NAV

Lomerizine

This drug entry is a stub and has not been fully annotated. It is scheduled to be annotated soon.

Identification

Generic Name
Lomerizine
DrugBank Accession Number
DB14065
Background

Lomerizine is a diphenylmethylpiperazine calcium channel blocker3,4 with relatively selective central nervous system (CNS) effects.4 This drug is used to prophylactically treat migraines1,2 and is also being investigated against eye-related diseases that are associated with local circulatory disturbances, an example being normal-tension glaucoma.3

Type
Small Molecule
Groups
Experimental
Structure
3D
Similar Structures
Weight
Average: 468.545
Monoisotopic: 468.22244916
Chemical Formula
C27H30F2N2O3
Synonyms
  • Lomerazine
  • Lomerizine
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Pharmacology

Indication

Not Available

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Contraindications & Blackbox Warnings
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Pharmacodynamics

Not Available

Mechanism of action
TargetActionsOrganism
AP-glycoprotein 1
inhibitor
Humans
Absorption

Not Available

Volume of distribution

Not Available

Protein binding

Not Available

Metabolism
Not Available
Route of elimination

Not Available

Half-life

Not Available

Clearance

Not Available

Adverse Effects
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Toxicity

Not Available

Pathways
Not Available
Pharmacogenomic Effects/ADRs
Not Available

Interactions

Drug Interactions
This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
DrugInteraction
Integrate drug-drug
interactions in your software
AbametapirThe serum concentration of Lomerizine can be increased when it is combined with Abametapir.
AcarboseThe risk or severity of hypoglycemia can be increased when Lomerizine is combined with Acarbose.
AcebutololAcebutolol may increase the arrhythmogenic activities of Lomerizine.
AceclofenacThe risk or severity of hyperkalemia can be increased when Aceclofenac is combined with Lomerizine.
AcemetacinThe risk or severity of hyperkalemia can be increased when Acemetacin is combined with Lomerizine.
Food Interactions
Not Available

Products

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Product Ingredients
IngredientUNIICASInChI Key
Lomerizine dihydrochloride3W473D5LIY101477-54-7LOGVKVSFYBBUAJ-UHFFFAOYSA-N

Categories

Drug Categories
Classification
Not classified
Affected organisms
Not Available

Chemical Identifiers

UNII
DEE37CY4VO
CAS number
101477-55-8
InChI Key
JQSAYKKFZOSZGJ-UHFFFAOYSA-N
InChI
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
IUPAC Name
1-[bis(4-fluorophenyl)methyl]-4-[(2,3,4-trimethoxyphenyl)methyl]piperazine
SMILES
COC1=CC=C(CN2CCN(CC2)C(C2=CC=C(F)C=C2)C2=CC=C(F)C=C2)C(OC)=C1OC

References

General References
  1. 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. [Article]
  2. 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. doi: 10.1254/jphs.09205sc. Epub 2009 Sep 26. [Article]
  3. 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. doi: 10.1089/10807680151125456. [Article]
  4. 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. [Article]
ChemSpider
3812
BindingDB
50095765
ChEBI
94682
ChEMBL
CHEMBL29188
ZINC
ZINC000019362693
Wikipedia
Lomerizine

Clinical Trials

Clinical Trials
PhaseStatusPurposeConditionsCount

Pharmacoeconomics

Manufacturers
Not Available
Packagers
Not Available
Dosage Forms
Not Available
Prices
Not Available
Patents
Not Available

Properties

State
Solid
Experimental Properties
Not Available
Predicted Properties
PropertyValueSource
Water Solubility0.00673 mg/mLALOGPS
logP4.47ALOGPS
logP5.08Chemaxon
logS-4.8ALOGPS
pKa (Strongest Basic)6.73Chemaxon
Physiological Charge1Chemaxon
Hydrogen Acceptor Count5Chemaxon
Hydrogen Donor Count0Chemaxon
Polar Surface Area34.17 Å2Chemaxon
Rotatable Bond Count8Chemaxon
Refractivity129.37 m3·mol-1Chemaxon
Polarizability49.19 Å3Chemaxon
Number of Rings4Chemaxon
Bioavailability1Chemaxon
Rule of FiveNoChemaxon
Ghose FilterYesChemaxon
Veber's RuleYesChemaxon
MDDR-like RuleYesChemaxon
Predicted ADMET Features
Not Available

Spectra

Mass Spec (NIST)
Not Available
Spectra
SpectrumSpectrum TypeSplash Key
Predicted MS/MS Spectrum - 10V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0000900000-ed0f45a04fabc2d45b80
Predicted MS/MS Spectrum - 10V, Negative (Annotated)Predicted LC-MS/MSsplash10-014i-0000900000-84a87c65dcc7cdedb984
Predicted MS/MS Spectrum - 20V, Positive (Annotated)Predicted LC-MS/MSsplash10-014i-0020900000-6f0f10845e34ce043e2d
Predicted MS/MS Spectrum - 20V, Negative (Annotated)Predicted LC-MS/MSsplash10-01bi-0011900000-f2655e03378fdc002a35
Predicted MS/MS Spectrum - 40V, Positive (Annotated)Predicted LC-MS/MSsplash10-0udi-5389800000-d2df483f9b232c6398c6
Predicted MS/MS Spectrum - 40V, Negative (Annotated)Predicted LC-MS/MSsplash10-0ukc-0394600000-3d76959b740d38fbbe2a
Predicted 1H NMR Spectrum1D NMRNot Applicable
Predicted 13C NMR Spectrum1D NMRNot Applicable
Chromatographic Properties
Collision Cross Sections (CCS)
Not Available

Targets

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Details1. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Yes
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Ji BS, He L, Li XQ, Liu GQ: CJZ3, a lomerizine derivative, modulates P-glycoprotein function in rat brain microvessel endothelial cells. Acta Pharmacol Sin. 2006 Apr;27(4):414-8. doi: 10.1111/j.1745-7254.2006.00294.x. [Article]
  2. 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. [Article]

Enzymes

Details1. Cytochrome P450 3A4
Kind
Protein
Organism
Humans
Pharmacological action
No
Actions
Substrate
General Function
Vitamin d3 25-hydroxylase activity
Specific Function
Cytochromes P450 are a group of heme-thiolate monooxygenases. In liver microsomes, this enzyme is involved in an NADPH-dependent electron transport pathway. It performs a variety of oxidation react...
Gene Name
CYP3A4
Uniprot ID
P08684
Uniprot Name
Cytochrome P450 3A4
Molecular Weight
57342.67 Da
References
  1. Uesawa Y, Takeuchi T, Mohri K: Integrated analysis on the physicochemical properties of dihydropyridine calcium channel blockers in grapefruit juice interactions. Curr Pharm Biotechnol. 2012 Jul;13(9):1705-17. [Article]

Transporters

Details1. P-glycoprotein 1
Kind
Protein
Organism
Humans
Pharmacological action
Unknown
Actions
Inhibitor
General Function
Xenobiotic-transporting atpase activity
Specific Function
Energy-dependent efflux pump responsible for decreased drug accumulation in multidrug-resistant cells.
Gene Name
ABCB1
Uniprot ID
P08183
Uniprot Name
Multidrug resistance protein 1
Molecular Weight
141477.255 Da
References
  1. Ji BS, Li M, He L: Interaction of CJZ3, a lomerizine derivative, with ATPase activity of human P-glycoprotein in doxorubicin-resistant human myelogenous leukemia (K562/DOX) cells. Pharmazie. 2010 Jul;65(7):515-9. [Article]
  2. 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. [Article]

Drug created at June 14, 2018 20:01 / Updated at February 15, 2022 14:48