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)
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 |
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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 |
---|---|---|
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 |
|
Cytokines and other biologic agents as immunotherapeutics for cutaneous T-cell lymphoma. | 2002 |
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Synthesis of new Targretin analogues that induce apoptosis in leukemia HL-60 cells. | 2002 Dec 16 |
|
Past, present, and future of gemcitabine and carboplatin regimens in advanced non-small cell lung cancer. | 2002 Nov |
|
Optimizing bexarotene therapy for cutaneous T-cell lymphoma. | 2002 Nov |
|
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 |
|
Mycosis fungoides with follicular mucinosis displaying aggressive tumor-stage transformation : successful treatment using radiation therapy plus oral bexarotene combination therapy. | 2003 |
|
Bexarotene is a new treatment option for lymphomatoid papulosis. | 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 |
|
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 |
|
Multicenter phase II study of oral bexarotene for patients with metastatic breast cancer. | 2003 Mar 15 |
|
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 |
|
Combination of bexarotene and psoralen-UVA therapy in a patient with Mycosis fungoides. | 2004 |
|
Bexarotene: a clinical review. | 2004 Apr |
|
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 |
|
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
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
by
admin
on
Edited
Fri Dec 16 17:30:36 UTC 2022
by
admin
on
Fri Dec 16 17:30:36 UTC 2022
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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 |
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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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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N0000007700
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DTXSID1040619
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747528
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M2468
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DB00307
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KK-21
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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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A61RXM4375
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233272
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CHEMBL1023
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ACTIVE MOIETY |
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Tmax | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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