Details
Stereochemistry | ACHIRAL |
Molecular Formula | C24H28O2 |
Molecular Weight | 348.4788 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
Cc1cc2c(cc1C(=C)c3ccc(cc3)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)
Molecular Formula | C24H28O2 |
Molecular Weight | 348.4788 |
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 |
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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 Date9.4642563E11 |
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 |
---|---|---|
Drug approval summaries: arsenic trioxide, tamoxifen citrate, anastrazole, paclitaxel, bexarotene. | 2001 |
|
Abrogation of transforming growth factor-alpha/epidermal growth factor receptor autocrine signaling by an RXR-selective retinoid (LGD1069, Targretin) in head and neck cancer cell lines. | 2001 Aug 1 |
|
Current treatment of Cutaneous T-Cell Lymphoma. | 2001 Feb |
|
Synergistic potentiation of thiazolidinedione-induced ST 13 preadipocyte differentiation by RAR synergists. | 2001 Jan 26 |
|
Bexarotene metabolism in rat, dog, and human, synthesis of oxidative metabolites, and in vitro activity at retinoid receptors. | 2001 Jul |
|
Retinoids induce fibroblast growth factor-2 production in endothelial cells via retinoic acid receptor alpha activation and stimulate angiogenesis in vitro and in vivo. | 2001 Mar 2 |
|
Bexarotene capsules and gel for previously treated patients with cutaneous T-cell lymphoma: results of the Australian patients treated on phase II trials. | 2001 May |
|
Bexarotene is effective and safe for treatment of refractory advanced-stage cutaneous T-cell lymphoma: multinational phase II-III trial results. | 2001 May 1 |
|
Multi-institutional phase I/II trial of oral bexarotene in combination with cisplatin and vinorelbine in previously untreated patients with advanced non-small-cell lung cancer. | 2001 May 15 |
|
Therapy options in cutaneous T-cell lymphoma. | 2001 Oct |
|
Mechanism of selective retinoid X receptor agonist-induced hypothyroidism in the rat. | 2002 Aug |
|
Immunomodulatory effects of RXR rexinoids: modulation of high-affinity IL-2R expression enhances susceptibility to denileukin diftitox. | 2002 Aug 15 |
|
Validated liquid chromatographic method for the determination of bexarotene in human plasma. | 2002 Aug 5 |
|
Bexarotene gel: a Food and Drug Administration-approved skin-directed therapy for early-stage cutaneous T-cell lymphoma. | 2002 Mar |
|
Response of CD30+ large cell lymphoma of skin to bexarotene. | 2002 May |
|
Induction of apoptosis by bexarotene in cutaneous T-cell lymphoma cells: relevance to mechanism of therapeutic action. | 2002 May |
|
Topical targretin and intralesional interferon alfa for cutaneous lymphoma of the scalp. | 2002 Nov |
|
Optimizing bexarotene therapy for cutaneous T-cell lymphoma. | 2002 Nov |
|
Treatment of mycosis fungoides with oral bexarotene combined with PUVA. | 2002 Sep |
|
Treatment planning in cutaneous T-cell lymphoma. | 2003 |
|
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 |
|
Extracorporeal photopheresis and multimodality immunomodulatory therapy in the treatment of cutaneous T-cell lymphoma. | 2003 Jul-Aug |
|
Gateways to clinical trials. | 2003 Jun |
|
Etiology, diagnosis, and treatment recommendations for central hypothyroidism associated with bexarotene therapy for cutaneous T-cell lymphoma. | 2003 Mar |
|
Long-term control of mycosis fungoides of the hands with topical bexarotene. | 2003 Mar |
|
Multicenter phase II study of oral bexarotene for patients with metastatic breast cancer. | 2003 Mar 15 |
|
Management of the primary cutaneous lymphomas. | 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 |
|
Pharmacology of oral chemotherapy agents. | 2003 Nov-Dec |
|
Current status of cutaneous T-cell lymphoma: molecular diagnosis, pathogenesis, therapy and future directions. | 2003 Oct |
|
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 |
|
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 |
|
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 |
|
Potential nonhormonal therapeutics for medical treatment of leiomyomas. | 2004 May |
|
Follicular mycosis fungoides: successful treatment with oral bexarotene. | 2004 May-Jun |
|
Potentiation of the teratogenic effects induced by coadministration of retinoic acid or phytanic acid/phytol with synthetic retinoid receptor ligands. | 2004 Nov |
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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admin
on
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Fri Jun 25 21:51:32 UTC 2021
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on
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Record UNII |
A61RXM4375
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Record Status |
Validated (UNII)
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Record Version |
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NDF-RT |
N0000007700
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LIVERTOX |
104
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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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FDA ORPHAN DRUG |
124699
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NDF-RT |
N0000007700
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153559-49-0
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153559-49-0
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M2468
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DB00307
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7782
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A61RXM4375
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SUB00795MIG
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2807
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C1635
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BEXAROTENE
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7453
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361
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C095105
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82146
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233272
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CHEMBL1023
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ACTIVE MOIETY |
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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