SML0282
Bexarotene
≥98% (HPLC), retinoid X receptor (RXR) agonist, powder
Sinónimos:
4-[1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]benzoic acid, LGD-1069, SR-11247
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Fórmula empírica (notación de Hill):
C24H28O2
Número CAS:
Peso molecular:
348.48
UNSPSC Code:
41106305
PubChem Substance ID:
NACRES:
NA.77
MDL number:
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Permítanos ayudarleNombre del producto
Bexarotene, ≥98% (HPLC)
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
assay
≥98% (HPLC)
form
powder
color
white to beige
solubility
DMSO: ≥15 mg/mL (warmed)
storage temp.
−20°C
Quality Level
Gene Information
human ... RXRA(6256), RXRB(6257), RXRG(6258)
Categorías relacionadas
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 and an antineoplastic agent.
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.
Clase de almacenamiento
11 - Combustible Solids
wgk
WGK 3
flash_point_f
Not applicable
flash_point_c
Not applicable
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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)
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)
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)
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)
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
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