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SML2883

Sigma-Aldrich

Paquinimod

≥98% (HPLC)

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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
Empirical Formula (Hill Notation):
C21H22N2O3
CAS Number:
Molecular Weight:
350.41
MDL number:

Quality Level

Assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 2 mg/mL, clear

storage temp.

2-8°C

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Paquinimod ≥98% (HPLC)

Sigma-Aldrich

SML2883

Paquinimod

Tasquinimod ≥98% (HPLC)

Sigma-Aldrich

SML2489

Tasquinimod

DDR1-IN-1 ≥98% (HPLC)

Sigma-Aldrich

SML2274

DDR1-IN-1

Laquinimod ≥98% (HPLC)

Sigma-Aldrich

SML2504

Laquinimod

form

powder

form

powder

form

powder

form

powder

color

white to beige

color

white to beige

color

white to beige

color

white to beige

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: 2 mg/mL, clear

solubility

DMSO: 2 mg/mL, clear (warmed)

storage temp.

2-8°C

storage temp.

−20°C

storage temp.

2-8°C

storage temp.

−20°C

Quality Level

100

Quality Level

-

Quality Level

-

Quality Level

-

Biochem/physiol Actions

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 Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable


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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
Per Björk et al.
PLoS biology, 7(4), e97-e97 (2009-05-01)
Despite more than 25 years of research, the molecular targets of quinoline-3-carboxamides have been elusive although these compounds are currently in Phase II and III development for treatment of autoimmune/inflammatory diseases in humans. Using photoaffinity cross-linking of a radioactively labelled

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