Semapimod tetrahydrochloride - ≥98% , CAS No.164301-51-3

CAS: 164301-51-3 Cat. No.: S649921 Molecular Weight: 890.74

GRADE & PURITY ≥98%

Synonyms

Decanediamide, N,N'-bis(3,5-bis(1-((aminoiminomethyl)hydrazono)ethyl)phenyl)-, tetrahydrochloride | DECANEDIAMIDE, N1,N10-BIS(3,5-BIS(1-(2-(AMINOIMINOMETHYL)HYDRAZINYLIDENE)ETHYL)PHENYL)-, HYDROCHLORIDE (1:4) | AKOS040754719 | DTXSID301028119 | CNI1493 |

Storage

Protected from light,Store at -20°C,Desiccated

Shipped In

Ice chest + Ice pads

Overview

Semapimod tetrahydrochloride (CNI-1493), an inhibitor of proinflammatory cytokine production, can inhibit TNF-α , IL-1β , and IL-6. Semapimod tetrahydrochloride inhibits TLR4 signaling (IC 50 ≈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 .

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. ?\nSemapimod tetrahydrochloride desensitizes TLR signaling via its effect on the TLR chaperone gp96. Semapimod tetrahydrochloride inhibits ATP-binding and ATPase activities of gp96 in vitro (IC 50 ≈0.2-0.4 μM). Semapimod tetrahydrochloride desensitizes TLR signaling via its effect on the TLR chaperone gp96. MCE has not independently confirmed the accuracy of these methods. They are for reference only.

In Vivo

Semapimod tetrahydrochloride (5 mg/kg; i.p; daily for 2 weeks) ameliorates endothelial dysfunction in Obese Zucker (OZ) rats . ?\nSemapimod tetrahydrochloride restores AM-induced akt phosphorylation and cGMP production in OZ rats . MCE has not independently confirmed the accuracy of these methods. They are for reference only. Animal Model: Male OZ rats Dosage: 5 mg/kg Administration: I.p; daily for 2 weeks Result: Restored endothelium-dependent vasorelaxation in OZ rats.

Form:Solid

Specifications

Synonyms

Decanediamide, N, N'-bis(3, 5-bis(1-((aminoiminomethyl)hydrazono)ethyl)phenyl)-, tetrahydrochloride | DECANEDIAMIDE, N1, N10-BIS(3, 5-BIS(1-(2-(AMINOIMINOMETHYL)HYDRAZINYLIDENE)ETHYL)PHENYL)-, HYDROCHLORIDE (1:4) | AKOS040754719 | DTXSID301028119 | CNI1493 |

Specifications & Purity

≥98%

Biochemical and Physiological Mechanisms

Semapimod tetrahydrochloride (CNI-1493), an inhibitor of proinflammatory cytokine production, can inhibit TNF-α , IL-1β , and IL-6 . Semapimod tetrahydrochloride inhibits TLR4 signaling (IC 50 ≈0.3 μM). Semapimod tetrahydrochloride inhibits p38 MAPK and n

Storage

Protected from light, Store at -20°C, Desiccated

Shipped In

Ice chest + Ice pads

This product requires cold chain shipping. Ground and other economy services are not available.

Purity

≥98%

Names and Identifiers

• Canonical Smiles: CC(=NN=C(N)N)C1=CC(=CC(=C1)NC(=O)CCCCCCCCC(=O)NC2=CC(=CC(=C2)C(=NN=C(N)N)C)C(=NN=C(N)N)C)C(=NN=C(N)N)C.Cl.Cl.Cl.Cl
• IUPAC Name: N,N'-bis[3,5-bis[(E)-N-(diaminomethylideneamino)-C-methylcarbonimidoyl]phenyl]decanediamide;tetrahydrochloride
• InChIKey: MAHASPGBAIQZLY-RTQZJKMDSA-N
• 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+
• Isomeric SMILES: C/C(=N\N=C(N)N)/C1=CC(=CC(=C1)NC(=O)CCCCCCCCC(=O)NC2=CC(=CC(=C2)/C(=N/N=C(N)N)/C)/C(=N/N=C(N)N)/C)/C(=N/N=C(N)N)/C.Cl.Cl.Cl.Cl
• Alternate CAS: 164301-51-3
• MeSH Entry Terms: AXD-455;AXD455;CNI 1493;CNI-1493;CPSI 2364;CPSI-2364;CPSI-2364 free base;CPSI2364;decanediamide, N1,N10-bis(3,5-bis(1-(2-(aminoiminomethyl)hydrazinylidene)ethyl)phenyl)-, hydrochloride (1:4);decanediamide, N1,N10-bis(3,5-bis(1-(2-(aminoiminomethyl)hydrazi
• Molecular Weight: 890.74
• Reaxy-Rn: 58197086
• Reaxys-RN_link_address: https://www.reaxys.com/reaxys/secured/hopinto.do?context=S&query=IDE.XRN=58197086&ln=

Taxonomic Classification

Taxonomy Tree

• Kingdom Organic compounds
  • Superclass Benzenoids
    • Class Benzene and substituted derivatives
      • Subclass Anilides

• Kingdom: Organic compounds
• Superclass: Benzenoids
• Class: Benzene and substituted derivatives
• Subclass: Anilides
• Intermediate Tree Nodes: Not available
• Direct Parent: Anilides
• Alternative Parents: N-arylamides Fatty amides Secondary carboxylic acid amides Guanidines Organic oxides Hydrochlorides Hydrocarbon derivatives Carbonyl compounds
• Molecular Framework: Aromatic homomonocyclic compounds
• Substituents: Anilide - N-arylamide - Fatty amide - Fatty acyl - Secondary carboxylic acid amide - Guanidine - Carboxamide group - Carboxylic acid derivative - Organic oxygen compound - Hydrochloride - Carbonyl group - Organic nitrogen compound - Organooxygen compound - Organonitrogen compound - Hydrocarbon derivative - Organic oxide - Aromatic homomonocyclic compound
• Description: This compound belongs to the class of organic compounds known as anilides. These are organic heterocyclic compounds derived from oxoacids RkE(=O)l(OH)m (l not 0) by replacing an OH group by the NHPh group or derivative formed by ring substitution.
• External Descriptors: Not available

Data sources

1. Djoumbou Feunang Y, Eisner R, Knox C, Chepelev L, Hastings J, Owen G, Fahy E, Steinbeck C, Subramanian S, Bolton E, Greiner R, and Wishart DS. ClassyFire: Automated Chemical Classification With A Comprehensive, Computable Taxonomy. Journal of Cheminformatics, 2016, 8:61.

DOI: 10.1186/s13321-016-0174-y

Chemical and Physical Properties

• Solubility: H2O : 2.17 mg/mL (2.44 mM; ultrasonic and warming and heat to 60°C)
• Molecular Weight: 890.700 g/mol
• Hydrogen Bond Donor Count: 14
• Hydrogen Bond Acceptor Count: 10
• Rotatable Bond Count: 19
• Exact Mass: 890.356 Da
• Monoisotopic Mass: 888.359 Da
• Topological Polar Surface Area: 365.000 Ų
• Heavy Atom Count: 58
• Formal Charge: 0
• Complexity: 1290.000
• Isotope Atom Count: 0
• Defined Atom Stereocenter Count: 0
• Undefined Atom Stereocenter Count: 0
• Defined Bond Stereocenter Count: 4
• Undefined Bond Stereocenter Count: 0
• The total count of all stereochemical bonds: 4
• Covalently-Bonded Unit Count: 5

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