Ciproxifan maleate
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MedKoo CAT#: 326719

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.

Chemical Structure

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Ciproxifan maleate
CAS# 184025-19-2 (maleate)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 326719
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

Price and Availability

Size Price Availability Quantity
100mg USD 950
200mg USD 1650
500mg USD 2150
1g USD 3250
2g USD 4950
5g USD 7450
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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.[

Product Data:
Product Data
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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/

Solubility Data

Solvent Max Conc. mg/mL Max Conc. mM
Solubility
DMSO 77.0 199.27
Ethanol 54.0 139.75
Water 2.3 5.93

Preparing Stock Solutions

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.

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: 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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1: Ding F, Zheng L, Liu M, Chen R, Leung LS, Luo T. Ciproxifan, an H3 receptor antagonist, improves short-term recognition memory impaired by isoflurane anesthesia. J Anesth. 2016 May 19. [Epub ahead of print] PubMed PMID: 27193325.

2: Mahmood D, Akhtar M, Jahan K, Goswami D. Histamine H3 receptor antagonists display antischizophrenic activities in rats treated with MK-801. J Basic Clin Physiol Pharmacol. 2016 Apr 18. pii: /j/jbcpp.ahead-of-print/jbcpp-2015-0045/jbcpp-2015-0045.xml. doi: 10.1515/jbcpp-2015-0045. [Epub ahead of print] PubMed PMID: 27089413.

3: Parmentier R, Zhao Y, Perier M, Akaoka H, Lintunen M, Hou Y, Panula P, Watanabe T, Franco P, Lin JS. Role of histamine H1-receptor on behavioral states and wake maintenance during deficiency of a brain activating system: A study using a knockout mouse model. Neuropharmacology. 2016 Jul;106:20-34. doi: 10.1016/j.neuropharm.2015.12.014. Epub 2015 Dec 23. PubMed PMID: 26723880.

4: Mahmood D, Pillai KK, Khanam R, Jahan K, Goswami D, Akhtar M. The Effect of Subchronic Dosing of Ciproxifan and Clobenpropit on Dopamine and Histamine Levels in Rats. J Exp Neurosci. 2015 Aug 31;9:73-80. doi: 10.4137/JEN.S27244. eCollection 2015. PubMed PMID: 26379444; PubMed Central PMCID: PMC4556212.

5: Aquino-Miranda G, Escamilla-Sánchez J, González-Pantoja R, Bueno-Nava A, Arias-Montaño JA. Histamine H3 receptor activation inhibits dopamine synthesis but not release or uptake in rat nucleus accumbens. Neuropharmacology. 2016 Jul;106:91-101. doi: 10.1016/j.neuropharm.2015.07.006. Epub 2015 Jul 10. PubMed PMID: 26169221.

6: Nuutinen S, Mäki T, Rozov S, Bäckström P, Hyytiä P, Piepponen P, Panula P. Histamine H3 receptor antagonist decreases cue-induced alcohol reinstatement in mice. Neuropharmacology. 2016 Jul;106:156-63. doi: 10.1016/j.neuropharm.2015.06.006. Epub 2015 Jun 21. PubMed PMID: 26107118.

7: Muindi F, Colas D, Ikeme J, Ruby NF, Heller HC. Loss of Melanopsin Photoreception and Antagonism of the Histamine H3 Receptor by Ciproxifan Inhibit Light-Induced Sleep in Mice. PLoS One. 2015 Jun 17;10(6):e0128175. doi: 10.1371/journal.pone.0128175. eCollection 2015. PubMed PMID: 26083020; PubMed Central PMCID: PMC4471207.

8: Lin JJ, Zhao TZ, Cai WK, Yang YX, Sun C, Zhang Z, Xu YQ, Chang T, Li ZY. Inhibition of histamine receptor 3 suppresses glioblastoma tumor growth, invasion, and epithelial-to-mesenchymal transition. Oncotarget. 2015 Jul 10;6(19):17107-20. PubMed PMID: 25940798; PubMed Central PMCID: PMC4627295.

9: Trofimiuk E, Braszko JJ. Ciproxifan differentially modifies cognitive impairment evoked by chronic stress and chronic corticosterone administration in rats. Behav Brain Res. 2015 Apr 15;283:145-53. doi: 10.1016/j.bbr.2015.01.038. Epub 2015 Jan 29. PubMed PMID: 25639546.

10: Baronio D, Castro K, Gonchoroski T, de Melo GM, Nunes GD, Bambini-Junior V, Gottfried C, Riesgo R. Effects of an H3R antagonist on the animal model of autism induced by prenatal exposure to valproic acid. PLoS One. 2015 Jan 5;10(1):e0116363. doi: 10.1371/journal.pone.0116363. eCollection 2015. PubMed PMID: 25560049; PubMed Central PMCID: PMC4283962.

11: Chauveau F, Laudereau K, Libourel PA, Gervasoni D, Thomasson J, Poly B, Pierard C, Beracochea D. Ciproxifan improves working memory through increased prefrontal cortex neural activity in sleep-restricted mice. Neuropharmacology. 2014 Oct;85:349-56. doi: 10.1016/j.neuropharm.2014.04.017. Epub 2014 May 4. PubMed PMID: 24796256.

12: Trofimiuk E, Braszko JJ. Single dose of H3 receptor antagonist--ciproxifan--abolishes negative effects of chronic stress on cognitive processes in rats. Psychopharmacology (Berl). 2014 Jan;231(1):209-19. doi: 10.1007/s00213-013-3227-1. Epub 2013 Aug 24. PubMed PMID: 23975035.

13: Flores-Clemente C, Osorio-Espinoza A, Escamilla-Sánchez J, Leurs R, Arias JM, Arias-Montaño JA. A single-point mutation (Ala280Val) in the third intracellular loop alters the signalling properties of the human histamine H₃ receptor stably expressed in CHO-K1 cells. Br J Pharmacol. 2013 Sep;170(1):127-35. doi: 10.1111/bph.12257. PubMed PMID: 23713487; PubMed Central PMCID: PMC3764854.

14: Chee SS, Menard JL. The histaminergic H1, H2, and H3 receptors of the lateral septum differentially mediate the anxiolytic-like effects of histamine on rats' defensive behaviors in the elevated plus maze and novelty-induced suppression of feeding paradigm. Physiol Behav. 2013 May 27;116-117:66-74. doi: 10.1016/j.physbeh.2013.03.016. Epub 2013 Mar 25. PubMed PMID: 23535246.

15: Karlstedt K, Jin C, Panula P. Expression of histamine receptor genes Hrh3 and Hrh4 in rat brain endothelial cells. Br J Pharmacol. 2013 Sep;170(1):58-66. doi: 10.1111/bph.12173. PubMed PMID: 23488566; PubMed Central PMCID: PMC3764849.

16: Gondard E, Anaclet C, Akaoka H, Guo RX, Zhang M, Buda C, Franco P, Kotani H, Lin JS. Enhanced histaminergic neurotransmission and sleep-wake alterations, a study in histamine H3-receptor knock-out mice. Neuropsychopharmacology. 2013 May;38(6):1015-31. doi: 10.1038/npp.2012.266. Epub 2013 Jan 2. PubMed PMID: 23303066; PubMed Central PMCID: PMC3629391.

17: Zhang DD, Sisignano M, Schuh CD, Sander K, Stark H, Scholich K. Overdose of the histamine H₃ inverse agonist pitolisant increases thermal pain thresholds. Inflamm Res. 2012 Nov;61(11):1283-91. doi: 10.1007/s00011-012-0528-5. Epub 2012 Jul 21. PubMed PMID: 22820944.

18: Fell MJ, Katner JS, Rasmussen K, Nikolayev A, Kuo MS, Nelson DL, Perry KW, Svensson KA. Typical and atypical antipsychotic drugs increase extracellular histamine levels in the rat medial prefrontal cortex: contribution of histamine h(1) receptor blockade. Front Psychiatry. 2012 May 17;3:49. doi: 10.3389/fpsyt.2012.00049. eCollection 2012. PubMed PMID: 22629251; PubMed Central PMCID: PMC3354526.

19: Mahmood D, Khanam R, Pillai KK, Akhtar M. Protective effects of histamine H3-receptor ligands in schizophrenic behaviors in experimental models. Pharmacol Rep. 2012;64(1):191-204. PubMed PMID: 22580536.

20: Griebel G, Decobert M, Jacquet A, Beeské S. Awakening properties of newly discovered highly selective H₃ receptor antagonists in rats. Behav Brain Res. 2012 Jul 1;232(2):416-20. doi: 10.1016/j.bbr.2012.04.033. Epub 2012 Apr 26. PubMed PMID: 22561131.