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
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)
| Molecular Formula | C24H28O2 |
| Molecular Weight | 348.4779 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
DescriptionCurator's Comment: description was created based on several sources, including
https://www.ncbi.nlm.nih.gov/pubmed/15056048
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.
CNS Activity
Originator
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2363070 Sources: https://www.ncbi.nlm.nih.gov/pubmed/16495926 |
Conditions
| Condition | Modality | Targets | Highest Phase | Product |
|---|---|---|---|---|
| Primary | TARGRETIN Approved UseTARGRETIN® (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 Date1999 |
Cmax
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Value | Dose | Co-administered | Analyte | Population |
|---|---|---|---|---|
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
| Dose | Population | Adverse 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 |
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 |
Disc. AE: Erythema, Triglyceride increased... AEs leading to discontinuation/dose reduction: Erythema (grade 2, 2.2%) Sources: Triglyceride increased (grade 2, 2.2%) |
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 |
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 |
DLT: Transaminitis, Hyperbilirubinemia... Dose limiting toxicities: Transaminitis (grade 3, 16.7%) Sources: Hyperbilirubinemia (grade 3, 16.7%) |
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 Health Status: unhealthy Sources: |
Disc. AE: Birth defects, Hyperlipidemia... AEs leading to discontinuation/dose reduction: Birth defects Sources: Hyperlipidemia Pancreatitis Hepatotoxicity Cholestasis Hepatic failure Hypothyroidism Neutropenia Photosensitivity |
AEs
| AE | Significance | Dose | Population |
|---|---|---|---|
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 |
| 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 Health Status: unhealthy Sources: |
| 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 Health Status: unhealthy Sources: |
| 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 Health Status: unhealthy Sources: |
| 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 Health Status: unhealthy Sources: |
| 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 Health Status: unhealthy Sources: |
| 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 Health Status: unhealthy Sources: |
| 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 Health Status: unhealthy Sources: |
| 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 Health Status: unhealthy Sources: |
| 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 Health Status: unhealthy Sources: |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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
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
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22142826
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.
| Substance Class |
Chemical
Created
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on
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Mon Mar 31 18:01:50 GMT 2025
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on
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| Record UNII |
A61RXM4375
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| Record Status |
Validated (UNII)
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NDF-RT |
N0000007700
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LIVERTOX |
NBK548336
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WHO-VATC |
QL01XX25
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NDF-RT |
N0000007700
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NDF-RT |
N0000175607
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NDF-RT |
N0000007700
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WHO-ATC |
L01XX25
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NCI_THESAURUS |
C804
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NDF-RT |
N0000007700
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EMA ASSESSMENT REPORTS |
TARGRETIN (AUTHORIZED: LYMPHOMA, T-CELL, CUTANEOUS)
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124699
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N0000007700
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153559-49-0
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DTXSID1040619
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747528
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m2468
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100000089393
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DB00307
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KK-21
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A61RXM4375
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C1635
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BEXAROTENE
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361
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C095105
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82146
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A61RXM4375
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233272
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CHEMBL1023
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TARGET -> AGONIST |
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TARGET -> AGONIST |
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TARGET -> AGONIST |
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METABOLITE -> PARENT |
MAJOR
PLASMA
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
PLASMA
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METABOLITE -> PARENT |
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ACTIVE MOIETY |
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| Name | Property Type | Amount | Referenced Substance | Defining | Parameters | References |
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| Tmax | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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| Biological Half-life | PHARMACOKINETIC |
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ORAL ADMINISTRATION |
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