Zimlovisertib

Zimlovisertib
Identifiers
	IUPAC name 1-[[(2S,3S,4S)-3-ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy]-7-methoxyisoquinoline-6-carboxamide;
CAS Number	1817626-54-2;
PubChem CID	118414016;
DrugBank	DB15143;
ChemSpider	58805665;
UNII	S3F315JJXI;
ChEMBL	ChEMBL4081711;
Chemical and physical data
Formula	C18H20FN3O4
Molar mass	361.373 g·mol−1
3D model (JSmol)	Interactive image;
	SMILES CC[C@H]1[C@H](NC(=O)[C@H]1F)COC2=NC=CC3=CC(=C(C=C32)OC)C(=O)N;
	InChI InChI=1S/C18H20FN3O4/c1-3-10-13(22-17(24)15(10)19)8-26-18-11-7-14(25-2)12(16(20)23)6-9(11)4-5-21-18/h4-7,10,13,15H,3,8H2,1-2H3,(H2,20,23)(H,22,24)/t10-,13+,15-/m0/s1; Key:JKDGKIBAOAFRPJ-ZBINZKHDSA-N;

Zimlovisertib (PF-06650833) is a drug which acts as a selective inhibitor of the enzyme Interleukin-1 receptor-associated kinase 4 (IRAK-4). It has antiinflammatory effects and has been trialed for various indications including hidradenitis suppurativa and treatment of COVID-19 infection, and while it has not been adopted into clinical use it continues to be used for research in this area.^[1]^[2]^[3]

References

^ Zapata-Acevedo CA, Guevara-Vela JM, Popelier PL, Rocha-Rinza T (December 2022). "Binding Energy Partition of Promising IRAK-4 Inhibitor (Zimlovisertib) for the Treatment of COVID-19 Pneumonia". ChemPhysChem. 23 (24): e202200455. doi:10.1002/cphc.202200455. PMC 9538207. PMID 36044560.
^ Kimball AB, Peeva E, Forman S, Moiin A, Khattri S, Porter ML, et al. (March 2024). "Brepocitinib, Zimlovisertib, and Ropsacitinib in Hidradenitis Suppurativa". NEJM Evidence. 3 (3): EVIDoa2300155. doi:10.1056/EVIDoa2300155. PMID 38335032.
^ Wright SW, Farley KA, Han S, Knafels JD, Lee KL (April 2024). "In Retrospect: Root-Cause Analysis of Structure-Activity Relationships in IRAK4 Inhibitor Zimlovisertib (PF-06650833)". ACS Medicinal Chemistry Letters. 15 (4): 540–545. doi:10.1021/acsmedchemlett.4c00036. PMC 11017396. PMID 38628800.

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[1] Zapata-Acevedo CA, Guevara-Vela JM, Popelier PL, Rocha-Rinza T (December 2022). "Binding Energy Partition of Promising IRAK-4 Inhibitor (Zimlovisertib) for the Treatment of COVID-19 Pneumonia". ChemPhysChem. 23 (24): e202200455. doi:10.1002/cphc.202200455. PMC 9538207. PMID 36044560.

[2] Kimball AB, Peeva E, Forman S, Moiin A, Khattri S, Porter ML, et al. (March 2024). "Brepocitinib, Zimlovisertib, and Ropsacitinib in Hidradenitis Suppurativa". NEJM Evidence. 3 (3): EVIDoa2300155. doi:10.1056/EVIDoa2300155. PMID 38335032.

[3] Wright SW, Farley KA, Han S, Knafels JD, Lee KL (April 2024). "In Retrospect: Root-Cause Analysis of Structure-Activity Relationships in IRAK4 Inhibitor Zimlovisertib (PF-06650833)". ACS Medicinal Chemistry Letters. 15 (4): 540–545. doi:10.1021/acsmedchemlett.4c00036. PMC 11017396. PMID 38628800.

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Identifiers

IUPAC name 1-[[(2S,3S,4S)-3-ethyl-4-fluoro-5-oxopyrrolidin-2-yl]methoxy]-7-methoxyisoquinoline-6-carboxamide
CAS Number	1817626-54-2
PubChem CID	118414016
DrugBank	DB15143
ChemSpider	58805665
UNII	S3F315JJXI
ChEMBL	ChEMBL4081711
Chemical and physical data
Formula	C₁₈H₂₀FN₃O₄
Molar mass	361.373 g·mol⁻¹
3D model (JSmol)	Interactive image
SMILES CC[C@H]1[C@H](NC(=O)[C@H]1F)COC2=NC=CC3=CC(=C(C=C32)OC)C(=O)N
InChI InChI=1S/C18H20FN3O4/c1-3-10-13(22-17(24)15(10)19)8-26-18-11-7-14(25-2)12(16(20)23)6-9(11)4-5-21-18/h4-7,10,13,15H,3,8H2,1-2H3,(H2,20,23)(H,22,24)/t10-,13+,15-/m0/s1 Key:JKDGKIBAOAFRPJ-ZBINZKHDSA-N

Zimlovisertib

See also

References