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=CC2=C(C=C1C(=C)C3=CC=C(C=C3)C(O)=O)C(C)(C)CCC2(C)C
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)
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
Approval Year
Targets
| Primary Target | Pharmacology | Condition | Potency |
|---|---|---|---|
Target ID: CHEMBL2363070 |
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: Page: p.1003 |
unhealthy, 56 n = 45 Health Status: unhealthy Condition: Breast Cancer Age Group: 56 Sex: F Population Size: 45 Sources: Page: p.1003 |
Disc. AE: Granulocytopenia... AEs leading to discontinuation/dose reduction: Granulocytopenia (severe, 2.2%) Sources: Page: p.1003 |
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: Page: p.1004 |
unhealthy, 56 n = 45 Health Status: unhealthy Condition: Breast Cancer Age Group: 56 Sex: F Population Size: 45 Sources: Page: p.1004 |
Disc. AE: Erythema, Triglyceride increased... AEs leading to discontinuation/dose reduction: Erythema (grade 2, 2.2%) Sources: Page: p.1004Triglyceride 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 Co-administed with:: Vinorelbine, i.v(15-30 mg/m2; once in 2 weeks) Sources: Page: p.2629, 2632cisplatin, i.v(100 mg/m2; once in 6 weeks) |
unhealthy, 59 n = 28 Health Status: unhealthy Condition: Non-small-cell lung cancer Age Group: 59 Sex: M+F Population Size: 28 Sources: Page: p.2629, 2632 |
DLT: Pancreatitis... Dose limiting toxicities: Pancreatitis (grade 2, 3.57%) Sources: Page: p.2629, 2632 |
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: Page: p.1660 |
unhealthy n = 6 Health Status: unhealthy Condition: Cancer Sex: M+F Population Size: 6 Sources: Page: p.1660 |
DLT: Transaminitis, Hyperbilirubinemia... Dose limiting toxicities: Transaminitis (grade 3, 16.7%) Sources: Page: p.1660Hyperbilirubinemia (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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Cutaneous T-cell lymphoma Sources: Page: p.1 |
Disc. AE: Birth defects, Hyperlipidemia... AEs leading to discontinuation/dose reduction: Birth defects Sources: Page: p.1Hyperlipidemia 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: Page: p.1003 |
unhealthy, 56 n = 45 Health Status: unhealthy Condition: Breast Cancer Age Group: 56 Sex: F Population Size: 45 Sources: Page: p.1003 |
| 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: Page: p.1004 |
unhealthy, 56 n = 45 Health Status: unhealthy Condition: Breast Cancer Age Group: 56 Sex: F Population Size: 45 Sources: Page: p.1004 |
| 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: Page: p.1004 |
unhealthy, 56 n = 45 Health Status: unhealthy Condition: Breast Cancer Age Group: 56 Sex: F Population Size: 45 Sources: Page: p.1004 |
| 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 Co-administed with:: Vinorelbine, i.v(15-30 mg/m2; once in 2 weeks) Sources: Page: p.2629, 2632cisplatin, i.v(100 mg/m2; once in 6 weeks) |
unhealthy, 59 n = 28 Health Status: unhealthy Condition: Non-small-cell lung cancer Age Group: 59 Sex: M+F Population Size: 28 Sources: Page: p.2629, 2632 |
| 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: Page: p.1660 |
unhealthy n = 6 Health Status: unhealthy Condition: Cancer Sex: M+F Population Size: 6 Sources: Page: p.1660 |
| 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: Page: p.1660 |
unhealthy n = 6 Health Status: unhealthy Condition: Cancer Sex: M+F Population Size: 6 Sources: Page: p.1660 |
| 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Cutaneous T-cell lymphoma Sources: Page: p.1 |
| 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Cutaneous T-cell lymphoma Sources: Page: p.1 |
| 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Cutaneous T-cell lymphoma Sources: Page: p.1 |
| 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Cutaneous T-cell lymphoma Sources: Page: p.1 |
| 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Cutaneous T-cell lymphoma Sources: Page: p.1 |
| 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Cutaneous T-cell lymphoma Sources: Page: p.1 |
| 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Cutaneous T-cell lymphoma Sources: Page: p.1 |
| 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Cutaneous T-cell lymphoma Sources: Page: p.1 |
| 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: Page: p.1 |
unhealthy Health Status: unhealthy Condition: Cutaneous T-cell lymphoma Sources: Page: p.1 |
PubMed
| Title | Date | PubMed |
|---|---|---|
| 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 Feb |
|
| Treatment of mycosis fungoides with oral bexarotene combined with PUVA. | 2002 Sep |
|
| 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 |
|
| Bexarotene gel: a new skin-directed treatment option for cutaneous T-cell lymphomas. | 2003 Apr |
|
| Therapy of cutaneous lymphoma--current practice and future developments. | 2003 Aug |
|
| Topical and systemic retinoid therapy for cutaneous T-cell lymphoma. | 2003 Dec |
|
| [Standard and experimental therapy of cutaneous T-cell lymphoma]. | 2003 Dec |
|
| Current data with bexarotene (Targretin) in non-small-cell lung cancer. | 2003 Jan |
|
| Bexarotene reverses alopecia in cutaneous T-cell lymphoma. | 2003 Jul |
|
| Extracorporeal photopheresis and multimodality immunomodulatory therapy in the treatment of cutaneous T-cell lymphoma. | 2003 Jul-Aug |
|
| Gateways to clinical trials. | 2003 Jun |
|
| 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 Jun |
|
| Management of the primary cutaneous lymphomas. | 2003 Nov |
|
| Topical bexarotene therapy for patients with refractory or persistent early-stage cutaneous T-cell lymphoma: results of the phase III clinical trial. | 2003 Nov |
|
| Effects of imatinib mesylate (STI571, Glivec) on the pharmacokinetics of simvastatin, a cytochrome p450 3A4 substrate, in patients with chronic myeloid leukaemia. | 2003 Nov 17 |
|
| Medication sheets for patients. Oral chemotherapy. | 2003 Nov-Dec |
|
| Pharmacology of oral chemotherapy agents. | 2003 Nov-Dec |
|
| Management of mycosis fungoides: Part 2. Treatment. | 2003 Oct |
|
| Current status of cutaneous T-cell lymphoma: molecular diagnosis, pathogenesis, therapy and future directions. | 2003 Oct |
|
| Experiences with monolithic LC phases in quantitative bioanalysis. | 2003 Oct 15 |
|
| A multiparameter flow cytometric analysis of the effect of bexarotene on the epidermis of the psoriatic lesion. | 2003 Sep |
|
| A phase 1 study of tazarotene in adults with advanced cancer. | 2003 Sep 1 |
|
| 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 Sep 15 |
|
| 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 |
|
| Bexarotene: a clinical review. | 2004 Apr |
|
| Systemic treatment of psoriatic patients with bexarotene decreases epidermal proliferation and parameters for inflammation, and improves differentiation in lesional skin. | 2004 Aug |
|
| A phase II multicenter clinical trial of systemic bexarotene in psoriasis. | 2004 Aug |
|
| 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 Aug |
|
| A selective retinoid X receptor agonist bexarotene (Targretin) prevents and overcomes acquired paclitaxel (Taxol) resistance in human non-small cell lung cancer. | 2004 Dec 15 |
|
| Rexinoids may be ready for prime time in prevention, but challenges remain. | 2004 Dec 15 |
|
| Comparison of selective retinoic acid receptor- and retinoic X receptor-mediated efficacy, tolerance, and survival in cutaneous t-cell lymphoma. | 2004 Jul |
|
| Bexarotene: new preparation. Cutaneous lymphoma: too many adverse effects. | 2004 Jun |
|
| Sustained remission of treatment-resistant cutaneous T-cell lymphoma with oral bexarotene. | 2004 Jun |
|
| How retinoids regulate breast cancer cell proliferation and apoptosis. | 2004 Jun |
|
| Therapy for mycosis fungoides. | 2004 Jun |
|
| Novel treatment of chronic severe hand dermatitis with bexarotene gel. | 2004 Mar |
|
| Management of refractory early-stage cutaneous T-cell lymphoma (mycosis fungoides) with a combination of oral bexarotene and psoralen plus ultraviolet bath therapy. | 2004 Mar |
|
| 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 Mar |
|
| Potential nonhormonal therapeutics for medical treatment of leiomyomas. | 2004 May |
|
| Current management strategies for cutaneous T-cell lymphoma. | 2004 May-Jun |
|
| Follicular mycosis fungoides: successful treatment with oral bexarotene. | 2004 May-Jun |
|
| Synergistic effect of a retinoid X receptor-selective ligand bexarotene (LGD1069, Targretin) and paclitaxel (Taxol) in mammary carcinoma. | 2004 Nov |
|
| Potentiation of the teratogenic effects induced by coadministration of retinoic acid or phytanic acid/phytol with synthetic retinoid receptor ligands. | 2004 Nov |
|
| Cutaneous T-cell lymphoma treatment using bexarotene and PUVA: a case series. | 2004 Oct |
|
| Optimizing bexarotene therapy for cutaneous T-cell lymphoma. | 2004 Sep |
|
| Mycosis fungoides and the Sézary syndrome. | 2004 Sep |
|
| Efficacy of Targretin on methylnitrosourea-induced mammary cancers: prevention and therapy dose-response curves and effects on proliferation and apoptosis. | 2005 Feb |
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.
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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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N0000175607
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N0000007700
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L01XX25
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NCI_THESAURUS |
C804
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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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BEXAROTENE
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CHEMBL1023
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ACTIVE MOIETY
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
METABOLITE (PARENT)
