TETRACAINE

/static/temp/default.svg Search structure
Synonyms
Status
Molecule Category Free-form
ATC C05AD02 D04AB06 N01BA03 S01HA03
UNII 0619F35CGV
EPA CompTox DTXSID1043883

Structure

InChI Key GKCBAIGFKIBETG-UHFFFAOYSA-N
Smiles CCCCNc1ccc(C(=O)OCCN(C)C)cc1
InChI
InChI=1S/C15H24N2O2/c1-4-5-10-16-14-8-6-13(7-9-14)15(18)19-12-11-17(2)3/h6-9,16H,4-5,10-12H2,1-3H3

Physicochemical Descriptors

Property Name Value
Molecular Formula C15H24N2O2
Molecular Weight 264.37
AlogP 2.62
Hydrogen Bond Acceptor 4.0
Hydrogen Bond Donor 1.0
Number of Rotational Bond 8.0
Polar Surface Area 41.57
Molecular species NEUTRAL
Aromatic Rings 1.0
Heavy Atoms 19.0

Bioactivity

Mechanism of Action Action Reference
Sodium channel alpha subunit blocker BLOCKER ISBN PubMed 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 Cyclic nucleotide-regulated channel
- - 6800-12000 - -
Ion channel Voltage-gated ion channel Voltage-gated sodium channel
- 56-7510 - 500-12000 72
Assay Description Organism Bioactivity Reference
Antagonism of batrachotoxin-mediated sodium ion uptake into cultured neuroblastoma cells None 400.0 nM
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 72.0 %
Cardiotoxicity in iv dosed Dunkin-Hartley guinea pig assessed as drug level required to evoke 50 ms QTc prolongation administered as 3 fold cumulative doses measured every 10 seconds at end of every 20 mins follow up period of individual dose by ECG Cavia porcellus 9.04 umol/Kg
Displacement of [3H]BTX from human Nav1.7 expressed in human HEK293 cells after 1 hr by MicroBeta analyzer Homo sapiens 500.0 nM
DRUGMATRIX: Monoamine Oxidase MAO-A enzyme inhibition (substrate: Kynuramine) None 317.0 nM
DRUGMATRIX: Serotonin (5-Hydroxytryptamine) 5-HT2A radioligand binding (ligand: [3H] Ketanserin) None 976.0 nM
DRUGMATRIX: Sigma1 radioligand binding (ligand: [3H] Haloperidol) None 703.0 nM
Inhibition of human NaV1.5 alpha subunit expressed in CHOK1 cells at -90 mV holding potential by patch clamp electrophysiological assay Homo sapiens 530.0 nM
Inhibition of recombinant human NaV1.7 alpha subunit expressed in HEK293 cells at -90 mV holding potential by patch clamp electrophysiological assay Homo sapiens 620.0 nM
Inhibition of recombinant human NaV1.7 alpha subunit expressed in HEK293 cells at -65 mV holding potential by patch clamp electrophysiological assay Homo sapiens 110.0 nM
Inhibition of recombinant human Nav1.7 expressed in HEK293F cells preincubated for 40 mins followed by DiSBAC2 substrate addition measured after 90 mins by FRET assay Homo sapiens 56.0 nM
Inhibition of human Nav1.7 expressed in HEK293F cells measured at -65 mV holding potential by voltage-patch clamp method Homo sapiens 320.0 nM
Inhibition of human Nav1.5 expressed in HEK293 cells by whole cell-patch clamp method Homo sapiens 650.0 nM
Inhibition of recombinant human Nav1.2 expressed in HEK293 cells preincubated for 40 mins followed by DiSBAC2 substrate addition measured after 90 mins by FRET assay Homo sapiens 490.0 nM
Inhibition of recombinant human Nav1.3 expressed in HEK293 cells preincubated for 40 mins followed by DiSBAC2 substrate addition measured after 90 mins by FRET assay Homo sapiens 740.0 nM
Inhibition of recombinant human Nav1.6 expressed in HEK293 cells preincubated for 40 mins followed by DiSBAC2 substrate addition measured after 90 mins by FRET assay Homo sapiens 520.0 nM
Inhibition of human Nav1.7 expressed in CHO-K1 cells at -120 mV holding potential incubated over 5 mins measured at 15 secs interval by Qpatch clamp assay Homo sapiens 200.0 nM
Inhibition of human Nav1.5 expressed in HEK293 cells at -120 mV holding potential incubated over 5 mins measured at 15 secs interval by Qpatch clamp assay Homo sapiens 200.0 nM
SARS-CoV-2 3CL-Pro protease inhibition percentage at 20µM by FRET kind of response from peptide substrate Severe acute respiratory syndrome coronavirus 2 2.35 %
Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.05 % Antiviral activity determined as inhibition of SARS-CoV-2 induced cytotoxicity of VERO-6 cells at 10 uM after 48 hours exposure to 0.01 MOI SARS CoV-2 virus by high content imaging Chlorocebus sabaeus -0.05 %

Related Entries

Cross References

Resources Reference
ChEBI 9468
ChEMBL CHEMBL698
DrugBank DB09085
DrugCentral 2610
FDA SRS 0619F35CGV
KEGG C07526
PDB TE4
PubChem 5411
SureChEMBL SCHEMBL34714
ZINC ZINC000001530811
CONTENTS