RESATORVID

Investigational

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

Structure Search

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

HIDE SMILES / InChI

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

Description
Sources: https://www.ncbi.nlm.nih.gov/pubmed/29437671 | https://www.ncbi.nlm.nih.gov/pubmed/24858944 | https://www.drugbank.ca/drugs/DB05943 | https://clinicaltrials.gov/ct2/show/NCT00143611 | https://clinicaltrials.gov/ct2/show/NCT00633477

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
Toll-like receptor 4 6 Target ID: CHEMBL5255 Sources: https://www.ncbi.nlm.nih.gov/pubmed/18299127	Inhibitor 8504

C_max

Value	Dose	Co-administered	Analyte	Population
54.1 ng/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/25586141/	3 mg/kg bw single, intraperitoneal dose: 3 mg/kg bw route of administration: Intraperitoneal experiment type: SINGLE co-administered:		RESATORVID plasma	Mus musculus population: UNHEALTHY age: ADULT sex: MALE food status: UNKNOWN

AUC

Value	Dose	Co-administered	Analyte	Population
6.08 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21950150/	3 mg/kg single, intravenous dose: 3 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		RESATORVID plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FED
1322 μg × h/mL EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21950150/	3 mg/kg single, intravenous dose: 3 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		RESATORVID plasma	Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FED

T_1/2

Value	Dose	Co-administered	Analyte	Population
5.6 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21950150/	3 mg/kg single, intravenous dose: 3 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		RESATORVID plasma	Rattus norvegicus population: HEALTHY age: ADULT sex: MALE food status: FED
158 h EXPERIMENT https://pubmed.ncbi.nlm.nih.gov/21950150/	3 mg/kg single, intravenous dose: 3 mg/kg route of administration: Intravenous experiment type: SINGLE co-administered:		RESATORVID plasma	Canis lupus population: HEALTHY age: ADULT sex: MALE food status: FED

PubMed

Title	Date	PubMed
Involvement of L-type Ca²⁺ channel and toll-like receptor-4 in nickel-induced interleukin-8 gene expression.	2016-01	25045119
The immunobiology of cobalt: demonstration of a potential aetiology for inflammatory pseudotumours after metal-on-metal replacement of the hip.	2014-09	25183586
Pro-inflammatory and pro-oxidant status of pancreatic islet in vitro is controlled by TLR-4 and HO-1 pathways.	2014	25343247
Crucial role of Toll-like receptors in the zinc/nickel-induced inflammatory response in vascular endothelial cells.	2013-12-15	24080332
Calcineurin inhibitors recruit protein kinases JAK2 and JNK, TLR signaling and the UPR to activate NF-κB-mediated inflammatory responses in kidney tubular cells.	2013-11-01	23958496
Lipopolysaccharide potentiates polychlorinated biphenyl-induced disruption of the blood-brain barrier via TLR4/IRF-3 signaling.	2012-12-16	22906770
Lipopolysaccharide induces H1 receptor expression and enhances histamine responsiveness in human coronary artery endothelial cells.	2011-04	21255012
Toll-like receptors in the pathogenesis of alcoholic liver disease.	2010	20827314
Toll-like receptor 4 modulation as a strategy to treat sepsis.	2010	20396414
Discovery and development of toll-like receptor 4 (TLR4) antagonists: a new paradigm for treating sepsis and other diseases.	2008-08	18493843
Bench-to-bedside review: sepsis, severe sepsis and septic shock - does the nature of the infecting organism matter?	2008	18466647
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.	2006-04	16373689
Optically active cyclohexene derivative as a new antisepsis agent: an efficient synthesis of ethyl (6R)-6-[N-(2-chloro-4-fluorophenyl)sulfamoyl]cyclohex-1-ene-1-carboxylate (TAK-242).	2006-01	16394550
Discovery of novel and potent small-molecule inhibitors of NO and cytokine production as antisepsis agents: synthesis and biological activity of alkyl 6-(N-substituted sulfamoyl)cyclohex-1-ene-1-carboxylate.	2005-11-17	16279805

Patents

Substance Class	Chemical Created by `admin` on `Mon Mar 31 18:21:53 GMT 2025` Edited by `admin` on `Mon Mar 31 18:21:53 GMT 2025`
Record UNII	H2MZ648C31
Record Status	`Validated (UNII)`
Record Version

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Name

Type

Language

RESATORVID

Official Name

English

TAK-242

Preferred Name

English

resatorvid [INN]

Common Name

English

CLI-095

Common Name

English

ETHYL (6R)-6-((2-CHLORO-4-FLUOROPHENYL)SULFAMOYL)CYCLOHEX-1-ENE-1-CARBOXYLATE

Systematic Name

English

Classification Tree Code System Code

NCI_THESAURUS

C308