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Details

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
Structure of VB-201

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

HIDE SMILES / InChI

Molecular Formula C29H60NO8P
Molecular Weight 581.7624
Charge 0
Count
Stereochemistry EPIMERIC
Additional Stereochemistry No
Defined Stereocenters 1 / 1
E/Z Centers 0
Optical Activity UNSPECIFIED

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.

Approval Year

PubMed

PubMed

TitleDatePubMed
A Lecinoxoid, an oxidized phospholipid small molecule, constrains CNS autoimmune disease.
2010 Sep 14
Patents

Patents

Substance Class Chemical
Created
by admin
on Fri Dec 15 15:40:08 GMT 2023
Edited
by admin
on Fri Dec 15 15:40:08 GMT 2023
Record UNII
SJ5A8151JO
Record Status Validated (UNII)
Record Version
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Name Type Language
VB-201
Common Name English
VB 201 [WHO-DD]
Common Name English
1-PALMITYL-2-(4-CARBOXYBUTYL)-SN-GLYCERO-3-PHOSPHOCHOLINE
Common Name English
Code System Code Type Description
PUBCHEM
45138527
Created by admin on Fri Dec 15 15:40:08 GMT 2023 , Edited by admin on Fri Dec 15 15:40:08 GMT 2023
PRIMARY
DRUG BANK
DB15259
Created by admin on Fri Dec 15 15:40:08 GMT 2023 , Edited by admin on Fri Dec 15 15:40:08 GMT 2023
PRIMARY
FDA UNII
SJ5A8151JO
Created by admin on Fri Dec 15 15:40:08 GMT 2023 , Edited by admin on Fri Dec 15 15:40:08 GMT 2023
PRIMARY
CAS
630112-41-3
Created by admin on Fri Dec 15 15:40:08 GMT 2023 , Edited by admin on Fri Dec 15 15:40:08 GMT 2023
PRIMARY
Related Record Type Details
ACTIVE MOIETY
In this study we demonstrate that VB-201, an oxidized phospholipid (Ox-PL) small molecule, inhibits TLR signalling restricted to TLR-2 and TLR-4 in human and mouse monocytes and DC. Mechanistically, we show that VB-201 binds directly to TLR-2 and CD14, the TLR-4 co-receptor, to impair downstream cues and cytokine production. In a rabbit model, oral administration of VB-201 constrained atherosclerosis progression. This effect was not due to reduced cholesterol abundance, as hyperlipidaemia was sustained. We suggest that VB-201 may counter inflammation where TLR-2 and/or CD14 complicity is essential, and is therefore beneficial for the treatment of atherosclerosis.