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MedKoo Cat#: 584550 | Name: Lomerizine

Description:

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

Lomerizine is a diphenylmethylpiperazine Ca2+ channel blocker that helps prevent migraines.

Chemical Structure

Lomerizine
Lomerizine
CAS#101477-55-8

Theoretical Analysis

MedKoo Cat#: 584550

Name: Lomerizine

CAS#: 101477-55-8

Chemical Formula: C27H30F2N2O3

Exact Mass: 468.2224

Molecular Weight: 468.54

Elemental Analysis: C, 69.21; H, 6.45; F, 8.11; N, 5.98; O, 10.24

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Lomerizine
IUPAC/Chemical Name
1-(Bis(p-fluorophenyl)-methyl)-4-(2,3,4-trimethoxybenzyl)piperazine
InChi Key
JQSAYKKFZOSZGJ-UHFFFAOYSA-N
InChi Code
InChI=1S/C27H30F2N2O3/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
SMILES Code
COC1=CC=C(C(OC)=C1OC)CN2CCN(C(C3=CC=C(F)C=C3)C4=CC=C(F)C=C4)CC2
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
>3 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
2934.99.03.00
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 468.54 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
1: 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. 2: 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. 3: Ishii M, Katoh H, Takagi M, Kawamura M, Shimizu S. Influence of the Tohoku-Pacific Ocean earthquake and its aftershocks on the response to prophylactic therapy with lomerizine in patients with migraine in Tokyo: a retrospective study. Eur Neurol. 2014;71(5-6):252-8. doi: 10.1159/000357209. Epub 2014 Feb 5. PubMed PMID: 24503777. 4: 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. 5: 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. 6: Inoue Y, Yabe T. Lomerizine therapy for the treatment of benign paroxysmal vertigo of childhood transitioning into atypical basilar migraine: A case report. Exp Ther Med. 2013 Jun;5(6):1573-1575. Epub 2013 Apr 2. PubMed PMID: 23837033; PubMed Central PMCID: PMC3702696. 7: Okano M, Thevis M, Sato M, Kageyama S. Analytical detection of trimetazidine produced by metabolic conversion of lomerizine in doping control analysis. Drug Test Anal. 2016 Aug;8(8):869-74. doi: 10.1002/dta.1893. Epub 2015 Nov 11. PubMed PMID: 26560081. 8: 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. 9: Shimizu H, Nagami S, Takahashi N. [A case of cerebral autosomal dominant arteriopathy with subcortical infarcts and leukoencephalopathy (CADASIL) in which lomerizine hydrochloride was suggested to prevent recurrent stroke]. Rinsho Shinkeigaku. 2014;54(1):22-6. Japanese. PubMed PMID: 24429644. 10: 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. 11: 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. 12: 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. 13: 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. 14: Hara H, Shimazawa M, Sasaoka M, Yamada C, Iwakura Y, Sakai T, Maeda Y, Yamaguchi T, Sukamoto T, Hashimoto M. Selective effects of lomerizine, a novel diphenylmethylpiperazine Ca2+ channel blocker, on cerebral blood flow in rats and dogs. Clin Exp Pharmacol Physiol. 1999 Nov;26(11):870-6. PubMed PMID: 10561807. 15: 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. 16: 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. 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: 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. 20: 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.

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