VTP-194204

Investigational

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 Search

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/26862735 | https://www.ncbi.nlm.nih.gov/pubmed/17947492

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

Originator

Approval Year

Targets

Primary Target	Pharmacology	Potency
Retinoid X receptor alpha 11 Target ID: CHEMBL2061 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11428923	Agonist 2678	0.2 nM [EC50]
Retinoid X receptor beta 3 Target ID: CHEMBL1870 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11428923	Agonist 2678	0.8 nM [EC50]
Retinoid X receptor gamma 8 Target ID: CHEMBL2004 Sources: https://www.ncbi.nlm.nih.gov/pubmed/11428923	Agonist 2678	0.08 nM [EC50]

Conditions

Condition	Modality	Highest Phase	Product
Parkinson's disease 226 Sources: https://www.ncbi.nlm.nih.gov/pubmed/26862735	Primary	Phase I 428	Unknown Approved Use Unknown
Non-small cell lung cancer 206 Sources: http://adisinsight.springer.com/drugs/800027968 https://clinicaltrials.gov/ct2/show/NCT02991651	Primary	Phase I 428	Unknown Approved Use Unknown
Prostate cancer 178 Sources: http://adisinsight.springer.com/drugs/800027968 https://clinicaltrials.gov/ct2/show/NCT01540071	Primary	Phase II 1132	Unknown Approved Use Unknown

Sourcing

Vendor/Aggregator	ID	URL
Axon MedChem	2408	https://www.axonmedchem.com/product/2408
Chem Scene	CS-0007745	http://www.chemscene.com/goproductList/searchProductList?productObj=CS-0007745
Lan Pharmatech	LQT-B42940
MedChem Express	HY-13717	https://www.medchemexpress.com/search.html?q=HY-13717&ft=&fa=&fp=
MolPort	MolPort-042-665-869	https://www.molport.com/shop/molecule-link/MolPort-042-665-869
MuseChem	I007364	https://www.musechem.com/product/I007364.html
Norris Pharm	NSZB-A233916
eMolecules	53927292	https://orderbb.emolecules.com/search/#?query=53927292

PubMed

Title	Date	PubMed
PPARbeta regulates vitamin A metabolism-related gene expression in hepatic stellate cells undergoing activation.	2003 Feb	12576510

Patents

Sample Use Guides

In Vivo Use Guide

VTP-194204 (IRX4204) 20 mg QD for Days 1-30

Route of Administration: Oral

In Vitro Use Guide

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 `Fri Dec 15 21:31:16 UTC 2023` Edited by `admin` on `Fri Dec 15 21:31:16 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