Semapimod (free base)

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MedKoo CAT#: 413211

CAS#: 352513-83-8 (free base)

Description: Semapimod (free base) is a macrophage-deactivating agent used to treat experimental autoimmune encephalomyelitis in mice; a tetravalent guanylhydrazone.

Chemical Structure

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Semapimod (free base)
CAS# 352513-83-8 (free base)
Instruction

Theoretical Analysis

MedKoo Cat#: 413211
Name: Semapimod (free base)
CAS#: 352513-83-8 (free base)
Chemical Formula: C34H52N18O2
Exact Mass: 744.45
Molecular Weight: 744.910
Elemental Analysis: C, 54.82; H, 7.04; N, 33.85; O, 4.30

Price and Availability

This product is not in stock, which may be available by custom synthesis. For cost-effective reason, minimum order is 1g (price is usually high, lead time is 2~3 months, depending on the technical challenge). Quote less than 1g will not be provided. To request quote, please email to sales @medkoo.com or click below button.
Note: Price will be listed if it is available in the future.

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Related CAS #: 164301-51-3 (HCl)   352513-83-8 (free base)   872830-76-7 (HCl hydrate)   872830-80-3 (mesylate)    

Synonym: Semapimod (free base); CNI1493; CNI 1493; CNI-1493

IUPAC/Chemical Name: N,N'-Bis{3,5-bis(1-(carbamimidoylhydrazono)ethyl)phenyl}decanediamide

InChi Key: PWDYHMBTPGXCSN-VCBMUGGBSA-N

InChi Code: InChI=1S/C34H52N18O2/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)/b45-19+,46-20+,47-21+,48-22+

SMILES Code: O=C(NC1=CC(/C(C)=N/NC(N)=N)=CC(/C(C)=N/NC(N)=N)=C1)CCCCCCCCC(NC2=CC(/C(C)=N/NC(N)=N)=CC(/C(C)=N/NC(N)=N)=C2)=O

Appearance: Solid powder

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

Shipping Condition: Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.

Storage Condition: Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).

Solubility: Soluble in DMSO

Shelf Life: >2 years if stored properly

Drug Formulation: This drug may be formulated in DMSO

Stock Solution Storage: 0 - 4 C for short term (days to weeks), or -20 C for long term (months).

HS Tariff Code: 2934.99.9001

More Info:

Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 744.91 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Sitaraman SV, Hoteit M, Gewirtz AT. Semapimod. Cytokine. Curr Opin Investig Drugs. 2003 Nov;4(11):1363-8. PMID: 14758776.

2: Miller IS, Didier S, Murray DW, Turner TH, Issaivanan M, Ruggieri R, Al-Abed Y, Symons M. Semapimod sensitizes glioblastoma tumors to ionizing radiation by targeting microglia. PLoS One. 2014 May 9;9(5):e95885. doi: 10.1371/journal.pone.0095885. PMID: 24816734; PMCID: PMC4015930.

3: Wang J, Grishin AV, Ford HR. Experimental Anti-Inflammatory Drug Semapimod Inhibits TLR Signaling by Targeting the TLR Chaperone gp96. J Immunol. 2016 Jun 15;196(12):5130-7. doi: 10.4049/jimmunol.1502135. Epub 2016 May 18. PMID: 27194788; PMCID: PMC4896225.

4: Vlachakis IK, Pitoulias GA, Kontopoulou KE, Kotakidou RE, Kosmidou EK, Kallaitzopoulou ME, Papadimitriou DK. Semapimod a new pretreatment modality of acute intestinal ischemia-reperfusion syndrome: experimental study in rabbits. Int Angiol. 2011 Feb;30(1):35-42. PMID: 21248671.

5: Erin N, Duymuş O, Oztürk S, Demir N. Activation of vagus nerve by semapimod alters substance P levels and decreases breast cancer metastasis. Regul Pept. 2012 Nov 10;179(1-3):101-8. doi: 10.1016/j.regpep.2012.08.001. Epub 2012 Sep 11. PMID: 22982142.

6: Löwenberg M, Verhaar A, van den Blink B, ten Kate F, van Deventer S, Peppelenbosch M, Hommes D. Specific inhibition of c-Raf activity by semapimod induces clinical remission in severe Crohn's disease. J Immunol. 2005 Aug 15;175(4):2293-300. doi: 10.4049/jimmunol.175.4.2293. PMID: 16081798.

7: van Westerloo DJ, Rauws EA, Hommes D, de Vos AF, van der Poll T, Powers BL, Fockens P, Dijkgraaf MG, Bruno MJ. Pre-ERCP infusion of semapimod, a mitogen- activated protein kinases inhibitor, lowers post-ERCP hyperamylasemia but not pancreatitis incidence. Gastrointest Endosc. 2008 Aug;68(2):246-54. doi: 10.1016/j.gie.2008.01.034. Epub 2008 May 2. PMID: 18455169.

8: Kherani AR, Moss GW, Zhou H, Gu A, Zhang G, Schulman AR, Fal JM, Sorabella R, Plasse T, Rui L, Homma S, Burkhoff D, Oz MC, Wang J. Macrophage inhibitor, semapimod, reduces tumor necrosis factor-alpha in myocardium in a rat model of ischemic heart failure. J Cardiovasc Pharmacol. 2004 Dec;44(6):665-71. doi: 10.1097/00005344-200412000-00007. PMID: 15550785.

9: Dotan I, Rachmilewitz D, Schreiber S, Eliakim R, van der Woude CJ, Kornbluth A, Buchman AL, Bar-Meir S, Bokemeyer B, Goldin E, Maaser C, Mahadevan U, Seidler U, Hoffman JC, Homoky D, Plasse T, Powers B, Rutgeerts P, Hommes D; Semapimod- CD04/CD05 Investigators. A randomised placebo-controlled multicentre trial of intravenous semapimod HCl for moderate to severe Crohn's disease. Gut. 2010 Jun;59(6):760-6. doi: 10.1136/gut.2009.179994. PMID: 20551461.

10: Singer AJ, McClain SA, Hacht G, Batchkina G, Simon M. Semapimod reduces the depth of injury resulting in enhanced re-epithelialization of partial-thickness burns in swine. J Burn Care Res. 2006 Jan-Feb;27(1):40-9. doi: 10.1097/01.bcr.0000194276.36691.fb. PMID: 16566536.