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Resatorvid

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Chemical compound Pharmaceutical compound
Resatorvid
Clinical data
Trade namesResatorvid
Identifiers
IUPAC name
  • ethyl (6R)-6-cyclohexene-1-carboxylate
CAS Number
PubChem CID
DrugBank
ChemSpider
UNII
ChEMBL
CompTox Dashboard (EPA)
Chemical and physical data
FormulaC15H17ClFNO4S
Molar mass361.81 g·mol
3D model (JSmol)
SMILES
  • CCOC(=O)C1=CCCC1S(=O)(=O)NC2=C(C=C(C=C2)F)Cl
InChI
  • 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
  • Key:LEEIJTHMHDMWLJ-CQSZACIVSA-N

Resatorvid (TAK-242) is a cyclohexane derivative that was invented by scientists at Takeda in a drug discovery campaign to identify inhibitors of the receptor TLR4. It binds directly to cysteine residue 747 intracellularly, preventing TLR4 binding with TIRAP and thus preventing downstream signal transduction.

A randomized, double-blinded Phase III trial of resatorvid in sepsis was halted early due to lack of efficacy, and the compound has become a widely used tool compound in biological research.

It has antiinflammatory and neuroprotective effects in preclinical models. It has been explored in preclinical studies of several forms of cancer, including multiple myeloma, breast cancer, and ovarian cancer, and has been suggested for study in skin cancers.

Efforts have been made to improve resatorvid by making prodrugs and deuterated derivatives.

See also

References

  1. ^ Wang X, Smith C, Yin H (June 2013). "Targeting Toll-like receptors with small molecule agents". Chemical Society Reviews. 42 (12): 4859–4866. doi:10.1039/c3cs60039d. PMC 3665707. PMID 23503527.
  2. Karimy JK, Reeves BC, Kahle KT (June 2020). "Targeting TLR4-dependent inflammation in post-hemorrhagic brain injury". Expert Opinion on Therapeutic Targets. 24 (6): 525–533. doi:10.1080/14728222.2020.1752182. PMC 8104018. PMID 32249624.
  3. ^ Miller S, Blanco MJ (June 2021). "Small molecule therapeutics for neuroinflammation-mediated neurodegenerative disorders". RSC Medicinal Chemistry. 12 (6): 871–886. doi:10.1039/d1md00036e. PMC 8221257. PMID 34223157.
  4. Innao V, Rizzo V, Allegra AG, Musolino C, Allegra A (February 2021). "Promising Anti-Mitochondrial Agents for Overcoming Acquired Drug Resistance in Multiple Myeloma". Cells. 10 (2): 439. doi:10.3390/cells10020439. PMC 7922387. PMID 33669515.
  5. Dickinson SE, Wondrak GT (2018). "TLR4-directed Molecular Strategies Targeting Skin Photodamage and Carcinogenesis". Current Medicinal Chemistry. 25 (40): 5487–5502. doi:10.2174/0929867324666170828125328. PMID 28847267. S2CID 670318.

Further reading

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