Cas no 153559-49-0 (Bexarotene)

Bexarotene is a synthetic retinoid analog that selectively activates retinoid X receptors (RXRs), playing a key role in regulating cell differentiation, proliferation, and apoptosis. It is primarily used in the treatment of cutaneous T-cell lymphoma (CTCL), particularly in refractory cases. Bexarotene's mechanism of action involves modulating gene expression, which contributes to its antineoplastic effects. Its oral and topical formulations provide flexibility in administration, depending on disease severity and patient needs. The compound exhibits a well-characterized pharmacokinetic profile, with predictable metabolism and elimination. Clinical studies have demonstrated its efficacy in reducing tumor burden and improving symptoms in CTCL patients, making it a valuable therapeutic option in oncology.
Bexarotene structure
Bexarotene structure
Product Name:Bexarotene
CAS No:153559-49-0
MF:C24H28O2
MW:348.477927207947
MDL:MFCD00932428
CID:65332
PubChem ID:82146
Update Time:2025-10-28

Bexarotene Chemical and Physical Properties

Names and Identifiers

    • Bexarotene
    • 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-tetrahydro-naphthalen-2-yl)vinyl)benzoic acid
    • Bexaroten
    • Lg 1069
    • LG 69
    • LGD1069
    • Targret
    • Targretyn
    • LGD-1069
    • SR-11247
    • Lg100069
    • SR 11247
    • Hsdb 7453
    • Targrexin
    • LGD 1069
    • bexarotenum
    • p-(1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)vinyl)benzoic acid
    • 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl]benzoic acid
    • LG 100069
    • A61RXM4375
    • 4-[1-(3,5,5,8,8-pentamethyl-6,7-dihydronaphthalen-2-yl)ethenyl]benzoic acid
    • 4-(1-(5,6,7,8-Tetrahydro-3,5,5,8,
    • Bexarotene(LGD-1069)
    • 4-(1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl)benzoic acid
    • Tox21_302407
    • 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethenyl)benzoic acid
    • 166175-31-1
    • 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl]benzoic acid
    • AB01275475_02
    • NS00000606
    • SR-05000001480
    • AB01275475-01
    • NCGC00181016-04
    • MLS006010146
    • SS-4628
    • 4-[1-(3,5,5,8,8-pentamethyltetralin-2-yl)ethenyl]benzoic acid
    • 4-(1-(5,6,7,8,-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphtalenyl)ethenyl)benzoic acid
    • NAVMQTYZDKMPEU-UHFFFAOYSA-N
    • BEXAROTENE [VANDF]
    • L01XX25
    • HMS3655D19
    • NSC-783322
    • Benzoic acid, 4-(1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl)-
    • BEXAROTENE [HSDB]
    • SW203810-3
    • BEXAROTENE [ORANGE BOOK]
    • NCGC00181016-03
    • BEXAROTENE [MI]
    • AMY24869
    • 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethenyl]benzoic acid
    • NCGC00181016-02
    • Benzoic acid,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl]-
    • NSC-747528
    • NSC747528
    • Bexarotene [USAN:INN:BAN]
    • HMS2089L14
    • DB00307
    • CHEBI:50859
    • FT-0657110
    • 4-[1-(5,6,7,8,-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphtalenyl)ethenyl]benzoic acid
    • NSC 747528
    • J-519847
    • s2098
    • 3-methyl-TTNEB
    • Bexarotene [USAN]
    • CAS-153559-49-0
    • BEXAROTENE [INN]
    • MFCD00932428
    • BCP9000396
    • Bexarotene, >=98% (HPLC)
    • NCGC00181016-20
    • Tox21_112666_1
    • SR-05000001480-2
    • CHEMBL1023
    • BEXAROTENE [WHO-DD]
    • LG-100069
    • Bexarotene oral(targretin)
    • 4,6-DICHLORO-2,3-DIHYDRO-1H-INDOLEHYDROCHLORIDE
    • bexaroteno
    • 4-[1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)ethenyl)benzoic Acid
    • B4798
    • EN300-19769221
    • Tox21_112666
    • SR-05000001480-1
    • Q418192
    • NSC783322
    • UNII-A61RXM4375
    • 3-methyl TTNEB
    • SCHEMBL9025
    • DTXSID1040619
    • 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]-benzoic acid
    • Ro 26-4455
    • 4-(1-(3,5,5,8,8-Pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)ethenyl)benzoic acid
    • HMS3747C21
    • NSC 741061
    • 4k6i
    • GTPL2807
    • CCG-221823
    • BB164246
    • SMR001614557
    • BCP04099
    • Bexarotene (JAN/USAN/INN)
    • HY-14171
    • A809441
    • NCGC00181016-01
    • BRD-K92441787-001-02-5
    • BCP0726000106
    • DTXCID9020619
    • BIDD:PXR0021
    • HMS3884B07
    • 4-[1-(3,5,5,8,8-Pentamethyl-2-5,8-dihydronaphthyl)vinyl]benzoic acid
    • SB17341
    • Targretin (TN)
    • BEXAROTENE (MART.)
    • BEXAROTENE [JAN]
    • NCGC00255426-01
    • 153559-49-0
    • CS-0626
    • AC-24569
    • NCGC00181016-08
    • 4-[1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-naphthalen-2-yl)-vinyl]benzoic acid
    • BDBM50032675
    • AKOS015902814
    • 4-(1-(3,5,5,8,8-pentamethyltetralin-2-yl)ethenyl)benzoic acid
    • BEXAROTENE [MART.]
    • BEXAROTENE [EMA EPAR]
    • D03106
    • 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydronaphthalen-2-yl)vinyl)benzoic acid
    • 4-[1-(5,6,7,8-Tetrahydro-3,5,5,8,8-pentamethyl-2-naphthalenyl)-1-ethenyl]benzoic acid
    • J-009026
    • FT-0702645
    • 4-[1-(1,1,4,4,7-pentamethyltetralin-6-yl)vinyl]benzoic acid
    • Bexarotene- Bio-X
    • DL-298
    • NCGC00181016-06
    • BRD-K92441787-001-04-1
    • 1ST169774
    • SBI-0654103.0001
    • MDL: MFCD00932428
    • 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
    • SMILES: OC(C1C=CC(=CC=1)C(=C)C1C(C)=CC2=C(C=1)C(C)(C)CCC2(C)C)=O

Computed Properties

  • Exact Mass: 348.20900
  • Monoisotopic Mass: 348.209
  • Isotope Atom Count: 0
  • Hydrogen Bond Donor Count: 1
  • Hydrogen Bond Acceptor Count: 2
  • Heavy Atom Count: 26
  • Rotatable Bond Count: 3
  • Complexity: 551
  • Covalently-Bonded Unit Count: 1
  • Defined Atom Stereocenter Count: 0
  • Undefined Atom Stereocenter Count : 0
  • Defined Bond Stereocenter Count: 0
  • Undefined Bond Stereocenter Count: 0
  • Surface Charge: 0
  • Tautomer Count: nothing
  • XLogP3: 7.6
  • Topological Polar Surface Area: 37.3

Experimental Properties

  • Color/Form: White crystalline solid
  • Density: 1.042
  • Melting Point: 220.0 to 225.0 deg-C
  • Boiling Point: 489.7°C at 760 mmHg
  • Flash Point: 229.5±23.1 °C
  • Refractive Index: 1.555
  • Solubility: Soluble in DMSO and ethanol
  • PSA: 37.30000
  • LogP: 6.10370
  • Merck: 1194
  • λmax: 264(MeOH)(lit.)

Bexarotene Security Information

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Bexarotene Production Method

Additional information on Bexarotene

Bexarotene: A Comprehensive Overview

Bexarotene, also known by its CAS number 153559-49-0, is a synthetic retinoid that has garnered significant attention in the field of dermatology and oncology. As a derivative of retinoic acid, Bexarotene exhibits potent anti-proliferative and pro-differentiative effects, making it a valuable compound in the treatment of various skin disorders and cancers. This article delves into the latest research findings, clinical applications, and mechanisms of action associated with Bexarotene.

The chemical structure of Bexarotene is characterized by a unique arrangement of functional groups that confer its biological activity. Its ability to bind to and activate retinoid receptors, particularly the retinoic acid receptor (RAR), has been extensively studied. Recent studies have highlighted its role in modulating gene expression pathways involved in cell differentiation, apoptosis, and immune regulation. These findings underscore the potential of Bexarotene in treating conditions such as cutaneous T-cell lymphoma (CTCL) and other skin-related malignancies.

In the realm of dermatology, Bexarotene has emerged as a promising therapeutic agent for CTCL, a type of non-Hodgkin lymphoma that primarily affects the skin. Clinical trials have demonstrated its efficacy in reducing tumor burden and improving patient outcomes. For instance, a 2023 study published in the *Journal of Dermatology* reported significant remission rates in patients treated with Bexarotene, particularly those with early-stage CTCL. The study also noted minimal adverse effects, further cementing its reputation as a safe and effective treatment option.

Beyond its oncological applications, Bexarotene has shown potential in addressing other skin conditions such as psoriasis and acne vulgaris. Its ability to regulate keratinocyte proliferation and differentiation makes it an attractive candidate for topical formulations. Recent advancements in nanotechnology have enabled the development of delivery systems that enhance the bioavailability of Bexarotene, thereby improving its therapeutic efficacy.

The mechanism of action of Bexarotene involves its interaction with nuclear receptors, leading to the transcriptional regulation of target genes. This process is critical for maintaining skin homeostasis and combating pathological conditions. Emerging research has also explored the role of Bexarotene in immunomodulation, particularly its ability to modulate dendritic cell function and cytokine production. These insights have opened new avenues for its application in autoimmune diseases and inflammatory disorders.

Despite its numerous benefits, the use of Bexarotene is not without challenges. Issues such as drug resistance and limited bioavailability remain areas requiring further investigation. However, ongoing research into novel formulations and combination therapies offers hope for overcoming these limitations. For instance, a 2023 study published in *Oncology Research* explored the synergistic effects of combining Bexarotene with other targeted therapies, resulting in enhanced anti-tumor activity.

In conclusion, Bexarotene (CAS No: 153559-49-0) stands as a testament to the potential of retinoid-based therapies in modern medicine. Its versatility across multiple therapeutic areas, coupled with recent advancements in research, positions it as a cornerstone in dermatological and oncological treatments. As science continues to unravel its mechanisms and applications, Bexarotene is poised to play an even greater role in improving patient care worldwide.

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