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Merck
CN

SML2883

Paquinimod

≥98% (HPLC), powder, immunomodulator

Synonym(s):

ABR 215757, ABR 25757, ABR-215757, ABR-25757, ABR215757, ABR25757, N,5-Diethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxo-N-phenyl-3-quinolinecarboxamide, N-Ethyl-N-phenyl-1,2-dihydro-5-ethyl-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxamide, N-Ethyl-N-phenyl-5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxamide

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About This Item

Empirical Formula (Hill Notation):
C21H22N2O3
CAS Number:
248282-01-1
Molecular Weight:
350.41
UNSPSC Code:
12352200
NACRES:
NA.77
MDL number:
MFCD18633277

Key Documents

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Product Name

Paquinimod, ≥98% (HPLC)

SMILES string

N1(c2c(c(ccc2)CC)C(=O)C(C1=O)C(=O)N(CC)c3ccccc3)C

InChI

1S/C21H22N2O3/c1-4-14-10-9-13-16-17(14)19(24)18(20(25)22(16)3)21(26)23(5-2)15-11-7-6-8-12-15/h6-13,18H,4-5H2,1-3H3

InChI key

RBHDLRDFJPBLNO-UHFFFAOYSA-N

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

Quality Level

100

Biochem/physiol Actions

Orally active S100A9 (Calgranulin B; MRP14) blocker with in vivo efficacy in murine models of autoimmune diseases.
Paquinimod (ABR-215757) is an orally active quinoline-3-carboxamide (Q substance) class immunomodulator that targets S100A9 (Calgranulin B; MRP14) via direct binding and blocks its interaction with receptor for advanced glycation end products (RAGE) and Toll-like receptor 4 (IC50 = 26 μM & 23 μM against 100 nM hS100A9 from binding immobilized hRAGE & hTLR4/MD2, respectively). Paquinimod in vivo efficacy is demonstrated in murine models of autoimmune/inflammatory diseases, including liver fibrosis, collagen-induced osteoarthritis, peritonitis, EAE, type 1 diabetes, lupus (0.04-25 mg/kg/day p.o.), and atherosclerosis (10 mg/kg i.p.).

Storage Class

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

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Certificates of Analysis (COA)

Lot/Batch Number
0000489698
0000489695
0000489698
0000489695
0000436851

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Sahar Tahvili et al.
PloS one, 13(5), e0196598-e0196598 (2018-05-10)
Quinoline-3-carboxamides (Q compounds) are immunomodulatory compounds that have shown efficacy both in autoimmune disease and cancer. We have in here investigated the impact of one such compound, paquinimod, on the development of diabetes in the NOD mouse model for type
Michael J Kraakman et al.
The Journal of clinical investigation, 127(6), 2133-2147 (2017-05-16)
Platelets play a critical role in atherogenesis and thrombosis-mediated myocardial ischemia, processes that are accelerated in diabetes. Whether hyperglycemia promotes platelet production and whether enhanced platelet production contributes to enhanced atherothrombosis remains unknown. Here we found that in response to
Sofia Helmersson et al.
The American journal of pathology, 182(5), 1671-1680 (2013-03-20)
Quinoline-3-carboxamide compounds (Q compounds) have demonstrated efficacy in treating autoimmune disease in both humans and mice. However, the mode of action of these compounds is poorly understood. Here, we show that preventive treatment with the Q compound paquinimod (ABR-215757) during
Christina Wache et al.
The Journal of infectious diseases, 212(2), 247-257 (2015-01-22)
Neutrophilic inflammation often persists for days despite effective antibiotic treatment and contributes to brain damage in bacterial meningitis. We propose here that myeloid-related protein 14 (MRP14), an abundant cytosolic protein in myeloid cells, acts as an endogenous danger signal, driving
R F Schelbergen et al.
Annals of the rheumatic diseases, 74(12), 2254-2258 (2015-05-15)
Alarmins S100A8/A9 regulate pathology in experimental osteoarthritis (OA). Paquinimod is an immunomodulatory compound preventing S100A9 binding to TLR-4. We investigated the effect of paquinimod on experimental OA and human OA synovium. Two OA mouse models differing in level of synovial
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