LIDOCAINE

/static/temp/default.svg Search structure
Trade Names
Synonyms
Status
Molecule Category Free-form
ATC C01BB01 C05AD01 D04AB01 N01BB02 R02AD02 S01HA07 S02DA01
UNII 98PI200987
EPA CompTox DTXSID1045166

Structure

InChI Key NNJVILVZKWQKPM-UHFFFAOYSA-N
Smiles CCN(CC)CC(=O)Nc1c(C)cccc1C
InChI
InChI=1S/C14H22N2O/c1-5-16(6-2)10-13(17)15-14-11(3)8-7-9-12(14)4/h7-9H,5-6,10H2,1-4H3,(H,15,17)

Physicochemical Descriptors

Property Name Value
Molecular Formula C14H22N2O
Molecular Weight 234.34
AlogP 2.58
Hydrogen Bond Acceptor 2.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 5.0
Polar Surface Area 32.34
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 17.0

Bioactivity

Mechanism of Action Action Reference
Sodium channel alpha subunit blocker BLOCKER PubMed PubMed
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 1 subunit alpha
Organism : Homo sapiens
P35498 ENSG00000144285
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 4 subunit alpha
Organism : Homo sapiens
P35499 ENSG00000007314
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 5 subunit alpha
Organism : Homo sapiens
Q14524 ENSG00000183873
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 9 subunit alpha
Organism : Homo sapiens
Q15858 ENSG00000169432
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 2 subunit alpha
Organism : Homo sapiens
Q99250 ENSG00000136531
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 3 subunit alpha
Organism : Homo sapiens
Q9NY46 ENSG00000153253
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 11 subunit alpha
Organism : Homo sapiens
Q9UI33 ENSG00000168356
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 8 subunit alpha
Organism : Homo sapiens
Q9UQD0 ENSG00000196876
Protein: Sodium channel alpha subunit
Description: Sodium channel protein type 10 subunit alpha
Organism : Homo sapiens
Q9Y5Y9 ENSG00000185313
Targets EC50(nM) IC50(nM) Kd(nM) Ki(nM) Inhibition(%)
Ion channel Voltage-gated ion channel Potassium channels Two-pore domain potassium channel
- - - - 62
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- 10500 - - 10-31
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC22 family of organic cation and anion transporters
- - - -
Transporter Electrochemical transporter SLC superfamily of solute carriers SLC47 family of multidrug and toxin extrusion transporters
- - - - 7
Unclassified protein
- - - - 0-1
Assay Description Organism Bioactivity Reference
Inhibition of beta-lactamase at 100 uM None 5.0 %
Inhibition of chymotrypsin at 250 uM unidentified 5.0 %
Inhibition of malate dehydrogenase (MDH) at 400 uM None 5.0 %
Percentage inhibition of specific binding of [3H]dofetilide (UK-68,798) from cardiac myocytes with blockade of delayed rectifier K+ channel Cavia porcellus 5.0 %
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high affinity sites on voltage dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 10 uM Cavia porcellus 9.8 %
Inhibition of binding of Batrachotoxinin [3H]BTX-B to high-affinity sites on voltage-dependent sodium channels in a vesicular preparation from guinea pig cerebral cortex at 100 uM Cavia porcellus 31.4 %
Percentage inhibition of specific binding of [3H]batrachotoxin [3H]BTX) in sodium channel from cardiac myocytes at 10 uM Rattus norvegicus 10.0 %
Inhibition of calcium-induced contraction of potassium ion depolarized guinea pig aortic strips at 100 uM Cavia porcellus 14.0 %
Negative inotropic activity assessed as decrease in developed tension in isolated guinea pig left atrium Cavia porcellus 17.0 nM
Inhibition of 4-(4-(dimethylamino)styryl)-N-methylpyridinium uptake at human OCT1 expressed in HEK293 cells at 100 uM by confocal microscopy Homo sapiens -2.3 %
Vasorelaxant activity in potassium depolarized guinea pig aortic strip assessed as inhibition of calcium-induced contraction at 50 uM Cavia porcellus 14.0 %
Negative inotropic activity against potassium-induced contraction in guinea pig left atrium assessed as decrease in developed tension Cavia porcellus 17.0 nM
Inhibition of polyhistidine tagged yeast prion protein Sup35 expressed in Escherichia coli BL21 (DE3) assessed as inhibition of amyloid polymerization at 50 uM by thioflavin T fluorescence assay relative to untreated control Saccharomyces cerevisiae 1.1 %
Inhibition of polyhistidine tagged yeast prion protein Sup35 expressed in Escherichia coli BL21 (DE3) assessed as inhibition of amyloid polymerization at 50 uM in presence of 5 mg/ml BSA by thioflavin T fluorescence assay relative to untreated control Saccharomyces cerevisiae 0.0 %
Inhibition of mouse prion protein (89-230) assessed as inhibition of amyloid polymerization at 25 uM by thioflavin T fluorescence assay relative to untreated control Mus musculus 0.0 %
Negative inotropic activity in guinea pig left atria assessed as decrease of 1 Hz current-induced developed tension Cavia porcellus 17.0 nM
Reduction in amplitude of compound action potential in bullfrog sciatic nerve at 0.5 mM after 15 mins by electrophysiology Rana catesbeiana 46.0 %
Inhibition of human MATE1-mediated ASP+ uptake expressed in HEK293 cells at 20 uM after 1.5 mins by fluorescence assay Homo sapiens 7.0 %
Antibacterial activity against Staphylococcus aureus MRSA ATCC 43300 (CO-ADD:GP_020); MIC in CAMBH media, using NBS plates, by OD(600) Staphylococcus aureus subsp. aureus 9.46 %
Antibacterial activity against Escherichia coli ATCC 25922 (CO-ADD:GN_001); MIC in CAMBH media using NBS plates, by OD(600) Escherichia coli -3.44 %
Antibacterial activity against Klebsiella pneumoniae MDR ATCC 70063 (CO-ADD:GN_003); MIC in CAMBH media using NBS plates, by OD(600) Klebsiella pneumoniae 14.92 %
Antibacterial activity against Pseudomonas aeruginosa ATCC 27853 (CO-ADD:GN_042); MIC in CAMBH media using NBS plates, by OD(600) Pseudomonas aeruginosa 23.12 %
Antibacterial activity against Acinetobacter baumannii ATCC 19606 (CO-ADD:GN_034); MIC in CAMBH media using NBS plates, by OD600 Acinetobacter baumannii 23.46 %
Antifungal activity against Candida albicans ATCC 90028 (CO-ADD:FG_001); MIC in YNB media using NBS plates, by OD630 Candida albicans 1.15 %
Antifungal activity against Cryptococcus neoformans H99 ATCC 208821 (CO-ADD:FG_002); MIC in YNB media using NBS plates, by Resazurin OD(600-570) Cryptococcus neoformans -4.85 %
Inhibition of rat TASK3 expressed in African green monkey COS7 cells at 1 mM by outside-out patches based electrophysiology assay relative to control Rattus norvegicus 62.0 %
Inhibition of ARAT in bovine RPE microsomes at 100 uM using retinol substrate in presence of dilauroyl-phosphatidyl choline incubated for 5 mins by HPLC analysis relative to control Bos taurus 12.0 %
Inhibition of LRAT in bovine RPE microsomes at 100 uM using retinol substrate in presence of Palmitoyl-CoA incubated for 5 mins by HPLC analysis relative to control Bos taurus 0.0 %

Related Entries

Environmental Exposure

Environmental Exposure Map
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Cross References

Resources Reference
ChEBI 6456
ChEMBL CHEMBL79
DrugBank DB00281
DrugCentral 1579
FDA SRS 98PI200987
Human Metabolome Database HMDB0014426
Guide to Pharmacology 2623
KEGG C07073
PDB LQZ
PharmGKB PA450226
PubChem 3676
SureChEMBL SCHEMBL17967359
ZINC ZINC000000020237
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