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MedKoo Cat#: 581833 | Name: Semapimod HCl hydrate

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Semapimod, known as CNI-1493, is a cytokine inhibitor. Semapimod is an investigational new drug which has anti-inflammatory, anti-cytokine, immunomodulatory, antiviral and antimalarial properties. Structurally, semapimod is synthetic guanylhydrazone mitogen-activated protein kinase blocker, as a potential treatment for Crohn's disease and other inflammatory conditions.

Chemical Structure

Semapimod HCl hydrate
CAS#872830-76-7 (HCl hydrate)

Theoretical Analysis

MedKoo Cat#: 581833

Name: Semapimod HCl hydrate

CAS#: 872830-76-7 (HCl hydrate)

Chemical Formula: C34H62Cl2N18O6

Exact Mass: 888.4477

Molecular Weight: 889.89

Elemental Analysis: C, 45.89; H, 7.02; Cl, 7.97; N, 28.33; O, 10.79

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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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 hydrochloride dihydrate; CNI1493; CNI-1493; CNI1493; AXD-455; AXD 455; AXD455; AIDS121302; AIDS-121302
IUPAC/Chemical Name
Decanediamide, N1,N10-bis(3,5-bis(1-(2-(aminoiminomethyl)hydrazinylidene)ethyl)phenyl)-, hydrochloride, hydrate (1:2:4)
InChi Key
KAMCPCQWHXZEMM-OBDKKVINSA-N
InChi Code
InChI=1S/C34H52N18O2.2ClH.4H2O/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);2*1H;4*1H2/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.[H]Cl.[H]Cl.[H]O[H].[H]O[H].[H]O[H].[H]O[H]
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
>3 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

Preparing Stock Solutions

The following data is based on the product molecular weight 889.89 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
1: Zheng EJ, Valeri JA, Andrews IW, Krishnan A, Bandyopadhyay P, Anahtar MN, Herneisen A, Schulte F, Linnehan B, Wong F, Stokes JM, Renner LD, Lourido S, Collins JJ. Discovery of antibiotics that selectively kill metabolically dormant bacteria. Cell Chem Biol. 2024 Apr 18;31(4):712-728.e9. doi: 10.1016/j.chembiol.2023.10.026. Epub 2023 Nov 28. PMID: 38029756; PMCID: PMC11031330. 2: Sankowski R, Herring A, Keyvani K, Frenzel K, Wu J, Röskam S, Noelker C, Bacher M, Al-Abed Y. The multi-target effects of CNI-1493: convergence of anti- amylodogenic and anti-inflammatory properties in animal models of Alzheimer's disease. Mol Med. 2016 Dec;22:776-788. doi: 10.2119/molmed.2016.00163. Epub 2016 Nov 15. PMID: 27847962; PMCID: PMC5193463. 3: Coniglio S, Miller I, Symons M, Segall JE. Coculture Assays to Study Macrophage and Microglia Stimulation of Glioblastoma Invasion. J Vis Exp. 2016 Oct 20;(116):53990. doi: 10.3791/53990. PMID: 27805587; PMCID: PMC5092226. 4: 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. 5: Schröder M, Kolodzik A, Windshügel B, Krepstakies M, Priyadarshini P, Hartjen P, van Lunzen J, Rarey M, Hauber J, Meier C. Linker-Region Modified Derivatives of the Deoxyhypusine Synthase Inhibitor CNI-1493 Suppress HIV-1 Replication. Arch Pharm (Weinheim). 2016 Feb;349(2):91-103. doi: 10.1002/ardp.201500323. Epub 2016 Jan 3. PMID: 26725082. 6: Hesketh AJ, Maloney C, Behr CA, Edelman MC, Glick RD, Al-Abed Y, Symons M, Soffer SZ, Steinberg BM. The Macrophage Inhibitor CNI-1493 Blocks Metastasis in a Mouse Model of Ewing Sarcoma through Inhibition of Extravasation. PLoS One. 2015 Dec 28;10(12):e0145197. doi: 10.1371/journal.pone.0145197. PMID: 26709919; PMCID: PMC4692435. 7: 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. 8: Vilz TO, Sommer N, Kahl P, Pantelis D, Kalff JC, Wehner S. Oral CPSI-2364 treatment prevents postoperative ileus in swine without impairment of anastomotic healing. Cell Physiol Biochem. 2013;32(5):1362-73. doi: 10.1159/000356575. Epub 2013 Nov 22. PMID: 24280834. 9: Websky Mv, Fujishiro J, Ohsawa I, Praktiknjo M, Wehner S, Abu-Elmagd K, Kitamura K, Kalff JC, Schaefer N, Pech T. The novel guanylhydrazone CPSI-2364 ameliorates ischemia reperfusion injury after experimental small bowel transplantation. Transplantation. 2013 Jun 15;95(11):1315-23. doi: 10.1097/TP.0b013e31828e72fa. PMID: 23598944. 10: Noelker C, Stuckenholz V, Reese JP, Alvarez-Fischer D, Sankowski R, Rausch T, Oertel WH, Hartmann A, van Patten S, Al-Abed Y, Bacher M. CNI-1493 attenuates neuroinflammation and dopaminergic neurodegeneration in the acute MPTP mouse model of Parkinson's disease. Neurodegener Dis. 2013;12(2):103-10. doi: 10.1159/000342714. Epub 2012 Nov 7. PMID: 23147695. 11: 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. 12: Wehner S, Vilz TO, Sommer N, Sielecki T, Hong GS, Lysson M, Stoffels B, Pantelis D, Kalff JC. The novel orally active guanylhydrazone CPSI-2364 prevents postoperative ileus in mice independently of anti-inflammatory vagus nerve signaling. Langenbecks Arch Surg. 2012 Oct;397(7):1139-47. doi: 10.1007/s00423-012-0989-6. Epub 2012 Aug 19. PMID: 22903876. 13: Ziegler P, Chahoud T, Wilhelm T, Pällman N, Braig M, Wiehle V, Ziegler S, Schröder M, Meier C, Kolodzik A, Rarey M, Panse J, Hauber J, Balabanov S, Brümmendorf TH. Evaluation of deoxyhypusine synthase inhibitors targeting BCR- ABL positive leukemias. Invest New Drugs. 2012 Dec;30(6):2274-83. doi: 10.1007/s10637-012-9810-1. Epub 2012 Mar 14. PMID: 22415796. 14: Oettinger CW, D'Souza MJ. Microencapsulated drug delivery: a new approach to pro-inflammatory cytokine inhibition. J Microencapsul. 2012;29(5):455-62. doi: 10.3109/02652048.2012.658443. Epub 2012 Feb 21. PMID: 22348221; PMCID: PMC3433085. 15: Bach JP, Mengel D, Wahle T, Kautz A, Balzer-Geldsetzer M, Al-Abed Y, Dodel R, Bacher M. The role of CNI-1493 in the function of primary microglia with respect to amyloid-β. J Alzheimers Dis. 2011;26(1):69-80. doi: 10.3233/JAD-2011-110179. PMID: 21593565. 16: Woriedh M, Hauber I, Martinez-Rocha AL, Voigt C, Maier FJ, Schröder M, Meier C, Hauber J, Schäfer W. Preventing Fusarium head blight of wheat and cob rot of maize by inhibition of fungal deoxyhypusine synthase. Mol Plant Microbe Interact. 2011 May;24(5):619-27. doi: 10.1094/MPMI-03-10-0068. PMID: 21463208. 17: The F, Cailotto C, van der Vliet J, de Jonge WJ, Bennink RJ, Buijs RM, Boeckxstaens GE. Central activation of the cholinergic anti-inflammatory pathway reduces surgical inflammation in experimental post-operative ileus. Br J Pharmacol. 2011 Jul;163(5):1007-16. doi: 10.1111/j.1476-5381.2011.01296.x. PMID: 21371006; PMCID: PMC3130947. 18: 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. 19: Tomillero A, Moral MA. Gateways to clinical trials. Methods Find Exp Clin Pharmacol. 2010 Nov;32(9):675-703. doi: 10.1358/mf.2010.32.9.1563109. PMID: 21225019. 20: dos Santos CC, Shan Y, Akram A, Slutsky AS, Haitsma JJ. Neuroimmune regulation of ventilator-induced lung injury. Am J Respir Crit Care Med. 2011 Feb 15;183(4):471-82. doi: 10.1164/rccm.201002-0314OC. Epub 2010 Sep 24. PMID: 20870758.