Name | Tamibarotene |
Synonyms | AM80 Amnolake NSC 608000 Tamibarotene Retinoid AM 80 Am 80 (pharmaceutical) 4-[(5,5,8,8-Tetramethyl-6,7-dihydronaphthalen-2-yl)carbamoyl]benzoic acid 4-[(5,5,8,8-tetramethyl-5,6,7,8-tetrahydronaphthalen-2-yl)carbamoyl]benzoic acid 4-[[(5,6,7,8-Tetrahydro-5,5,8,8-tetramethyl-2-naphthalenyl)amino]carbonyl]benzoic Acid |
CAS | 94497-51-5 |
EINECS | 1806241-263-5 |
InChI | InChI=1/C22H25NO3/c1-21(2)11-12-22(3,4)18-13-16(9-10-17(18)21)23-19(24)14-5-7-15(8-6-14)20(25)26/h5-10,13H,11-12H2,1-4H3,(H,23,24)(H,25,26) |
Molecular Formula | C22H25NO3 |
Molar Mass | 351.44 |
Density | 1.154±0.06 g/cm3(Predicted) |
Melting Point | 231-232°C |
Boling Point | 449.6±45.0 °C(Predicted) |
Flash Point | 225.7°C |
Solubility | Soluble in 1.1eq. NaOH (100 mM), DMSO (50 mM), methanol, and water (slightly). |
Vapor Presure | 7.2E-09mmHg at 25°C |
Appearance | powder |
Color | white to off-white |
pKa | 3.83±0.10(Predicted) |
Storage Condition | room temp |
Refractive Index | 1.593 |
MDL | MFCD00866188 |
Use | Tamibarotene are specific RAR-alpha/beta agonists for the treatment of all-trans retinoic acid-tolerant acute leukemia. |
In vitro study | Tamibarotene slightly inhibited the growth of myeloma cells and endothelial cells and significantly inhibited the growth of endothelial cells stimulated by vascular endothelial growth factor. Tamibarotene had a small growth inhibition on bone marrow stromal cells (BMSCs) but significantly inhibited endothelial cell migration by co-cultured myeloma cells. Tamibarotene inhibits VEGF-induced phosphorylation of vascular endothelial growth factor receptors. In the mouse cornea, VEGF significantly inhibited the formation of VEGF-induced in vivo outer tube-like structures and neovascularization. The ability of Tamibarotene to induce HL-60 cell adhesion to endothelial cell was 38% lower than that of all-trans retinoic acid (ATRA), and the ability of Tamibarotene to induce NB4 cell adhesion to endothelial cell was comparable to that of ATRA, it induces transcription of the CD38 gene in HL-60 cells, early gene transcription by DR-RARE containing intron 1, and late gene expression by RARE lacking the 5 '-flanking region. Tamibarotene induces early gene expression in HL-60 cells, resulting in lower CD38 induction than ATRA. Tamibarotene had negligible growth inhibition on peripheral blood mononuclear cells but strong growth inhibition on markers HTLV-I infected T-cell lines and ATL cells. In HTLV-I infected T cell lines, Tamibarotene caused the cells to stay in the G1 phase of the cell cycle and induced apoptosis. Tamibarotene also inhibits phosphorylation of IkappaBalpha and NF-κB-DNA binding, and reduces the expression of transitional and apoptotic proteins involved in the G1/S phase of the cell cycle. Tamibarotene also inhibits the expression of JunD, thereby inhibiting AP-1 DNA binding. |
In vivo study | Tamibarotene treatment significantly reduced insoluble Aβ levels in the brain of mice, particularly Aβ(42), while it had no significant effect on soluble Aβ levels. |
WGK Germany | 3 |
RTECS | DH6940000 |
1mg | 5mg | 10mg | |
---|---|---|---|
1 mM | 2.845 ml | 14.227 ml | 28.454 ml |
5 mM | 0.569 ml | 2.845 ml | 5.691 ml |
10 mM | 0.285 ml | 1.423 ml | 2.845 ml |
5 mM | 0.057 ml | 0.285 ml | 0.569 ml |