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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:
153559-49-0
Molecular Weight:
348.48
MDL number:
MFCD00932428
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)

Related Categories

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

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Inhibition of histone deacetylase 3 causes replication stress in cutaneous T cell lymphoma
Wells CE, et al.
PLoS ONE, 8(7), e68915-e68915 (2013)
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)
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)
Retinoids induce antagonism between FOXO3A and FOXM1 transcription factors in human oral squamous cell carcinoma (OSCC) cells
Osei-Sarfo K, et al.
PLoS ONE, 14(4), e0215234-e0215234 (2019)
The rexinoid bexarotene represses cyclin D1 transcription by inducing the DEC2 transcriptional repressor
Li Y, et al.
Breast Cancer Research and Treatment, 128(3), 667-677 (2011)
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