Details
Stereochemistry | ABSOLUTE |
Molecular Formula | C15H17ClFNO4S |
Molecular Weight | 361.816 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCOC(=O)C1=CCCC[C@H]1S(=O)(=O)NC2=CC=C(F)C=C2Cl
InChI
InChIKey=LEEIJTHMHDMWLJ-CQSZACIVSA-N
InChI=1S/C15H17ClFNO4S/c1-2-22-15(19)11-5-3-4-6-14(11)23(20,21)18-13-8-7-10(17)9-12(13)16/h5,7-9,14,18H,2-4,6H2,1H3/t14-/m1/s1
Molecular Formula | C15H17ClFNO4S |
Molecular Weight | 361.816 |
Charge | 0 |
Count |
|
Stereochemistry | ABSOLUTE |
Additional Stereochemistry | No |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Optical Activity | UNSPECIFIED |
Resatorvid (TAK-242) is a Toll-like receptor 4 (TLR4) antagonist that was designed for the treatment of severe sepsis because of its inhibitory effect on suppressing cytokine levels. This compound suppresses production of inflammatory mediators by inhibiting signal transduction through TLR4. It has also been shown that topical resatorvid, in a UV-induced skin tumorigenesis model, displays photochemopreventive activity, suppressing tumor area and multiplicity. Resatorvid has furthermore shown neuroprotective effects after traumatic brain injury (in a mouse model). Phase III studies evaluating the effects of resatorvid on sepsis have been completed. One such study was ended after it was determined that there was insufficient cytokine suppression in the first stage of the study.
Approval Year
Targets
Primary Target | Pharmacology | Condition | Potency |
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Target ID: CHEMBL5255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18299127 |
PubMed
Title | Date | PubMed |
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A novel cyclohexene derivative, ethyl (6R)-6-[N-(2-Chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate (TAK-242), selectively inhibits toll-like receptor 4-mediated cytokine production through suppression of intracellular signaling. | 2006 Apr |
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Discovery and development of toll-like receptor 4 (TLR4) antagonists: a new paradigm for treating sepsis and other diseases. | 2008 Aug |
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Lipopolysaccharide potentiates polychlorinated biphenyl-induced disruption of the blood-brain barrier via TLR4/IRF-3 signaling. | 2012 Dec 16 |
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Crucial role of Toll-like receptors in the zinc/nickel-induced inflammatory response in vascular endothelial cells. | 2013 Dec 15 |
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Calcineurin inhibitors recruit protein kinases JAK2 and JNK, TLR signaling and the UPR to activate NF-κB-mediated inflammatory responses in kidney tubular cells. | 2013 Nov 1 |
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Pro-inflammatory and pro-oxidant status of pancreatic islet in vitro is controlled by TLR-4 and HO-1 pathways. | 2014 |
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The immunobiology of cobalt: demonstration of a potential aetiology for inflammatory pseudotumours after metal-on-metal replacement of the hip. | 2014 Sep |
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Involvement of L-type Ca²⁺ channel and toll-like receptor-4 in nickel-induced interleukin-8 gene expression. | 2016 Jan |
Patents
Substance Class |
Chemical
Created
by
admin
on
Edited
Fri Dec 15 16:12:33 GMT 2023
by
admin
on
Fri Dec 15 16:12:33 GMT 2023
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Record UNII |
H2MZ648C31
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Record Status |
Validated (UNII)
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Record Version |
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Systematic Name | English |
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NCI_THESAURUS |
C308
Created by
admin on Fri Dec 15 16:12:33 GMT 2023 , Edited by admin on Fri Dec 15 16:12:33 GMT 2023
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FDA ORPHAN DRUG |
503515
Created by
admin on Fri Dec 15 16:12:33 GMT 2023 , Edited by admin on Fri Dec 15 16:12:33 GMT 2023
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Code System | Code | Type | Description | ||
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11703255
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243984-11-4
Created by
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C87682
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100000175795
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C507035
Created by
admin on Fri Dec 15 16:12:33 GMT 2023 , Edited by admin on Fri Dec 15 16:12:33 GMT 2023
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Resatorvid
Created by
admin on Fri Dec 15 16:12:33 GMT 2023 , Edited by admin on Fri Dec 15 16:12:33 GMT 2023
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8785
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DTXSID00947269
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DB05943
Created by
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H2MZ648C31
Created by
admin on Fri Dec 15 16:12:33 GMT 2023 , Edited by admin on Fri Dec 15 16:12:33 GMT 2023
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PRIMARY |
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Related Record | Type | Details | ||
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ACTIVE MOIETY |