Skip to Content
MilliporeSigma
All Photos(1)

Key Documents

View All Documentation

SML0282

Sigma-Aldrich

Bexarotene

≥98% (HPLC)

Synonym(s):

4-[1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]benzoic acid, LGD-1069, SR-11247

Sign Into View Organizational & Contract Pricing
All Photos(1)

About This Item

Empirical Formula (Hill Notation):
C24H28O2
CAS Number:
153559-49-0
Molecular Weight:
348.48
MDL number:
MFCD00932428
UNSPSC Code:
41106305
PubChem Substance ID:
329825290
NACRES:
NA.77

Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: ≥15 mg/mL (warmed)

storage temp.

−20°C

SMILES string

C=C(C1=CC=C(C(O)=O)C=C1)C2=C(C)C=C3C(C(C)(C)CCC3(C)C)=C2

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)

InChI key

NAVMQTYZDKMPEU-UHFFFAOYSA-N

Gene Information

human ... RXRA(6256) , RXRB(6257) , RXRG(6258)

Application

Bexarotene has been used as retinoid x receptor (RXR) agonist:
  • to study its effect on human oral squamous cell carcinoma (OSCC) cell lines
  • to test for cooperative cell killing of cutaneous T cell lymphoma (CTCL) with 966
  • as a standard in HPLC for determining its potential impurities in drug substances and drug products

Bexarotene has been used:
  • to investigate its effects on the changes in renal, cardiac, hepatic, and pulmonary expression/activity of inducible nitric oxide synthase (iNOS) and CYP4F6
  • to analyze the involvement of retinoid x receptor (RXR) homo or permissive heterodimers
  • to study its potential impurities in drug substances and drug products

Biochem/physiol Actions

Bexarotene is a highly selective retinoid X receptor (RXR) agonist. It is an antineoplastic agent, already approved as an oral antineoplastic agent for cutaneous T cell lymphoma and being investigated against other cancers. A study has found that bexarotene in a mouse Alzheimer′s model lowered the most toxic form of β-amyloid peptide and increased cognitive ability. The activity in the mouse Alzheimer′s models are believed to be by activating PPARγ:RXR and LXR:RXR dimers which induces the expression of apoE and facilitates Aβ clearance and promotes microglial phagocytosis.
Bexarotene is used to treat breast cancer.

Features and Benefits

This compound is a featured product for Cyclic Nucleotide research. Click here to discover more featured Cyclic Nucleotide products. Learn more about bioactive small molecules for other areas of research at sigma.com/discover-bsm.
This compound is featured on the Nuclear Receptors (Non-Steroids) page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

Already Own This Product?

Find documentation for the products that you have recently purchased in the Document Library.

Visit the Document Library

M Maekawa et al.
Translational psychiatry, 7(9), e1229-e1229 (2017-09-06)
The risk of schizophrenia is increased in offspring whose mothers experience malnutrition during pregnancy. Polyunsaturated fatty acids (PUFAs) are dietary components that are crucial for the structural and functional integrity of neural cells, and PUFA deficiency has been shown to
Katherine D LaClair et al.
Molecular neurodegeneration, 8, 18-18 (2013-06-15)
Though the precise cause(s) of Alzheimer's disease (AD) remain unknown, there is strong evidence that decreased clearance of β-amyloid (Aβ) from the brain can contribute to the disease. Therapeutic strategies to promote natural Aβ clearance mechanisms, such as the protein
Protective effects of retinoid x receptors on retina pigment epithelium cells
Ayala-Pena VB, et al.
Biochimica et Biophysica Acta - Molecular Cell Research, 1863(6), 1134-1145 (2016)
Shawn C Owen et al.
ACS chemical biology, 7(8), 1429-1435 (2012-05-26)
Many small molecules, including bioactive molecules and approved drugs, spontaneously form colloidal aggregates in aqueous solution at micromolar concentrations. Though it is widely accepted that aggregation leads to artifacts in screens for ligands of soluble proteins, the effects of colloid
Inhibition of histone deacetylase 3 causes replication stress in cutaneous T cell lymphoma
Wells CE, et al.
PLoS ONE, 8(7), e68915-e68915 (2013)
View All Related Papers

Related Content

Discover Bioactive Small Molecules for Cyclic Nucleotides

Cyclic nucleotides, including cyclic AMP (cAMP), cyclic GMP (cGMP) and cyclic ADP-ribose, have been extensively studied as second messengers of intracellular events initiated by activation of GPCRs. cAMP modifies cell function in all eukaryotic cells, principally through the activation of cAMP-dependent protein kinase (PKA), but also through cAMP-gated ion channels and guanine nucleotide exchange factors directly activated by cAMP.

Our team of scientists has experience in all areas of research including Life Science, Material Science, Chemical Synthesis, Chromatography, Analytical and many others.

Contact Technical Service