U.S. Department of Health & Human Services Divider Arrow National Institutes of Health Divider Arrow NCATS

Details

Stereochemistry ACHIRAL
Molecular Formula C24H28O2
Molecular Weight 348.4779
Optical Activity NONE
Defined Stereocenters 0 / 0
E/Z Centers 0
Charge 0

SHOW SMILES / InChI
Structure of BEXAROTENE

SMILES

CC1=C(C=C2C(=C1)C(C)(C)CCC2(C)C)C(=C)C3=CC=C(C=C3)C(O)=O

InChI

InChIKey=NAVMQTYZDKMPEU-UHFFFAOYSA-N
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)

HIDE SMILES / InChI

Description
Curator's Comment: description was created based on several sources, including https://www.ncbi.nlm.nih.gov/pubmed/15056048

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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
TARGRETIN

Approved Use

TARGRETIN® (bexarotene) Capsules are indicated for the treatment of cutaneous manifestations of cutaneous T-cell lymphoma in patients who are refractory to at least one prior systemic therapy. TARGRETIN (bexarotene) is a retinoid indicated for the treatment of cutaneous manifestations of cutaneous T-cell lymphoma in patients who are refractory to at least one prior systemic therapy. (1)

Launch Date

1999
Cmax

Cmax

ValueDoseCo-administeredAnalytePopulation
652.44 ng/mL
300 mg/m² 1 times / day multiple, oral
dose: 300 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BEXAROTENE plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
AUC

AUC

ValueDoseCo-administeredAnalytePopulation
2133.34 ng × h/mL
300 mg/m² 1 times / day multiple, oral
dose: 300 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BEXAROTENE plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
T1/2

T1/2

ValueDoseCo-administeredAnalytePopulation
3.18 h
300 mg/m² 1 times / day multiple, oral
dose: 300 mg/m²
route of administration: Oral
experiment type: MULTIPLE
co-administered:
BEXAROTENE plasma
Homo sapiens
population: UNHEALTHY
age: UNKNOWN
sex: UNKNOWN
food status: UNKNOWN
Doses

Doses

DosePopulationAdverse events​
500 mg/m2 1 times / day multiple, oral
Studied dose
Dose: 500 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 500 mg/m2, 1 times / day
Sources:
unhealthy, 56
Health Status: unhealthy
Age Group: 56
Sex: F
Sources:
Disc. AE: Granulocytopenia...
AEs leading to
discontinuation/dose reduction:
Granulocytopenia (severe, 2.2%)
Sources:
500 mg/m2 1 times / day multiple, oral
Studied dose
Dose: 500 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 500 mg/m2, 1 times / day
Sources:
unhealthy, 56
Health Status: unhealthy
Age Group: 56
Sex: F
Sources:
Disc. AE: Erythema, Triglyceride increased...
AEs leading to
discontinuation/dose reduction:
Erythema (grade 2, 2.2%)
Triglyceride increased (grade 2, 2.2%)
Sources:
400 mg/m2 1 times / day multiple, oral
MTD
Dose: 400 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 400 mg/m2, 1 times / day
Sources:
unhealthy, 59
Health Status: unhealthy
Age Group: 59
Sex: M+F
Sources:
DLT: Pancreatitis...
Dose limiting toxicities:
Pancreatitis (grade 2, 3.57%)
Sources:
1000 mg/m2 1 times / day multiple, oral
Highest studied dose
Dose: 1000 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 1000 mg/m2, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
DLT: Transaminitis, Hyperbilirubinemia...
Dose limiting toxicities:
Transaminitis (grade 3, 16.7%)
Hyperbilirubinemia (grade 3, 16.7%)
Sources:
300 mg/m2 1 times / day multiple, oral
Recommended
Dose: 300 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg/m2, 1 times / day
Sources:
unhealthy
Disc. AE: Birth defects, Hyperlipidemia...
AEs leading to
discontinuation/dose reduction:
Birth defects
Hyperlipidemia
Pancreatitis
Hepatotoxicity
Cholestasis
Hepatic failure
Hypothyroidism
Neutropenia
Photosensitivity
Sources:
AEs

AEs

AESignificanceDosePopulation
Granulocytopenia severe, 2.2%
Disc. AE
500 mg/m2 1 times / day multiple, oral
Studied dose
Dose: 500 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 500 mg/m2, 1 times / day
Sources:
unhealthy, 56
Health Status: unhealthy
Age Group: 56
Sex: F
Sources:
Erythema grade 2, 2.2%
Disc. AE
500 mg/m2 1 times / day multiple, oral
Studied dose
Dose: 500 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 500 mg/m2, 1 times / day
Sources:
unhealthy, 56
Health Status: unhealthy
Age Group: 56
Sex: F
Sources:
Triglyceride increased grade 2, 2.2%
Disc. AE
500 mg/m2 1 times / day multiple, oral
Studied dose
Dose: 500 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 500 mg/m2, 1 times / day
Sources:
unhealthy, 56
Health Status: unhealthy
Age Group: 56
Sex: F
Sources:
Pancreatitis grade 2, 3.57%
DLT, Disc. AE
400 mg/m2 1 times / day multiple, oral
MTD
Dose: 400 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 400 mg/m2, 1 times / day
Sources:
unhealthy, 59
Health Status: unhealthy
Age Group: 59
Sex: M+F
Sources:
Hyperbilirubinemia grade 3, 16.7%
DLT
1000 mg/m2 1 times / day multiple, oral
Highest studied dose
Dose: 1000 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 1000 mg/m2, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
Transaminitis grade 3, 16.7%
DLT
1000 mg/m2 1 times / day multiple, oral
Highest studied dose
Dose: 1000 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 1000 mg/m2, 1 times / day
Sources:
unhealthy
Health Status: unhealthy
Sex: M+F
Sources:
Birth defects Disc. AE
300 mg/m2 1 times / day multiple, oral
Recommended
Dose: 300 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg/m2, 1 times / day
Sources:
unhealthy
Cholestasis Disc. AE
300 mg/m2 1 times / day multiple, oral
Recommended
Dose: 300 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg/m2, 1 times / day
Sources:
unhealthy
Hepatic failure Disc. AE
300 mg/m2 1 times / day multiple, oral
Recommended
Dose: 300 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg/m2, 1 times / day
Sources:
unhealthy
Hepatotoxicity Disc. AE
300 mg/m2 1 times / day multiple, oral
Recommended
Dose: 300 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg/m2, 1 times / day
Sources:
unhealthy
Hyperlipidemia Disc. AE
300 mg/m2 1 times / day multiple, oral
Recommended
Dose: 300 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg/m2, 1 times / day
Sources:
unhealthy
Hypothyroidism Disc. AE
300 mg/m2 1 times / day multiple, oral
Recommended
Dose: 300 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg/m2, 1 times / day
Sources:
unhealthy
Neutropenia Disc. AE
300 mg/m2 1 times / day multiple, oral
Recommended
Dose: 300 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg/m2, 1 times / day
Sources:
unhealthy
Pancreatitis Disc. AE
300 mg/m2 1 times / day multiple, oral
Recommended
Dose: 300 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg/m2, 1 times / day
Sources:
unhealthy
Photosensitivity Disc. AE
300 mg/m2 1 times / day multiple, oral
Recommended
Dose: 300 mg/m2, 1 times / day
Route: oral
Route: multiple
Dose: 300 mg/m2, 1 times / day
Sources:
unhealthy
PubMed

PubMed

TitleDatePubMed
Efficacy of Targretin on methylnitrosourea-induced mammary cancers: prevention and therapy dose-response curves and effects on proliferation and apoptosis.
2005-02
A selective retinoid X receptor agonist bexarotene (Targretin) prevents and overcomes acquired paclitaxel (Taxol) resistance in human non-small cell lung cancer.
2004-12-15
Rexinoids may be ready for prime time in prevention, but challenges remain.
2004-12-15
Synergistic effect of a retinoid X receptor-selective ligand bexarotene (LGD1069, Targretin) and paclitaxel (Taxol) in mammary carcinoma.
2004-11
Potentiation of the teratogenic effects induced by coadministration of retinoic acid or phytanic acid/phytol with synthetic retinoid receptor ligands.
2004-11
Cutaneous T-cell lymphoma treatment using bexarotene and PUVA: a case series.
2004-10
Optimizing bexarotene therapy for cutaneous T-cell lymphoma.
2004-09
Mycosis fungoides and the Sézary syndrome.
2004-09
Systemic treatment of psoriatic patients with bexarotene decreases epidermal proliferation and parameters for inflammation, and improves differentiation in lesional skin.
2004-08
A phase II multicenter clinical trial of systemic bexarotene in psoriasis.
2004-08
The novel synthetic oleanane triterpenoid CDDO (2-cyano-3, 12-dioxoolean-1, 9-dien-28-oic acid) induces apoptosis in Mycosis fungoides/Sézary syndrome cells.
2004-08
Current management strategies for cutaneous T-cell lymphoma.
2004-07-21
Comparison of selective retinoic acid receptor- and retinoic X receptor-mediated efficacy, tolerance, and survival in cutaneous t-cell lymphoma.
2004-07
Follicular mycosis fungoides: successful treatment with oral bexarotene.
2004-06-05
Bexarotene: new preparation. Cutaneous lymphoma: too many adverse effects.
2004-06
Sustained remission of treatment-resistant cutaneous T-cell lymphoma with oral bexarotene.
2004-06
How retinoids regulate breast cancer cell proliferation and apoptosis.
2004-06
Therapy for mycosis fungoides.
2004-06
Potential nonhormonal therapeutics for medical treatment of leiomyomas.
2004-05
Bexarotene: a clinical review.
2004-04
Novel treatment of chronic severe hand dermatitis with bexarotene gel.
2004-03
Management of refractory early-stage cutaneous T-cell lymphoma (mycosis fungoides) with a combination of oral bexarotene and psoralen plus ultraviolet bath therapy.
2004-03
Low-dose oral bexarotene in combination with low-dose interferon alfa in the treatment of cutaneous T-cell lymphoma: clinical synergism and possible immunologic mechanisms.
2004-03
Medication sheets for patients. Oral chemotherapy.
2004-01-07
Pharmacology of oral chemotherapy agents.
2004-01-07
A retinoid X receptor (RXR)-selective retinoid reveals that RXR-alpha is potentially a therapeutic target in breast cancer cell lines, and that it potentiates antiproliferative and apoptotic responses to peroxisome proliferator-activated receptor ligands.
2004
Combination of bexarotene and psoralen-UVA therapy in a patient with Mycosis fungoides.
2004
Topical and systemic retinoid therapy for cutaneous T-cell lymphoma.
2003-12
[Standard and experimental therapy of cutaneous T-cell lymphoma].
2003-12
Effects of imatinib mesylate (STI571, Glivec) on the pharmacokinetics of simvastatin, a cytochrome p450 3A4 substrate, in patients with chronic myeloid leukaemia.
2003-11-17
Management of the primary cutaneous lymphomas.
2003-11
Topical bexarotene therapy for patients with refractory or persistent early-stage cutaneous T-cell lymphoma: results of the phase III clinical trial.
2003-11
Experiences with monolithic LC phases in quantitative bioanalysis.
2003-10-15
Management of mycosis fungoides: Part 2. Treatment.
2003-10
Current status of cutaneous T-cell lymphoma: molecular diagnosis, pathogenesis, therapy and future directions.
2003-10
Responsiveness to the retinoic acid receptor-selective retinoid LGD1550 correlates with abrogation of transforming growth factor alpha/epidermal growth factor receptor autocrine signaling in head and neck squamous carcinoma cells.
2003-09-15
Extracorporeal photopheresis and multimodality immunomodulatory therapy in the treatment of cutaneous T-cell lymphoma.
2003-09-06
A phase 1 study of tazarotene in adults with advanced cancer.
2003-09-01
A multiparameter flow cytometric analysis of the effect of bexarotene on the epidermis of the psoriatic lesion.
2003-09
Therapy of cutaneous lymphoma--current practice and future developments.
2003-08
Bexarotene reverses alopecia in cutaneous T-cell lymphoma.
2003-07
Gateways to clinical trials.
2003-06
Psoralen plus long-wave UV-A (PUVA) and bexarotene therapy: An effective and synergistic combined adjunct to therapy for patients with advanced cutaneous T-cell lymphoma.
2003-06
Bexarotene gel: a new skin-directed treatment option for cutaneous T-cell lymphomas.
2003-04
Current data with bexarotene (Targretin) in non-small-cell lung cancer.
2003-01
Overview of cutaneous T-cell lymphoma: prognostic factors and novel therapeutic approaches.
2003
Retinoids: therapeutic applications and mechanisms of action in cutaneous T-cell lymphoma.
2003
Treatment planning in cutaneous T-cell lymphoma.
2003
Treatment of mycosis fungoides with oral bexarotene combined with PUVA.
2002-09
Placebo-controlled trial of bexarotene, a retinoid x receptor agonist, as maintenance therapy for patients treated with chemotherapy for advanced non-small-cell lung cancer.
2001-02
Patents

Patents

Sample Use Guides

The recommended initial dose of Targretin (bexarotene) capsules is 300 mg/m2 /day. Capsules should be taken as a single oral daily dose with a meal.
Route of Administration: Oral
Bexarotene (10−6 mol/L) inhibits the transactivation potential of NF-κB in an RXR-dependent manner through decreased promoter permissiveness without interfering with NF-κB nuclear translocation and binding to its responsive elements. Inhibition of transcription results from the release of 300 coactivator from NF-κB target gene promoters and subsequent histone deacetylation.
Name Type Language
BEXAROTENE
EMA EPAR   HSDB   INN   MART.   MI   ORANGE BOOK   USAN   VANDF   WHO-DD  
USAN   INN  
Official Name English
TARGRETIN
Preferred Name English
BEXAROTENE [EMA EPAR]
Common Name English
Bexarotene [WHO-DD]
Common Name English
BEXAROTENE [MART.]
Common Name English
BEXAROTENE [VANDF]
Common Name English
BEXAROTENE [ORANGE BOOK]
Common Name English
LGD-1069
Code English
LGD1069
Code English
bexarotene [INN]
Common Name English
P-(1-(5,6,7,8-TETRAHYDRO-3,5,5,8,8-PENTAMETHYL-2-NAPHTHYL)VINYL)BENZOIC ACID
Common Name English
BEXAROTENE [USAN]
Common Name English
LG-100069
Code English
LG100069
Code English
4-(1-(5,6,7,8-TETRAHYDRO-3,5,5,8,8-PENTAMETHYL-2-NAPHTHALENYL)ETHENYL)BENZOIC ACID
Systematic Name English
BEXAROTENE [HSDB]
Common Name English
BEXAROTENE [MI]
Common Name English
BEXAROTENE [JAN]
Common Name English
NSC-747528
Code English
Classification Tree Code System Code
NDF-RT N0000007700
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
LIVERTOX NBK548336
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
WHO-VATC QL01XX25
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
NDF-RT N0000007700
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
NDF-RT N0000175607
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
NDF-RT N0000007700
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
WHO-ATC L01XX25
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
NCI_THESAURUS C804
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
NDF-RT N0000007700
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
EMA ASSESSMENT REPORTS TARGRETIN (AUTHORIZED: LYMPHOMA, T-CELL, CUTANEOUS)
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
FDA ORPHAN DRUG 124699
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
NDF-RT N0000007700
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
Code System Code Type Description
CAS
153559-49-0
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY
EPA CompTox
DTXSID1040619
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY
NSC
747528
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY
MERCK INDEX
m2468
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY Merck Index
SMS_ID
100000089393
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY
DRUG BANK
DB00307
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY
INN
7782
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY
CHEBI
50859
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY
USAN
KK-21
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY
FDA UNII
A61RXM4375
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY
EVMPD
SUB00795MIG
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY
IUPHAR
2807
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY
NCI_THESAURUS
C1635
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY
WIKIPEDIA
BEXAROTENE
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY
HSDB
7453
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY
DRUG CENTRAL
361
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY
MESH
C095105
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY
PUBCHEM
82146
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY
DAILYMED
A61RXM4375
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY
RXCUI
233272
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY RxNorm
ChEMBL
CHEMBL1023
Created by admin on Mon Mar 31 18:01:50 GMT 2025 , Edited by admin on Mon Mar 31 18:01:50 GMT 2025
PRIMARY