WARNING: This product is for research use only, not for human or veterinary use.
Hodoodo CAT#: H326719
CAS#: 184025-19-2 (maleate)
Description: Ciproxifan, also known as FUB-359, is an extremely potent histamine H3 inverse agonist/antagonist. Ciproxifan produces wakefulness and attentiveness in animal studies, and produced cognitive enhancing effects without prominent stimulant effects at relatively low levels of receptor occupancy, and pronounced wakefulness at higher doses. It has therefore been proposed as a potential treatment for sleep disorders such as narcolepsy and to improve vigilance in old age, particularly in the treatment of conditions such as Alzheimer's disease. It also potentiated the effects of antipsychotic drugs, and has been suggested as an adjuvant treatment for schizophrenia.
Hodoodo Cat#: H326719
Name: Ciproxifan maleate
CAS#: 184025-19-2 (maleate)
Chemical Formula: C20H22N2O6
Exact Mass: 270.14
Molecular Weight: 386.404
Elemental Analysis: C, 62.17; H, 5.74; N, 7.25; O, 24.84
Related CAS #: 184025-18-1 (free base) 184025-19-2 (maleate)
Synonym: FUB-359; FUB 359; FUB359; Ciproxifan. Ciproxifan maleate
IUPAC/Chemical Name: Cyclopropyl-(4-(3-1H-imidazol-4-yl)propyloxyphenyl)ketone maleate
InChi Key: RLQFKEYRALXXEJ-BTJKTKAUSA-N
InChi Code: InChI=1S/C16H18N2O2.C4H4O4/c19-16(12-3-4-12)13-5-7-15(8-6-13)20-9-1-2-14-10-17-11-18-14;5-3(6)1-2-4(7)8/h5-8,10-12H,1-4,9H2,(H,17,18);1-2H,(H,5,6)(H,7,8)/b;2-1-
SMILES Code: O=C(C1CC1)C2=CC=C(OCCCC3=CNC=N3)C=C2.O=C(O)/C=C\C(O)=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, not in water
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: Related: 184025-18-1 (Ciproxifan free) 184025-19-2 (maleate) The histamine H3 receptor is an inhibitory autoreceptor located on histaminergic nerve terminals, and is believed to be involved in modulating the release of histamine in the brain. Histamine has an excitatory effect in the brain via H1 receptors in the cerebral cortex, and so drugs such as ciproxifan which block the H3 receptor and consequently allow more histamine to be released have an alertness-promoting effect.[
Biological target: | Ciproxifan maleate (FUB 359 maleate) is a competitive antagonist of histamine H3-receptor, with an IC50 of 9.2 nM. |
In vitro activity: | Ciproxifan significantly improved the behavioural parameters in RAM. Ciproxifan increased ACh and showed anti-oxidant properties by reducing NO and LPO levels as well as enhancing antioxidant levels. The neuroinflammatory analysis showed that ciproxifan reduced both COX-1 and COX-2 activities, decreased the level of pro-inflammatory cytokines IL-1α, IL-1β and IL-6 and increased the level of anti-inflammatory cytokine TGF-1β. Reference: Life Sci. 2017 Jul 1;180:23-35. https://pubmed.ncbi.nlm.nih.gov/28501482/ |
In vivo activity: | Ciproxifan increased memory retrieval of D2 in nonstress condition and of D1 in stress one. Ciproxifan mitigated the stress-induced increase of Fos expression in the prelimbic and infralimbic cortex, the central and basolateral amygdala and the CA1 of mouse dorsal hippocampus. Reference: CNS Neurosci Ther. 2019 Aug;25(8):832-841. https://pubmed.ncbi.nlm.nih.gov/31094061/ |
Solvent | Max Conc. mg/mL | Max Conc. mM | |
---|---|---|---|
Solubility | |||
DMSO | 77.0 | 199.27 | |
Ethanol | 54.0 | 139.75 | |
Water | 2.3 | 5.93 |
The following data is based on the product molecular weight 386.40 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.
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: | 1. Mani V, Jaafar SM, Azahan NSM, Ramasamy K, Lim SM, Ming LC, Majeed ABA. Ciproxifan improves cholinergic transmission, attenuates neuroinflammation and oxidative stress but does not reduce amyloid level in transgenic mice. Life Sci. 2017 Jul 1;180:23-35. doi: 10.1016/j.lfs.2017.05.013. Epub 2017 May 10. PMID: 28501482. 2. Chauveau F, De Job E, Poly-Thomasson B, Cavroy R, Thomasson J, Fromage D, Beracochea D. Procognitive impact of ciproxifan (a histaminergic H3 receptor antagonist) on contextual memory retrieval after acute stress. CNS Neurosci Ther. 2019 Aug;25(8):832-841. doi: 10.1111/cns.13113. Epub 2019 May 15. PMID: 31094061; PMCID: PMC6630007. 3. Lu CW, Lin TY, Chang CY, Huang SK, Wang SJ. Ciproxifan, a histamine H3 receptor antagonist and inverse agonist, presynaptically inhibits glutamate release in rat hippocampus. Toxicol Appl Pharmacol. 2017 Mar 15;319:12-21. doi: 10.1016/j.taap.2017.01.017. Epub 2017 Jan 27. PMID: 28132918. |
In vitro protocol: | 1. Mani V, Jaafar SM, Azahan NSM, Ramasamy K, Lim SM, Ming LC, Majeed ABA. Ciproxifan improves cholinergic transmission, attenuates neuroinflammation and oxidative stress but does not reduce amyloid level in transgenic mice. Life Sci. 2017 Jul 1;180:23-35. doi: 10.1016/j.lfs.2017.05.013. Epub 2017 May 10. PMID: 28501482. |
In vivo protocol: | 1. Chauveau F, De Job E, Poly-Thomasson B, Cavroy R, Thomasson J, Fromage D, Beracochea D. Procognitive impact of ciproxifan (a histaminergic H3 receptor antagonist) on contextual memory retrieval after acute stress. CNS Neurosci Ther. 2019 Aug;25(8):832-841. doi: 10.1111/cns.13113. Epub 2019 May 15. PMID: 31094061; PMCID: PMC6630007. 2. Lu CW, Lin TY, Chang CY, Huang SK, Wang SJ. Ciproxifan, a histamine H3 receptor antagonist and inverse agonist, presynaptically inhibits glutamate release in rat hippocampus. Toxicol Appl Pharmacol. 2017 Mar 15;319:12-21. doi: 10.1016/j.taap.2017.01.017. Epub 2017 Jan 27. PMID: 28132918. |
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