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.

Structure

Similar Structures

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

External IDs

LG 100069 / LG-100069 / LG100069 / LGD 1069 / LGD-1069 / LGD1069

Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Targretin	Capsule	75 mg/1	Oral	Cardinal Health	2006-03-28	2006-07-18
Targretin	Gel	10 mg/1g	Topical	Ligand Pharmaceuticals	2006-03-28	Not applicable
Targretin	Capsule, liquid filled	75 mg/1	Oral	Valeant Pharmaceuticals North America	1999-12-29	Not applicable
Targretin	Gel	1 g/100g	Topical	Valeant Pharmaceuticals North America LLC	2000-06-28	Not applicable
Targretin	Capsule	75 mg	Oral	Eisai Limited	2001-03-29	Not applicable
Targretin	Capsule, liquid filled	75 mg/1	Oral	Eisai Limited	1999-12-29	2014-12-01
Targretin	Gel	1 g/100g	Topical	Eisai Limited	2000-06-28	2017-04-30

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Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Generic Prescription Products

Name	Dosage	Strength	Route	Labeller	Marketing Start	Marketing End
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Bexarotene	Capsule	75 mg/1	Oral	Upsher Smith Laboratories	2018-07-25	Not applicable
Bexarotene	Gel	1 g/100g	Topical	Oceanside Pharmaceuticals	2000-06-28	2018-03-16
Bexarotene	Capsule, liquid filled	75 mg/1	Oral	Amerigen Pharmaceuticals Inc.	2018-05-10	Not applicable
Bexarotene	Capsule	75 mg/1	Oral	Amneal Pharmaceuticals NY LLC	2018-09-04	Not applicable
Bexarotene	Capsule, liquid filled	75 mg/1	Oral	Oceanside Pharmaceuticals	2015-12-17	Not applicable
Bexarotene	Capsule, liquid filled	75 mg/1	Oral	Mylan Institutional Inc.	2016-04-15	Not applicable
Bexarotene	Capsule, liquid filled	75 mg/1	Oral	Mylan Pharmaceuticals Inc.	2015-07-09	Not applicable

Additional Data Available

Application Number

A unique ID assigned by the FDA when a product is submitted for approval by the labeller.

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Product Code

A governmentally-recognized ID which uniquely identifies the product within its regulatory market.

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Categories

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.

Associated Conditions

Refractory peripheral cutaneous T-cell lymphoma

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 (RXR_α, RXR_β, RXR_γ). 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: RXR_α, RXR_β, RXR_γ. 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	agonist	Humans
ARetinoic acid receptor RXR-beta	agonist	Humans
ARetinoic acid receptor RXR-gamma	agonist	Humans

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Additional Data Available

Adverse Effects

Comprehensive structured data on known drug adverse effects with statistical prevalence. MedDRA and ICD10 ids are provided for adverse effect conditions and symptoms.

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Additional Data Available

Contraindications

Structured data covering drug contraindications. Each contraindication describes a scenario in which the drug is not to be used. Includes restrictions on co-administration, contraindicated populations, and more.

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Blackbox Warnings

Structured data representing warnings from the black box section of drug labels. These warnings cover important and dangerous risks, contraindications, or adverse effects.

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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

This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.

Drug	Interaction
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(R)-warfarin	The metabolism of (R)-warfarin can be increased when combined with Bexarotene.
(S)-Warfarin	The metabolism of (S)-Warfarin can be increased when combined with Bexarotene.
2-Methoxyethanol	The risk or severity of adverse effects can be increased when Bexarotene is combined with 2-Methoxyethanol.
3,5-diiodothyropropionic acid	The metabolism of 3,5-diiodothyropropionic acid can be increased when combined with Bexarotene.
4-hydroxycoumarin	The metabolism of 4-hydroxycoumarin can be increased when combined with Bexarotene.
5-androstenedione	The metabolism of 5-androstenedione can be increased when combined with Bexarotene.
6-Deoxyerythronolide B	The metabolism of Bexarotene can be decreased when combined with 6-Deoxyerythronolide B.
6-O-benzylguanine	The metabolism of 6-O-benzylguanine can be increased when combined with Bexarotene.
7-ethyl-10-hydroxycamptothecin	The metabolism of 7-ethyl-10-hydroxycamptothecin can be increased when combined with Bexarotene.
9-(N-methyl-L-isoleucine)-cyclosporin A	The risk or severity of adverse effects can be increased when Bexarotene is combined with 9-(N-methyl-L-isoleucine)-cyclosporin A.

Additional Data Available

Extended Description

Extended description of the mechanism of action and particular properties of each drug interaction.

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Severity

A severity rating for each drug interaction, from minor to major.

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Evidence Level

A rating for the strength of the evidence supporting each drug interaction.

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Action

An effect category for each drug interaction. Know how this interaction affects the subject drug.

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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
KEGG Drug: D03106
PubChem Compound: 82146
PubChem Substance: 46509119
ChemSpider: 74139
BindingDB: 50032675
ChEBI: 50859
ChEMBL: CHEMBL1023
Therapeutic Targets Database: DAP000276
PharmGKB: PA164752250
Guide to Pharmacology: GtP Drug Page
HET: 9RA
RxList: RxList Drug Page
Drugs.com: Drugs.com Drug Page
Wikipedia: Bexarotene

ATC Codes

L01XX25 — Bexarotene

PDB Entries

3h0a / 4k6i

FDA label

Download (40.2 KB)

Clinical Trials

Clinical Trials

Phase	Status	Purpose	Conditions	Count
0	Completed	Treatment	Thyroid Cancers	1
1	Completed	Not Available	Alzheimer's Disease (AD)	1
1	Completed	Prevention	Cancer, Breast	1
1	Completed	Treatment	Advanced, Malignant Aerodigestive Tract Tumor (Lung, Head and Neck and Esophagus)	1
1	Completed	Treatment	Cutaneous T-Cell Lymphoma (CTCL) / Mycosis Fungoides (MF) / Primary Cutaneous Anaplastic Large Cell Lymphoma / Sezary Syndrome	1
1	Completed	Treatment	Leukemia Acute Myeloid Leukemia (AML)	2
1	Recruiting	Prevention	Atypical Ductal Breast Hyperplasia / Atypical Lobular Breast Hyperplasia / BRCA1 Gene Mutation / Brca2 Gene Mutation / Ductal Breast Carcinoma In Situ / Invasive Breast Carcinoma / Lobular Breast Carcinoma In Situ / No Evidence of Disease	1
1	Terminated	Treatment	Malignant Lymphomas	1
1	Terminated	Treatment	Malignant Lymphomas / Multiple Myeloma (MM) / Tumors, Solid	1
1, 2	Completed	Treatment	Cutaneous T-Cell Lymphoma (CTCL)	1
1, 2	Completed	Treatment	Lung Cancers	1
1, 2	Terminated	Treatment	Lung Cancer Non-Small Cell Cancer (NSCLC)	1
1, 2	Unknown Status	Not Available	Cushing's Disease	1
2	Completed	Treatment	Alzheimer's Disease (AD)	1
2	Completed	Treatment	Cancer, Breast	1
2	Completed	Treatment	Cutaneous T-Cell Lymphoma (CTCL) / Mycosis Fungoides (MF) / Sezary Syndrome	1
2	Completed	Treatment	Human Immunodeficiency Virus (HIV) Infections / Kaposi s Sarcoma (KS)	1
2	Completed	Treatment	Leukemia Acute Myeloid Leukemia (AML)	1
2	Completed	Treatment	Leukemias / Myelodysplastic Syndromes / Myelodysplastic/Myeloproliferative Diseases	1
2	Completed	Treatment	Lung Cancer Non-Small Cell Cancer (NSCLC)	1
2	Completed	Treatment	Lung Cancers	1
2	Completed	Treatment	Malignant Lymphomas	3
2	Terminated	Treatment	Parapsoriasis	1
2	Unknown Status	Treatment	Lung Cancers	1
2	Unknown Status	Treatment	Malignant Lymphomas	1
2, 3	Completed	Treatment	Alopecia Areata (AA)	1
3	Completed	Prevention	Schizophrenic Disorders	1
3	Completed	Treatment	Cutaneous T-Cell Lymphoma (CTCL) / Mycosis Fungoides (MF) / Primary Cutaneous Anaplastic Large Cell Lymphoma	1
3	Completed	Treatment	Lung Cancer Non-Small Cell Cancer (NSCLC)	2
3	Terminated	Treatment	Malignant Lymphomas	1
3	Unknown Status	Treatment	Schizophrenic Disorders	1
3	Withdrawn	Treatment	Cognition / Schizoaffective Disorders / Schizophrenic Disorders	1
4	Completed	Treatment	Refractory peripheral cutaneous T-cell lymphoma	1
Not Available	Completed	Treatment	Lung Cancer Non-Small Cell Cancer (NSCLC)	1

Pharmacoeconomics

Manufacturers

Eisai inc

Packagers

Catalent Pharma Solutions
Contract Pharm
Eisai Inc.

Dosage forms

Form	Route	Strength
Capsule, liquid filled	Oral	75 mg/1
Capsule	Oral	75 mg/1
Capsule	Oral	75 mg
Gel	Topical	1 g/100g
Gel	Topical	10 mg/1g

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)
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US6043279	No	2000-03-28	2012-04-22
US5780676	No	1998-07-14	2015-07-14
US5962731	No	1999-10-05	2016-10-05

Additional Data Available

Filed On

The date on which a patent was filed with the relevant government.

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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

ADMET data is predicted using admetSAR, a free tool for evaluating chemical ADMET properties. (23092397)

Spectra

Mass Spec (NIST)

Not Available

Spectra

Spectrum	Spectrum Type	Splash Key
Predicted GC-MS Spectrum - GC-MS	Predicted GC-MS	Not Available
Predicted MS/MS Spectrum - 10V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Positive (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 10V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 20V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
Predicted MS/MS Spectrum - 40V, Negative (Annotated)	Predicted LC-MS/MS	Not Available
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0002-0009000000-f46ef667393584a6300e
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0udj-0009000000-9b87e4750a290eb82a7e
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0udi-0009000000-3ce7b47cafecba720b63
LC-MS/MS Spectrum - LC-ESI-QFT , negative	LC-MS/MS	splash10-0udi-0009000000-91e32292babb45759b5d
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0002-0009000000-885779b7401a85dbf649
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0002-0029000000-e65f7a4f9e6ecad40c0b
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-00os-1594000000-b4c3e389bf263ae949a1
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-00kb-1941000000-7e96ac6cea878d4fd773
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0f6w-1920000000-ca6fbe2847a1daae3bd0
LC-MS/MS Spectrum - LC-ESI-QFT , positive	LC-MS/MS	splash10-0f97-1920000000-f8a80e931ae20d42408c
MS/MS Spectrum - , positive	LC-MS/MS	splash10-0002-0239000000-3289f3a345e8948cb1c5

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

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	19.8	N/A	N/A	20656484
EC 50 (nM)	2.7	N/A	N/A	21218783
EC 50 (nM)	28	N/A	N/A	7636877 / 10052980
EC 50 (nM)	33	N/A	N/A	8071941
EC 50 (nM)	42	N/A	N/A	7650690
EC 50 (nM)	52	N/A	N/A	19791803
Kd (nM)	14	N/A	N/A	8071941
Kd (nM)	18	7.4	4	9479476
Kd (nM)	26	7.4	4	9479476
Kd (nM)	28	7.4	4	9479476
Kd (nM)	36	N/A	N/A	7636877 / 12182871
Kd (nM)	36	7.4	4	9479476
Kd (nM)	42	7.4	4	9479476
Kd (nM)	51	7.4	4	9479476
Kd (nM)	7	7.4	4	9479476
Ki (nM)	16	N/A	N/A	9435893
Ki (nM)	21	N/A	N/A	19791803
Ki (nM)	36	N/A	N/A	10052980

Details1. Retinoic acid receptor RXR-alpha

Kind: Protein
Organism: Humans
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]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	112	N/A	N/A	7650690
EC 50 (nM)	25	N/A	N/A	10052980
Ki (nM)	21	N/A	N/A	10052980
Ki (nM)	5.9	N/A	N/A	9435893

Details2. Retinoic acid receptor RXR-beta

Kind: Protein
Organism: Humans
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]

Property	Measurement	pH	Temperature (°C)	References
EC 50 (nM)	122	N/A	N/A	7650690
EC 50 (nM)	20	N/A	N/A	10052980
Ki (nM)	29	N/A	N/A	10052980
Ki (nM)	8.3	N/A	N/A	9435893

Details3. Retinoic acid receptor RXR-gamma

Kind: Protein
Organism: Humans
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

Details1. Cytochrome P450 3A4

Kind: Protein
Organism: Humans
Pharmacological action: Unknown
Actions: Substrate
Inducer

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

Wakelee HA, Takimoto CH, Lopez-Anaya A, Chu Q, Middleton G, Dunlop D, Ramlau R, Leighl N, Rowinsky EK, Hao D, Zatloukal P, Jacobs CD, Rodon J: The effect of bexarotene on atorvastatin pharmacokinetics: results from a phase I trial of bexarotene plus chemotherapy in patients with advanced non-small cell lung cancer. Cancer Chemother Pharmacol. 2012 Feb;69(2):563-71. doi: 10.1007/s00280-011-1772-z. Epub 2011 Nov 6. [PubMed:22057855]
Maminakis C, Whitman AC, Islam N: Bexarotene-Induced Hypertriglyceridemia: A Case Report. Case Rep Oncol. 2018 Apr 11;11(1):234-238. doi: 10.1159/000488447. eCollection 2018 Jan-Apr. [PubMed:29805374]

Details2. Cytochrome P450 2C8

Kind: Protein
Organism: Humans
Pharmacological action: No
Actions: Inhibitor

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: CYP2C8
Uniprot ID: P10632
Uniprot Name: Cytochrome P450 2C8
Molecular Weight: 55824.275 Da

Drug created on June 13, 2005 07:24 / Updated on September 02, 2019 16:39

Bexarotene

Identification

Structure for Bexarotene (DB00307)

Pharmacology

Interactions

References

Clinical Trials

Pharmacoeconomics

Properties

Spectra

Taxonomy

Targets

References

References

References

Enzymes

References