Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C24H32O2 |
Molecular Weight | 352.5097 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 2 / 2 |
E/Z Centers | 2 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CC(\C=C\[C@@H]1C[C@]1(C)C2=CC3=C(C=C2)C(C)(C)CCC3(C)C)=C/C(O)=O
InChI
InChIKey=BOOOLEGQBVUTKC-NVQSDHBMSA-N
InChI=1S/C24H32O2/c1-16(13-21(25)26)7-8-18-15-24(18,6)17-9-10-19-20(14-17)23(4,5)12-11-22(19,2)3/h7-10,13-14,18H,11-12,15H2,1-6H3,(H,25,26)/b8-7+,16-13+/t18-,24-/m1/s1
VTP-194204 (NRX 194204, IRX4204) is a second-generation retinoid X receptor (RXR) agonist that has no cross-reactivity with retinoic acid receptors, farnesoid X receptor, liver X receptors or peroxisome proliferator-activated receptor PPARγ. Rexinoid NRX 194204 selectively binds to and activates RXRs. Because RXRs can form heterodimers with several nuclear receptors (NRs), RXR activation by this agent may result in a broad range of gene expression depending on the effector DNA response elements activated. Rexinoid NRX 194204 may inhibit the tumour-necrosis factor (TNF)-mediated release of nitric oxide (NO) and interleukin 6 (IL6) and may inhibit tumour cell proliferation. This agent appears to be less toxic than RAR-selective ligands. VTP-194204 (IRX-4204) is in phase II clinical trials by Io Therapeutics for the treatment of prostate cancer. It is also in preclinical trials for the treatment of Alzheimer's disease, autoimmune diseases and multiple sclerosis.
CNS Activity
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26862735
Curator's Comment: Brain bioavailability studies demonstrate that VTP-194204 (IRX4204) can cross the blood brain barrier and reach the brain at nM concentration. IRX4204 represents a novel, potent and selective pharmacological means to activate cellular RXR-Nurr1 signaling and promote SN DA neuron survival in PD prevention and/or treatment.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
---|---|---|---|
Target ID: CHEMBL2061 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11428923 |
0.2 nM [EC50] | ||
Target ID: CHEMBL1870 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11428923 |
0.8 nM [EC50] | ||
Target ID: CHEMBL2004 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11428923 |
0.08 nM [EC50] |
Conditions
Condition | Modality | Targets | Highest Phase | Product |
---|---|---|---|---|
Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
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Primary | Unknown Approved UseUnknown |
PubMed
Title | Date | PubMed |
---|---|---|
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 |
Patents
Sample Use Guides
In Vivo Use Guide
Sources: https://clinicaltrials.gov/ct2/show/NCT02438215
VTP-194204 (IRX4204) 20 mg QD for Days 1-30
Route of Administration:
Oral
In Vitro Use Guide
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26862735
VTP-194204 (IRX4204) can partially activate RXRs at a concentration of 0.1 nM and fully activates all three RXRs (α, β and γ) at a concentration of 1 nM
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220619-73-8
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877M97Z38Y
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DB11806
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C74076
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9863341
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260262-39-3
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NON-SPECIFIC STEREOCHEMISTRY |
ACTIVE MOIETY