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bexarotene

Trade name: targretin

Small moleculeapprovedOrphan Drug FDA

Approved

Dec 29, 1999

Bexarotene (Targretin) is an antineoplastic agent indicated by the FDA for Cutaneous T cell lymphoma. It has been used off-label for lung cancer, breast cancer, and Kaposi's sarcoma. Bexarotene is a member of a subclass of retinoids that selectively activate retinoid X receptors (RXRs). These retinoid receptors have biologic activity distinct from that of retinoic acid receptors (RARs). Bexarotene selectively binds and activates retinoid X receptor subtypes (RXRa, RXRb, RXRg). RXRs can form heterodimers with various receptor partners such as retinoic acid receptors (RARs), vitamin D receptor, thyroid receptor, and peroxisome proliferator activator receptors (PPARs). Once activated, these receptors function as transcription factors that regulate the expression of genes that control cellular differentiation and proliferation. Bexarotene inhibits the growth in vitro of some tumor cell lines of hematopoietic and squamous cell origin. It also induces tumor regression in vivo in some animal models. The exact mechanism of action of bexarotene in the treatment of cutaneous T-cell lymphoma (CTCL) is unknown. — NCATS

Clinical trial activity

44 trials · 49 clinical orgs · 11 marketing orgs

Phase 1
16
Phase 2
28
Phase 3
8
Phase 4
1

Earliest trial started Oct 1, 1998 (NCT00003752)

Timeline

1990s

  1. Jan 1, 1998

    Ligand Pharmaceuticals — Earliest Phase 2 Sponsor(trial)

  2. Jun 18, 1999

    Orphan Drug Designation

  3. Dec 29, 1999

    Ligand Pharmaceuticals — Earliest FDA Approval

  4. Dec 29, 1999

    Ligand Pharmaceuticals — NDA Organization

  5. Dec 29, 1999

    Bausch Health Companies — NDA Secondary Org

2000s

  1. Jan 1, 2001

    Earliest Phase 1 Sponsor(trial)

  2. Jan 1, 2002

    Earliest Phase 3 Sponsor(trial)

2010s

  1. Aug 12, 2014

    Bionpharma Inc — Marketing Organization

  2. May 8, 2018

    Ani Pharmaceuticals — Marketing Organization

  3. May 8, 2018

    Amerigen Pharmaceuticals — Marketing Organization

  4. Jul 25, 2018

    Upsher-Smith Laboratories — Marketing Organization

  5. Sep 4, 2018

    Amneal Pharmaceuticals — Marketing Organization

2020s

  1. Jun 16, 2020

    Hikma — Marketing Organization

  2. Jan 14, 2021

    Teva — Marketing Organization

  3. Sep 6, 2024

    Ascent Pharmahealth — Marketing Organization

  4. Dec 10, 2024

    Cipla — Marketing Organization

Indications

Approved for

Studied for

Mechanism of action

Approval history

  • approvedPriority reviewDec 29, 1999

Chemistry & pharmacology

Loading structure…

SMILES

CC1=C(C=C2C(=C1)C(C)(C)CCC2(C)C)C(=C)C3=CC=C(C=C3)C(O)=O
Mol. weight
348.4779 g/mol
Lipinski Ro5
1 violation(s)
Rule of 3
No
Chirality
Achiral Molecule
Inorganic
No
Polymer
No
Delivery
Oral, Topical
Availability
Prescription Only

Oral

Yes

Parenteral

No

Topical

Yes

Black box warning

Sources

Also known as

  • 3-methyl-ttneb
  • 4-(1-(3,5,5,8,8-pentamethyl-5,6,7,8-tetrahydro-2-naphthyl)ethenyl)benzoic acid
  • 4-[1-(3,5,5,8,8-pentamethyltetralin-2-yl)ethenyl]benzoic acid
  • 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
  • 4-[1-(5,6,7,8,-tetrahydro-3,5,5,8,8-pentamethyl-2-naphtalenyl)ethenyl]benzoic acid
  • bexaroten
  • bexaroten
  • bexarotene
  • bexarotene
  • bexarotene
  • bexarotene
  • bexarotene
  • bexarotene
  • bexarotene
  • bexarotene
  • bexarotene
  • bexarotene
  • bexarotene
  • bexarotène
  • bexarotène
  • bexaroteno
  • bexaroteno
  • bexarotenum
  • bexarotenum
  • elan brand of bexarotene
  • lg100069
  • lg100069
  • lg-100069
  • lg-100069
  • lg69 compound
  • lgd1069
  • lgd1069
  • lgd1069
  • lgd 1069
  • lgd 1069
  • lgd 1069
  • lgd 1069
  • lgd 1069
  • lgd 1069
  • lgd-1069
  • lgd-1069
  • lgd-1069
  • ligand brand of bexarotene
  • p-(1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)vinyl)benzoic acid
  • p-(1-(5,6,7,8-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)vinyl)benzoic acid
  • p-[1-(5,6,7,8,-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)vinyl]benzoic acid
  • p-[1-(5,6,7,8,-tetrahydro-3,5,5,8,8-pentamethyl-2-naphthyl)vinyl]benzoic acid
  • targretin
  • targretin
  • targretin
  • targretin
  • targretin
  • targretine
  • targretyn
  • targretyn
  • targretyn
  • targrexin
  • targrexin
  • targrexin

Clinical trials

NCT IDPhaseStart dateSponsor(s)
NCT05296304Phase 1Mar 16, 2022Memorial Sloan-Kettering Cancer Center
NCT05106192N/AJan 1, 2022Case Western Reserve University
NCT04664829Phase 1Oct 1, 2020Government of Singapore
NCT03323658Phase 1Jun 15, 2018National Cancer Institute (NCI), University of Texas at Houston
NCT02061878Phase 1Aug 1, 2014Compass Research, ReXceptor, Inc.
NCT01782742Phase 2Feb 1, 2013University of Rochester
NCT01578499Phase 3Aug 1, 2012Millennium Pharmaceuticals, Seattle Genetics
NCT01504490Phase 1Dec 1, 2011Daiichi Sankyo, Georgetown University
NCT01283698Phase 2Jan 1, 2011Almirall
NCT01119339Phase 2Jul 1, 2010Almirall
NCT01001143Phase 1May 1, 2010Washington University in St. Louis
NCT01134341Phase 1Mar 1, 2010Spectrum Pharmaceuticals
NCT01007448Phase 4Dec 1, 2009Bausch Health Companies
NCT00718770Early Phase 1 (Phase 1)Nov 1, 2008American Cancer Society, Inc., Eisai, University of Colorado, Denver
NCT00535574Phase 3Nov 1, 2008Ben Gurion University
NCT00845351Phase 1/Phase 2 (Phase 2)Nov 1, 2008University of Virginia
NCT00660231Phase 2Mar 1, 2008The Christie NHS Foundation Trust, University of London
NCT00615784Phase 2Jan 1, 2008University of Pennsylvania
NCT00534898Phase 3Sep 24, 2007Ben Gurion University
NCT00514293Phase 2Jan 1, 2007National Cancer Institute (NCI)
Showing 20 of 44 trials
Page 1 / 3

Organizations

Research & Development (49)

OrganizationOrg typeTrialsAs lead sponsorPhasesEarliest year
Ligand PharmaceuticalsFor profit13241998
National Cancer Institute (NCI)Government6222001
Dartmouth UniversityAcademic/Hospital4432001
University of Texas at HoustonAcademic/Hospital4232003
Ben Gurion UniversityAcademic/Hospital3312005
EisaiFor profit3222002
GenentechFor profit3032003
AlmirallFor profit2212010
Cornell UniversityAcademic/Hospital2212001
Rutgers UniversityAcademic/Hospital2012003
University of LondonAcademic/Hospital2122003
University of PennsylvaniaAcademic/Hospital2222004
American Cancer Society, Inc.Academic/Hospital1012008
AstraZenecaFor profit1012004
Bausch Health CompaniesFor profit1112009
Baylor UniversityAcademic/Hospital1112001
Boston UniversityAcademic/Hospital1112001
Bristol-Myers SquibbFor profit1012001
Case Western Reserve UniversityAcademic/Hospital1112022
Compass ResearchFor profit1012014
49 organizations
Page 1 / 3

Marketing (16)

OrganizationOrg typeRelationshipDate
Amerigen PharmaceuticalsFor profitMKTGMay 8, 2018
Amneal PharmaceuticalsFor profitSYNApr 27, 2022
Amneal PharmaceuticalsFor profitMKTGSep 4, 2018
Ani PharmaceuticalsFor profitMKTGMay 8, 2018
Ani PharmaceuticalsFor profitSYNMay 8, 2018
Ascent PharmahealthFor profitMKTGSep 6, 2024
Bausch Health CompaniesFor profitNDA2Dec 29, 1999
Bausch Health CompaniesFor profitSYNJun 28, 2000
Bionpharma IncFor profitMKTGAug 12, 2014
Bionpharma IncFor profitSYNAug 12, 2014
CiplaFor profitMKTGDec 10, 2024
HikmaFor profitMKTGJun 16, 2020
HikmaFor profitSYNJun 16, 2020
Ligand PharmaceuticalsFor profitNDADec 29, 1999
TevaFor profitMKTGJan 14, 2021
Upsher-Smith LaboratoriesFor profitMKTGJul 25, 2018