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 |
---|---|---|
Therapeutic advances in biological response modifiers in the treatment of cutaneous T-cell lymphoma. | 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 |
|
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 |
|
Bexarotene metabolism in rat, dog, and human, synthesis of oxidative metabolites, and in vitro activity at retinoid receptors. | 2001 Jul |
|
Therapy options in cutaneous T-cell lymphoma. | 2001 Oct |
|
Cutaneous T-cell lymphoma. New immunomodulators. | 2001 Oct |
|
Where to next with retinoids for cancer therapy? | 2001 Oct |
|
Oral bexarotene in the treatment of cutaneous T-cell lymphoma. | 2001 Sep |
|
A review of cancer chemopreventive agents. | 2001 Sep |
|
Retinoids--which dermatological indications will benefit in the near future? | 2001 Sep-Oct |
|
Retinoid signalling and gene expression in neuroblastoma cells: RXR agonist and antagonist effects on CRABP-II and RARbeta expression. | 2002 |
|
Risk management strategies in the Physicians' Desk Reference product labels for pregnancy category X drugs. | 2002 |
|
Treatment of cutaneous T cell lymphoma: 2001. | 2002 |
|
Treatment of cutaneous T cell lymphoma: current status and future directions. | 2002 |
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Mechanism of selective retinoid X receptor agonist-induced hypothyroidism in the rat. | 2002 Aug |
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Immunomodulatory effects of RXR rexinoids: modulation of high-affinity IL-2R expression enhances susceptibility to denileukin diftitox. | 2002 Aug 15 |
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Validated liquid chromatographic method for the determination of bexarotene in human plasma. | 2002 Aug 5 |
|
Novel multimodality biologic response modifier therapy, including bexarotene and long-wave ultraviolet A for a patient with refractory stage IVa cutaneous T-cell lymphoma. | 2002 Dec |
|
A pharmacophore for human pregnane X receptor ligands. | 2002 Jan |
|
Bexarotene gel: a Food and Drug Administration-approved skin-directed therapy for early-stage cutaneous T-cell lymphoma. | 2002 Mar |
|
Induction of apoptosis by bexarotene in cutaneous T-cell lymphoma cells: relevance to mechanism of therapeutic action. | 2002 May |
|
T0070907, a selective ligand for peroxisome proliferator-activated receptor gamma, functions as an antagonist of biochemical and cellular activities. | 2002 May 31 |
|
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 |
|
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 |
|
[Standard and experimental therapy of cutaneous T-cell lymphoma]. | 2003 Dec |
|
Effects of oral bexarotene (targretin) on the minimal erythema dose for broadspectrum UVB light. | 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 |
|
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 |
|
Topical bexarotene therapy for patients with refractory or persistent early-stage cutaneous T-cell lymphoma: results of the phase III clinical trial. | 2003 Nov |
|
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 |
|
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 |
|
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 |
|
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 |
|
How retinoids regulate breast cancer cell proliferation and apoptosis. | 2004 Jun |
|
Therapy for mycosis fungoides. | 2004 Jun |
|
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 |
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
Wed Jul 05 23:04:12 UTC 2023
by
admin
on
Wed Jul 05 23:04:12 UTC 2023
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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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NDF-RT |
N0000007700
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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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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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Tmax | PHARMACOKINETIC |
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Biological Half-life | PHARMACOKINETIC |
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