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Summary
General Info

PubChem

PubChem Compound 10337961

Name:	bexarotene
PubChem Compound ID:	10337961
Molecular formula:	C₂₄H₂₈O₂
Molecular weight:	350.47 g/mol

DrugBank

Identification

Name:	bexarotene
Name (isomeric):	DB00307
Drug Type:	small molecule
Brand:	Targretyn, Targretin, Targret, Targretin-gel, Targrexin
Category:	Anticarcinogenic Agents
CAS number:	153559-49-0

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.
Pharmacology:	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 o... show more » 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. show less «
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.
Protein binding:	>99%
Route of elimination:	Urinary elimination of bexarotene and its known metabolites is a minor excretory pathway (<1% of administered dose).
Half Life:	7 hours
Affected organisms:	Humans and other mammals

Interactions

Drug interaction:

Norgestimate	Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of norgestimate, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Etonogestrel	Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of etonogestrel, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Doxycycline	Tetracycline derivatives like doxycycline may enhance the adverse/toxic effect of Retinoic Acid Derivatives. Due to the risk of developing pseudotumor cerebri (also known as intracranial hypertension), avoid this combination of drugs if possible. If used concomitantly, monitor for evidence of this interaction (eg, dizziness, diplopia, headache).
estrogen	Bexarotene may decrease the serum concentration of contraceptives (estrogens) and is teratogenic. Women of childbearing age receiving bexarotene should use two forms of contraception, including at least one non-hormonal form.
Ethynodiol Diacetate	Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of ethynodiol diacetate it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).

Norgestimate	Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of norgestimate, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Etonogestrel	Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of etonogestrel, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Doxycycline	Tetracycline derivatives like doxycycline may enhance the adverse/toxic effect of Retinoic Acid Derivatives. Due to the risk of developing pseudotumor cerebri (also known as intracranial hypertension), avoid this combination of drugs if possible. If used concomitantly, monitor for evidence of this interaction (eg, dizziness, diplopia, headache).
estrogen	Bexarotene may decrease the serum concentration of contraceptives (estrogens) and is teratogenic. Women of childbearing age receiving bexarotene should use two forms of contraception, including at least one non-hormonal form.
Ethynodiol Diacetate	Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of ethynodiol diacetate it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Levonorgestrel	Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of levonorgestrel, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Gemfibrozil	Gemfibrozil may increase the serum concentration of bexarotene. This combination should be avoided.
Drospirenone	Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of drospirenone, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Vitamin A	Bexarotene increases the risk of vitamin A toxicity. Avoid vitamin A supplementation while taking bexarotene.
Conivaptan	Conivaptan may increase the serum concentration of CYP3A4 substrates such as bexarotene. Upon completion/discontinuation of conivaptan, allow at least 7 days before initiating therapy with drugs that are CYP3A4 substrates. Consider therapy modification.
Desogestrel	Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of desogestrel, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Norelgestromin	Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of norelgestromin, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Tetracycline	Tetracycline may enhance the adverse/toxic effect of Retinoic Acid Derivatives. Due to the risk of developing pseudotumor cerebri (also known as intracranial hypertension), avoid this combination of drugs if possible. If used concomitantly, monitor for evidence of this interaction (eg, dizziness, diplopia, headache).
Medroxyprogesterone	Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of medroxyprogesterone, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Minocycline	Tetracycline derivatives like minocycline may enhance the adverse/toxic effect of Retinoic Acid Derivatives. Due to the risk of developing pseudotumor cerebri (also known as intracranial hypertension), avoid this combination of drugs if possible. If used concomitantly, monitor for evidence of this interaction (eg, dizziness, diplopia, headache).
Tigecycline	Tigecycline may enhance the adverse/toxic effect of Retinoic Acid Derivatives. The development of pseudotumor cerebri (intracranial hypertension) is of particular concern. Avoid this combination.
Demeclocycline	Tetracycline derivatives like demeclocycline may enhance the adverse/toxic effect of Retinoic Acid Derivatives. Due to the risk of developing pseudotumor cerebri (also known as intracranial hypertension), avoid this combination of drugs if possible. If used concomitantly, monitor for evidence of this interaction (eg, dizziness, diplopia, headache).
Norgestrel	Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of norgestrel, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).
Norethindrone	Bexarotene may decrease the serum concentration of Contraceptives (Progestins). Since bexarotene is teratogenic and can lower serum concentrations of norethindrone, it is advised that women of childbearing potential use two forms of contraception (including at least one non-hormonal form).

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Targets

Retinoic acid receptor RXR-alpha

Nuclear hormone receptor. Involved in the retinoic acid response pathway. Binds 9-cis retinoic acid (9C-RA). ARF6 acts as a key regulator of the tissue-specific adipocyte P2 (aP2) enhancer

UniProt ID:

P19793

Gene:

RXRA

Actions:

agonist

References:

Lowe MN, Plosker GL: Bexarotene. Am J Clin Dermatol. 2000 Jul-Aug;1(4):245-50; discussion 251-2.
View Article

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.
View Article

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.
View Article

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.
View Article

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.
View Article

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.
View Article

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.
View Article

Rigas JR, Dragnev KH: Emerging role of rexinoids in non-small cell lung cancer: focus on bexarotene. Oncologist. 2005 Jan;10(1):22-33.
View Article

Farol LT, Hymes KB: Bexarotene: a clinical review. Expert Rev Anticancer Ther. 2004 Apr;4(2):180-8.
View Article

Retinoic acid receptor RXR-beta

Nuclear hormone receptor. Involved in the retinoic acid response pathway. Binds 9-cis retinoic acid (9C-RA)

UniProt ID:

P28702

Gene:

RXRB

Actions:

agonist

References:

Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6.
View Article

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.
View Article

Rigas JR, Dragnev KH: Emerging role of rexinoids in non-small cell lung cancer: focus on bexarotene. Oncologist. 2005 Jan;10(1):22-33.
View Article

Farol LT, Hymes KB: Bexarotene: a clinical review. Expert Rev Anticancer Ther. 2004 Apr;4(2):180-8.
View Article

Lowe MN, Plosker GL: Bexarotene. Am J Clin Dermatol. 2000 Jul-Aug;1(4):245-50; discussion 251-2.
View Article

Retinoic acid receptor RXR-gamma

Nuclear hormone receptor. Involved in the retinoic acid response pathway. Binds 9-cis retinoic acid (9C-RA)

UniProt ID:

P48443

Gene:

RXRG

Actions:

agonist

References:

Lowe MN, Plosker GL: Bexarotene. Am J Clin Dermatol. 2000 Jul-Aug;1(4):245-50; discussion 251-2.
View Article

Rigas JR, Dragnev KH: Emerging role of rexinoids in non-small cell lung cancer: focus on bexarotene. Oncologist. 2005 Jan;10(1):22-33.
View Article

Farol LT, Hymes KB: Bexarotene: a clinical review. Expert Rev Anticancer Ther. 2004 Apr;4(2):180-8.
View Article

Enzymes

Cytochrome P450 3A4

Cytochrome P450 2C9