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153559-49-0 (Bexarotene)

1

Identification

Bexarotene Bexarotene
Name Bexarotene
Formula C24H28O2
MW 348.48
CAS No. 153559-49-0
EINECS
Smiles CC1(C)C2=CC(C(C3=CC=C(C(O)=O)C=C3)=C)=C(C)C=C2C(C)(C)CC1
Synonyms 4-[1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]benzoic acid; Targretin; 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoic acid
InChI 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)
2

Introduction

Bexarotene (Targretin) is a selective RXR agonist approved for the treatment of CTCL. IC50 value: Target: retinoid X receptor Exposure of NSCLC cell lines to bexarotene as a single agent had modest growth inhibitory effects (at > 1 μM).

Background Information

A synthetic retinoic acid ligand ......by AOBIOUS INC
Bexarotene is a highly selective retinoid X receptor (RXR) agonist. ......by AdooQ BioScience, LLC
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 ......by Affix Scientific
Bexarotene is a retinoid specifically selective for retinoid X receptors, used as an oral antineoplastic agent in the treatment of cutaneous T-cell lymphoma. ......by BOC Sciences
Bexarotene is a synthetic retinoid analog with specific affinity for the retinoid X receptor and belongs to a group of compounds called rexinoids. It is an oral, noncytotoxic drug that was approved in Europe and in the U.S.A. for the treatment of refractory advanced-stage cutaneous T-cell lymphomas. The receptor-selective retinoids might be particularly useful in preventing ER-negative breast cancer. ......by BioVision, Inc.,
Bexarotene, also known as LGD-1069, is a synthetic retinoic acid agent with potential antineoplastic, chemopreventive, teratogenic and embryotoxic properties. Bexarotene selectively binds to and activates retinoid X receptors (RXRs), thereby inducing changes in gene expression that lead to cell differentiation, decreased cell proliferation, apoptosis of some cancer cell types, and tumor regression. ......by MedKoo Biosciences, Inc.
Bexarotene is a retinoid specifically selective for retinoid X receptors, used as an oral antineoplastic agent in the treatment of cutaneous T-cell lymphoma. ......by Selleck Chemicals LLC
Bexarotene is a retinoid specifically selective for retinoid X receptors, used as an oral antineoplastic agent in the treatment of cutaneous T-cell lymphoma. ......by Target Molecule Corp.
Potent and selective RXR agonist (EC50 values are 24, 25 and 33 nM for RXRβ, RXRγ and RXRα, respectively). Exhibits >300-fold selectivity for RXR over RAR receptors. Inhibits tumor cell invasion and migration in vitro, and inhibits metastasis and angiogenesis in mouse models. Also promotes brown adipogenic differentiation and induces brown adipogenic reprogramming from myoblasts. ......by Tocris Bioscience Inc.
3

Protocol(Only for Reference)

Cell Experiment

Animal Experiment

4

Physical and Chemical Properties

Appearance:White to off-white Solid EBNumber:EB000028540

Storage condition

Up to one week at 4°C or six months at -20°C. by Affix Scientific
Store at or below -20 oC. by LC Laboratoies

Solubility

Soluble in DMSO at 65 mg/mL; soluble in ethanol at 10 mg/mL with warming; very poorly soluble in water; maximum solubility in plain water is estimated to be about 10-50 μM; buffers, serum, or other additives may increase or decrease the aqueous solubility. by LC Laboratoies
(25°C) * In vitro DMSO 8 mg/mL (22.98 mM); Water<1 mg/mL (<1 mM); Ethanol<1 mg/mL (<1 mM) by Selleck Chemicals LLC
5

Mechanism and Indication

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Clinical Information

Product Name Sponsor & Collaborators Indications Start Date End Date Phase
Bexarotene Eisai Inc Cutaneous T-cell lymphoma 2009/12/31 2013/11/30 Phase 4 Clinical
Bexarotene European Organization for Research and Treatment of Cancer Mycosis fungoides 2003/1/31 2011/6/30 Phase 3 Clinical
Bexarotene Millennium Pharmaceuticals Inc Cutaneous T-cell lymphoma 2012/8/31 2015/6/30 Phase 3 Clinical
Bexarotene Beersheva Mental Health Center Schizophrenia 2007/9/24 Phase 3 Clinical
Bexarotene Eisai Inc Metastatic non small cell lung cancer 2002/5/31 2005/3/31 Phase 3 Clinical
Bexarotene - Launched
7

Safety Data of Bexarotene

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Spectral Information

9

Suppliers List

Company Price and Availability Country/Region
AOBIOUS INC 1mg/USD9() USA
AdooQ BioScience, LLC USA
Affix Scientific 1g/USD600(In stock) USA
Ark Pharm, Inc. USA
BOC Sciences
BioVision, Inc., USA
Biochempartner Co., Ltd China
CHEMSCENE, LLC 50mg/USD72();100mg/USD108() USA
Cayman Chemical Company USA
LC Laboratoies 100mg/USD57(In stock);300mg/USD72(In stock);500mg/USD98(In stock);1g/USD147(In stock);2g/USD283(In stock);5g/USD655(In stock);10g/USD994(In stock) USA
MedChemexpress Co., Ltd. 50mg/USD72();100mg/USD108() USA
MedKoo Biosciences, Inc. USA
Selleck Chemicals LLC 50mg/USD97(In stock);10mM/1mLIn DMSO/USD130(In stock) USA
Shanghai Haoyuan Chemexpress Co., Ltd. 50mg/USD72();100mg/USD108() China
Shanghai Taiheng Industry Co., Ltd. China
Shanghai Yingxuan Chempharm Co., Ltd. China
Target Molecule Corp. 10mg/USD28();100mg/USD93() USA
Tocris Bioscience Inc. USA
Wuhan Sunrise Technology Development Company Limited China
Wuxi Mizat Chemicals Technology Co., Ltd. China
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Related Products

Other Forms of 153559-49-0

Name CAS No Formula MW

Recommended Compounds in RAR/RXR Autophagy

Name CAS No Formula MW
AGN 205728 859498-05-8 C29H27NO3 437.53
AGN 196996 958295-17-5 C24H20BrNO5 482.32
AGN 194310 229961-45-9 C28H24O2S 424.55
Acitretin (sodium) 925701-88-8 C21H25NaO3 348.41
Acitretin 55079-83-9 C21H26O3 326.43
Adapalene (sodium salt) 911110-93-5 C28H27NaO3 434.5
Adapalene 106685-40-9 C28H28O3 412.52
TTNPB 71441-28-6 C24H28O2 348.48
Magnolol 528-43-8 C18H18O2 266.33
Tazarotene 118292-40-3 C21H21NO2S 351.46
Fenretinide 65646-68-6 C26H33NO2 391.55
LG 100268 153559-76-3 C24H29NO2 363.49
Isotretinoin 4759-48-2 C20H28O2 300.44
Palovarotene 410528-02-8 C27H30N2O2 414.54
Retinoic acid 302-79-4 C20H28O2 300.44
AM580 102121-60-8 C22H25NO3 351.44
(R)-Flurbiprofen 51543-40-9 C15H13FO2 244.2609
Tamibarotene 94497-51-5 C22H25NO3 351.44
AGN 195183 367273-07-2 C22H22ClF2NO4 437.86
AR7 80306-38-3 C15H12ClNO 0.0

Recommended Compounds in Same Indication

Name CAS No Formula MW
LDK378 1032900-25-6 C28H36ClN5O3S 558.14
Pemetrexed (disodium) 150399-23-8 C20H19N5Na2O6 471.37
Rifabutin 72559-06-9 C46H62N4O11 847.0
Volasertib 755038-65-4 C34H50N8O3 618.81
ALK inhibitor 1 761436-81-1 C23H28BrN7O3S 562.48
Olaparib 763113-22-0 C24H23FN4O3 434.46
Afatinib (dimaleate) 850140-73-7 C32H33ClFN5O11 718.08
Asenapine (maleate) 85650-56-2 C21H20ClNO5 401.84
MGCD-265 analog 875337-44-3 C26H20FN5O2S2 517.5977
Cariprazine 839712-12-8 C21H32Cl2N4O 427.41
PF-2545920 898562-94-2 C25H20N4O 392.45
AT-101 90141-22-3 C30H30O8 518.55
Tivantinib 905854-02-6 C23H19N3O2 369.42
lumateperone (Tosylate) 1187020-80-9 C31H36FN3O4S 565.6987
Lu AE58054 467459-31-0 C20H19F5N2O 398.37
EVP-6124 550999-75-2 C16H17ClN2OS 320.84
Sunitinib 557795-19-4 C22H27FN4O2 398.47
Asenapine 65576-45-6 C17H16ClNO 285.77
FK866 658084-64-1 C24H29N3O2 391.51
Motesanib (Diphosphate) 857876-30-3 C22H29N5O9P2 569.44
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Route of Synthesis

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References

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More Information

Bexarotene

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