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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
Structure of VTP-194204

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

HIDE SMILES / InChI

Molecular Formula C24H32O2
Molecular Weight 352.5097
Charge 0
Count
Stereochemistry ABSOLUTE
Additional Stereochemistry No
Defined Stereocenters 2 / 2
E/Z Centers 2
Optical Activity UNSPECIFIED

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

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

Targets

Primary TargetPharmacologyConditionPotency
0.2 nM [EC50]
0.8 nM [EC50]
0.08 nM [EC50]
Conditions
PubMed

PubMed

TitleDatePubMed
Retinoid x receptor agonists increase bcl2a1 expression and decrease apoptosis of naive T lymphocytes.
2005 Dec 15
Combination therapy of insulin-like growth factor binding protein-3 and retinoid X receptor ligands synergize on prostate cancer cell apoptosis in vitro and in vivo.
2005 Jul 1
Retinoid-mediated stimulation of steroid sulfatase activity in myeloid leukemic cell lines requires RARalpha and RXR and involves the phosphoinositide 3-kinase and ERK-MAP kinase pathways.
2006 Feb 1
Patents

Sample Use Guides

VTP-194204 (IRX4204) 20 mg QD for Days 1-30
Route of Administration: Oral
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
Substance Class Chemical
Created
by admin
on Thu Jul 06 04:20:42 UTC 2023
Edited
by admin
on Thu Jul 06 04:20:42 UTC 2023
Record UNII
877M97Z38Y
Record Status Validated (UNII)
Record Version
  • Download
Name Type Language
VTP-194204
Code English
AGN194204
Code English
NRX-194204
Code English
(+)-VTP-194204
Common Name English
2,4-PENTADIENOIC ACID, 3-METHYL-5-((1S,2S)-2-METHYL-2-(5,6,7,8-TETRAHYDRO-3,5,5,8,8-PENTAMETHYL-2-NAPHTHALENYL)CYCLOPROPYL)-
Common Name English
2,4-PENTADIENOIC ACID, 3-METHYL-5-((1S,2S)-2-METHYL-2-(5,6,7,8-TETRAHYDRO-5,5,8,8-TETRAMETHYL-2-NAPHTHALENYL)CYCLOPROPYL)-, (2E,4E)-
Systematic Name English
NRX194204
Code English
AGN-194204
Code English
Code System Code Type Description
CAS
220619-73-8
Created by admin on Thu Jul 06 04:20:42 UTC 2023 , Edited by admin on Thu Jul 06 04:20:42 UTC 2023
PRIMARY
FDA UNII
877M97Z38Y
Created by admin on Thu Jul 06 04:20:42 UTC 2023 , Edited by admin on Thu Jul 06 04:20:42 UTC 2023
PRIMARY
DRUG BANK
DB11806
Created by admin on Thu Jul 06 04:20:42 UTC 2023 , Edited by admin on Thu Jul 06 04:20:42 UTC 2023
PRIMARY
NCI_THESAURUS
C74076
Created by admin on Thu Jul 06 04:20:42 UTC 2023 , Edited by admin on Thu Jul 06 04:20:42 UTC 2023
PRIMARY NCIT
PUBCHEM
9863341
Created by admin on Thu Jul 06 04:20:42 UTC 2023 , Edited by admin on Thu Jul 06 04:20:42 UTC 2023
PRIMARY
CAS
260262-39-3
Created by admin on Thu Jul 06 04:20:42 UTC 2023 , Edited by admin on Thu Jul 06 04:20:42 UTC 2023
NON-SPECIFIC STEREOCHEMISTRY
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TARGET -> AGONIST
TARGET -> AGONIST
TARGET -> AGONIST
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ACTIVE MOIETY