Details
| Stereochemistry | ACHIRAL |
| Molecular Formula | C28H24O2 |
| Molecular Weight | 392.489 |
| Optical Activity | NONE |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Charge | 0 |
SHOW SMILES / InChI
SMILES
CC1=CC=C(C=C1)C2=CCC(C)(C)C3=C2C=C(C=C3)C#CC4=CC=C(C=C4)C(O)=O
InChI
InChIKey=NCEQLLNVRRTCKJ-UHFFFAOYSA-N
InChI=1S/C28H24O2/c1-19-4-11-22(12-5-19)24-16-17-28(2,3)26-15-10-21(18-25(24)26)7-6-20-8-13-23(14-9-20)27(29)30/h4-5,8-16,18H,17H2,1-3H3,(H,29,30)
| Molecular Formula | C28H24O2 |
| Molecular Weight | 392.489 |
| Charge | 0 |
| Count |
|
| Stereochemistry | ACHIRAL |
| Additional Stereochemistry | No |
| Defined Stereocenters | 0 / 0 |
| E/Z Centers | 0 |
| Optical Activity | NONE |
The synthetic retinoid AGN-193109 is a potent pan retinoic acid receptor (RAR) antagonist. It has been shown to block the antiproliferative effect of retinoids in cultured human cervical cancer cells. AGN-193109 is a potent RAR antagonist and a potential antidote of retinoid intoxication in vivo. In addition to potential clinical applications in the prevention and treatment of retinoid toxicity, AGN-193109 should provide a powerful experimental tool for the elucidation of retinoid biology.
Originator
Approval Year
PubMed
| Title | Date | PubMed |
|---|---|---|
| N-(4-hydroxyphenyl)retinamide induces apoptosis in human retinal pigment epithelial cells: retinoic acid receptors regulate apoptosis, reactive oxygen species generation, and the expression of heme oxygenase-1 and Gadd153. | 2006-12 |
|
| PPARgamma controls CD1d expression by turning on retinoic acid synthesis in developing human dendritic cells. | 2006-10-02 |
|
| 13-cis Retinoic acid induces apoptosis and cell cycle arrest in human SEB-1 sebocytes. | 2006-10 |
|
| Kinase-dependent, retinoic acid receptor-independent up-regulation of cyclooxygenase-2 by all-trans retinoic acid in human mesangial cells. | 2006-09 |
|
| 9-cis-retinoic acid up-regulates expression of transcriptional coregulator PELP1, a novel coactivator of the retinoid X receptor alpha pathway. | 2006-06-02 |
|
| Retinoic acid is required early during adult neurogenesis in the dentate gyrus. | 2006-03-07 |
|
| Retinoic acid receptors and tissue-transglutaminase mediate short-term effect of retinoic acid on migration and invasion of neuroblastoma SH-SY5Y cells. | 2006-01-12 |
|
| Activation of retinoic acid receptor-dependent transcription by organochlorine pesticides. | 2005-01-01 |
|
| PPARbeta regulates vitamin A metabolism-related gene expression in hepatic stellate cells undergoing activation. | 2003-02 |
|
| Retinoid X receptor agonist elevation of serum triglycerides in rats by potentiation of retinoic acid receptor agonist induction or by action as single agents. | 2001-12-01 |
|
| Recruitment of nuclear receptor corepressor and coactivator to the retinoic acid receptor by retinoid ligands. Influence of DNA-heterodimer interactions. | 2000-06-23 |
|
| Therapeutic applications for ligands of retinoid receptors. | 2000-01 |
|
| Identification and functional separation of retinoic acid receptor neutral antagonists and inverse agonists. | 1996-09-13 |
Patents
Sample Use Guides
Mice: treatment of pregnant mice with a single oral 1 mg/kg dose of AGN-193109 on day 8 postcoitum results in severe craniofacial (median cleft face or frontonasal deficiency) and eye malformations in virtually all exposed fetuses.
Route of Administration:
Oral
In ECE16-1 cells addition of increasing concentrations of
AGN-193109 in the presence of 10 nM TTNPB prevents the
TTNPB-dependent suppression of proliferation.
The growth suppression is half-reversed by 10 nM and completely
reversed by 100 nM AGN-193109. Although it can antagonize
the effects of TTNPB, 1 uM AGN-193109 given alone has
no effect on cell proliferation.
| Substance Class |
Chemical
Created
by
admin
on
Edited
Mon Mar 31 22:41:25 GMT 2025
by
admin
on
Mon Mar 31 22:41:25 GMT 2025
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| Record UNII |
ZC6062V1O9
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| Record Status |
Validated (UNII)
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| Record Version |
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ZC6062V1O9
Created by
admin on Mon Mar 31 22:41:25 GMT 2025 , Edited by admin on Mon Mar 31 22:41:25 GMT 2025
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