Semapimod tetrahydrochloride

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.

Product information

CAS Number: 164301-51-3

Molecular Weight: 890.74

Formula: C34H56Cl4N18O2

Synonym:

CNI-1493

CPSI-2364 tetrahydrochloride

Chemical Name: N1, N10-bis(3, 5-bis((E)-1-(2-carbamimidoylhydrazono)ethyl)phenyl)decanediamide tetrahydrochloride

Smiles: Cl.Cl.Cl.Cl.C/C(=N\NC(N)=N)/C1=CC(=CC(=C1)/C(/C)=N/NC(N)=N)NC(=O)CCCCCCCCC(=O)NC1C=C(C=C(C=1)/C(/C)=N/NC(N)=N)/C(/C)=N/NC(N)=N

InChiKey: MAHASPGBAIQZLY-RTQZJKMDSA-N

InChi: InChI=1S/C34H52N18O2.4ClH/c1-19(45-49-31(35)36)23-13-24(20(2)46-50-32(37)38)16-27(15-23)43-29(53)11-9-7-5-6-8-10-12-30(54)44-28-17-25(21(3)47-51-33(39)40)14-26(18-28)22(4)48-52-34(41)42;;;;/h13-18H,5-12H2,1-4H3,(H,43,53)(H,44,54)(H4,35,36,49)(H4,37,38,50)(H4,39,40,51)(H4,41,42,52);4*1H/b45-19+,46-20+,47-21+,48-22+;;;;

Technical Data

Appearance: Solid Power

Purity: ≥98% (or refer to the Certificate of Analysis)

Solubility: H2O : 14.29 mg/mL (16.04 mM; Need ultrasonic)

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical or refer to Certificate of Analysis

Storage Condition: Dry, dark and -20 ^oC for 1 year or refer to the Certificate of Analysis.

Shelf Life: ≥360 days if stored properly.

Stock Solution Storage: 0 - 4 ^oC for 1 month or refer to the Certificate of Analysis.

Drug Formulation: To be determined

HS Tariff Code: 382200

How to use

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. 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.

In Vivo:

Semapimod tetrahydrochloride (5 mg/kg; i.p; daily for 2 weeks) ameliorates endothelial dysfunction in Obese Zucker (OZ) rats. Semapimod tetrahydrochloride restores AM-induced akt phosphorylation and cGMP production 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.

Products are for research use only. Not for human use.