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L6295

Sigma-Aldrich

Lomerizine dihydrochloride

≥98% (HPLC), powder

Synonym(s):

1-[Bis(4-fluorophenyl)methyl]-4-[(2,3,4-trimethoxyphenyl)methyl]piperazine dihydrochloride

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About This Item

Empirical Formula (Hill Notation):
C27H30F2N2O3·2HCl
CAS Number:
101477-54-7
Molecular Weight:
541.46
MDL number:
MFCD01703867
UNSPSC Code:
12352200
PubChem Substance ID:
329817637
NACRES:
NA.25

assay

≥98% (HPLC)

form

powder

color

white to tan

solubility

DMSO: ≥30 mg/mL

storage temp.

2-8°C

SMILES string

Cl.Cl.COc1ccc(CN2CCN(CC2)C(c3ccc(F)cc3)c4ccc(F)cc4)c(OC)c1OC

InChI

1S/C27H30F2N2O3.2ClH/c1-32-24-13-8-21(26(33-2)27(24)34-3)18-30-14-16-31(17-15-30)25(19-4-9-22(28)10-5-19)20-6-11-23(29)12-7-20;;/h4-13,25H,14-18H2,1-3H3;2*1H

InChI key

LOGVKVSFYBBUAJ-UHFFFAOYSA-N

Biochem/physiol Actions

Lomerizine dihydrochloride is a voltage-dependent calcium channel blocker and selective cerebral vasodilator. It is one of the most selective calcium channel blockers for the CNS and cerebral arteries. It has been reported to inhibit both T-type and L-type Ca2+ currents in rat hippocampal CA1 pyramidal neurons, to prevent glutamate-induced neurotoxicity in rat hippocampal primary cell cultures, and to exhibit protective effects in animal models of migraine, ischemia and hypoxia. In Japan, lomerizine has been used as the first-line prophylactic drug for migraines.

pictograms

Exclamation markEnvironment
GHS07,GHS09

signalword

Warning

hcodes

H302,H410

Hazard Classifications

Acute Tox. 4 Oral - Aquatic Acute 1 - Aquatic Chronic 1

Storage Class

11 - Combustible Solids

wgk_germany

WGK 3

flash_point_f

Not applicable

flash_point_c

Not applicable

Certificates of Analysis (COA)

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Yasuhiro Tamaki et al.
Investigative ophthalmology & visual science, 44(11), 4864-4871 (2003-10-28)
To investigate the effects of lomerizine, a Ca2+ antagonist, on the ocular tissue circulation in rabbits and on the circulation in the optic nerve head (ONH) and choroid in healthy volunteers. Lomerizine (0.1 [n=10] or 0.3 [n=11] mg/kg) or vehicle
Toshiki Mizuno et al.
Clinical neuropharmacology, 32(2), 113-116 (2009-06-11)
A 64-year-old woman was admitted to our hospital for recurrent stroke and cognitive impairment and was diagnosed with cerebral autosomal dominant arteriopathy with subcortical infarcts and leukoencephalopathy (CADASIL). Iodine-123 iodoamphetamine single photon emission computed tomography showed hypoperfusion in the whole
Bian-Sheng Ji et al.
Die Pharmazie, 65(7), 515-519 (2010-07-29)
P-Glycoprotein, a 170-180 kDa membrane glycoprotein that mediates multidrug resistance, hydrolyses ATP to efflux a broad spectrum of hydrophobic agents. To observe the interaction of a P-gp reversal agent with P-gp ATPase activity should provide further insights into the mechanisms
Melinda Fitzgerald et al.
Experimental neurology, 216(1), 219-230 (2009-01-03)
Secondary degeneration is a form of 'bystander' damage that can affect neural tissue both nearby and remote from an initial injury. Partial optic nerve transection is an excellent model in which to unequivocally differentiate events occurring during secondary degeneration from
Melinda Fitzgerald et al.
Investigative ophthalmology & visual science, 50(11), 5456-5462 (2009-05-29)
After partial optic nerve (ON) injury, intact retinal ganglion cells (RGCs) undergo secondary death, but the topographic distribution of this death is unknown, and it is unclear which cell death pathways are involved. Although the calcium channel blocker lomerizine reduces
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