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IdentificationPharmacologyInteractionsReferencesTrialsEconomicsPropertiesSpectraTaxonomyIdentification
- Name
- Bexarotene
- Accession Number
- DB00307 (APRD00114)
- Type
- Small Molecule
- Groups
- Approved, 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
Structure for DB00307 (Bexarotene)
- 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 IDs
- LG 100069 / LG-100069 / LG100069 / LGD 1069 / LGD-1069 / LGD1069
- Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Targretin Capsule, liquid filled 75 mg/1 Oral Eisai Limited 1999-12-29 2017-02-11 US 
Targretin Gel 1 g/100g Topical Eisai Limited 2000-06-28 2017-04-30 US Targretin Capsule, liquid filled 75 mg/1 Oral Valeant Pharmaceuticals North America 1999-12-29 Not applicable US Targretin Capsule 75 mg Oral Eisai Limited 2001-03-29 Not applicable EU 
Targretin Gel 1 g/100g Topical Valeant Pharmaceuticals North America 2000-06-28 Not applicable US - Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Bexarotene Capsule, liquid filled 75 mg/1 Oral Mylan Institutional 2016-04-15 Not applicable US Bexarotene Gel 1 g/100g Topical Oceanside Pharmaceuticals 2000-06-28 2018-03-22 US Bexarotene Capsule, liquid filled 75 mg/1 Oral Oceanside Pharmaceuticals 1999-12-29 Not applicable US Bexarotene Capsule, liquid filled 75 mg/1 Oral Mylan Pharmaceuticals 2015-07-09 Not applicable US - Categories
- Anticarcinogenic Agents
- Antineoplastic Agents
- Antineoplastic and Immunomodulating Agents
- Cytochrome P-450 CYP2C9 Substrates
- Cytochrome P-450 CYP3A Inducers
- Cytochrome P-450 CYP3A4 Inducers (moderate)
- Cytochrome P-450 CYP3A4 Substrates
- Cytochrome P-450 Enzyme Inducers
- Myelosuppressive Agents
- Naphthalenes
- Protective Agents
- Retinoic Acid Derivatives
- Retinoids
- UNII
- A61RXM4375
- CAS number
- 153559-49-0
- Weight
- Average: 348.4779
Monoisotopic: 348.20893014 - Chemical Formula
- C24H28O2
- InChI Key
- 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
Pharmacology
- Indication
Used 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.
- Structured Indications
- Pharmacodynamics
Bexarotene 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 action
Bexarotene 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.
Target Actions Organism ARetinoic acid receptor RXR-alpha agonistHuman ARetinoic acid receptor RXR-beta agonistHuman ARetinoic acid receptor RXR-gamma agonistHuman - Absorption
- Not Available
- Volume of distribution
- Not Available
- Protein binding
>99%
- Metabolism
- Not Available
- Route of elimination
Urinary elimination of bexarotene and its known metabolites is a minor excretory pathway (<1% of administered dose).
- Half life
7 hours
- Clearance
- Not Available
- Toxicity
- Not Available
- Affected organisms
- Humans and other mammals
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs
- Not Available
Interactions
- Drug Interactions
Drug Interaction Drug group Abiraterone The metabolism of Bexarotene can be decreased when combined with Abiraterone. Approved Acetyldigitoxin Acetyldigitoxin may decrease the cardiotoxic activities of Bexarotene. Approved Acetyldigoxin Acetyldigoxin may decrease the cardiotoxic activities of Bexarotene. Experimental Amiodarone The metabolism of Bexarotene can be decreased when combined with Amiodarone. Approved, Investigational Ancestim The risk or severity of cytotoxicity can be increased when Ancestim is combined with Bexarotene. Approved, Investigational, Withdrawn Apalutamide The serum concentration of Bexarotene can be decreased when it is combined with Apalutamide. Approved, Investigational Aprepitant The serum concentration of Bexarotene can be increased when it is combined with Aprepitant. Approved, Investigational Aripiprazole The serum concentration of Aripiprazole can be decreased when it is combined with Bexarotene. Approved, Investigational Asunaprevir The serum concentration of Asunaprevir can be decreased when it is combined with Bexarotene. Approved, Investigational, Withdrawn Atazanavir The metabolism of Bexarotene can be decreased when combined with Atazanavir. Approved, Investigational Atomoxetine The metabolism of Bexarotene can be decreased when combined with Atomoxetine. Approved Atorvastatin The serum concentration of Atorvastatin can be decreased when it is combined with Bexarotene. Approved Bevacizumab Bevacizumab may increase the cardiotoxic activities of Bexarotene. Approved, Investigational Boceprevir The metabolism of Bexarotene can be decreased when combined with Boceprevir. Approved, Withdrawn Bortezomib The metabolism of Bexarotene can be decreased when combined with Bortezomib. Approved, Investigational Bosentan The serum concentration of Bexarotene can be decreased when it is combined with Bosentan. Approved, Investigational Cabazitaxel The risk or severity of adverse effects can be increased when Cabazitaxel is combined with Bexarotene. Approved Capecitabine The metabolism of Bexarotene can be decreased when combined with Capecitabine. Approved, Investigational Carbamazepine The metabolism of Bexarotene can be increased when combined with Carbamazepine. Approved, Investigational Carboplatin The serum concentration of Bexarotene can be increased when it is combined with Carboplatin. Approved Ceritinib The serum concentration of Bexarotene can be increased when it is combined with Ceritinib. Approved Chlorotrianisene The serum concentration of Chlorotrianisene can be decreased when it is combined with Bexarotene. Investigational, Withdrawn Chlortetracycline The risk or severity of adverse effects can be increased when Chlortetracycline is combined with Bexarotene. Approved, Investigational, Vet Approved Cholecalciferol The metabolism of Bexarotene can be decreased when combined with Cholecalciferol. Approved, Nutraceutical Clarithromycin The metabolism of Bexarotene can be decreased when combined with Clarithromycin. Approved Clemastine The metabolism of Bexarotene can be decreased when combined with Clemastine. Approved, Investigational Clotrimazole The metabolism of Bexarotene can be decreased when combined with Clotrimazole. Approved, Vet Approved Clozapine The risk or severity of adverse effects can be increased when Bexarotene is combined with Clozapine. Approved Cobicistat The metabolism of Bexarotene can be decreased when combined with Cobicistat. Approved Conivaptan The serum concentration of Conivaptan can be increased when it is combined with Bexarotene. Approved, Investigational Conjugated estrogens The serum concentration of Conjugated estrogens can be decreased when it is combined with Bexarotene. Approved Crisaborole The metabolism of Bexarotene can be decreased when combined with Crisaborole. Approved, Investigational Crizotinib The metabolism of Bexarotene can be decreased when combined with Crizotinib. Approved Cyclophosphamide Cyclophosphamide may increase the cardiotoxic activities of Bexarotene. Approved, Investigational Cyclosporine The metabolism of Bexarotene can be decreased when combined with Cyclosporine. Approved, Investigational, Vet Approved Cymarin Cymarin may decrease the cardiotoxic activities of Bexarotene. Experimental Dabrafenib The serum concentration of Bexarotene can be decreased when it is combined with Dabrafenib. Approved, Investigational Darunavir The metabolism of Bexarotene can be decreased when combined with Darunavir. Approved Dasatinib The serum concentration of Bexarotene can be increased when it is combined with Dasatinib. Approved, Investigational Deferasirox The serum concentration of Bexarotene can be decreased when it is combined with Deferasirox. Approved, Investigational Delavirdine The metabolism of Bexarotene can be decreased when combined with Delavirdine. Approved Demeclocycline The risk or severity of adverse effects can be increased when Demeclocycline is combined with Bexarotene. Approved Deslanoside Deslanoside may decrease the cardiotoxic activities of Bexarotene. Approved Desogestrel The serum concentration of Desogestrel can be decreased when it is combined with Bexarotene. Approved Dienestrol The serum concentration of Dienestrol can be decreased when it is combined with Bexarotene. Approved, Investigational Dienogest The serum concentration of Dienogest can be decreased when it is combined with Bexarotene. Approved Diethylstilbestrol The serum concentration of Diethylstilbestrol can be decreased when it is combined with Bexarotene. Approved, Investigational Digitoxin Digitoxin may decrease the cardiotoxic activities of Bexarotene. Approved, Investigational Digoxin Digoxin may decrease the cardiotoxic activities of Bexarotene. Approved Digoxin Immune Fab (Ovine) Digoxin Immune Fab (Ovine) may decrease the cardiotoxic activities of Bexarotene. Approved Dihydroergotamine The metabolism of Bexarotene can be decreased when combined with Dihydroergotamine. Approved, Investigational Diltiazem The metabolism of Bexarotene can be decreased when combined with Diltiazem. Approved, Investigational Docetaxel The risk or severity of adverse effects can be increased when Docetaxel is combined with Bexarotene. Approved, Investigational Dosulepin The metabolism of Bexarotene can be decreased when combined with Dosulepin. Approved Doxycycline The risk or severity of adverse effects can be increased when Doxycycline is combined with Bexarotene. Approved, Investigational, Vet Approved Dronedarone The metabolism of Bexarotene can be decreased when combined with Dronedarone. Approved Drospirenone The serum concentration of Drospirenone can be decreased when it is combined with Bexarotene. Approved Efavirenz The metabolism of Bexarotene can be decreased when combined with Efavirenz. Approved, Investigational Enzalutamide The serum concentration of Bexarotene can be decreased when it is combined with Enzalutamide. Approved Erythromycin The metabolism of Bexarotene can be decreased when combined with Erythromycin. Approved, Investigational, Vet Approved Estradiol The serum concentration of Estradiol can be decreased when it is combined with Bexarotene. Approved, Investigational, Vet Approved Estramustine The serum concentration of Estramustine can be decreased when it is combined with Bexarotene. Approved, Investigational Estrogens, esterified The serum concentration of Estrogens, esterified can be decreased when it is combined with Bexarotene. Approved Estrone sulfate The serum concentration of Estrone sulfate can be decreased when it is combined with Bexarotene. Approved Ethinyl Estradiol The serum concentration of Ethinyl Estradiol can be decreased when it is combined with Bexarotene. Approved Ethynodiol diacetate The serum concentration of Ethynodiol diacetate can be decreased when it is combined with Bexarotene. Approved Etonogestrel The serum concentration of Etonogestrel can be decreased when it is combined with Bexarotene. Approved, Investigational Etravirine The metabolism of Bexarotene can be decreased when combined with Etravirine. Approved Floxuridine The metabolism of Bexarotene can be decreased when combined with Floxuridine. Approved Fluconazole The metabolism of Bexarotene can be decreased when combined with Fluconazole. Approved, Investigational Fluorouracil The metabolism of Bexarotene can be decreased when combined with Fluorouracil. Approved Fluvastatin The metabolism of Bexarotene can be decreased when combined with Fluvastatin. Approved Fluvoxamine The metabolism of Bexarotene can be decreased when combined with Fluvoxamine. Approved, Investigational Fosamprenavir The metabolism of Bexarotene can be decreased when combined with Fosamprenavir. Approved Fosaprepitant The serum concentration of Bexarotene can be increased when it is combined with Fosaprepitant. Approved Fosphenytoin The metabolism of Bexarotene can be increased when combined with Fosphenytoin. Approved, Investigational Fusidic Acid The serum concentration of Bexarotene can be increased when it is combined with Fusidic Acid. Approved, Investigational Gemfibrozil The serum concentration of Bexarotene can be increased when it is combined with Gemfibrozil. Approved Gestodene The serum concentration of Gestodene can be decreased when it is combined with Bexarotene. Approved, Investigational Gitoformate Gitoformate may decrease the cardiotoxic activities of Bexarotene. Experimental Hexestrol The serum concentration of Hexestrol can be decreased when it is combined with Bexarotene. Withdrawn Idelalisib The metabolism of Bexarotene can be decreased when combined with Idelalisib. Approved Imatinib The metabolism of Bexarotene can be decreased when combined with Imatinib. Approved Indinavir The metabolism of Bexarotene can be decreased when combined with Indinavir. Approved Irbesartan The metabolism of Bexarotene can be decreased when combined with Irbesartan. Approved, Investigational Isavuconazole The serum concentration of Bexarotene can be increased when it is combined with Isavuconazole. Approved, Investigational Isavuconazonium The metabolism of Bexarotene can be decreased when combined with Isavuconazonium. Approved, Investigational Isradipine The metabolism of Bexarotene can be decreased when combined with Isradipine. Approved, Investigational Itraconazole The metabolism of Bexarotene can be decreased when combined with Itraconazole. Approved, Investigational Ivacaftor The serum concentration of Bexarotene can be increased when it is combined with Ivacaftor. Approved Ketoconazole The metabolism of Bexarotene can be decreased when combined with Ketoconazole. Approved, Investigational Lanatoside C Lanatoside C may decrease the cardiotoxic activities of Bexarotene. Experimental Leflunomide The metabolism of Bexarotene can be decreased when combined with Leflunomide. Approved, Investigational Levonorgestrel The serum concentration of Levonorgestrel can be decreased when it is combined with Bexarotene. Approved, Investigational Lipegfilgrastim Bexarotene may increase the myelosuppressive activities of Lipegfilgrastim. Approved, Investigational Lobeglitazone The metabolism of Bexarotene can be decreased when combined with Lobeglitazone. Approved, Investigational Lopinavir The metabolism of Bexarotene can be decreased when combined with Lopinavir. Approved Lorpiprazole The serum concentration of Bexarotene can be increased when it is combined with Lorpiprazole. Approved Losartan The metabolism of Bexarotene can be decreased when combined with Losartan. Approved Lovastatin The metabolism of Bexarotene can be decreased when combined with Lovastatin. Approved, Investigational Luliconazole The serum concentration of Bexarotene can be increased when it is combined with Luliconazole. Approved Lumacaftor The serum concentration of Bexarotene can be decreased when it is combined with Lumacaftor. Approved Lynestrenol The serum concentration of Lynestrenol can be decreased when it is combined with Bexarotene. Approved, Investigational Manidipine The metabolism of Bexarotene can be decreased when combined with Manidipine. Approved, Investigational Medroxyprogesterone acetate The serum concentration of Medroxyprogesterone acetate can be decreased when it is combined with Bexarotene. Approved, Investigational Mestranol The serum concentration of Mestranol can be decreased when it is combined with Bexarotene. Approved Metamizole The risk or severity of myelosuppression can be increased when Metamizole is combined with Bexarotene. Approved, Investigational, Withdrawn Methallenestril The serum concentration of Methallenestril can be decreased when it is combined with Bexarotene. Experimental Metildigoxin Metildigoxin may decrease the cardiotoxic activities of Bexarotene. Experimental Midostaurin The metabolism of Bexarotene can be decreased when combined with Midostaurin. Approved, Investigational Mifepristone The serum concentration of Bexarotene can be increased when it is combined with Mifepristone. Approved, Investigational Minocycline The risk or severity of adverse effects can be increased when Minocycline is combined with Bexarotene. Approved, Investigational Mitotane The serum concentration of Bexarotene can be decreased when it is combined with Mitotane. Approved Nabilone The metabolism of Bexarotene can be decreased when combined with Nabilone. Approved, Investigational Nefazodone The metabolism of Bexarotene can be decreased when combined with Nefazodone. Approved, Withdrawn Nelfinavir The metabolism of Bexarotene can be decreased when combined with Nelfinavir. Approved Netupitant The serum concentration of Bexarotene can be increased when it is combined with Netupitant. Approved, Investigational Nevirapine The metabolism of Bexarotene can be increased when combined with Nevirapine. Approved Nicardipine The metabolism of Bexarotene can be decreased when combined with Nicardipine. Approved, Investigational Nilotinib The metabolism of Bexarotene can be decreased when combined with Nilotinib. Approved, Investigational Norelgestromin The serum concentration of Norelgestromin can be decreased when it is combined with Bexarotene. Approved, Investigational Norgestimate The serum concentration of Norgestimate can be decreased when it is combined with Bexarotene. Approved, Investigational Norgestrel The serum concentration of Norgestrel can be decreased when it is combined with Bexarotene. Approved Olaparib The metabolism of Bexarotene can be decreased when combined with Olaparib. Approved Oleandrin Oleandrin may decrease the cardiotoxic activities of Bexarotene. Experimental, Investigational Omeprazole The metabolism of Bexarotene can be decreased when combined with Omeprazole. Approved, Investigational, Vet Approved Osimertinib The serum concentration of Bexarotene can be increased when it is combined with Osimertinib. Approved Ouabain Ouabain may decrease the cardiotoxic activities of Bexarotene. Approved Paclitaxel The risk or severity of adverse effects can be increased when Paclitaxel is combined with Bexarotene. Approved, Vet Approved Paclitaxel The serum concentration of Bexarotene can be increased when it is combined with Paclitaxel. Approved, Vet Approved Palbociclib The serum concentration of Bexarotene can be increased when it is combined with Palbociclib. Approved, Investigational Pentobarbital The metabolism of Bexarotene can be increased when combined with Pentobarbital. Approved, Investigational, Vet Approved Peruvoside Peruvoside may decrease the cardiotoxic activities of Bexarotene. Experimental Phenobarbital The metabolism of Bexarotene can be increased when combined with Phenobarbital. Approved, Investigational Phenytoin The metabolism of Bexarotene can be increased when combined with Phenytoin. Approved, Vet Approved Pitolisant The serum concentration of Bexarotene can be decreased when it is combined with Pitolisant. Approved, Investigational Posaconazole The metabolism of Bexarotene can be decreased when combined with Posaconazole. Approved, Investigational, Vet Approved Primidone The metabolism of Bexarotene can be increased when combined with Primidone. Approved, Vet Approved Proscillaridin Proscillaridin may decrease the cardiotoxic activities of Bexarotene. Experimental Pyrimethamine The metabolism of Bexarotene can be decreased when combined with Pyrimethamine. Approved, Investigational, Vet Approved Quinine The metabolism of Bexarotene can be decreased when combined with Quinine. Approved Ranolazine The metabolism of Bexarotene can be decreased when combined with Ranolazine. Approved, Investigational Rifabutin The metabolism of Bexarotene can be increased when combined with Rifabutin. Approved, Investigational Rifampicin The metabolism of Bexarotene can be increased when combined with Rifampicin. Approved Rifapentine The metabolism of Bexarotene can be increased when combined with Rifapentine. Approved, Investigational Rilpivirine The serum concentration of Rilpivirine can be decreased when it is combined with Bexarotene. Approved Rucaparib The metabolism of Bexarotene can be decreased when combined with Rucaparib. Approved, Investigational Saquinavir The metabolism of Bexarotene can be decreased when combined with Saquinavir. Approved, Investigational Sarilumab The therapeutic efficacy of Bexarotene can be decreased when used in combination with Sarilumab. Approved, Investigational Saxagliptin The serum concentration of Saxagliptin can be decreased when it is combined with Bexarotene. Approved Secobarbital The metabolism of Bexarotene can be increased when combined with Secobarbital. Approved, Vet Approved Sildenafil The metabolism of Bexarotene can be decreased when combined with Sildenafil. Approved, Investigational Siltuximab The serum concentration of Bexarotene can be decreased when it is combined with Siltuximab. Approved, Investigational Simeprevir The serum concentration of Bexarotene can be increased when it is combined with Simeprevir. Approved Sorafenib The metabolism of Bexarotene can be decreased when combined with Sorafenib. Approved, Investigational St. John's Wort The serum concentration of Bexarotene can be decreased when it is combined with St. John's Wort. Approved, Investigational, Nutraceutical Stiripentol The serum concentration of Bexarotene can be increased when it is combined with Stiripentol. Approved Sulfadiazine The metabolism of Bexarotene can be decreased when combined with Sulfadiazine. Approved, Investigational, Vet Approved Sulfamethoxazole The metabolism of Bexarotene can be decreased when combined with Sulfamethoxazole. Approved Sulfisoxazole The metabolism of Bexarotene can be decreased when combined with Sulfisoxazole. Approved, Vet Approved Synthetic Conjugated Estrogens, A The serum concentration of Synthetic Conjugated Estrogens, A can be decreased when it is combined with Bexarotene. Approved Tamoxifen The serum concentration of Tamoxifen can be decreased when it is combined with Bexarotene. Approved Telaprevir The metabolism of Bexarotene can be decreased when combined with Telaprevir. Approved, Withdrawn Telithromycin The metabolism of Bexarotene can be decreased when combined with Telithromycin. Approved Ticagrelor The metabolism of Bexarotene can be decreased when combined with Ticagrelor. Approved Ticlopidine The metabolism of Bexarotene can be decreased when combined with Ticlopidine. Approved Tocilizumab The serum concentration of Bexarotene can be decreased when it is combined with Tocilizumab. Approved Tolbutamide The metabolism of Bexarotene can be decreased when combined with Tolbutamide. Approved, Investigational Topiroxostat The metabolism of Bexarotene can be decreased when combined with Topiroxostat. Approved, Investigational Trastuzumab Trastuzumab may increase the cardiotoxic activities of Bexarotene. Approved, Investigational Trimethoprim The metabolism of Bexarotene can be decreased when combined with Trimethoprim. Approved, Vet Approved Valproic Acid The metabolism of Bexarotene can be decreased when combined with Valproic Acid. Approved, Investigational Valsartan The metabolism of Bexarotene can be decreased when combined with Valsartan. Approved, Investigational Vemurafenib The serum concentration of Bexarotene can be decreased when it is combined with Vemurafenib. Approved Venlafaxine The metabolism of Bexarotene can be decreased when combined with Venlafaxine. Approved Verapamil The metabolism of Bexarotene can be decreased when combined with Verapamil. Approved Vitamin A The risk or severity of adverse effects can be increased when Vitamin A is combined with Bexarotene. Approved, Nutraceutical, Vet Approved Voriconazole The metabolism of Bexarotene can be decreased when combined with Voriconazole. Approved, Investigational Zafirlukast The metabolism of Bexarotene can be decreased when combined with Zafirlukast. Approved, Investigational Ziprasidone The metabolism of Bexarotene can be decreased when combined with Ziprasidone. Approved - Food Interactions
- Not Available
References
- Synthesis Reference
- US5466861
- General References
- 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]
- 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]
- 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]
- Lowe MN, Plosker GL: Bexarotene. Am J Clin Dermatol. 2000 Jul-Aug;1(4):245-50; discussion 251-2. [PubMed:11702369]
- 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]
- Farol LT, Hymes KB: Bexarotene: a clinical review. Expert Rev Anticancer Ther. 2004 Apr;4(2):180-8. [PubMed:15056048]
- External Links
- Human Metabolome Database
- HMDB0014452
- PubChem Compound
- 82146
- PubChem Substance
- 46509119
- ChemSpider
- 74139
- BindingDB
- 50032675
- ChEBI
- 50859
- ChEMBL
- CHEMBL1023
- Therapeutic Targets Database
- DAP000276
- PharmGKB
- PA164752250
- IUPHAR
- 2807
- Guide to Pharmacology
- GtP Drug Page
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- RxList Drug Page
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- Drugs.com Drug Page
- Wikipedia
- Bexarotene
- ATC Codes
- L01XX25 — Bexarotene
- PDB Entries
- 3h0a / 4k6i
- FDA label
- Download (40.2 KB)
Clinical Trials
- Clinical Trials
Pharmacoeconomics
- Manufacturers
- Eisai inc
- Packagers
- Catalent Pharma Solutions
- Contract Pharm
- Eisai Inc.
- Dosage forms
Form Route Strength Gel Topical 1 g/100g Capsule Oral 75 mg Capsule, liquid filled Oral 75 mg/1 - Prices
Unit description Cost Unit Targretin 75 mg capsule 38.0USD capsule Targretin 75 mg softgel 36.54USD softget capsule Targretin 1% gel 30.08USD g DrugBank does not sell nor buy drugs. Pricing information is supplied for informational purposes only.- Patents
Patent Number Pediatric Extension Approved Expires (estimated) US6043279 No 1995-04-22 2012-04-22 US US5780676 No 1995-07-14 2015-07-14 US US5962731 No 1996-10-05 2016-10-05 US
Properties
- State
- Solid
- Experimental Properties
Property Value Source logP 6.9 Not Available - Predicted Properties
Property Value Source Water Solubility 0.000149 mg/mL ALOGPS logP 6.86 ALOGPS logP 6.94 ChemAxon logS -6.4 ALOGPS pKa (Strongest Acidic) 4.07 ChemAxon Physiological Charge -1 ChemAxon Hydrogen Acceptor Count 2 ChemAxon Hydrogen Donor Count 1 ChemAxon Polar Surface Area 37.3 Å2 ChemAxon Rotatable Bond Count 3 ChemAxon Refractivity 117.12 m3·mol-1 ChemAxon Polarizability 40.89 Å3 ChemAxon Number of Rings 3 ChemAxon Bioavailability 1 ChemAxon Rule of Five No ChemAxon Ghose Filter No ChemAxon Veber's Rule Yes ChemAxon MDDR-like Rule No ChemAxon - Predicted ADMET features
Property Value Probability Human Intestinal Absorption + 0.9954 Blood Brain Barrier + 0.9022 Caco-2 permeable + 0.794 P-glycoprotein substrate Substrate 0.6283 P-glycoprotein inhibitor I Non-inhibitor 0.5369 P-glycoprotein inhibitor II Non-inhibitor 0.7182 Renal organic cation transporter Non-inhibitor 0.8496 CYP450 2C9 substrate Non-substrate 0.7722 CYP450 2D6 substrate Non-substrate 0.9116 CYP450 3A4 substrate Substrate 0.6786 CYP450 1A2 substrate Non-inhibitor 0.8171 CYP450 2C9 inhibitor Non-inhibitor 0.8724 CYP450 2D6 inhibitor Inhibitor 0.5589 CYP450 2C19 inhibitor Inhibitor 0.8351 CYP450 3A4 inhibitor Non-inhibitor 0.8138 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.6458 Ames test Non AMES toxic 0.8592 Carcinogenicity Non-carcinogens 0.7898 Biodegradation Not ready biodegradable 0.933 Rat acute toxicity 2.2119 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9703 hERG inhibition (predictor II) Non-inhibitor 0.9034
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
Taxonomy
- Description
- This 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.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Prenol lipids
- Sub Class
- Retinoids
- Direct Parent
- Retinoids
- Alternative Parents
- Sesquiterpenoids / Tetralins / Benzoic acids / Styrenes / Benzoyl derivatives / Monocarboxylic acids and derivatives / Carboxylic acids / Organooxygen compounds / Organic oxides / Hydrocarbon derivatives
- Substituents
- Bexarotene / Sesquiterpenoid / Bisabolane sesquiterpenoid / Tetralin / Benzoic acid / Benzoic acid or derivatives / Styrene / Benzoyl / Monocyclic benzene moiety / Benzenoid
- Molecular Framework
- Aromatic homopolycyclic compounds
- External Descriptors
- retinoid, naphthalenes, benzoic acids (CHEBI:50859)
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 expressi...
- Gene Name
- RXRA
- Uniprot ID
- P19793
- Uniprot Name
- Retinoic acid receptor RXR-alpha
- Molecular Weight
- 50810.835 Da
References
- Lowe MN, Plosker GL: Bexarotene. Am J Clin Dermatol. 2000 Jul-Aug;1(4):245-50; discussion 251-2. [PubMed:11702369]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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 expressi...
- Gene Name
- RXRB
- Uniprot ID
- P28702
- Uniprot Name
- Retinoic acid receptor RXR-beta
- Molecular Weight
- 56921.38 Da
References
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- Farol LT, Hymes KB: Bexarotene: a clinical review. Expert Rev Anticancer Ther. 2004 Apr;4(2):180-8. [PubMed:15056048]
- 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 expressi...
- Gene Name
- RXRG
- Uniprot ID
- P48443
- Uniprot Name
- Retinoic acid receptor RXR-gamma
- Molecular Weight
- 50870.72 Da
References
- Lowe MN, Plosker GL: Bexarotene. Am J Clin Dermatol. 2000 Jul-Aug;1(4):245-50; discussion 251-2. [PubMed:11702369]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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]
- 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 react...
- Gene Name
- CYP3A4
- Uniprot ID
- P08684
- Uniprot Name
- Cytochrome P450 3A4
- Molecular Weight
- 57342.67 Da
References
- 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 un...
- Gene Name
- CYP2C9
- Uniprot ID
- P11712
- Uniprot Name
- Cytochrome P450 2C9
- Molecular Weight
- 55627.365 Da
References
- 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]
Drug created on June 13, 2005 07:24 / Updated on May 01, 2018 22:09