Bexarotene

Names

[ Name ]:
Bexarotene

[Synonym ]:
Targretin
Bexarotene
4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl]benzoic acid
LG 69
4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-2-naphthalenyl)vinyl]benzoic acid
Lg 1069
4-[1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-benzoic acid
Targretyn
Bexaroten
Targret
Benzoic acid, 4-[1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-
4-[1-(3,5,5,8,8-Pentamethyl-2-5,8-dihydronaphthyl)vinyl]benzoic acid
4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoic acid
LGD1069

Biological Activity

[Description]:

Bexarotene is a selective retinoid X receptors (RXR) agonist for the treatment of cutaneous T-cell lymphoma.

[Related Catalog]:

Signaling Pathways >> Autophagy >> Autophagy

Signaling Pathways >> Metabolic Enzyme/Protease >> RAR/RXR

Research Areas >> Cancer

[References]

[1]. Vakeva L, Ranki A, Hahtola S.Ten-year experience of bexarotene therapy for cutaneous T-cell lymphoma in Finland.Acta Derm Venereol. 2012 May;92(3):258-63. doi: 10.2340/00015555-1359.

[2]. Zhang X, Schlaak M, Fabri M, Mauch C, Kurschat P.Successful Treatment of a Panniculitis-Like Primary Cutaneous T-Cell Lymphoma of the α/β Type with Bexarotene.Case Rep Dermatol. 2012 Jan;4(1):56-60.

[3]. Orendas P, Kubatka P, Kajo K, Stollarova N, Kassayova M, Bojkova B, Pec M, Nosal V, Kiskova T, Zihlavnikova K, Karsnakova R.Melatonin enhanced bexarotene efficacy in experimental mammary carcinogenesis.Neoplasma. 2012;59(4):469-74.

[4]. Cras A, Politis B, Balitrand N, Darsin-Bettinger D, Boelle PY, Cassinat B, Toubert ME, Chomienne C.Bexarotene via CBP/p300 induces suppression of NF-κB-dependent cell growth and invasion in thyroid cancer.Clin Cancer Res. 2012 Jan 15;18(2):442-53.

[5]. Gui Y, et al. Bexarotent attenuated CCI-induced spinal neuroinflammation and neuropathic pain by targeting MKP-1. J Pain. 2019 Jan 17. pii: S1526-5900(18)30607-2.

[Related Small Molecules]

Chemical & Physical Properties

[ Density]:
1.0±0.1 g/cm3

[ Boiling Point ]:
489.7±44.0 °C at 760 mmHg

[ Melting Point ]:
230-231ºC

[ Molecular Formula ]:
C₂₄H₂₈O₂

[ Molecular Weight ]:
348.478

[ Flash Point ]:
229.5±23.1 °C

[ Exact Mass ]:
348.208923

[ PSA ]:
37.30000

[ LogP ]:
8.55

[ Vapour Pressure ]:
0.0±1.3 mmHg at 25°C

[ Index of Refraction ]:
1.556

MSDS

Click to get detail MSDS

Safety Information

[ Hazard Codes ]:
Xn

[ RIDADR ]:
NONH for all modes of transport

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Articles

Retinoids Bias Integrin Expression and Function in Cutaneous T-Cell Lymphoma.

J. Invest. Dermatol. 135 , 2102-8, (2015)

Cutaneous T-cell lymphoma (CTCL) is a heterogeneous group of malignancies characterized by accumulation of malignant T-cells within the skin. Retinoids, metabolic derivatives, and synthetic analogs of...

RNA-sequencing reveals transcriptional up-regulation of Trem2 in response to bexarotene treatment.

Neurobiol. Dis. 82 , 132-40, (2015)

We have recently demonstrated that short term bexarotene treatment of APP/PS1 mice significantly improves their cognitive performance. While there were no changes in plaque load, or insoluble Aβ level...

Retinoid X receptors orchestrate osteoclast differentiation and postnatal bone remodeling.

J. Clin. Invest. 125(2) , 809-23, (2015)

Osteoclasts are bone-resorbing cells that are important for maintenance of bone remodeling and mineral homeostasis. Regulation of osteoclast differentiation and activity is important for the pathogene...