Lomerizine dihydrochloride | CAS#101477-54-7 | L-type antagonist | T-type Ca 2+ channels | TRp5 channel

MedKoo Cat#: 540273 | Name: Lomerizine dihydrochloride

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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Lomerizine dihydrochloride is a antagonist at L-type and T-type Ca 2+ channels and TRp5 channels used to treat migraines and vertigo. It also decreases glutamate excitotoxicity, Ca 2+ overload, and mitochondrial dysfunction and protects against NMDA-induced retinal damage and neurodegenration.

Chemical Structure

Lomerizine dihydrochloride

CAS#101477-54-7

Theoretical Analysis

MedKoo Cat#: 540273

Name: Lomerizine dihydrochloride

CAS#: 101477-54-7

Chemical Formula: C27H32Cl2F2N2O3

Exact Mass: 540.1758

Molecular Weight: 541.46

Elemental Analysis: C, 59.89; H, 5.96; Cl, 13.09; F, 7.02; N, 5.17; O, 8.86

Price and Availability

Size	Price	Availability
250mg	USD 250.00	2 weeks
500mg	USD 500.00	2 weeks
1g	USD 850.00	2 Weeks

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Related CAS #

No Data

Synonym

B 2796; B2796; B-2796; Lomerizine dihydrochloride; Lomerizine HCl

IUPAC/Chemical Name

1-(bis(4-fluorophenyl)methyl)-4-(2,3,4-trimethoxybenzyl)piperazine dihydrochloride

InChi Key

LOGVKVSFYBBUAJ-UHFFFAOYSA-N

InChi Code

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

SMILES Code

COC1=CC=C(CN2CCN(C(C3=CC=C(F)C=C3)C4=CC=C(F)C=C4)CC2)C(OC)=C1OC.[H]Cl.[H]Cl

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

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

Product Data

Product Data

Instruction

View handling instruction

Biological target:

Lomerizine dihydrochloride is an antagonist of L- and T-type voltagegated calcium channels.

In vitro activity:

Lom (lomerizine) increased the cytotoxicity of ADM and the apoptosis induced by ADM or VCR in K562/ADM cells. At the concentration of 3, 10 and 30 micromol x L(-1), Lom reduced the IC50 value of ADM from 79.03 micromol x L(-1) to 28.14, 8.16 and 3.16 micromol x L(-1), respectively. Lom increased the intracellular accumulation of ADM and inhibited the efflux of Rh123 in K562/ ADM cells. Reference: Yao Xue Xue Bao. 2004 May;39(5):333-7. https://pubmed.ncbi.nlm.nih.gov/15338873/

In vivo activity:

Lomerizine reduced glutamate excitotoxicity in cultured mouse motor neurons by reducing the accumulation of cytoplasmic Ca(2+) and protected motor neurons against multiple measures of mutant SOD1 toxicity: Ca(2+) overload, impaired mitochondrial trafficking, mitochondrial fragmentation, formation of mutant SOD1 inclusions, and loss of viability. Reference: J Neurochem. 2014 Aug;130(3):455-66. https://pubmed.ncbi.nlm.nih.gov/24716897/

	Solvent	mg/mL	mM
Solubility
	DMF	20.0	36.94
	DMSO	72.5	133.90
	Ethanol	1.0	1.85

Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 541.46 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. Tan XP, He Y, Huang YN, Zheng CC, Li JQ, Liu QW, He ML, Li B, Xu WW. Lomerizine 2HCl inhibits cell proliferation and induces protective autophagy in colorectal cancer via the PI3K/Akt/mTOR signaling pathway. MedComm (2020). 2021 Jul 15;2(3):453-466. doi: 10.1002/mco2.83. PMID: 34766155; PMCID: PMC8554656. 2. Zhu HJ, Wu YL, Liu GQ. [Reversal of multidrug resistance by lomerizine in K562/ADM cells]. Yao Xue Xue Bao. 2004 May;39(5):333-7. Chinese. PMID: 15338873. 3. Tran LT, Gentil BJ, Sullivan KE, Durham HD. The voltage-gated calcium channel blocker lomerizine is neuroprotective in motor neurons expressing mutant SOD1, but not TDP-43. J Neurochem. 2014 Aug;130(3):455-66. doi: 10.1111/jnc.12738. Epub 2014 May 9. PMID: 24716897. 4. Fitzgerald M, Payne SC, Bartlett CA, Evill L, Harvey AR, Dunlop SA. Secondary retinal ganglion cell death and the neuroprotective effects of the calcium channel blocker lomerizine. Invest Ophthalmol Vis Sci. 2009 Nov;50(11):5456-62. doi: 10.1167/iovs.09-3717. Epub 2009 May 27. PMID: 19474405.

In vitro protocol:

In vivo protocol:

1. Tran LT, Gentil BJ, Sullivan KE, Durham HD. The voltage-gated calcium channel blocker lomerizine is neuroprotective in motor neurons expressing mutant SOD1, but not TDP-43. J Neurochem. 2014 Aug;130(3):455-66. doi: 10.1111/jnc.12738. Epub 2014 May 9. PMID: 24716897. 2. Fitzgerald M, Payne SC, Bartlett CA, Evill L, Harvey AR, Dunlop SA. Secondary retinal ganglion cell death and the neuroprotective effects of the calcium channel blocker lomerizine. Invest Ophthalmol Vis Sci. 2009 Nov;50(11):5456-62. doi: 10.1167/iovs.09-3717. Epub 2009 May 27. PMID: 19474405.

1: Furuishi T, Kato Y, Fukami T, Suzuki T, Endo T, Nagase H, Ueda H, Tomono K. Effect of terpenes on the skin permeation of lomerizine dihydrochloride. J Pharm Pharm Sci. 2013;16(4):551-63. PubMed PMID: 24210063. 2: Ito Y, Nakamura S, Tanaka H, Tsuruma K, Shimazawa M, Araie M, Hara H. Lomerizine, a Ca2+ channel blocker, protects against neuronal degeneration within the visual center of the brain after retinal damage in mice. CNS Neurosci Ther. 2010 Apr;16(2):103-14. doi: 10.1111/j.1755-5949.2009.00081.x. Epub 2009 Sep 24. PubMed PMID: 19788586. 3: Ishii M, Iizuka R, Kiuchi Y, Mori Y, Shimizu S. Neuroprotection by lomerizine, a prophylactic drug for migraine, against hydrogen peroxide-induced hippocampal neurotoxicity. Mol Cell Biochem. 2011 Dec;358(1-2):1-11. doi: 10.1007/s11010-011-0913-3. Epub 2011 Jun 9. PubMed PMID: 21656126. 4: Ren Y, Liu T, Song G, Hu Y, Liang J. Determination of lomerizine in human plasma by liquid chromatography/tandem mass spectrometry and its application to a pharmacokinetic study. J Chromatogr B Analyt Technol Biomed Life Sci. 2014 Feb 1;947-948:96-102. doi: 10.1016/j.jchromb.2013.12.026. Epub 2013 Dec 26. PubMed PMID: 24412691. 5: Aoyagi J, Ikeda K, Kiyozuka T, Hirayama T, Ishikawa Y, Sato R, Yoshii Y, Kawabe K, Iwasaki Y. Alleviation of brain hypoperfusion after preventative treatment with lomerizine in an elderly migraineur with aura. Int J Mol Imaging. 2011;2011:782758. doi: 10.1155/2011/782758. Epub 2010 Dec 27. PubMed PMID: 21490733; PubMed Central PMCID: PMC3065840. 6: Ishii M, Katoh H, Kurihara T, Kawamura M, Shimizu S. Characteristics of inconsistent responders to prophylaxis therapy with lomerizine in patients with migraine: a retrospective study in Japan. J Neurol Sci. 2013 Dec 15;335(1-2):118-23. doi: 10.1016/j.jns.2013.09.007. Epub 2013 Sep 12. PubMed PMID: 24074550. 7: Ishii M, Kobayashi S, Ohkura M, Yamamoto R, Shimizu S, Kiuchi Y. Inhibitory effect of lomerizine, a prophylactic drug for migraines, on serotonin-induced contraction of the basilar artery. J Pharmacol Sci. 2009 Oct;111(2):221-5. Epub 2009 Sep 26. PubMed PMID: 19783864. 8: Tamaki Y, Araie M, Fukaya Y, Nagahara M, Imamura A, Honda M, Obata R, Tomita K. Effects of lomerizine, a calcium channel antagonist, on retinal and optic nerve head circulation in rabbits and humans. Invest Ophthalmol Vis Sci. 2003 Nov;44(11):4864-71. PubMed PMID: 14578410. 9: Tran LT, Gentil BJ, Sullivan KE, Durham HD. The voltage-gated calcium channel blocker lomerizine is neuroprotective in motor neurons expressing mutant SOD1, but not TDP-43. J Neurochem. 2014 Aug;130(3):455-66. doi: 10.1111/jnc.12738. Epub 2014 May 9. PubMed PMID: 24716897. 10: Iwasaki S, Ushio M, Chihara Y, Ito K, Sugasawa K, Murofushi T. Migraine-associated vertigo: clinical characteristics of Japanese patients and effect of lomerizine, a calcium channel antagonist. Acta Otolaryngol Suppl. 2007 Dec;(559):45-9. doi: 10.1080/03655230701596491. PubMed PMID: 18340570. 11: Shiraki N, Hamada A, Ohmura T, Tokunaga J, Oyama N, Nakano M. Increase in doxorubicin cytotoxicity by inhibition of P-glycoprotein activity with lomerizine. Biol Pharm Bull. 2001 May;24(5):555-7. PubMed PMID: 11379779. 12: Hara H, Shimazawa M, Hashimoto M, Sukamoto T. [Anti-migraine effects of lomerizine]. Nihon Yakurigaku Zasshi. 1998 Oct;112 Suppl 1:138P-142P. Japanese. PubMed PMID: 10190151. 13: Awata N, Sakai T, Satomi O, Kawashima T. [Metabolism of lomerizine hydrochloride (KB-2796) in rats]. Yakugaku Zasshi. 1995 Feb;115(2):120-9. Japanese. PubMed PMID: 7722879. 14: Watano T, Hara H, Sukamoto T. Inhibitory effect of lomerizine, a diphenylpiperazine Ca2+-channel blocker, on Ba2+ current through voltage-gated Ca2+ channels in PC12 cells. Jpn J Pharmacol. 1997 Oct;75(2):209-13. PubMed PMID: 9414039. 15: Fitzgerald M, Bartlett CA, Evill L, Rodger J, Harvey AR, Dunlop SA. Secondary degeneration of the optic nerve following partial transection: the benefits of lomerizine. Exp Neurol. 2009 Mar;216(1):219-30. doi: 10.1016/j.expneurol.2008.11.026. Epub 2008 Dec 11. PubMed PMID: 19118550. 16: Hara H, Toriu N, Shimazawa M. Clinical potential of lomerizine, a Ca2+ channel blocker as an anti-glaucoma drug: effects on ocular circulation and retinal neuronal damage. Cardiovasc Drug Rev. 2004 Fall;22(3):199-214. Review. PubMed PMID: 15492768. 17: Selt M, Bartlett CA, Harvey AR, Dunlop SA, Fitzgerald M. Limited restoration of visual function after partial optic nerve injury; a time course study using the calcium channel blocker lomerizine. Brain Res Bull. 2010 Mar 16;81(4-5):467-71. doi: 10.1016/j.brainresbull.2009.11.004. Epub 2009 Nov 11. PubMed PMID: 19913075. 18: Toriu N, Sasaoka M, Shimazawa M, Sugiyama T, Hara H. Effects of lomerizine, a novel Ca2+ channel blocker, on the normal and endothelin-1-disturbed circulation in the optic nerve head of rabbits. J Ocul Pharmacol Ther. 2001 Apr;17(2):131-49. PubMed PMID: 11324981. 19: Toriu N, Akaike A, Yasuyoshi H, Zhang S, Kashii S, Honda Y, Shimazawa M, Hara H. Lomerizine, a Ca2+ channel blocker, reduces glutamate-induced neurotoxicity and ischemia/reperfusion damage in rat retina. Exp Eye Res. 2000 Apr;70(4):475-84. PubMed PMID: 10865996. 20: Karim Z, Sawada A, Kawakami H, Yamamoto T, Taniguchi T. A new calcium channel antagonist, lomerizine, alleviates secondary retinal ganglion cell death after optic nerve injury in the rat. Curr Eye Res. 2006 Mar;31(3):273-83. PubMed PMID: 16531285.