| Identification | Back Directory | [Name]
CHF 5074 | [CAS]
749269-83-8 | [Synonyms]
CHF 5074
GHF-5074
CSP-1103
Itanapraced
1-[4-(3,4-dichlorophenyl)-3-fluorophenyl]cyclopropane-1-carboxylic Acid
1-(3′,4′-Dichloro-2-fluoro[1,1′-biphenyl]-4-yl)-cyclopropanecarboxylic acid
Cyclopropanecarboxylic acid, 1-(3',4'-dichloro-2-fluoro[1,1'-biphenyl]-4-yl)-
1-[4-(3,4-dichlorophenyl)-3-fluorophenyl]cyclopropane-1-carboxylic acid GHF-5074 | [Molecular Formula]
C16H11Cl2FO2 | [MDL Number]
MFCD18633206 | [MOL File]
749269-83-8.mol | [Molecular Weight]
325.16 |
| Chemical Properties | Back Directory | [Boiling point ]
466.4±45.0 °C(Predicted) | [density ]
1.467±0.06 g/cm3(Predicted) | [storage temp. ]
2-8°C | [solubility ]
DMSO:59.0(Max Conc. mg/mL);181.45(Max Conc. mM) | [form ]
A solid | [pka]
2.30±0.20(Predicted) | [color ]
White to off-white | [InChI]
InChI=1S/C16H11Cl2FO2/c17-12-4-1-9(7-13(12)18)11-3-2-10(8-14(11)19)16(5-6-16)15(20)21/h1-4,7-8H,5-6H2,(H,20,21) | [InChIKey]
LIYLTQQDABRNRX-UHFFFAOYSA-N | [SMILES]
C1(C2=CC=C(C3=CC=C(Cl)C(Cl)=C3)C(F)=C2)(C(O)=O)CC1 |
| Hazard Information | Back Directory | [Uses]
Itanapraced (CHF5074) is an orally active γ-secretase modulator and a non-steroidal anti-inflammatory derivative. Itanapraced reduces Aβ42 and Aβ40 secretion with IC50 values of 3.6 and 18.4 μM, respectively. Itanapraced inhibits cell apoptosis of hippocampal neurons induced by oxygen and glucose deprivation (OGD). Itanapraced can be used for the research of Alzheimer's disease[1][2]. | [Biological Activity]
Itanapraced (CHF 5074, CSP-1103) is a gamma-secretase modulator that reduces Aβ42 and Aβ40 secretion. It inhibits COX1 and COX2 with IC50 greater than 100 μM. | [in vitro]
In glioma cells expressing APPswe (H4swe), CHF5074 reduces Aβ42 release with IC50 of 3.6 μM. It had no inhibitory activity against COX-1 and COX-2 at concentrations up to 100 μM and 300 μM. | [in vivo]
In rats, CHF5074 is well absorbed orally (50%) and is slowly eliminated from plasma (half-life approximately 20 hours). In Tg2576 transgenic mice, chronic treatment of CHF5074 significantly reduced the total amount of Aβ in the brain, and at the histological level, no Notch-mediated toxic effects were found. | [target]
| Target | Value | γ secretase
() | < /table>[References]
[1] Imbimbo BP, et al. 1-(3',4'-Dichloro-2-fluoro[1,1'-biphenyl]-4-yl)-cyclopropanecarboxylic acid (CHF5074), a novel gamma-secretasemodulator, reduces brain beta-amyloid pathology in a transgenic mouse model of Alzheimer's disease withoutcausing peripheral toxicity. J Pharmacol Exp Ther. 2007 Dec;323(3):822-830. DOI:10.1124/jpet.107.129007
[2] Mango D, et al. Electrophysiological and metabolic effects of CHF5074 in the hippocampus: protection against in vitro ischemia. Pharmacol Res. 2014 Mar;81:83-90. DOI:10.1016/j.phrs.2014.02.010 |
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Tags:749269-83-8
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