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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
Structure of ADAROTENE

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+

HIDE SMILES / InChI

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

Description
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.

Approval Year

Targets

Targets

Primary TargetPharmacologyConditionPotency
Conditions

Conditions

ConditionModalityTargetsHighest PhaseProduct
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
Primary
Unknown

Approved Use

Unknown
PubMed

PubMed

TitleDatePubMed
ST1926, a novel and orally active retinoid-related molecule inducing apoptosis in myeloid leukemia cells: modulation of intracellular calcium homeostasis.
2004 Jan 1
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
Synthesis and structure-activity relationships of new antiproliferative and proapoptotic retinoid-related biphenyl-4-yl-acrylic acids.
2007 Jul 15
Patents

Sample Use Guides

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
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
by admin
on Fri Dec 15 17:18:44 GMT 2023
Edited
by admin
on Fri Dec 15 17:18:44 GMT 2023
Record UNII
W6SU73VG8H
Record Status Validated (UNII)
Record Version
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Name Type Language
ADAROTENE
INN   WHO-DD  
INN  
Official Name English
(2E)-3-(3'-(ADAMANTAN-1-YL)-4'-HYDROXY-1,1'-BIPHENYL-4-YL)PROP-2-ENOIC ACID
Systematic Name English
adarotene [INN]
Common Name English
Adarotene [WHO-DD]
Common Name English
Classification Tree Code System Code
NCI_THESAURUS C804
Created by admin on Fri Dec 15 17:18:44 GMT 2023 , Edited by admin on Fri Dec 15 17:18:44 GMT 2023
Code System Code Type Description
MESH
C573390
Created by admin on Fri Dec 15 17:18:44 GMT 2023 , Edited by admin on Fri Dec 15 17:18:44 GMT 2023
PRIMARY
FDA UNII
W6SU73VG8H
Created by admin on Fri Dec 15 17:18:44 GMT 2023 , Edited by admin on Fri Dec 15 17:18:44 GMT 2023
PRIMARY
EPA CompTox
DTXSID9040390
Created by admin on Fri Dec 15 17:18:44 GMT 2023 , Edited by admin on Fri Dec 15 17:18:44 GMT 2023
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WIKIPEDIA
Adarotene
Created by admin on Fri Dec 15 17:18:44 GMT 2023 , Edited by admin on Fri Dec 15 17:18:44 GMT 2023
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SMS_ID
100000175605
Created by admin on Fri Dec 15 17:18:44 GMT 2023 , Edited by admin on Fri Dec 15 17:18:44 GMT 2023
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INN
9058
Created by admin on Fri Dec 15 17:18:44 GMT 2023 , Edited by admin on Fri Dec 15 17:18:44 GMT 2023
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CAS
496868-77-0
Created by admin on Fri Dec 15 17:18:44 GMT 2023 , Edited by admin on Fri Dec 15 17:18:44 GMT 2023
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NCI_THESAURUS
C96706
Created by admin on Fri Dec 15 17:18:44 GMT 2023 , Edited by admin on Fri Dec 15 17:18:44 GMT 2023
PRIMARY
PUBCHEM
9864378
Created by admin on Fri Dec 15 17:18:44 GMT 2023 , Edited by admin on Fri Dec 15 17:18:44 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY