164301-51-3

164301-51-3 structure

Name: Semapimod tetrahydrochloride
Chemical Name: N,N'-bis[3,5-bis[(E)-N-(diaminomethylideneamino)-C-methylcarbonimidoyl]phenyl]decanediamide,tetrahydrochloride
CAS Number: 164301-51-3
Molecular Formula: C₃₄H₅₆Cl₄N₁₈O₂
Molecular Weight: 890.74000
Catalog: Signaling Pathways Immunology/Inflammation Interleukin Related
Create Date: 2017-05-19 05:31:03
Modify Date: 2024-01-09 15:56:49
Semapimod tetrahydrochloride (CNI-1493), an inhibitor of proinflammatory cytokine production, can inhibit TNF-α, IL-1β, and IL-6. Semapimod tetrahydrochloride inhibits TLR4 signaling (IC50≈0.3 μM). Semapimod tetrahydrochloride inhibits p38 MAPK and nitric oxide production in macrophages. Semapimod tetrahydrochloride has potential in a variety of inflammatory and autoimmune disorders[1][2][3].

Name	N,N'-bis[3,5-bis[(E)-N-(diaminomethylideneamino)-C-methylcarbonimidoyl]phenyl]decanediamide,tetrahydrochloride
Synonyms	Semapimod HCl Decanediamide,N,N'-bis(3,5-bis(1-((aminoiminomethyl)hydrazono)ethyl)phenyl)-,tetrahydrochloride CNI 1493 AXD 455 N,N'-Bis(3,5-bis(1-((aminoiminomethyl)hydrazono)ethyl)phenyl)decanediamide tetrahydrochloride Semapimod tetrahydrochloride Semapimod hydrochloride

Description	Semapimod tetrahydrochloride (CNI-1493), an inhibitor of proinflammatory cytokine production, can inhibit TNF-α, IL-1β, and IL-6. Semapimod tetrahydrochloride inhibits TLR4 signaling (IC50≈0.3 μM). Semapimod tetrahydrochloride inhibits p38 MAPK and nitric oxide production in macrophages. Semapimod tetrahydrochloride has potential in a variety of inflammatory and autoimmune disorders[1][2][3].
Related Catalog	Signaling Pathways >> Immunology/Inflammation >> Interleukin Related Signaling Pathways >> MAPK/ERK Pathway >> p38 MAPK Research Areas >> Inflammation/Immunology
In Vitro	Semapimod tetrahydrochloride leads to a significant decrease of p38-MAPK phosphorylation in macrophages, proinflammatory gene expression of macrophage inflammatory protein-1alpha, interleukin-6, monocyte chemoattractant protein-1, and intercellular adhesion molecule-1, and neutrophil infiltration. Semapimod tetrahydrochloride completely abrogated nitric oxide production within the tunica muscularis[2]. Semapimod tetrahydrochloride desensitizes TLR signaling via its effect on the TLR chaperone gp96. Semapimod tetrahydrochloride inhibits ATP-binding and ATPase activities of gp96 in vitro (IC50≈0.2-0.4 μM). Semapimod tetrahydrochloride desensitizes TLR signaling via its effect on the TLR chaperone gp96[3].
In Vivo	Semapimod tetrahydrochloride (5 mg/kg; i.p; daily for 2 weeks) ameliorates endothelial dysfunction in Obese Zucker (OZ) rats[1]. Semapimod tetrahydrochloride restores AM-induced akt phosphorylation and cGMP production in OZ rats[1]. Animal Model: Male OZ rats[1] Dosage: 5 mg/kg Administration: I.p; daily for 2 weeks Result: Restored endothelium-dependent vasorelaxation in OZ rats.
References	[1]. Nishimatsu H, et al. Blockade of endogenous proinflammatory cytokines ameliorates endothelial dysfunction in obese Zucker rats. Hypertens Res. 2008;31(4):737‐743. [2]. Wehner S, Set al. Inhibition of p38 mitogen-activated protein kinase pathway as prophylaxis of postoperative ileus in mice. Gastroenterology. 2009;136(2):619‐629. [3]. Wang J, et al. Experimental Anti-Inflammatory Drug Semapimod Inhibits TLR Signaling by Targeting the TLR Chaperone gp96. J Immunol. 2016;196(12):5130‐5137.

Boiling Point	1025.8ºC at 760mmHg
Molecular Formula	C₃₄H₅₆Cl₄N₁₈O₂
Molecular Weight	890.74000
Flash Point	574.2ºC
Exact Mass	888.35900
PSA	362.22000
LogP	11.48360
Vapour Pressure	0mmHg at 25°C

Hazard Codes	Xi

164301-51-3	872830-80-3
352513-83-8	16632-23-8
306-67-2	117399-50-5
15446-43-2	28564-83-2
36509-15-6	117654-79-2