Stereochemistry | ABSOLUTE |
Molecular Formula | C29H60NO8P |
Molecular Weight | 581.7624 |
Optical Activity | UNSPECIFIED |
Defined Stereocenters | 1 / 1 |
E/Z Centers | 0 |
Charge | 0 |
SHOW SMILES / InChI
SMILES
CCCCCCCCCCCCCCCCOC[C@H](COP([O-])(=O)OCC[N+](C)(C)C)OCCCCC(O)=O
InChI
InChIKey=JGGNOCUEWOGWPL-MUUNZHRXSA-N
InChI=1S/C29H60NO8P/c1-5-6-7-8-9-10-11-12-13-14-15-16-17-19-23-35-26-28(36-24-20-18-21-29(31)32)27-38-39(33,34)37-25-22-30(2,3)4/h28H,5-27H2,1-4H3,(H-,31,32,33,34)/t28-/m1/s1
CI-201 (also known as VB-201) is pure synthetic Lecinoxoid, oxidized phospholipid analog, for prevention and treatment of atherosclerosis and central nervous system (CNS) autoimmune inflammatory disease. In preclinical models, CI-201 ameliorated the severity of experimental autoimmune encephalomyelitis (EAE) induced by myelin oligodendrocyte glycoprotein (MOG) peptide, and constrained the infiltration of pathogenic CD4+ T-cells into the CNS and impaired their IFN-γ production. CI-201 inhibits Toll-like receptor (TLR) signaling restricted to TLR-2 and TLR-4 in human monocytes and dendritic cells, and exhibits up to 90% inhibition of monocyte chemotaxis in vitro. Interestingly, CI-201 did not inhibit monocyte adhesion or phagocytosis and had no effect on chemotaxis of neutrophils. In vivo, oral treatment with CI-201 reduced monocyte migration in a peritonitis model and inhibited atheroma development in ApoE(-/-) mice, without affecting cholesterol or triglyceride levels. CI-201 is developed by Vascular Biogenics for the oral treatment of atherosclerosis, rheumatoid arthritis (RA), plaque psoriasis and multiple sclerosis (MS). However, in Phase 2 clinical trials CI-201 failed to demonstrate a statistically significant reduction in vascular inflammation associated with atherosclerotic lesions over placebo. As a result, Vascular Biogenics discontinued the development of CI-201 in psoriasis and atherosclerosis. No information about rheumatoid arthritis and multiple sclerosis clinical trials are currently available.