RANOLAZINE

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Trade Names
Synonyms
Status
Molecule Category UNKNOWN
ATC C01EB18
UNII A6IEZ5M406
EPA CompTox DTXSID3045196

Structure

InChI Key XKLMZUWKNUAPSZ-UHFFFAOYSA-N
Smiles COc1ccccc1OCC(O)CN1CCN(CC(=O)Nc2c(C)cccc2C)CC1
InChI
InChI=1S/C24H33N3O4/c1-18-7-6-8-19(2)24(18)25-23(29)16-27-13-11-26(12-14-27)15-20(28)17-31-22-10-5-4-9-21(22)30-3/h4-10,20,28H,11-17H2,1-3H3,(H,25,29)

Physicochemical Descriptors

Property Name Value
Molecular Formula C24H33N3O4
Molecular Weight 427.55
AlogP 2.31
Hydrogen Bond Acceptor 6.0
Hydrogen Bond Donor 2.0
Number of Rotational Bond 9.0
Polar Surface Area 74.27
Molecular species NEUTRAL
Aromatic Rings 2.0
Heavy Atoms 31.0

Bioactivity

Mechanism of Action Action Reference
Sodium channel protein type IV alpha subunit blocker BLOCKER PubMed
Protein: Sodium channel protein type IV alpha subunit
Description: Sodium channel protein type 4 subunit alpha
Organism : Homo sapiens
P35499 ENSG00000007314
Protein: Sodium channel protein type V alpha subunit
Description: Sodium channel protein type 5 subunit alpha
Organism : Homo sapiens
Q14524 ENSG00000183873
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Enzyme Kinase Protein Kinase AGC protein kinase group AGC protein kinase PKC family AGC protein kinase PKC iota subfamily
- 6900 - - -
Ion channel Voltage-gated ion channel Potassium channels Voltage-gated potassium channel
- 12000 - - -
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- - - - 11-19
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC21/SLCO family of organic anion transporting polypeptides
- - - - -15-83
Assay Description Organism Bioactivity Reference
Inhibition of human sodium Nav1.5 channel expressed in HEK293 cells assessed as inhibition of veratridine-induced late sodium current elicited at -30 mV from holding potential of -110 mV at 10 uM by patch clamp technique Homo sapiens 11.0 %
Inhibition of human sodium Nav1.5 channel expressed in HEK293 cells assessed as inhibition of veratridine-induced late sodium current elicited at -30 mV from holding potential of -90 mV at 10 uM by patch clamp technique Homo sapiens 19.0 %
Inhibition of human liver OATP1B1 expressed in HEK293 Flp-In cells assessed as reduction in E17-betaG uptake at 20 uM by scintillation counting Homo sapiens 4.3 %
Inhibition of human liver OATP1B3 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E17-betaG uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens -14.9 %
Inhibition of human liver OATP2B1 expressed in HEK293 Flp-In cells assessed as reduction in [3H]E3S uptake at 20 uM incubated for 5 mins by scintillation counting Homo sapiens 41.6 %
Inhibition of sodium fluorescein uptake in OATP1B1-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 70.75 %
Inhibition of sodium fluorescein uptake in OATP1B3-transfected CHO cells at an equimolar substrate-inhibitor concentration of 10 uM Cricetulus griseus 83.1 %
Inhibition of 0.1 Hz stimulated human Nav1.5alpha expressed in HEK293 cells assessed as inhibition of late sodium current at 10 uM with 3 compound additions for 7 to 8 mins at holding potential -120 mV in presence of late sodium current activator tefluthrin/ATX2 measured immediately after third compound addition by PatchXpress method relative to control Homo sapiens 17.0 %
Inhibition of Nav 1.5 in langerdorff isolated heart model (unknown origin) assessed as reversal of ATX-2 induced increase in monophasic action potential duration Not specified 60.0 %
Inhibition of 0.1 Hz stimulated human Nav1.5alpha expressed in HEK293 cells assessed as inhibition of late sodium current at 10 uM with 3 compound additions for 7 to 8 mins at holding potential -120 mV in presence of late sodium current activator tefluthrin/ATX2 measured immediately after third compound addition by PatchXpress method relative to control Homo sapiens 17.0 %
Inhibition of Nav1.5 in isolated rabbit heart assessed as inhibition of ATX2-induced prolongation of mean action potential duration at 10 to 100000 nM relative to control Oryctolagus cuniculus 60.0 %
Cardioprotective activity in New Zealand rabbit model of LAD coronary artery occlusion-induced ischemia-reperfusion injury assessed as inhibition of ST segment elevation at 12 uM for 30 mins followed by induction of ischemia for 15 mins and subsequent reperfusion for 15 mins by electrocardiographic analysis Oryctolagus cuniculus 60.0 %

Cross References

Resources Reference
ChEBI 87690
ChEMBL CHEMBL1404
DrugBank DB00243
DrugCentral 2359
FDA SRS A6IEZ5M406
Human Metabolome Database HMDB0014388
Guide to Pharmacology 7291
PharmGKB PA164746007
PubChem 56959
SureChEMBL SCHEMBL124665
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