Paquinimod
- Product Name
- Paquinimod
- CAS No.
- 248282-01-1
- Chemical Name
- Paquinimod
- Synonyms
- ABR25757;ABR 25757;ABR-25757;ABR?215757;Paquinimod;Paquinimod - Bio-X ?;Paquinimod, 10 mM in DMSO;ABR?215757; ABR 215757; ABR215757; PAQUINIMOD.;ABR-25757,Inhibitor,ABR25757,inhibit,Paquinimod;ABR 25757;ABR-25757;ABR25757;PAQUINIMOD;248282-01-1
- CBNumber
- CB92498835
- Molecular Formula
- C21H22N2O3
- Formula Weight
- 350.41
- MOL File
- 248282-01-1.mol
Paquinimod Property
- Boiling point:
- 487.3±45.0 °C(Predicted)
- Density
- 1.267±0.06 g/cm3(Predicted)
- storage temp.
- 2-8°C
- solubility
- DMSO:15.0(Max Conc. mg/mL);42.8(Max Conc. mM)
- form
- A solid
- pka
- 4.50±1.00(Predicted)
- color
- White to off-white
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H302Harmful if swallowed
H315Causes skin irritation
H319Causes serious eye irritation
H335May cause respiratory irritation
- Precautionary statements
-
P261Avoid breathing dust/fume/gas/mist/vapours/spray.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
N-Bromosuccinimide Price
- Product number
- SML2883
- Product name
- Paquinimod
- Purity
- ≥98% (HPLC)
- Packaging
- 5 mg
- Price
- $96.8
- Updated
- 2025/07/31
- Product number
- SML2883
- Product name
- Paquinimod
- Purity
- ≥98% (HPLC)
- Packaging
- 25 mg
- Price
- $392
- Updated
- 2025/07/31
- Product number
- 28443
- Product name
- Paquinimod
- Packaging
- 1mg
- Price
- $55
- Updated
- 2024/03/01
- Product number
- 28443
- Product name
- Paquinimod
- Packaging
- 25mg
- Price
- $914
- Updated
- 2024/03/01
- Product number
- 28443
- Product name
- Paquinimod
- Packaging
- 5mg
- Price
- $224
- Updated
- 2024/03/01
Paquinimod Chemical Properties,Usage,Production
Uses
Paquinimod is a S100A9 inhibitor preventing S100A9 binding to TLR-4. Paquinimod reduces pathology in experimental collagenase-induced osteoarthritis. Paquinimod treatment of collagenase-induced OA (CIOA) resulted in significantly reduced synovial thickening (57%), osteophyte size at the medial femur (66%) and cruciate ligaments (67%) and cartilage damage at the medial tibia (47%) and femur (75%; n=7, untreated n=6). Paquinimod reduces leukocyte recruitment during sterile inflammation. Paquinimod also reduced priming of proinflammatory effector CD4(+) T cells.
Biological Activity
Paquinimod (ABR-215757) is an orally active quinoline-3-carboxamide (Q substance) class immunomodulator th at 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.).
Synthesis
1354639-60-3
103-69-5
248282-01-1
1. 5-Ethyl-4-hydroxy-1-methyl-2-oxo-1,2-dihydroquinoline-3-carboxylic acid methyl ester (5.00 g) was dissolved in n-heptane (200 mL) with N-ethylaniline (4.7 g), 4A molecular sieves (22.9 g) were added and placed in a Soxhlet extraction device under reflux. 2. After refluxing for 2.0 hours the heating was stopped and the reaction mixture was cooled to room temperature. 3. The crystalline suspension in the reaction mixture was filtered and the solid product was collected. 4. The precipitate was washed with n-heptane and subsequently dried under vacuum to afford N-ethyl-N-phenyl-5-ethyl-1,2-dihydro-4-hydroxy-1-methyl-2-oxoquinoline-3-carboxamide (A) in a yield of 5.53 g (82% yield). 5. The isolated product was analyzed by 1H-NMR and was shown to contain 2% unreacted ester. 1H-NMR (d-DMSO) data were as follows: broad peaks appeared at 11.1 (1H), 7.41 (1H), 7.29 (2H), 7.21 (3H), 7.14 (1H), 6.96 (1H), 3.80 (2H), 3.42 (3H), 3.08 ( 2H), 1.07 (3H) ppm. 6. According to U.S. Patent No. 6,875,869, a 2 hour reaction from n-heptane by conventional distillation under the same reaction conditions resulted in a product yield of 85% (based on Compound A). 1H-NMR analysis showed the product to be a mixture of Compound A (75 mol%) and the feedstock ester (25 mol%).
in vivo
S100A9 is a calcium-binding protein of the S100 family. Paquinimod is an immunomodulatory compound preventing S100A9 binding to TLR-4. Prophylactic treatment with S100A9 inhibitor Paquinimod reduces pathology in experimental collagenase-induced osteoarthritis[1]. Paquinimod is a potent inhibitor of insulitis and diabetes development in the NOD mouse. To assess the preventive efficacy of Paquinimod on diabetes development in female NOD mice, groups of mice are treated with daily doses of 0.04, 0.2, 1, and 5 mg/kg/day of Paquinimod from week 10 of age until week 20 of age. Glycosuria is analyzed on a weekly basis from 10 weeks of age until the endpoint of the experiment at 40 weeks of age. There is a clear dose-dependent reduction in diabetes development in the Paquinimod-treated mice[2].
References
[1] Patent: WO2012/4338, 2012, A1. Location in patent: Page/Page column 13; 15
Paquinimod Preparation Products And Raw materials
Raw materials
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