Details
Stereochemistry | ACHIRAL |
Molecular Formula | C25H26O3 |
Molecular Weight | 374.4721 |
Optical Activity | NONE |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
OC(=O)\C=C\C1=CC=C(C=C1)C2=CC=C(O)C(=C2)C34CC5CC(CC(C5)C3)C4
InChI
InChIKey=QAWBIEIZDDIEMW-FPYGCLRLSA-N
InChI=1S/C25H26O3/c26-23-7-6-21(20-4-1-16(2-5-20)3-8-24(27)28)12-22(23)25-13-17-9-18(14-25)11-19(10-17)15-25/h1-8,12,17-19,26H,9-11,13-15H2,(H,27,28)/b8-3+
Molecular Formula | C25H26O3 |
Molecular Weight | 374.4721 |
Charge | 0 |
Count |
|
Stereochemistry | ACHIRAL |
Additional Stereochemistry | No |
Defined Stereocenters | 0 / 0 |
E/Z Centers | 1 |
Optical Activity | NONE |
DescriptionSources: https://www.ncbi.nlm.nih.gov/pubmed/22365912Curator's Comment: description was created based on several sources, including
http://www.sigma-tau.it/documenti/bilancio_2008.pdf
Sources: https://www.ncbi.nlm.nih.gov/pubmed/22365912
Curator's Comment: description was created based on several sources, including
http://www.sigma-tau.it/documenti/bilancio_2008.pdf
Adarotene (ST1926) is a new pro-apoptotic and cytodifferentiating antitumour drug, belongs to the so-called class of atypical retinoids. Adarotene is active on its own or in combination with other chemotherapeutics for the treatment of a vast number of experimental tumors. It was found in preclinical investigations the potential therapeutic use it in chronic myeloid leukemia (CML), against Rhabdomyosarcoma and for treatment of Adult T-cell leukemia/lymphoma (ATL). ST1926 induced an early DNA damage response, which led to increase in apoptosis, in addition to S-phase cell cycle arrest and a reduction in protein levels of the cell cycle kinase CDK1. The presence of the phenolic hydroxyl group on adarotene structure allows a rapid O-glucuronidation as a major mechanism of elimination of the drug, favoring a fast excretion of its glucuronide metabolite in the urines.
Originator
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: GO:0006915 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26453552 |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
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ST1926, a novel and orally active retinoid-related molecule inducing apoptosis in myeloid leukemia cells: modulation of intracellular calcium homeostasis. | 2004 Jan 1 |
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Antitumor activity of the retinoid-related molecules (E)-3-(4'-hydroxy-3'-adamantylbiphenyl-4-yl)acrylic acid (ST1926) and 6-[3-(1-adamantyl)-4-hydroxyphenyl]-2-naphthalene carboxylic acid (CD437) in F9 teratocarcinoma: Role of retinoic acid receptor gamma and retinoid-independent pathways. | 2006 Sep |
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Synthesis and structure-activity relationships of new antiproliferative and proapoptotic retinoid-related biphenyl-4-yl-acrylic acids. | 2007 Jul 15 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25035162
for mice: Stock ST1926 (ADAROTENE) solution was diluted in 1:1 cremophor/ethanol solution (10 µL stock ST1926 containing 0.6 mg in 40 µL cremophor/ethanol). Each animal received by gavage 50 µL of ST1926 solutions, equivalent to 30 mg/kg body weight (average mouse weight, 20 g) as this dosage was reported to cause survival advantage in AML mice with no signs of toxicity
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/25035162
Were used 3 HTLV-1–transformed cell lines (HuT-102, MT-2, and C8166) and 3 HTLV-1–negative cell lines (CEM, Jurkat, and MOLT-4) to test for the effects of ST1926 (ADAROTENE) on cell growth and viability. ST1926 concentrations ranging from 0 05 to 5 µM as these are pharmacologically achievable were used. ST1926 treatment resulted in a time-dependent growth inhibition of all tested cell lines. In general, both HTLV-1–negative and –positive cell lines were equally sensitive to ST1926. A threshold level at 0.5 µM concentration was noted, with similar growth suppressive effects as 10-fold higher concentrations, except for CEM cells. 1 µM ST1926 caused a growth inhibition that was almost complete in primary ATL cells from the newly diagnosed acute ATL patients and >60% in the relapsed one. In contrast, resting and phytohemagglutinin-stimulated normal T cells from 3 healthy donors were resistant to ST1926 up to 10 μM.
Substance Class |
Chemical
Created
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admin
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Edited
Fri Dec 15 17:18:44 GMT 2023
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on
Fri Dec 15 17:18:44 GMT 2023
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Record UNII |
W6SU73VG8H
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Record Status |
Validated (UNII)
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Record Version |
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NCI_THESAURUS |
C804
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C573390
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W6SU73VG8H
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DTXSID9040390
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Adarotene
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496868-77-0
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C96706
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9864378
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Related Record | Type | Details | ||
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ACTIVE MOIETY |