThe serum concentration of Vinorelbine can be decreased when it is combined with Bexarotene.
Vitamin AThe risk or severity of adverse effects can be increased when Vitamin A is combined with Bexarotene.
VortioxetineThe serum concentration of Vortioxetine can be decreased when it is combined with Bexarotene.
ZolpidemThe serum concentration of Zolpidem can be decreased when it is combined with Bexarotene.
ZonisamideThe serum concentration of Zonisamide can be decreased when it is combined with Bexarotene.
ZopicloneThe serum concentration of Zopiclone can be decreased when it is combined with Bexarotene.
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. The high affinity ligand for RXR...
Gene Name:
RXRA
Uniprot ID:
P19793
Molecular Weight:
50810.835 Da
References
  1. Lowe MN, Plosker GL: Bexarotene. Am J Clin Dermatol. 2000 Jul-Aug;1(4):245-50; discussion 251-2. [PubMed:11702369 ]
  2. Tsai DE, Luger SM, Andreadis C, Vogl DT, Kemner A, Potuzak M, Goradia A, Loren AW, Perl AE, Schuster SJ, Porter DL, Stadtmauer EA, Goldstein SC, Thompson JE, Swider C, Bagg A, Mato AR, Carroll M: A phase I study of bexarotene, a retinoic X receptor agonist, in non-M3 acute myeloid leukemia. Clin Cancer Res. 2008 Sep 1;14(17):5619-25. doi: 10.1158/1078-0432.CCR-07-5185. [PubMed:18765556 ]
  3. Tooker P, Yen WC, Ng SC, Negro-Vilar A, Hermann TW: Bexarotene (LGD1069, Targretin), a selective retinoid X receptor agonist, prevents and reverses gemcitabine resistance in NSCLC cells by modulating gene amplification. Cancer Res. 2007 May 1;67(9):4425-33. [PubMed:17483357 ]
  4. Lalloyer F, Fievet C, Lestavel S, Torpier G, van der Veen J, Touche V, Bultel S, Yous S, Kuipers F, Paumelle R, Fruchart JC, Staels B, Tailleux A: The RXR agonist bexarotene improves cholesterol homeostasis and inhibits atherosclerosis progression in a mouse model of mixed dyslipidemia. Arterioscler Thromb Vasc Biol. 2006 Dec;26(12):2731-7. Epub 2006 Sep 28. [PubMed:17008586 ]
  5. Yen WC, Lamph WW: The selective retinoid X receptor agonist bexarotene (LGD1069, Targretin) prevents and overcomes multidrug resistance in advanced breast carcinoma. Mol Cancer Ther. 2005 May;4(5):824-34. [PubMed:15897247 ]
  6. Yen WC, Prudente RY, Corpuz MR, Negro-Vilar A, Lamph WW: A selective retinoid X receptor agonist bexarotene (LGD1069, targretin) inhibits angiogenesis and metastasis in solid tumours. Br J Cancer. 2006 Mar 13;94(5):654-60. [PubMed:16495926 ]
  7. Rizvi N, Hawkins MJ, Eisenberg PD, Yocum RC, Reich SD: Placebo-controlled trial of bexarotene, a retinoid x receptor agonist, as maintenance therapy for patients treated with chemotherapy for advanced non-small-cell lung cancer. Clin Lung Cancer. 2001 Feb;2(3):210-5. [PubMed:14700480 ]
  8. Rigas JR, Dragnev KH: Emerging role of rexinoids in non-small cell lung cancer: focus on bexarotene. Oncologist. 2005 Jan;10(1):22-33. [PubMed:15632250 ]
  9. Farol LT, Hymes KB: Bexarotene: a clinical review. Expert Rev Anticancer Ther. 2004 Apr;4(2):180-8. [PubMed:15056048 ]
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. Tsai DE, Luger SM, Andreadis C, Vogl DT, Kemner A, Potuzak M, Goradia A, Loren AW, Perl AE, Schuster SJ, Porter DL, Stadtmauer EA, Goldstein SC, Thompson JE, Swider C, Bagg A, Mato AR, Carroll M: A phase I study of bexarotene, a retinoic X receptor agonist, in non-M3 acute myeloid leukemia. Clin Cancer Res. 2008 Sep 1;14(17):5619-25. doi: 10.1158/1078-0432.CCR-07-5185. [PubMed:18765556 ]
  4. Tooker P, Yen WC, Ng SC, Negro-Vilar A, Hermann TW: Bexarotene (LGD1069, Targretin), a selective retinoid X receptor agonist, prevents and reverses gemcitabine resistance in NSCLC cells by modulating gene amplification. Cancer Res. 2007 May 1;67(9):4425-33. [PubMed:17483357 ]
  5. Lalloyer F, Fievet C, Lestavel S, Torpier G, van der Veen J, Touche V, Bultel S, Yous S, Kuipers F, Paumelle R, Fruchart JC, Staels B, Tailleux A: The RXR agonist bexarotene improves cholesterol homeostasis and inhibits atherosclerosis progression in a mouse model of mixed dyslipidemia. Arterioscler Thromb Vasc Biol. 2006 Dec;26(12):2731-7. Epub 2006 Sep 28. [PubMed:17008586 ]
  6. Yen WC, Lamph WW: The selective retinoid X receptor agonist bexarotene (LGD1069, Targretin) prevents and overcomes multidrug resistance in advanced breast carcinoma. Mol Cancer Ther. 2005 May;4(5):824-34. [PubMed:15897247 ]
  7. Yen WC, Prudente RY, Corpuz MR, Negro-Vilar A, Lamph WW: A selective retinoid X receptor agonist bexarotene (LGD1069, targretin) inhibits angiogenesis and metastasis in solid tumours. Br J Cancer. 2006 Mar 13;94(5):654-60. [PubMed:16495926 ]
  8. Rizvi N, Hawkins MJ, Eisenberg PD, Yocum RC, Reich SD: Placebo-controlled trial of bexarotene, a retinoid x receptor agonist, as maintenance therapy for patients treated with chemotherapy for advanced non-small-cell lung cancer. Clin Lung Cancer. 2001 Feb;2(3):210-5. [PubMed:14700480 ]
  9. Rigas JR, Dragnev KH: Emerging role of rexinoids in non-small cell lung cancer: focus on bexarotene. Oncologist. 2005 Jan;10(1):22-33. [PubMed:15632250 ]
  10. Farol LT, Hymes KB: Bexarotene: a clinical review. Expert Rev Anticancer Ther. 2004 Apr;4(2):180-8. [PubMed:15056048 ]
  11. Lowe MN, Plosker GL: Bexarotene. Am J Clin Dermatol. 2000 Jul-Aug;1(4):245-50; discussion 251-2. [PubMed:11702369 ]
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. Lowe MN, Plosker GL: Bexarotene. Am J Clin Dermatol. 2000 Jul-Aug;1(4):245-50; discussion 251-2. [PubMed:11702369 ]
  2. Tsai DE, Luger SM, Andreadis C, Vogl DT, Kemner A, Potuzak M, Goradia A, Loren AW, Perl AE, Schuster SJ, Porter DL, Stadtmauer EA, Goldstein SC, Thompson JE, Swider C, Bagg A, Mato AR, Carroll M: A phase I study of bexarotene, a retinoic X receptor agonist, in non-M3 acute myeloid leukemia. Clin Cancer Res. 2008 Sep 1;14(17):5619-25. doi: 10.1158/1078-0432.CCR-07-5185. [PubMed:18765556 ]
  3. Tooker P, Yen WC, Ng SC, Negro-Vilar A, Hermann TW: Bexarotene (LGD1069, Targretin), a selective retinoid X receptor agonist, prevents and reverses gemcitabine resistance in NSCLC cells by modulating gene amplification. Cancer Res. 2007 May 1;67(9):4425-33. [PubMed:17483357 ]
  4. Lalloyer F, Fievet C, Lestavel S, Torpier G, van der Veen J, Touche V, Bultel S, Yous S, Kuipers F, Paumelle R, Fruchart JC, Staels B, Tailleux A: The RXR agonist bexarotene improves cholesterol homeostasis and inhibits atherosclerosis progression in a mouse model of mixed dyslipidemia. Arterioscler Thromb Vasc Biol. 2006 Dec;26(12):2731-7. Epub 2006 Sep 28. [PubMed:17008586 ]
  5. Yen WC, Lamph WW: The selective retinoid X receptor agonist bexarotene (LGD1069, Targretin) prevents and overcomes multidrug resistance in advanced breast carcinoma. Mol Cancer Ther. 2005 May;4(5):824-34. [PubMed:15897247 ]
  6. Yen WC, Prudente RY, Corpuz MR, Negro-Vilar A, Lamph WW: A selective retinoid X receptor agonist bexarotene (LGD1069, targretin) inhibits angiogenesis and metastasis in solid tumours. Br J Cancer. 2006 Mar 13;94(5):654-60. [PubMed:16495926 ]
  7. Rizvi N, Hawkins MJ, Eisenberg PD, Yocum RC, Reich SD: Placebo-controlled trial of bexarotene, a retinoid x receptor agonist, as maintenance therapy for patients treated with chemotherapy for advanced non-small-cell lung cancer. Clin Lung Cancer. 2001 Feb;2(3):210-5. [PubMed:14700480 ]
  8. Rigas JR, Dragnev KH: Emerging role of rexinoids in non-small cell lung cancer: focus on bexarotene. Oncologist. 2005 Jan;10(1):22-33. [PubMed:15632250 ]
  9. Farol LT, Hymes KB: Bexarotene: a clinical review. Expert Rev Anticancer Ther. 2004 Apr;4(2):180-8. [PubMed:15056048 ]

Enzymes

Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrateinducer
General Function:
Vitamin d3 25-hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation reactions (e.g. caffeine 8-oxidation, omeprazole sulphoxidation, midazolam 1'-hydroxylation and midazolam 4-hydroxylation) of structurally unrelated compounds, including steroids, fatty acids, and xenobiot...
Gene Name:
CYP3A4
Uniprot ID:
P08684
Molecular Weight:
57342.67 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
Kind
Protein
Organism
Human
Pharmacological action
unknown
Actions
substrate
General Function:
Steroid hydroxylase activity
Specific Function:
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It oxidizes a variety of structurally unrelated compounds, including steroids, fatty acids, and xenobiotics. This enzyme contributes to the wide pharmacokinetics variability of the metabolism of drugs such as S-warfarin, diclofenac, phenyto...
Gene Name:
CYP2C9
Uniprot ID:
P11712
Molecular Weight:
55627.365 Da
References
  1. Preissner S, Kroll K, Dunkel M, Senger C, Goldsobel G, Kuzman D, Guenther S, Winnenburg R, Schroeder M, Preissner R: SuperCYP: a comprehensive database on Cytochrome P450 enzymes including a tool for analysis of CYP-drug interactions. Nucleic Acids Res. 2010 Jan;38(Database issue):D237-43. doi: 10.1093/nar/gkp970. Epub 2009 Nov 24. [PubMed:19934256 ]
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Drug created on June 13, 2005 07:24 / Updated on May 27, 2016 02:16