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SML0282

Sigma-Aldrich

Bexarotene

≥98% (HPLC)

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Synonym(s):
4-[1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]benzoic acid, LGD-1069, SR-11247
Empirical Formula (Hill Notation):
C24H28O2
CAS Number:
Molecular Weight:
348.48
MDL number:
PubChem Substance ID:
NACRES:
NA.77

Quality Level

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

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This Item
200499S8951SML1149
Bexarotene ≥98% (HPLC)

SML0282

Bexarotene

Bexarotene A retinoid X receptor (RXR) agonist that can permeate the blood-brain barrier and rapidly reduce Aβ40 and Aβ42 levels in APP/PS1 mice in an ApoE-dependent manner.

200499

Bexarotene

SR11237 ≥98% (HPLC)

S8951

SR11237

BMS-189453 ≥98% (HPLC)

SML1149

BMS-189453

form

powder

form

powder

form

powder

form

powder

Quality Level

100

Quality Level

100

Quality Level

100

Quality Level

100

storage temp.

−20°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

solubility

DMSO: ≥15 mg/mL (warmed)

solubility

DMSO: 50 mg/mL, clear, colorless

solubility

DMSO: >28 mg/mL (warmed)

solubility

DMSO: 10 mg/mL, clear

color

white to beige

color

white

color

white to off-white

color

white to beige

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


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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)
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
Development and Validation of a Stability-Indicating LC Method for Determination of Bexarotene in Softgel Dosage Formulation
Rao KL, et al.
Chromatographia, 80(8), 1211-1224 (2017)
Bexarotene, a Selective RXRalpha Agonist, Reverses Hypotension Associated with Inflammation and Tissue Injury in a Rat Model of Septic Shock
Tunctan B, et al.
Inflammation, 41(1), 337-355 (2018)

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