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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

Signal Word

Warning

Hazard Statements

H302,H410

Hazard Classifications

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

Storage Class Code

11 - Combustible Solids

WGK

WGK 3

Flash Point(F)

Not applicable

Flash Point(C)

Not applicable

Certificates of Analysis (COA)

Search for Certificates of Analysis (COA) by entering the products Lot/Batch Number. Lot and Batch Numbers can be found on a product’s label following the words ‘Lot’ or ‘Batch’.

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N Shiraki et al.
Biological & pharmaceutical bulletin, 24(5), 555-557 (2001-05-31)
Acquired resistance to chemotherapy is a major problem during cancer treatment. One mechanism for drug resistance is overexpression of the MDR (multidrug resistance)1 gene encoding the transmembrane efflux pump, P-glycoprotein (P-gp). Calcium channel blockers such as verapamil, nifedipine and nicardipine
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
Tomoko Hibino et al.
Journal of pharmacological sciences, 108(1), 89-94 (2008-09-09)
The effects of goshuyuto and chotosan, traditional Japanese medicines, on collagen-induced platelet aggregation were examined using guinea-pig blood. Goshuyuto at the concentration of 1,000 mug/mL inhibited collagen-induced platelet hyper-aggregation to the same degree as aspirin at the concentration of 100
Bian-Sheng Ji et al.
Acta pharmacologica Sinica, 27(4), 414-418 (2006-03-17)
To investigate the modulatory effect of CJZ3, a lomerizine derivative, on P-glycoprotein (P-gp) function in rat brain microvessel endothelial cells (RBMEC). RBMEC were isolated and cultured in Dulbecco modified Eagle medium/F12 (1:1) medium, and the amount of intracellular rhodamine 123
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
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