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C6848

Ciproxifan maleate

≥98% (HPLC), powder

Sinónimos:

Cyclopropyl (4-[3-(1H-imidazol-4-yl)propyloxy]phenyl) ketone maleate salt, FUB 359 maleate salt

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Fórmula empírica (notación de Hill):
C16H18N2O2 · C4H4O4
Número CAS:
184025-19-2
Peso molecular:
386.40
NACRES:
NA.77
PubChem Substance ID:
24892901
UNSPSC Code:
12352200
MDL number:
MFCD06411563
Assay:
≥98% (HPLC)
Form:
powder
Quality level:
100
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Quality Level

100

assay

≥98% (HPLC)

form

powder

color

white to beige

solubility

DMSO: 32 mg/mL, H2O: insoluble

SMILES string

OC(=O)\C=C/C(O)=O.O=C(C1CC1)c2ccc(OCCCc3c[nH]cn3)cc2

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-

InChI key

RLQFKEYRALXXEJ-BTJKTKAUSA-N

Application

Ciproxifan maleate has been used as a selective H3R antagonist to investigate the antidepressant potential of ciproxifan in chronic unpredictable stress (CUS) model of depression in mice. It has also been used as an H3R antagonist to develop in vivo receptor occupancy assay for histamine H3 receptors (H3R)/to determine the occupancy of exogenous H3R antagonists using non-radiolabeled GSK189254 as a tracer in the rat.

Biochem/physiol Actions

Cyclopropyl 4-(3-(1H-imidazol-4-yl)propyloxy)phenyl methanone (Ciproxifan) is a species-specific histamine H3 receptor (H3R) inverse agonist. It is mainly used as a reference H3R antagonist in rodent models for neurological diseases, Alzheimer′s disease, attention deficit hyperactivity disorder (ADHD), and sleep-wake disorders. It can block monoamine oxidase A (MAO-A) and monoamine oxidase B (MAO-B) enzyme isoforms reversibly in humans and rats.
Potent, selective H3 histamine receptor antagonist.

Features and Benefits

This compound is featured on the Histamine Receptors page of the Handbook of Receptor Classification and Signal Transduction. To browse other handbook pages, click here.

pictograms

Exclamation mark
GHS07

signalword

Warning

Hazard Classifications

Acute Tox. 4 Oral - Eye Irrit. 2 - Skin Irrit. 2 - Skin Sens. 1 - STOT SE 3

target_organs

Respiratory system

Clase de almacenamiento

11 - Combustible Solids

wgk

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

ppe

dust mask type N95 (US), Eyeshields, Faceshields, Gloves

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Certificados de análisis (COA)

Lot/Batch Number
0000113404
043M4762V
125K46062
125K4606
125K46061

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S Hagenow et al.
Scientific reports, 7, 40541-40541 (2017-01-14)
Ciproxifan is a well-investigated histamine H3 receptor (H3R) inverse agonist/antagonist, showing an exclusively high species-specific affinity at rodent compared to human H3R. It is well studied as reference compound for H3R in rodent models for neurological diseases connected with neurotransmitter
Ramakrishna Nirogi et al.
Journal of pharmacological and toxicological methods, 65(3), 115-121 (2012-04-11)
Rapid and reliable preclinical receptor occupancy measurement at the target organ in relevant species is critical in accelerating the drug hunting process. The aim of this study was to develop in vivo receptor occupancy assay for histamine H₃ receptors (H₃R)
X Ligneau et al.
The Journal of pharmacology and experimental therapeutics, 287(2), 658-666 (1998-11-10)
Ciproxifan, i.e., cyclopropyl-(4-(3-1H-imidazol-4-yl)propyloxy) phenyl) ketone, belongs to a novel chemical series of histamine H3-receptor antagonists. In vitro, it behaved as a competitive antagonist at the H3 autoreceptor controlling [3H]histamine release from synaptosomes and displayed similar Ki values (0.5-1.9 nM) at
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